Adi Pradhan

Founder of Socratify. Building an AI career skills agent for interview prep and professional upskilling.

I’m not sorry for following curiosity over looking smart.

Three winning principles

01

The unexamined life is not worth living (Socrates).

Outsourcing your thoughts and opinions to LLMs and podcasters has never been easier. To be ‘un-LLMable’ you have to struggle through messy human thought and introspection.

02

Do or Do Not. There is No Try (Master Yoda).

Don’t give yourself an excuse by simply “trying.” Do it, recognize if it didn’t work and keep moving.

03

Not all friction is bad.

Be intentional with friction you embrace vs. automate. Don’t miss the view by taking a helicopter up the mountain.

One thing to takeaway

Adi is the Founder of Socratify, a career skills agent that uses AI-powered debate, interview simulations, and personalized coaching to build critical thinking, structured reasoning, and communication skills. A University of Michigan Ross alum and McKinsey alum, he has also written on developing AI at scale.

Aimee Langevin

Founder and CEO of Skintuition. Building AI-powered skincare support for people tired of trial-and-error routines.

I’m not sorry for choosing real over impressive.

Three winning principles

01

If you don’t believe you can win, you’ve already lost.

Everything starts with belief. It sets the standard for how you show up, how you think, and what you go after. Sometimes you need an unreasonable level of confidence because that’s what lets you take the actions that create results.

02

Consistency compounds. What feels small daily becomes everything over time.

Most people underestimate how much progress comes from showing up every day. The unglamourous work is what builds momentum. Failing and learning from your mistakes. Sticking with it when nothing seems to be working. You don’t notice it day to day, but over time it separates people completely.

03

I’d rather take ownership and fail than succeed inside something I don’t believe in.

There’s a different kind of pressure when it’s yours. You can’t wait for direction or hide when something goes wrong. But that’s also where the meaning is. Even if it doesn’t work, I’d rather know I went all in on something I cared about than be successful building someone else’s vision.

One thing to takeaway

Aimee is the Founder & CEO of Skintuition, an AI-powered skincare support tool that helps users understand routines, ingredients, habits, and skin progress over time. A Carnegie Mellon alum and James R. Swartz Fellow, she is building Skintuition with support from CMU’s AI Venture Studio and Jackson Square Ventures Launchpad.

Alex Chieng

Co-founder and Managing Partner of Pawsible Ventures. Backing and co-building early-stage pet health and animal health companies.

I’m not sorry for believing pet health deserves more innovation.

Three winning principles

01

Work hard. Really hard.

Hard work is still the greatest advantage. If you have to wake up earlier, do it. If you have to stay up later, do it. There are many things in life and business that are out of your control. How hard you work is one of the few that is entirely within it.

02

Remember why you started.

People sometimes forget why they started. Remind yourself every day what you’re working toward. Whether it’s for your family, your parents, your pets, or the people you want to help, staying connected to that motivation will carry you through the difficult days.

03

Surround yourself with great people.

Nothing meaningful is built alone. Surround yourself with people who challenge you, believe in what you’re building, and care deeply about the mission. The right partners and teammates make everything possible.

One thing to takeaway

Alex is the Co-Founder & Managing Partner of Pawsible Ventures, a pet-health fund and studio backing and co-building companies across veterinary care, diagnostics, AI, insurance, and consumer wellness. He previously co-founded Vetsie, one of North America’s first veterinary telemedicine platforms, bringing founder/operator experience to animal health venture building.

Alexandre Carey

Co-founder and CEO of AnchorPoint. Building AI agents and analytics tools for retail and business operations.

I’m not sorry for betting on Canada’s economic potential.

01

Never let a good crisis go to waste.

The world is loud with bad news. Markets crash, deals fall through, entire industries shift overnight. I’ve learned that the people who win aren’t the ones with the best starting hand; they’re the ones who see opportunity where everyone else sees chaos. Optimism isn’t naive. It’s a competitive advantage. The darkest moments have always preceded my biggest moves.

02

Radical transparency.

Life is too short to operate in half-truths. I tell clients what they need to hear, not what they want to hear. I tell my team when something isn’t working. I tell myself the truth first. It’s uncomfortable sometimes, but honesty is the only foundation that holds up long-term. Every relationship I’ve built that actually lasted was built on that.

03

Love and passion beat resources every time.

I’ve been outspent, out-networked, and out-credentialed more times than I can count. But I’ve never been out-cared. When you genuinely love what you’re building: the product, the people, the craft, and it shows up in the work. That energy is contagious and it’s impossible to fake. The biggest players in any room can throw money at a problem. They can’t manufacture heart.

One thing to takeaway

Alexandre is the Co-Founder & CEO of AnchorPoint Data, building voice AI agents and semantic analytics for operational teams. He previously spent nearly five years at SSENSE, including work leading analytics and operations systems across order, inventory, warehouse, and supply-chain workflows. He brings an industrial engineering and retail operations lens to applied AI.

Alexandre Cooper-Roy

Founder and CEO of UpScale Quantum Solutions. Building hardware to make quantum computing scalable.

I’m not sorry for going my own way, even when it meant choosing the hard path.

Three winning principles

01

Choose your path and own it.

Follow the direction you believe in, and take responsibility for the outcomes. Learn to savour that tension in your stomach.

02

Trust your judgment.

Make decisions before anything is proven, stay close to people who get it, and keep going when things start falling apart.

03

Devote yourself to things that are real and difficult.

There is little pride in choosing the easy path.

One thing to takeaway

Alexandre is the founder and CEO of UpScale Quantum Solutions and a Senior Technical Lead at the University of Waterloo’s Institute for Quantum Computing. An MIT-trained physicist (PhD, Nuclear Science), he is building the hardware infrastructure required to make quantum computers work at scale. His work focuses on developing the modular “interconnects” that allow quantum processors to communicate—solving the critical technical bottleneck that currently keeps quantum computing confined to the lab.

Ammaar Khan

Co-founder of The ADHD Weasel. Building a fast-growing ADHD media brand that helps readers turn overwhelm into clear, doable wins.

I’m not sorry for dedicating my career to a community that research overlooked for decades.

Three winning principles

01

Listen before you build.

We started with a food waste app nobody used. The people who did use it were adults with ADHD. Instead of forcing the original idea, we followed them. That pivot became a top #50 Substack newsletter.

02

Treat hard conversations as a feature, not a bug.

Most people dread them. A conversation about ownership, a missed deadline, a direction change. But avoiding them costs more than having them. Prepare with structure, open with facts, and let the other person propose solutions. Avoiding the hard conversation is usually the limiting factor.

03

Every problem you face, someone else has faced and wrote a book about.

When our meetings kept going off track, I found the answer in High Output Management. When a conversation felt impossible, Crucial Conversations gave me a framework that actually worked. Reading compounds faster than money.

One thing to takeaway

Ammaar is the Co-Founder of The ADHD Weasel, a weekly newsletter and media brand for ADHDers navigating focus, motivation, habits, and mental health. Launched in 2025, The ADHD Weasel has grown to 28,000+ subscribers with practical content, worksheets, and tools designed to make daily ADHD challenges feel more manageable.

Andrew Lockhead

Co-founder and CEO of Stay22. Building the monetization layer that helps creators and publishers turn travel intent into revenue.

I’m not sorry for chasing what most call impossible.

Three winning principles

01

Outcome over output.

Busy is easy, results are hard. It’s very easy to build a culture around activity. Meetings, tasks, updates, a lot of activity that feels productive but doesn’t translate into real impact. We try to stay disciplined about tying everything back to what actually moves the needle: revenue, product, or people. If it doesn’t clearly ladder up to one of those, it’s probably noise. A lot of teams know this, very few actually operate this way.

02

Speed is a strategy.

Perfect is a luxury. Most companies don’t lose because they’re wrong, they lose because they’re too slow. We ship quickly, learn and adjust. Fast decisions compound, over time that becomes a real competitive advantage. Speed isn’t chaos. It’s discipline applied faster.

03

Ask for forgiveness instead of permission.

There’s always a reason to wait, more data, more alignment, better timing but waiting is often just hesitation dressed up as discipline. Take the shot, figure it out as you go and clean up the mess if needed. Progress comes from motion, not from perfect planning. Most of the upside in life sits on the other side of “just go.”

One thing to takeaway

Andrew is the Co-Founder & CEO of Stay22, a Montreal travel-tech company helping creators, publishers, and event organizers monetize audience intent through AI-powered affiliate tools, interactive maps, and travel booking products. Stay22 works with 5,000+ creators and processes US$1B+ in yearly transactions; in 2026, the company announced a $122M minority growth investment from Summit Partners.

Andrew Walls

Founder and Partner at Boardroom Labs. Building ventures and operating systems for mission-driven organizations.

I’m not sorry for building ambitiously while living fully.

Three winning principles

01

You don’t have to be productive to justify your existence.

For a long time, I mistook motion for progress and exhaustion for commitment. Building a venture studio requires relentless drive, but I’ve learned that sustainable ambition demands a different math. True success isn’t just about revenue or scale; it’s about creating enduring value while maintaining the capacity to actually enjoy the things you create. If your work comes at the cost of your inner peace, your relationships, or your ability to be fully present, the math just doesn’t work out.

02

Follow your curiosity, wherever it leads.

Specialization is useful, but cross-disciplinary curiosity is how you spot the most interesting opportunities. Whether it’s diving into transition design, writing speculative fiction about the future, or learning to scuba dive and rock climb, I try to follow what fascinates me. The world’s most complex problems aren’t solved in a single lane. If something makes you lose track of time, take it seriously.

03

Show up for the future you want.

The systems we rely on are struggling to adapt to a rapidly changing world. You cannot optimize your way out of systemic failure; you have to build new models. Whether that means launching ventures that transform proactive healthcare, creating equitable infrastructure, or simply showing up for systemic reform in your community, you have to put your energy where your convictions are. The future gets made by people who decide to build it.

One thing to takeaway

Andrew is a strategist and innovator at Boardroom Labs, working at the intersection of design thinking, venture building, and future-focused strategy to help organizations create systemic change across healthcare, economics, and infrastructure.

Angela Nader

Co-founder of Ad-Lib. Built creative automation technology that became part of Smartly’s AI advertising platform.

I’m not sorry for proving ambition and humility can coexist.

Three winning principles

01

Stay low ego and stay in the game.

The best founders I know aren’t the loudest in the room. Ego closes you off but humility keeps you learning, iterating, and earning trust.

02

Keep a player-coach mentality.

I don’t believe in leading from a distance. I’m in the work alongside my team. That’s how you spot real problems, build real culture, and stay sharp enough to make good calls. It also means you’re close enough to pull in perspectives that would never reach a leader operating from a distance and those are often the ones with the most honest read on what’s actually happening.

03

Make the call and own the outcome.

Waiting for alignment is comfortable but the best moves I’ve made were ones nobody else fully believed in yet: bootstrapping, selling on our terms, betting on my own judgment before anyone else did.

One thing to takeaway

Angela is a consumer tech operator, revenue leader, and Co-Founder of Ad-Lib, a creative automation company that became part of Smartly and is now integrated into its Creative Suite and AI Studio. Based in London, she has built and restructured commercial organizations across global platforms, with experience spanning TikTok, Spotify, Deloitte, and EY.

April Hicke

Founder and CEO of Toast. Helping women and nonbinary professionals get hired, paid, and promoted in tech.

I’m not sorry for lifting up women in tech.

Three winning principles

01

Hope is a strategy.

Cynicism is easy. Building something better is harder. The future doesn’t change because people complain about it, it changes because someone decides to build something different. Progress almost always starts with someone refusing to accept the status quo.

02

Build things that matter.

Starting a company is one of the most direct ways to turn ideas into reality. If you’re going to spend years building something, it should make the world better for someone else. Businesses can shape opportunity, culture, and who gets to participate in the economy.

03

Bet on people.

Talent is everywhere, opportunity is not. Some of the most capable people are overlooked because they don’t fit traditional hiring patterns. When you build systems that see people properly, companies - and entire industries - get stronger.

One thing to takeaway

April is the Founder & CEO of Toast, a tech recruitment platform focused on increasing gender diversity in tech. Toast has helped women land roles and negotiate compensation, putting $25M+ into women’s hands. A former PwC, WestJet, and ATB leader with 15+ years across leadership, mentoring, and change management, she is building a hiring platform around equity, advocacy, and measurable career outcomes.

Ashima Chopra

Founder and CEO of FanVerse. Building predictive fan intelligence, focusing on female fandom across all sports.

I’m not sorry for taking up space and wanting more.

Three winning principles

01

Alignment matters more than applause.

I’ve learned that being praised for something is not the same as being fulfilled by it. There were seasons of my life where, on paper, things looked impressive, but internally I knew I was building a life that didn’t fully fit. One of the biggest lessons I’ve learned is that external validation can be very loud, but is not always honest. Alignment has a different kind of truth to it. I make decisions now by asking whether something expands me, challenges me in the right ways, and feels connected to who I actually am becoming, not just whether it looks good to other people.

02

The right rooms will challenge you, not shrink you.

I’ve become much more discerning about the environments I choose. Not every opportunity is worth saying yes to, and not every room that looks impressive is actually expansive. I pay attention to what a space invites in versus what it rewards. I’ve also learned not to put people on pedestals in those rooms. Titles and proximity to power can create the illusion that others have it all figured out. What’s shifted is not just how I see others, but how I see myself. I don’t walk into rooms assuming I have less to offer. I walk in as a peer, not a spectator, grounded in my value, able to contribute and hold my own without needing to prove it first.

03

You don’t need permission to evolve.

One of the hardest things I’ve learned is that growth often requires disappointing people’s expectations of who you used to be. You don’t owe anyone consistency at the expense of your own evolution. You’re allowed to change your mind, outgrow old identities, and move toward something that makes more sense for who you are now.

One thing to takeaway

Ashima is the Founder & CEO of FanVerse, a predictive data intelligence company helping sports, media, and commerce brands understand, engage, and grow female fandom. A lawyer with experience across human rights and venture capital, she studied at Queen Mary University of London and is building around one of sports’ most under-measured audiences.

Bryn Davis Williams

Co-founder and CEO of DOUBL. Building personalized fit technology that helps shoppers find clothing based on their proportions.

I’m not sorry for rejecting the status quo.

Three winning principles

01

Do an energy audit.

What we actually need to balance isn’t work versus life, it’s the give and the take of energy. There are things at work that fill me up and things in my personal life that drain me, and pitting “work” against “life” misses that entirely. The more you understand what gives you energy and what takes it, and the more intentionally you carve out time for the givers, the better off you’ll be. An energy audit won’t solve every scheduling conflict, but it’s one of the most useful things I do when planning ahead and setting boundaries that actually hold.

02

Question everything.

Stay curious, always. You’ve been dropped into the world in a minuscule sliver of time, and everything you do will barely be remembered. I find that genuinely exciting. What can I push? What can I change in the time I have? We stand in our own way more often than anything else stands in it for us, hiding behind rules we think can never change. We had it right as kids. Keep asking why.

03

Compare yourself to yourself.

Everyone has a different starting point, and social media makes it easy to forget that. You see someone ahead of you and feel behind, but you have no idea where they began. The only honest data point you have is your own. We’re so focused on the gap between where we are and where we want to go that we forget to look back at how far we’ve actually come. Beating yourself, knowing exactly what it took to do it, is more fulfilling than beating anyone else could ever be.

One thing to takeaway

Bryn is the Co-Founder & CEO of DOUBL, a personalized fit platform that creates a virtual body double from a phone scan to help shoppers find better-fitting clothing across brands. An Ivey HBA and former Unilever brand marketer, she brings consumer brand and growth experience to a company rethinking sizing, fit, and apparel recommendations.

Charles Antoine Malenfant

Co-founder and CTO of GhostEye. Building AI-powered human-layer security software for phishing, scam-call, text, and deepfake risk.

I’m not sorry for representing French Canadians on the biggest stages.

Three winning principles

01

When in doubt, choose the harder option.

I’ve been following this principle for as long as I can remember. When faced with uncertainty (what major to choose, what career to pursue, etc.), going for the harder option will tend to be rewarded by either opening more doors or by acquiring useful skills.

02

Humility and integrity are very underrated virtues to live by.

Consistent and genuine display of humility and integrity engenders trust which is key to have success in any sphere of life. This said, unshakable confidence is also a huge part of it and striking the right balance between confidence and humility is what one should always strive towards.

03

Increase your surface area of luck.

When it comes to the startup world, YC has taught us to stay alive long enough to get lucky. I think this one applies beyond startups. A lot of creating your own luck involves stepping out of your comfort zone and putting yourself out there. Doing this consistently will dramatically increase the likelihood of getting lucky.

One thing to takeaway

Charles is the Co-Founder & CTO of GhostEye, a YC S25 cybersecurity company building vulnerability management for the human layer. A former Senior AI Engineer at BlackRock, he builds AI systems that map employee exposure and run personalized phishing, scam-call, text, and deepfake simulations to help security teams measure human risk.

Chinni Kanu

Co-founder and CEO of Ceezaa. Building a consumer app that translates spending behavior into taste and identity.

I’m not sorry for walking away from the traditional path.

Three winning principles

01

The safest path is the most dangerous one.

I had the path laid out. Queen’s Commerce. M&A investment banking at PJT Partners in New York. The next step was supposed to be private equity or B-school. Everyone around me followed the playbook. I left because I realized the playbook was someone else’s dream, not mine. The “safe” route felt like the biggest risk I could take because it meant spending my best years building someone else’s vision. The real risk isn’t leaving the path. It’s staying on one that was never yours. The best time to chase your dreams was yesterday, and the next best time is right now.

02

Disconnect to perform.

The best ideas I’ve ever had didn’t come from a 16-hour day at my laptop. They came on the basketball court, in the gym, time with friends, on a walk where I wasn’t thinking about work at all. Stepping away isn’t a break from building; it’s part of building. Your brain needs space to connect the dots. Protect the time away so you show up sharper when it counts. It’s a marathon, not a sprint.

03

Representation isn’t optional.

Where you come from and who you see around you shape what you believe is possible. I didn’t see enough people who looked like me in the spaces I wanted to be in, especially in finance. That’s a big part of why I founded the Smith Black Business Association at Queen’s, and later Blackleaf Capital, to bridge the gap for Black students across Canada interested in finance. Not just to create access, but to make those paths feel normal, visible, and attainable for the next generation coming up. Sometimes, seeing is believing.

One thing to takeaway

Chinni is the Co-Founder & CEO of Ceezaa, a consumer app that translates spend behavior into a living record of taste and identity. He previously worked in investment banking at PJT Partners and founded Blackleaf Capital, a nonprofit investment fund and finance education program for Black university students across Canada, while studying Commerce at Queen’s.

Christian Alphonse

Co-founder of WattShare. Building peer-to-peer EV charging software for apartments and underused private chargers.

I’m not sorry for believing win-win scenarios always exist.

Three winning principles

01

Lead with the humility to be wrong.

Stop trying to be the smartest person in the room or convincing others that you have all the answers. It’s the worst way to build trust and create genuine connections. Instead, focus on having the humility to be wrong and the vulnerability to admit when you don’t know something. You’ll be surprised how far that honesty takes you in both life and business.

02

Relentless Curiosity: Protect your time to learn.

I block 30 minutes to 2 hours every single day strictly to learn. Whether I’m picking up something new, deepening my understanding of a subject, or seeking a fresh perspective from others (young or old), nurturing your curious side is essential for growth; if you don’t prioritize it, you’ll stay stuck in the same place.

03

Be courageous, especially when the odds are against you.

I started dreaming of universal access to energy when I was a child experiencing blackouts in Haiti. It sounded crazy to many people when I said I wanted to start a cleantech company just as Fintech and AI startups were taking off. To me, being courageous is about having the conviction to keep going even when the rest of the world seems opposed to your vision.

One thing to takeaway

Christian is the Co-Founder of WattShare, a Toronto-based EV charger sharing platform that connects EV drivers with private charger owners. WattShare helps hosts monetize underused chargers while giving drivers a bookable way to access charging across homes, apartments, fleets, commercial properties, and multi-unit buildings.

Craig Kerr

Product lead at Lila Sciences. Building AI x bio products for autonomous scientific discovery.

I’m not sorry for always striving to learn.

Three winning principles

01

Decisiveness: choose action over stagnation.

Inaction is the only path that offers no data, no growth, and no closure. A wrong turn can be corrected, but standing still leaves you stranded while the world moves on. We rarely regret the risks that failed; we regret the moments we were too afraid to try. Fortune favors the bold because even a mistake provides a lesson, whereas hesitation only provides a haunt.

02

Beginner’s Mindset: there is no such thing as a stupid question.

Curiosity is the engine of growth, but it only runs when we give ourselves permission to not already know the answer. A beginner’s mindset means setting aside ego and the fear of looking foolish and recognizing that the moment you stop asking questions is the moment you stop learning. Every expert was once a beginner who dared to ask the obvious, and the “stupid” question is often the most honest one in the room — the one everyone else is too proud to voice. Asking it doesn’t reveal ignorance, instead it reveals courage and a genuine desire to understand. This is also a reflection of how we treat others: when someone asks something you consider basic, that question deserves patience, not condescension, and clarity, not eye-rolls, because knowledge is only valuable when it’s shared freely. Stay curious. Stay humble. Ask the question.

03

Pay It Forward: Be kind and build your network.

Kindness is rarely forgotten. The generosity and care you extend to others quietly builds something larger than yourself, a web of trust and mutual support that you may one day need to lean on. Life has a way of humbling even the most self-sufficient; the people you show up for today become the community that shows up for you when needed the most. So be generous with your time and empathy while you have them to give, because building a support network isn’t a sign of weakness; it’s one of the wisest things you cando. Stay open. Stay connected. You won’t always be the one with the answers, and that’s exactly why it matters how you treat people on the days that you are.

One thing to takeaway

Craig is a product leader at Lila Sciences, an AI science company building autonomous labs and scientific superintelligence tools across biology, chemistry, and materials. A UBC PhD in Biochemistry and Molecular Biology with postdoctoral experience at Stanford, he has published across RNA biology, translation, mRNA design, and ribosome-associated protein research.

Eliana Field-Marsham

Co-founder and COO of SONNI. Building mineral SPF skincare designed to make daily sun protection wearable and invisible.

I’m not sorry for maintaining balance.

Three winning principles

01

Figure out what makes you whole and prioritize it relentlessly.

Building SONNI has pushed me to get honest about this in a way nothing else has. You can’t be amazing at every role in your life every day, but if you think of it as an exchange of energy, balance starts to feel achievable.

My approach is simple:

1. Pick three things you want to prioritize in this season of life

2. At the end of each day or week, check in on where your energy actually went

3. Use that to inform where it goes next

I know what it feels like to be heads down, grinding, completely on autopilot. And I know what all play, no work feels like too. Neither one is it for me. I’m my best self when I’m working hard, taking care of myself, and maintaining a full life outside of work. That’s how I reach my flow state, and that’s what allows me to show up as the cofounder and COO that SONNI needs.

02

Women can do anything and then some.

I went to an all-girls school in Toronto, grew up in a house full of sisters, and spent the rest of my life choosing all-women environments: my sorority in college, my first startup role at Little Spoon, and now with our team at SONNI. That wasn’t an accident. These spaces shape how I see myself and what I believe is possible.

Operations is still a male-dominated field, even in the consumer space. Fundraising as a young female founder isn’t for the faint of heart. Walking into rooms full of investors who don’t look like you is uncomfortable. But other women have done it, so I know I can too. (My dream is to build an all-women Ops team. I’m working on it.)

03

If you don’t like something, change it. If you can’t change it, change the way you think about it.

There are moments - as a founder, as a person - when I catch myself complaining or getting complacent. But I control more than I think I do, and when I genuinely can’t control something, there’s almost always another way to look at it - a silver lining, a lesson, something worth keeping. That reframe is a muscle: the more you use it, the stronger it gets.

One thing to takeaway

Eliana is the Co-Founder & COO of SONNI, a next-generation suncare brand making mineral SPF feel like skincare. A Stanford GSB graduate with prior experience at McKinsey and Little Spoon, she leads operations for a launch focused on invisible, non-greasy mineral sun protection that works across skin tones and daily routines.

Ian Burgess

Founder and President of Ascendance Foundry. Building AI-first apprenticeship programs that place emerging technical talent into real company projects.

I’m not sorry for showing that Canada’s youth can be shockingly productive before completing four years of University.

Three winning principles

01

I believe in the Second Law of Thermodynamics.

Disorder is the default. Order is expensive. Many organizational failures come from suspension of belief in the Second Law, including those that killed hundreds of millions under communism in the 20th century. Some examples:

• Change management is hard. If you introduce a process change complex enough that one person can do it correctly 90% of the time, then the odds that 100 people can all do it correctly is ~0.002% (0.9^100).

• Obsess with your customer, not your technology. There are infinite bad solutions for your customer’s problem and vanishingly few great ones. If you are not obsessed with finding the best solution for your customer every day, the odds you will build something valuable to them is ~0.

• If you don’t prioritize growth, your organization (or economy) will shrink. There are infinitely more possible ways to destroy value than to create value. Of all the possible ways to run a business, most are not effective. Of all the possible ways to run a society, most leave everyone poor. Therefore if you are not focused on growth, odds are your organization will shrink (get poorer).

02

Say it like it is.

It is already difficult enough to lead a team of driven people to solve a very hard problem. Don’t make it harder by beating around the bush.

• Be obsessed with finding the best solution, not with defending your current solution.

• If you are only saying things when you are certain everyone else agrees, you are not a leader by definition.

• If you really believe someone has potential for greatness, you will tell them when what they are doing is not great. Communicating low expectations is not kindness.

03

Fix mistakes fast. Take full advantage of good fortune when it comes.

In my experience, success correlates with the time average of successes and failures more than the number of successes and failures.

• The most successful people I know are good at failing fast - identifying and fixing mistakes quickly - and then taking full advantage when things go their way.

• The easiest way to underachieve your potential is to dwell on one failure or one bad idea for a really long time.

• Most people are too afraid of making mistakes and not afraid enough of moving too slowly.

One thing to takeaway

Ian is the Founder & President of Ascendance Foundry, an AI-first apprenticeship venture that recruits and trains students, then places them into real company projects as fellows. A Harvard PhD in Applied Physics and co-founder of Validere, he brings deep technical, startup, and mentorship experience across photonics, AI, energy data, and early-career talent development.

Jay Gerbrandt

Founder and CEO of Fruitbloom. Bringing proven allied technologies into Canadian minerals, energy, photonics, and compute markets.

I’m not sorry for picking Canada’s lowest-hanging fruit.

Three winning principles

01

Grow curiously.

Engage people with earnest curiosity. Trust them to be experts on their fields, and show up by doing some research of your own. The best parts of my story have come from saying “yes” to things outside my comfort zone: I wasn’t ready for a French-immersion Cree JV gold mine. I wasn’t planning to build an online map of Indigenous place names. One led to the other.

02

Pursue coherence.

Had my 7-year-old self not insisted on a mall trip that day, trusted my little gut, what would my life be? “You! With the boy! Stop!” The lithe, stubbly Brit ran over to us, introducing himself as the director of a movie, “with John Cusack.” He told my parents that here, in the Eaton Centre in August 2000, was the kid he needed for the part: me. So I’m the kid in the elevator, in the devil costume. Irony: my casting in Serendipity being serendipitous.

03

Vibecode responsibly.

Having given many devs at Rivian and EvenUp thoughtful feedback is a stealth superpower when it comes to getting Claude to make what I want. In a month, I have been able to replace almost all the software I pay for with my own versions. But you need to make informed design choices from the beginning. You are responsible for security, for interfaces, and for knowing your tools.

One thing to takeaway

Jay is the Founder & CEO of Fruitbloom Canadian Resources, which facilitates technology-transfer partnerships from allied democracies into Canada across urban mining, rugged power, photonics, and sovereign compute. A Harvard history grad, he previously worked in strategy consulting at Bain, contributed to IPO and brand work at Rivian, and built investor collateral for EvenUp’s Series B.

Jeffrey Fasegha

Co-founder and CEO of Deducta. Building procurement data intelligence software for enterprise spend teams.

I’m not sorry for trying my best.

Three winning principles

01

Integrity is key.

02

Learn the rules of the game.

03

Touch grass often.

One thing to takeaway

Jeffrey is the Co-Founder & CEO of Deducta, a London-based procurement data intelligence platform helping enterprises unify spend data, normalize suppliers, identify opportunities, and track initiatives. A Canadian Rhodes Scholar and U of T/Rotman Commerce alum, he previously founded the Black Career Conference and co-founded Black Rotman Commerce.

Jenn Nguyen

Co-founder and CEO of LookbookAI. Building AI-powered visual tools for luxury and fashion brands.

I’m not sorry for being fashionably late.

Three winning principles

01

Everything happens for you, not to you.

Nothing is against you, unless you decide it is. Life is about framing – view a bad experience as a setback, or see it as a step forward. If it changes you, then it’s an opportunity to become better.

02

Luck is preparation meets opportunity.

The hard work you do behind the scenes always rewards itself. Always be ready for when that moment can come, it could be your golden ticket.

03

Be the most authentic version of you.

There is no competition when you are fully yourself. No one else has your perspective, your voice, your way of seeing the world. Being the real you is the advantage.

One thing to takeaway

Jenn is the Co-Founder & CEO of LookbookAI, where she leads product and strategy for AI-powered image and video tools for fashion and luxury brands. A product, UX, and e-commerce leader, she is building technology that helps brands create on-brand, editorial-quality imagery at scale across e-commerce, campaigns, and video.

Jeremy Auger

Co-founder and Managing Partner at Lucid Ventures. D2L co-founder backing AI-native B2B and frontier-tech founders.

I’m not sorry for refusing to treat Canada like a farm team.

Three winning principles

01

Authenticity is a Force Multiplier.

There is a tired myth that to be a “serious” executive, you must be a stoic, humorless robot. I reject that. You can be the most rigorous person in the boardroom and still be the person who cracks a joke or leads with kindness. When you show up as the same person across all your personas - founder, board member, mentor, colleague, boss, friend - you build a level of trust and speed that “professional masking” can never achieve. Being nice isn’t a weakness; it’s a strategic advantage.

02

Great Ideas Must Earn Their Keep.

Ideas are free, but they shouldn’t be coddled. The best outcomes aren’t born in polite consensus; they are forged through vigorous debate and relentless challenge. I strive to build environments where we separate the person from the protocol where we can be “kind to the person, but brutal to the idea.” If an idea can’t survive a room full of smart people trying to poke holes in it, it isn’t ready for the market.

03

Don’t Wait for the Roadmap—Write It.

Growth lives at the edge of what’s comfortable. Whether it was the early days of the internet or today’s AI-native revolution, the most significant breakthroughs come from those who refuse to accept “the way things have always been done” as a valid constraint. Don’t wait for the roadmap to be written by someone else; be the one holding the pen. If you aren’t slightly uncomfortable with the pace of change, you aren’t leading it.

One thing to takeaway

Jeremy is the Co-Founder & Managing Partner at Lucid Ventures, a seed-stage fund backing AI-native B2B software and commercial frontier technologies. He previously co-founded D2L, helping scale it from startup to public global edtech company, and held CTO, COO, and CSO roles. A named inventor on 30+ patents, he brings operator, product, M&A, and global expansion experience to early-stage founders.

Jia Ming Huang

Co-founder of Diaminate. Building AI tools for investor-founder matching and event intelligence.

I’m not sorry for giving my all to my people.

Three winning principles

01

The world is abundant.

Opportunities surface when we build in public. Every business is only a small piece of a huge pie, we can each have our little piece.

02

Be an interesting person.

When you’re building, people want to follow your journey of a being an interesting person. For the same reason Day in the Life videos are popular. People want to resonate with a story. Seeing someone make it inspires.

03

You can just do things

Don’t be trapped with analysis paralysis. When you just do things, you know what you don’t know, you know what you don’t like, and you leave with a story to tell and a lesson learned.

One thing to takeaway

Jia Ming is the Co-Founder & CPO of Diaminate, an AI-driven platform for investor-founder matching and event intelligence. Diaminate’s products include Fundraise, TalkMatch, and EventIQ, with TalkMatch live for event matchmaking. He is also a Cursor Ambassador organizing community events in Calgary and Toronto, including a 400+ person Cursor meetup during Toronto Tech Week 2026.

Justin Allen

Co-founder of GlucoSolutions. Building non-invasive glucose monitoring technology for prediabetes prevention.

I’m not sorry for being too early.

Three winning principles

01

Do what you’re thinking about.

If you spend too much time thinking about something, you’ll convince yourself you got it done without anything to show for it. Stop thinking about how great it’s going to be, first make it badly.

02

Make something you want your family to use.

If I wouldn’t feel comfortable letting people I know use my product, it needs to be refined more. The most important standard is the one I’m holding myself to.

03

I don’t know enough about anything to stop learning about it.

Learning will happen over and over for any skill I have, no matter how good I am at it. If you don’t let yourself be a student again, your biggest strength will be a crutch.

One thing to takeaway

Justin is the Co-Founder of Gluco Solutions Inc., a company developing non-invasive glucose monitoring technology for prediabetes. With an engineering background from Toronto Metropolitan University, he is focused on building tools that help people track glucose levels without traditional invasive methods.

Kasey Boyle

Founder and CEO of Bantor. Building AI software that helps field sales reps capture conference conversations and automate follow-ups.

I’m not sorry for wanting more for myself, my people, my country, and what I’m building.

Three winning principles

01

Think about your deathbed.

We spend so much energy avoiding the thought of death when acknowledging it is actually the most clarifying thing you can do. Life is finite. When I’m stuck on a decision, I ask myself: how would I feel on my deathbed if I didn’t do it? The answer usually cuts right through the noise. I would rather try and fail than never try at all.

02

Let yourself be seen.

Hiding who you are is exhausting, and it’s a ceiling. There is real power in naming your vulnerabilities instead of managing them. People can’t show up for you if they don’t understand you, and you can’t build anything meaningful alone. Give yourself the grace to be seen. And try, as hard as you can, to see others beyond what they show on the surface.

03

Stop thinking, start doing.

Every minute you spend deliberating is a minute you could be moving. Once you’ve made a decision, you’ve made it. Toying with it after the fact is just wasted energy. Make the call, do the thing, and face what comes next.

One thing to takeaway

Kasey is the Founder & CEO of Bantor, AI software that helps field sales teams capture conference conversations, track key details, and draft follow-ups. A Harvard MBA and former BCG consultant, she brings a strategy and GTM lens to a workflow every rep feels: turning in-person conversations into pipeline.

Kristin O'Neill

Forward for Team Canada and the New York Sirens. Olympic silver medalist and five-time World Champion.

I’m not sorry for never giving up on my dreams.

Three winning principles

01

Kindness: make people feel heard and valued.

Nothing big is built alone. Teammates, coaches, and mentors invest in you when they feel respected, not used. People forget the details, but they remember how you made them feel. Kindness builds trust, and trust is what holds teams together.

02

Courage: say the dream out loud.

I started saying “Team Canada” when I was a kid. It sounded impossible, but my family and coaches didn’t laugh; they asked what the next step was. Saying the goal out loud forces you to take it seriously, and it helps the people around you help you. If you won’t name it, you won’t chase it.

03

Process over outcome: let preparation create confidence.

I can’t control selection. I can control my habits: training, recovery, film, and the small details every day. When you focus on what you can control and do it consistently, confidence builds. On game day, you know you’re ready.

One thing to takeaway

Kristin is a forward for the New York Sirens and a core member of Team Canada. She helped lead Canada to a silver medal at the 2026 Milano Cortina Olympics, and scored Canada’s only goal in the gold medal game. With five World Championship medals to her name, she’s established herself as one of the most reliable two-way players in professional hockey.

Lauren Nunziata

Founder of Tiny Laundry. Scaling a portfolio of consumer brands and distinctive real assets.

I’m not sorry for choosing risk over security.

Three winning principles

01

Test, iterate, repeat - fast.

Ideas are only as good as the feedback they get. Move quickly, learn quickly, fail even faster, adjust, and keep improving. Small, deliberate wins compound over time. Every tiny feedback-based improvement - product tweak, customer interaction, team process...adds up.

02

Happiness is reducing the gap between expectation and reality.

Borrowing a page from Mo Gawdat, happiness comes from either aligning expectations with reality or shifting your perception of reality. By staying humble, practicing gratitude, and adjusting expectations, it becomes possible to find contentment even amidst uncertainty.

03

Say “thank you” more than you think you should.

Gratitude builds trust, loyalty, and energy in every relationship - from your team and partners to your customers.

One thing to takeaway

Lauren is the Founder of Tiny Laundry, a developmental babywear brand she acquired in 2025. An Ivey HBA with experience at Google and Unilever, she spent four years leading go-to-market operations and helping launch YouTube Shorts in Canada. Today, she manages a portfolio of niche consumer businesses and distinctive real assets, including Long Lake Cabin and Technic Revolution. Based in North Vancouver, Lauren applies her background in global brand marketing and operations to build thoughtful products, grow small businesses, and develop memorable physical spaces.

Lindsay Kruit

Founder and CEO of Stowe Health. Building the platform to organize and simplify healthcare for Canadians.

I’m not sorry for relentlessly persisting.

I grew up in a small town on Vancouver Island and had a very narrow perspective on the outside world. I didn’t know what the options for a career could be, and as I navigated my path, I often felt like I was sprinting through the fog - I wasn’t sure exactly where I was headed, but I pushed forward regardless (yes, sometimes tripping over obstacles along the way.)

Apparently one of my earliest phrases as a toddler was “I do it!” Independent and strong willed from the start, I drove my parents and eventually my bosses crazy with my insistence on doing it my way. I was never willing to settle in, I always wanted to push the limit and try for more.

I’ve heard it all over the years: “Who does she think she is?” “You’re too intense.” “You should try being more approachable.” Charting your own path can be tedious and lonely. You often think you’re doing it all wrong. You often get told there’s a different way you should go about it. You either need a robust support system or you need thick skin and relentless persistence. Over the years, I have developed the latter.

And don’t get me wrong, I have had my fair share of handwringing and worries along the way. Why can’t I just go with the flow more? Why do I have to be so strong headed? Why can’t I be more likeable? Believe me, being strong headed resulted in many, many mistakes along the way. Yet, I have learned that the compulsion I had toward personal agency was more of a strength than a weakness once I learned how to wield it well. And those mistakes became teaching moments so long as I was willing to remain open to change along the way.

From that small town to downtown Toronto, from being an accounts receivable clerk to a two-time CFO and now an entrepreneur, I have been incredibly fortunate to have the career I have had. It has, however, not been an easy road. I have fought very hard for where I am now, and chalk it up to my relentless persistence along the way.

I think some of what has made it possible has been the security and opportunity available (if you grasp it) in the country we live in. Canada is one of the greatest countries in the world, and I am deeply proud to call myself a Canadian. That said, it does have its opportunities for improvement.

Canadian niceness is world renowned, but it comes with a flip side / a shadow side. The same cultural forces that produce politeness, modesty, and conflict aversion also tend to drive deference to rank / institution / process, results in some gatekeeping, and provokes passive aggression as a release valve. If someone is seen as rocking the boat, getting too big for their britches, or not playing by the rules, especially when that person is a woman, there’s often a price to pay for that. It’s a little bit of Tall Poppy Syndrome meets crabs in a bucket (except the crabs say sorry as they’re pulling you back in).

While it’s far from the only reason, I believe this is one of the contributing factors for why some of Canada’s boldest and brightest have gone south of the border, where ambitious behaviours are celebrated, not scorned. Either that, or some take their foot off the gas, tired of going against the current.

I, for one, am going to keep fighting. I hope for a future where Canadians dream bigger and support each other along the way. Where ambition and audacity are celebrated, especially when they’re directed toward making the future brighter for humanity. I relentlessly persist in making this dream a reality, and I hope others will too.

Three winning principles

01

Try not to focus too much on being likeable.

• It is impossible to please everyone and get everyone to like you.

• Love yourself and believe in yourself first. If others also believe in you, that’s a cherry on top, but that intrinsic confidence is paramount.

02

Focus on “Opportunities for Improvement”.

• Take the positive view on how to learn and grow in every situation, don’t focus on blame, excuses, faults or failures.

• A negative mindset is demoralising, whereas the positive perspective is motivating and even inspiring.

03

Always keep learning and growing.

• You don’t have to be perfect, and it’s okay to fail, but you do have to try.

• Always keep learning, never plateau or flatline.

• The only constant is change - if you’re not moving forward, you’re moving backward.

One thing to takeaway

Lindsay is the CEO of Stowe Health and a Rotman MBA. A two-time former CFO, she transitioned from senior financial leadership to build a technical solution for Canada’s medical system. Stowe Health enables users to organize fragmented medical records and navigate complex healthcare data. Based in Toronto, she is putting a CFO’s discipline to work on the system’s inefficiencies, and on giving patients more control over their own care.

Lisa-Marie Assenza

Founder and CEO of Impacked. Building the B2B marketplace for sustainable packaging.

I’m not sorry for my small town Canadian roots that made me who I am.

Three winning principles

01

A person who never gives up is hard to beat

Keep putting in the work and never stop believing in yourself. Where there’s a will, there’s always a way.

02

Over-invest in relationships.

Friends, family, partners, colleagues. In the end, people make the difference. Sometimes being “too nice” is a superpower.

03

Your energy creates your reality.

Energy is palpable. A person on a mission vibrates at a different frequency, and the right people and opportunities find you when you’re just being you.

One thing to takeaway

Lisa-Marie is the CEO of Impacked. An Ivey MBA and packaging strategist, she is building a marketplace to simplify primary packaging procurement for consumer brands. She specializes in packaging-led growth and sustainability, helping firms navigate fragmented supply chains. Based in New York City, her platform digitizes the procurement lifecycle to reduce lead times and environmental impact.

Liza Akhvledziani Carew

Co-founder and CEO of Chexy. Building the platform that turns rent into rewards and credit.

I’m not sorry for building what everyone said was impossible. They were wrong.

Three winning principles

01

Say the uncomfortable thing first.

In a negotiation, a hire, or a board meeting, the thing you’re tiptoeing around is always the thing that needs to be said out loud. Candor isn’t rude. Avoidance is expensive.

02

Distribution is the product.

A great feature no one finds is a graveyard. I spend as much time thinking about how people discover us as I do about what we’re building.

03

The market that doesn’t exist yet is the one worth building for.

Rent, mortgage, bills didn’t earn rewards because no one built the infrastructure to make it possible. The biggest opportunities aren’t hiding in competition - they’re hiding in assumptions everyone stopped questioning.

One thing to takeaway

Liza is the CEO and Co-founder of Chexy. A CFA charterholder and UBC Chancellor’s Scholar, she founded the platform to enable tenants to earn rewards and build credit through rent payments. Based in Toronto, she leads the firm’s expansion in the Canadian rental market by integrating financial incentives into residential leasing. Liza is a member of Emerging Women in Finance and worked in institutional investment management before launching Chexy to modernize the rental experience.

Mathew Mozaffari

Founder at Speer. Advisor at Grata, revolutionizing traditional multifamily and student properties.

I’m not sorry for following signals over noise.

Three winning principles

01

Anything in life worth doing is worth overdoing.

If something shows even a signal - traction, clarity, money, momentum - lean into it completely. Most people hesitate. You shouldn’t. If a product has legs, it will tell you, often subtly. Your job is to notice and double down.

02

Failure is data.

Failure isn’t wasted effort - it’s direction. It tells you what doesn’t work and often points to what might happen if you do the exact opposite of what you just attempted. Progress is iterative and scientific. Enough failed attempts, applied consistently, lead to the one outcome that moves everything forward.

03

Grit compounds.

Most people don’t fail - they stop. They try once, twice, maybe three times, then walk away. Grit is what keeps you going when it’s uncomfortable, unclear, or unrewarding. The ability to get back up, and learn how to, matters more than avoiding the fall.

One thing to takeaway

Mathew is the Founder of Speer and an advisor at Grata. He is a technology professional based in Toronto with a background in STEM community leadership including roles at Ryerson University and the Ryerson Science Society. He has appeared on CBC discussing the impact of technology on Canadian daily life.

Megan Black

Founder and CEO of SONNI. Building high-performance mineral SPF for daily use.

I’m not sorry for questioning things that are “just the way they are.”

Three winning principles

01

A lot of things stick around simply because no one questions them.

The products we use, the systems we operate within, the routines we follow. Over time, you get used to how something feels, even if it’s not actually that good. I try to notice that friction instead of normalizing it. Once you start paying attention, you realize how much of the world is built on “good enough.”

02

Just because something makes sense on paper doesn’t mean it’s right for you.

For a long time, I was on a very clear, conventional path. It looked right from the outside, and it’s what a lot of people around me were doing. But eventually I realized I didn’t actually want that version of my life. Not because it was bad, just because it wasn’t mine. That realization changed how I make decisions.

03

Build for real life, not ideal conditions.

It’s not enough for something to be conceptually good. It has to work on busy days, in imperfect routines, when people aren’t thinking about it. That extra level of thoughtfulness is usually what makes something stick.

One thing to takeaway

Megan is the Founder and CEO of SONNI. A Kellogg MBA with experience at Estée Lauder, she left corporate retail to address technical flaws in mineral sunscreen. She merges product strategy with global retail experience to build habit-forming suncare that matches prestige skincare quality. Her mission is to remove the friction that prevents daily sunscreen use.

Mikayla Stewart

Founder of Athena Collective. Helping founders scale through AI-driven operations.

I’m not sorry for trying to spend my career focused on others instead of myself.

Three winning principles

01

Just start helping.

I have spent my career centered around the idea that you can learn so much by offering to help figure something out for someone. Most of the contracts I worked on - I had no idea what I was going into, and I was working with founders who had no idea how to solve the solution. The Difference? I had the time to figure out a solution for them, they didn’t have the bandwidth. It is okay to ask for help, but it is also okay to come in and offer the help of “I don’t know how to fix this, but let me find out for you” (It’s also a great way to learn a lot of different skills very early in your career. It does however require a lot of ‘volunteering’ while you learn these pieces)

02

Don’t seek money.

Don’t let it be your guiding principle. By doing that you are forced to not support people you would have otherwise, you let yourself get a little corrupted. Follow what feeds your soul and the money will follow that. I’ve really been a big proponent of just offering help regardless of the resources someone has to compensate for it. I’ve done countless hours of free advising, support and just straight up work for companies. I honestly wouldn’t trade a moment of it for some cushy high paying job. Because it meant that I got to learn so much about how to support founders that I get to turn around and tailor for the women in Athena Collective. I get to take all these pieces and build a product that works alongside you, and the money follows now but it was and is not the reason I do anything. It’s just a bonus that feeds an already full heart.

03

Motivation is a Choice.

It is an active decision every moment of every day. Willing to tackle something you don’t want to do is critical for success, but it’s never going to just magically happen. You have to choose, and it’s okay to say “I’m not choosing to tackle more than I believe I can handle”, but know that at the end of the day it’s a choice you made. There are many days that I choose to allocate my energy.

One thing to takeaway

Mikayla is the CTO of Athena Collective and Founder of Coldstart. A former Arctic Security specialist, she builds AI-powered operating systems for high-growth ventures. She has helped 75+ startups raise $150M+ by designing autonomous agents that automate manual workflows and intake. By applying systems logic to operations, Mikayla enables companies to scale without increasing headcount. She currently leads a global network of 1,000+ female founders, owners, and operators.

Mike Lyons

Co-founder and CTO of hi finance. Automating the search for non-repayable student funding.

I’m not sorry for building finance that serves the next generation.

Three winning principles

01

Development Driven Development.

Build to learn. Ship fast, learn everything you can, then iterate. We don’t spend weeks in design docs - we get something in users’ hands and learn from real feedback. If you aren’t getting things wrong 70% of the time, you aren’t iterating fast enough.

02

Quality IS speed.

The “speed vs quality” dichotomy is false. High quality work today means we can build faster tomorrow instead of maintaining broken things. Slow is smooth, smooth is fast.

03

Never be blocked.

We don’t wait for others to get started. We don’t let “not knowing something” stop us. We happen to the world, the world doesn’t happen to us. If our integration partners are slow, we do their job for them or cut them out.

One thing to takeaway

Mike is the Co-founder and CTO of hi finance, a platform dedicated to the mission that “tuition should never be a barrier to education.” A “full-stack” engineer with a background at Verkada and Apple, he is building the technical infrastructure that matches students with the grants, scholarships, and bursaries they don’t have to pay back. Based in Edmonton and born out of the University of Alberta, hi finance has already helped over 2,000 students secure more than $4 million in funding, allowing them to focus on their degrees rather than their debt.

Mike Wessinger

Co-founder and Executive Chair of PointClickCare. Built the company to nearly $1B+ in revenue.

I’m not sorry for building a powerhouse from Canada.

Three winning principles

01

Lifestyle vs category killer is a decision.

Nothing is wrong with either but your actions will be very different depending on what you choose. Know it’s a choice.

02

Don’t over index in fundraising.

Over index on your customer and customer delight. Make sure you know where you add value to the world and be the best at it!

03

Develop a strong support network.

This can include investors, team members and leaders of similar companies that are 4-16 quarters ahead of you.

One thing to takeaway

Mike is the Co-Founder and Executive Chair of PointClickCare, which he built into one of North America’s largest private tech companies with over $1 billion in revenue. He pioneered cloud-based healthcare records when the industry still relied on paper, and today mentors the next generation of Canadian tech founders as Co-Chair of C100 while guiding PointClickCare’s expansion into AI-driven healthcare solutions.

Minh Phan

Founder of Studio.init(). Building the software layer for global critical infrastructure at Octave.

I’m not sorry for being a creative.

Three winning principles

01

Leaders are made from mistakes, not meetings.

You have to live through the bad calls. That’s what builds real judgment, you can’t inherit it from a deck.

02

Friction in design is information.

When the work gets hard, I’ve learned to treat that as a signal that the problem is wrong, not the solution.

03

The best design system is Nature

I return to it for both the forms that feel right, and the logic underneath them.

One thing to takeaway

Minh is a product builder who recently joined Octave following the merger of his venture studio, Studio.init(). A former lead for Google Maps on iOS and the architect behind the viral Web3 breakout Milk Road (acquired by Bitwise), he has spent his career at the intersection of high-growth tech and consumer psychology. Having shipped over 50 startups and led commerce at Coinbase, Minh is now applying his “0 to 1” expertise to the industrial sector, building the digital thread for the world’s most mission-critical infrastructure.

Nasib Ahmed

Founder of Quantigo AI. Building the human-centric data layer for the world’s most advanced AI labs.

I’m not sorry for taking the long way instead of taking shortcuts.

Three winning principles

01

Stay in long enough and you figure it out.

Most people don’t fail because they lack ability. They stop too early. I learned by staying in, repeating the work, and letting things become clear over time.

02

Do the work no one sees.

The real work is quiet. It’s the hard conversations and small improvements that never get attention. That’s what actually builds the business.

03

Stay uncomfortable. That’s where growth is.

If things feel easy for too long, you’re probably not pushing yourself. Growth usually shows up as uncertainty, pressure, or friction. Over time, you learn to trust that feeling instead of avoiding it.

One thing to takeaway

Nasib is the Founder and CEO of Quantigo AI, a global leader in high-precision training data for machine learning. He began his career as the first employee at Ecopia AI, where he helped scale the company into a geospatial data powerhouse before launching Quantigo in 2017. Today, Nasib leads a global team that bridges the gap between raw data and model performance, providing the human-in-the-loop validation that top-tier AI companies—from Silicon Valley to Toronto—use to ensure their models are accurate, ethical, and ready for production.

Neil Cawse

Founder and CEO of Geotab. Built to $1B+ revenue without outside capital.

I’m not sorry for ruthless transparency.

Being honest is not the same as being cruel. It means being straight with people early, while there is still time to help them get better. If someone is doing the wrong thing and you avoid the uncomfortable conversation, you are not protecting them. You are letting the problem grow until it becomes much harder to fix.

Three winning principles

01

Do the right thing for the long run.

Never compromise on what matters long term: your customers, your people, your family, your health, or your technology. Do not take the quick buck. Do not take the shortcut. Build for the long run as much as you can.

02

Check your ego at the door.

The worst, most powerful evil is to believe that you are somehow special, that you’re always right, or that you can’t be questioned. The more successful you become, the easier it is to fall into this trap. The more successful Geotab becomes, and the bigger we grow, the more important it is for me to keep reminding myself of this point. Surround yourself with people who can tell you the truth, and listen when they do.

03

Measure, reflect, and improve.

You cannot manage what you do not measure. Build feedback loops into everything: your work, your company, your relationships, your health. Look at what is happening, understand it, change the input, and measure again.

One thing to takeaway

Neil is the Founder and CEO of Geotab, a company he started in 2000 and built into a global powerhouse with over $1B in revenue. An electrical engineer by training (University of the Witwatersrand), Neil grew the business for two decades without outside funding, transforming it into an industry leader that now serves customers on every continent.

Neil Vidyarthi

Co-founder of Feel Good Interactive. Building AI that transforms passive screen time into active storytelling.

I’m not sorry for rational optimism.

Three winning principles

01

Gratitude is empowering.

02

You can control the shot, but can’t control the outcome.

03

We have SO much more in common than not.

One thing to takeaway

Neil is the Co-founder and CEO of Feel Good Interactive, the studio behind Little Magic Stories. A consumer tech veteran who has scaled platforms for millions at EA Mobile, Dapper Labs (NBA Top Shot), and Todoist, he is now applying that high-growth expertise to the future of childhood development. Based in Waterloo, Neil is building an “AI-native” library where children are no longer passive viewers, but active protagonists who shape their own literary adventures through real-time generative technology.

Nivit Kochhar

Founder of Supercharged Studio and Nomad Wildheart. Building design and gear for the global remote workforce.

I’m not sorry for thinking life should be designed, not defaulted.

Three winning principles

01

If it’s scary and exciting but also feels right, the answer is always ‘yes’.

Most of the best things in my life came from decisions that were uncomfortable at the time such as moving countries, starting businesses, travelling alone, speaking to people I didn’t know, taking opportunities before I felt ready. Fear usually means you’re about to grow. Excitement means you actually want it. When both are there, it’s usually a sign you should go for it.

02

Live a life that’ll make your 8 year-old self and your 80 year-old self happy.

I try to live in a way where my younger self would think my life is exciting and my older self would think my life was meaningful. At the end of life, you don’t regret the things you tried, you regret the things you didn’t do. I want to be able to look back and honestly say I minimised the number of times I said, “I wish I did that.”

03

The journey is better than the destination.

Goals are important, but the day-to-day process of building, learning, travelling, meeting people, and growing is actually the best part. If you only live for the big milestones, you miss most of life. I try to enjoy the process: building companies, improving my craft, exploring new places, and becoming a little better every year.

One thing to takeaway

Nivit is the Founder of Supercharged Studio and Nomad Wildheart, a travel-inspired apparel brand launched in early 2025. A specialist in the intersection of design, cognition, and AI, he has led high-stakes projects for Rakuten and Tony Robbins, helping startups raise over $40M through strategic brand identities. Now a fixture in the global nomad community, he draws on years of working remote-first to build products, digital and physical, for the next generation of borderless entrepreneurs.

Nomaan Ahmed

Founder of Orbits. Building the AI-powered operating system for the modern household.

I’m not sorry for pulling up a chair.

Three winning principles

01

Stay uncomfortable.

I’ve always measured myself against who I’ll be in five years. If future me isn’t impressed by the distance I’ve covered, I haven’t pushed hard enough. I went from pension plans and executive assistants to splitting the cost of a domain name with my cofounder. If I was optimizing for comfort, I would’ve been satisfied a long time ago. I optimize for impact, and impact isn’t comfortable.

02

Nothing is off the table. Not even you.

Growing up named “Nomaan”, you learn pretty quick that nobody ‘s saving you a seat at the table. But nobody tells you that you can pull up your own chair - so I did. Knock on every door, have every conversation. Genuine connection will open doors that no resume or pedigree ever could. That’ s how I approach building a business, and it’s how I approach everything else.

03

Never stop learning. Ever.

Be a sponge. Every person you meet knows something you don’t. The moment you think you’ve figured it out is the moment you stop growing. Stay curious, keep absorbing, and never convince yourself you’ve arrived.

One thing to takeaway

Nomaan is the Founder of Orbits, an AI-powered assistant designed to automate the “mental load” of running a home. He recently left his role as Director of Engineering at Super.com—where he led the technical scaling of the all-in-one savings platform—to focus entirely on solving the complex logistics of family life. With a background at Mastercard and a track record of scaling teams from early-stage startups to Fortune 500 giants, Nomaan is now applying high-velocity engineering principles to the home, building Orbits to put schedules, maintenance, and family coordination on autopilot.

Oday Brahem

Founder of OP8 Industries. Building the operating system for autonomous heavy machinery.

I’m not sorry for carrying the mission before I’m asked.

Three winning principles

01

Build with integrity before velocity.

Figure out what you stand for before you start building. Chaos will test it. So will urgency, praise, partnerships, and shortcuts. Values are the filter before the plan. If the move cannot survive scrutiny, it is not the move.

02

Use what you’ve got. Bring Receipts.

Do not wait for perfect conditions: team, title, capital, invitation. Start with what is in front of you. Build the proof, map the risks, and put something real on the table. Permission usually comes after the pattern is visible.

03

Hold the whole board.

The technical problem is never only technical. The business problem is never only business. Timing, people, trust, quality, incentives, and mission all touch. Compress the noise until the next responsible move is clear. Then move.

One thing to takeaway

Oday is the Founder of OP8 Industries, where he is developing the “Autonomy Operating System” (AOS) to power the next generation of industrial robots. Based in Vancouver, he previously held roles at VersaFile and Collabware, specializing in bridging the gap between complex software and enterprise operations. A systems architect by trade, Oday is now applying that technical foundation to the world of heavy machinery, creating the edge AI required for cranes and excavators to navigate and operate in unstructured environments without human intervention.

Rob Khazzam

Co-founder and CEO of Float. Building intelligent spend management software for Canadian businesses.

I’m not sorry for having high expectations for Canada or insisting we unleash our >1M SMBs’ full potential.

Three winning principles

01

Where there’s a will, there’s a way.

• Most things that look impossible are just unsolved.

• The job of a founder is to refuse the default constraints and keep pushing until a path forward is found.

• Resourcefulness beats resources almost every time.

02

Winning is a conscious choice.

• You will encounter failure constantly; it is inevitable in life and your career.

• What matters is whether you learn fast, adjust, and keep going.

• The people and teams that ultimately win are the ones that simply refuse to stop.

03

Courage is rare, bet on yourself.

• Intelligence is abundant. Courage is not.

• The willingness to take risks, speak plainly, and pursue ambitious ideas when others doubt you is what creates progress in the world.

One thing to takeaway

Rob is the Co-Founder and CEO of Float, one of Canada’s fastest-growing fintech companies. Float combines corporate cards with spend management software to help businesses control expenses and automate financial operations. He previously spent over five years at Uber, leading international expansion across Eastern Europe and serving as General Manager in Canada. A CFA charterholder and Ivey Business School graduate, Rob is building financial tools designed specifically for Canadian teams.

Robert Ciborowski

Co-founder and CEO of Chatforce. Building an AI game studio for viral creations.

I’m not sorry for building something for people like me.

Three winning principles

01

The embarrassing thing is usually the right thing.

Every time I’ve felt most self-conscious about a decision, it turned out to be the right one. Tinkering with startup ideas in a community centre while all our friends had jobs at prestigious companies. Being “gamer founders” when everyone around us was building enterprise SaaS. Presenting our barely-functioning prototype in front of 200 people, only for it to attract our lead investor. The pattern held every time: if it made me cringe, it was worth doing.

02

Give your silly ideas a chance.

The ideas that feel like a waste of time can be your best bets. When we finished the first version of Chatforce, I spent two weeks using it to build Grand Theft Toronto, a meme game where you deliver Tim Hortons orders while dodging carjackers. It got us into the news and was the first Chatforce game to go viral.

03

Make friends along the way.

Building a company will pull you away from old friendships. Don’t let that make you lonely. Go to events, get to know people properly, and befriend the ones you connect with. Having even a few friends with your level of ambition makes the pursuit of your dreams so much easier.

One thing to takeaway

Robert is the Co-founder and CEO of Chatforce, an AI-powered studio where autonomous agents build and monetize viral video games. A University of Toronto Computer Science alumnus, he skipped the traditional corporate track to launch the company straight out of school. Backed by $2.1M in pre-seed funding, Robert is now leading a platform where AI agents collaborate to turn imagination into playable hits, like the viral Grand Theft Toronto.

Sachin Arora

CEO of Maple. Building the e-commerce engine for Canada’s legacy retail brands.

I’m not sorry for refusing to let Canada be anything less than excellent.

Three winning principles

01

Everyone is an entrepreneur — and I mean that.

Not in the “build the next billion-dollar startup” way. I’m talking about the willingness to take a risk, try something new, push for change, and actually give a damn about the outcome. That instinct doesn’t belong to founders. It belongs to anyone who decides to bring it. I think everyone should feel that way about something in their life — and I’m drawn to people who do.

02

Canada is not an afterthought.

It’s one of the most diverse, interesting, and budding markets in the world. Brands that get this have a unique opportunity — to test products across essentially every demographic, scale in an affluent and growing country, and build something real. This isn’t a stepping stone to the US. The brands we work with know this. The rest of the world should too.

03

Being competitive is good. Stop apologizing for it.

There’s a quiet discomfort in Canada with actually wanting to win — and I’ve never understood it. Wanting to be the best, for your clients, your team, the work itself — that raises everyone’s game. I’m not interested in second place, and I don’t think you should be either.

One thing to takeaway

Sachin is the CEO of Maple, a company that manages the online operations for some of Canada’s most established retail brands. An alumnus of the Smith School of Business at Queen’s University, he is a veteran e-commerce operator who specializes in building the digital storefronts and logistics networks traditional retailers need to compete. Under his leadership, Maple acts as the dedicated online arm for iconic labels, handling their technology, growth, and fulfillment from end to end.

Sam Anderson

Co-founder of CarbonGraph. Automating carbon tracking for global supply chains.

I’m not sorry for believing climate change matters and that business models can change to address it.

Three winning principles

01

See the good in people.

Deep down, almost everyone is a fundamentally good person. We all want to make the world a better place, but most of us don’t have the time, energy, or know-how to diverge from the crowd in all but a few aspects of our lives. The most impactful innovations are those that make it as easy as possible for people to do the right thing, like a plant-based burger so good a carnivore can’t resist it, a transit system so fast you’d be a fool to hop on the highway, or a local business that is both a great employer and the best product on the market. If you strive to make doing the right thing easy, people will rally behind it.

02

No one is an expert in everything.

Building something big means figuring out how to ask for help or advice from people smarter than you in almost every aspect of the project. If you’re the linchpin in most areas of the venture, that’s a bottleneck; not an asset. A strong leader has a few core competencies related to their field but is first and foremost a humble, empathetic, and inspirational communicator who can leverage the passion of others into something bigger than the sum of its parts.

03

Do it for our grandparents.

Our grandparents cared immensely about the world they built for us and we owe it to our grandchildren to do the same. Success means enjoying the great things life has to offer and ensuring they’ll still be around in some form for others to enjoy after we’re gone. Growth and innovation are valuable, but a stable and peaceful society with abundant resources and a healthy natural world has been achieved many times in the past, is largely intact today, and is more than enough to leave for tomorrow.

One thing to takeaway

Sam is the Co-founder of CarbonGraph, a platform that automates carbon footprint tracking for complex products and supply chains. An engineer and data scientist by training (Queen’s University), he previously worked at Hatch, leading emission reduction projects for major mining companies across 12 countries. Sam is now applying that deep industrial expertise to build the data infrastructure required for businesses to reach net-zero targets.

Samim Safaei

Co-founder and CEO of siift.ai. Building AI tools to de-risk entrepreneurship.

I’m not sorry for being a stubborn founder.

Three winning principles

01

Stay honest.

Honesty is a dying skill; it’s not about filtering what you say but rather facing reality and maintaining integrity - especially as a business owner. Don’t let “story-telling” replace trust as your primary currency, you won’t last long. How does this help you win? Most lies are told to ourselves... Think twice about where to play, how you show up and what you offer. It’s not black & white, but even greyscale takes calibration.

02

Commit to growth.

If you don’t consistently believe in yourself and keep trying to improve, chances are others won’t either. A “growth mindset” isn’t showing off, it’s about relentlessly improving yourself through self-awareness and self-love. How does this help you win? Your vision of success probably requires you to become a different, better version of yourself... someone who’s put themselves out there, failed & tried again 1000x.

03

Focus on empathy.

Being a student of human behavior and understanding people can be a superpower for entrepreneurs - IF they turn off their criticisms and zoom in on individuals and emotions, things don’t have to make sense. How does this help you win? As AI automates technical work and floods everything, what will stand out is what makes you feel human connection, your identity, values, background, taste, brand... society is at the verge of redefining what it means to be human - keep up.

One thing to takeaway

Samim is the Co-founder and CEO of siift.ai, his fifth startup venture. He recently left his role leading Generative AI product strategy at TELUS Business Solutions to focus entirely on building “The New Business OS”, an Agentic AI platform designed to help early-stage entrepreneurs validate and scale their ideas. An engineer by training with a history of building Deeptech in Music, IoT and fire safety, Samim is now pointing his AI product experience at what actually stalls new founders: no clarity on the next step, and no guidance they can reach.

Sarah Bartnicka

Founder of Milk Bag. Building independent business media for the Canadian market.

I’m not sorry for betting on newsletters before anyone thought they could be a real business.

Three winning principles

01

Work harder than anyone else.

Working hard doesn’t guarantee results, but when you’re starting out in your career or with a new idea, you can come out ahead of people who are smarter, more talented, or better connected than you with more effort. I spent a year convincing the company that gave me my first break to hire me. I see people give up so fast, and in moments that could change everything for them.

02

Hold yourself to a high standard.

Everywhere I look, standards are slipping and ‘good enough’ has become the default, so people who obsess over details stand out immediately. It is exceptionally difficult to do this when nobody is asking it of you, and even harder when you’re told to dial it back. To me there’s no alternative, and if you hold firm you’ll eventually land with people who care as much as you do.

03

Identify a mission that lights you up.

When the work means something to you, everything else is easier: the early mornings, the hard conversations, the moments where nothing is going right. I’ve also seen it affect the way I show up with others: I’m more curious, present, and generous with my resources and time. You can’t fake that energy and I find it reinforces whatever it is you’re working on.

One thing to takeaway

Sarah is the founder of Milk Bag and the former founding editor of The Peak, which she helped build into Canada’s most-read daily business newsletter. A writer and editor with work in The Globe and Mail and BetaKit, she has spent her career defining the modern voice of business reporting. Now based in Toronto, she is taking what she learned building a newsletter to national scale and setting a new bar for independent business storytelling.

Shiva Bhardwaj

Founder and CEO of Pitstop. Predicting vehicle failure with 94% accuracy.

I’m not sorry for choosing discipline over hype and capital.

Three winning principles

01

Architecture beats headcount.

You don’t need many engineers. You need the right system design and the discipline to say no to everything that doesn’t compound. A small team with leverage will outrun a big team without it. This is obvious today in an AI-first world. Five years ago, I was the “fool” going against the grain.

02

Stay in the room longer than everyone else.

If your vision for the world is an inevitable future, it’s your job to make it reality. You don’t control timing, but you control outcomes. The founders who win are the ones still standing no matter the market wave.

03

Build for your customer, but most importantly build for the future.

Take the customer and market on a journey to the future of their job. Inspire them. That’s harder and littered with more mistakes, but way more fulfilling. This mindset has allowed me to build a truly innovative company in an industrial field like fleet and vehicle maintenance, not just a transactional one.

One thing to takeaway

Shiva is the Founder and CEO of Pitstop, an AI-powered platform that predicts vehicle failures before they occur. An electrical and computer engineer (University of Waterloo), he spent time at NVIDIA and BlackBerry before launching the company in 2015. Inspired by his childhood in his father’s repair shop, Shiva built Pitstop into a leader in fleet intelligence—culminating in its acquisition by Fullbay in 2026. He has been recognized as the Vaughan Entrepreneur of the Year and a SEMA 35 Under 35 leader.

Sruti Pujari

Founder and CEO of Feel Your Best. Building an integrative mental wellbeing platform.

I’m not sorry for refusing to accept that suffering is permanent.

Three winning principles

01

Know your why, and know it well.

There is a real difference between understanding something intellectually and knowing it in your bones. My 20 years of battle with depression and anxiety is not incidental to what I am building. It is the whole reason behind why I’m building a mental health company. And on days when doubt creeps in, I come back to the same question: why did I start this in the first place? That answer has never changed. Knowing your why with that kind of clarity is not a nice-to-have. It is the only thing that keeps you honest when everything else gets loud.

02

When you can’t run, walk. When you can’t walk, crawl.

Entrepreneurship is a marathon. There will be years before your effort compounds into anything visible. Hurdles are not a bug in this journey - they’re a feature. The pace will change. Some stretches you run. Others you walk. Occasionally, you crawl. None of that is failure. And I want to be clear: I am not saying that hoping for success is a strategy. I am saying that stopping is the only option that is truly off the table. Forward motion, at whatever speed you can manage on a given day, is the whole game.

03

Customers over investors. ALWAYS.

Never cut corners on customer experience to please a cap table. The customer is the business. Everything else is a means to serve them. I don’t just preach this. I have returned investor money because I could see, clearly enough, that the vision I was building towards would not survive the criteria being placed on it. That was not an easy call. But getting that agency back has been one of the most empowering things I have done in this journey.

One thing to takeaway

Sruti is the Founder and CEO of Feel Your Best (FYB), a mental wellbeing platform focused on integrative and holistic health. A graduate of IIM Lucknow (PGDM) with a professional background at TD Bank and HDFC Bank, she is putting that training in strategy and operations to work on mental wellbeing. Now based in Toronto, she is scaling FYB to sit between traditional mental health care and something people will actually use every day.

Stephen Szeto

Physician at North East Medical Services. Specializing in physical medicine and medical device innovation.

I’m not sorry for choosing fun.

Three winning principles

01

I like to think of my life as a story in a book.

When I eventually go back and read mine, I hope it’s interesting. In life, there are always options. I tend to choose paths that feel unique and uncharted. It makes for a better story.

02

Ball is life. Literally.

For those who know me, there’s no greater escape than a basketball and a hoop. Finding something that keeps me grounded through life’s everyday pressures has been an irreplaceable blessing, one I hope everyone can find for themselves.

03

Be curious about your limits.

Knowledge falls into three disproportionate buckets: what we know, what we don’t know, and (by far the largest) what we don’t know we don’t know. Curiosity is what allows us to grow into that last, unknown space, and it’s often where the most interesting opportunities come from.

One thing to takeaway

Stephen is a physician at North East Medical Services specializing in physical medicine and rehabilitation. A Stanford Biodesign Fellow trained at the University of Toronto and Stanford, he focuses on treating musculoskeletal injuries through ultrasound-guided procedures and electrodiagnostics. He combines his clinical practice with a background in medical device innovation to advance patient recovery and functional independence in the San Francisco Bay Area.

Tal Schwartz

Co-founder of North Exit Ventures. Driving capital and conversation across Canadian fintech.

I’m not sorry for treating almost everything in life like starting a business.

Three winning principles

01

Start before you feel ready.

Clarity usually comes from doing, not from thinking about doing.

02

Take ownership early.

Most things improve quickly when someone decides they are responsible for the outcome.

03

Distribution matters more than the product.

It is not enough to build something good if no one sees it.

One thing to takeaway

Tal is a General Partner at North Exit Ventures and the author of the Canadian Fintech Newsletter, one of the industry’s most widely read publications. He founded Lenders API, which he sold to Trust Science, and established the Canadian Lenders Association, scaling it into the country’s largest financial services trade group. He knows Canadian financial regulation and how the market moves, and he uses the newsletter to walk early-stage founders through what building and scaling inside it actually takes.

Tim Lichti

Co-founder and CEO of Swap Robotics. Scaling solar energy through autonomous robot fleets.

I’m not sorry for having an outrageous mission to 10x the clean energy industry.

Three winning principles

01

The Paradox of Ambition: Why Audacious Goals Are Easier to Hit.

Choosing an “outrageously ambitious” mission is actually a shortcut to success. Realistic goals are boring; meaning-driven moonshots—like Swap Robotics’ mission to 10x clean energy—act as a magnet for world-class talent. When your vision is massive, you can recruit the wildly ambitious people that a cash-strapped startup normally couldn’t afford. Plus, if the mission creates genuine social value, you can’t lose: you either change the world or walk away proud that you gave it everything.

02

Identify “10x” Opportunities.

High-growth companies scale by tackling the two biggest problems their customers face. In a world of limited corporate focus, “nice-to-have” products struggle to close. If you want sales to become your superpower rather than your bottleneck, align your product with your customer’s top annual priority. Create a solution so radically better—at least 10x—that the transition becomes a mathematical necessity rather than a hard sell.

03

Master the Win-Win Architecture.

Sustainable growth is built on transactions where both sides thrive. Whether you’re negotiating with a supplier or hiring a new teammate, your goal should be to structure deals that maximize total value over time. Short-term wins at a partner’s expense are self-limiting; instead, develop the skill of identifying “aggregate gain.” If you consistently leave your partners in a stronger position, you’ll find that doors stay open and your reputation does the heavy lifting for you.

One thing to takeaway

Tim is the Co-Founder and CEO of Swap Robotics, where he is deploying autonomous robot fleets to scale North America’s solar infrastructure. A University of Waterloo alumnus and serial entrepreneur, he has a proven track record of building four separate ventures from scratch, earning recognition as one of the Globe and Mail’s Top 12 Innovators. Tim is now bridging the gap between heavy operations and climate tech to solve the critical labor and emissions challenges facing the energy sector.

Tudor Lungu

Co-founder and CEO of Tofu. Building social discovery platforms to solve the global crisis of social isolation.

I’m not sorry for ignoring convention.

Three winning principles

01

The Will of an Olympian: Strength Through Failure.

You learn more from failure than from success. I spent a big part of my life swimming, training up to four hours a day with the Olympics as my goal, until a sudden allergy forced me to stop overnight. Rather than lamenting it, I didn’t quit; I pivoted. I poured that same resilience into building software solutions for problems. After years of making apps, I launched a gamified social platform in Toronto at the height of COVID. I bootstrapped it to 7-figure profitability and scaled it to over half a million annual members. An obstacle isn’t just in the way; it can show you the way. The only real failure is not getting back up when things get you down.

02

The Heart of a Human: Build For People, Not Users.

Nowadays, what can be easily lost is the courage to be vulnerable and stay human. I try to build things that actually matter in real life, not just capture attention and “shareholder value”. Currently I am developing an “offline social media” and researching social innovation at Keio in Japan. Don’t lose yourself chasing metrics that don’t feed the soul.

03

The Passion of an Inventor.

Refuse Default Constraints Being atypical isn’t a weakness; it’s leverage. Growing up in Canada, with its cultural mosaic, I learned that diversity is strength. As the youngest admit to the hyper-global INSEAD MBA, instead of feeling isolated, I leaned into my different perspective. Take ownership of your “lucky differences”; build upon them brick by brick. When you stop trying to conform to the norm, you can start creating something that actually matters.

One thing to takeaway

Tudor is the Co-Founder and CEO of Tofu, where he builds social discovery platforms designed to tackle the challenge of social isolation. A serial entrepreneur, he built a seven-figure business while an undergraduate at the London School of Economics and became the youngest MBA candidate in INSEAD’s history at 22. Now based in Ottawa, Tudor is applying a history of rapid execution to ventures like Up, an app created to help people find community and connection in the real world.

Will Hanna

Co-founder and COO of Miniswap. Building the global marketplace for the tabletop gaming community.

I’m not sorry for choosing what interested me over what was expected of me.

Three winning principles

01

See the world before you settle into it.

I grew up in North Toronto. It was all I knew, and I didn’t appreciate how small my slice was. Then I moved to France at 18 and everything I thought I understood about myself was challenged. Living in a foreign environment as a young person was a fast track to personal growth and maturation. The same thing was true when I moved to Quebec, Cambridge, London and now San Francisco. I am a Torontonian, Ontarian, Canadian but I am also much more than that. Exploring the world has given me the confidence to see myself beyond the boundaries of where I grew up, and the courage to venture into the unknown. If you’ve never lived somewhere that made you feel like a stranger, go. If not abroad, to another province. You can always come back. You’ll be better when you do.

02

Stay close to what engages you.

I studied philosophy because it kept me up at night. I dropped out of law school because it didn’t. I ran a painting company one summer and a tutoring business the next because I wanted to be my own boss. I started Miniswap with my best friend because the work absorbed us both completely. The through-line of my trajectory is not a career plan but a series of moments where I followed what fully engaged me and walked away from what didn’t, even when walking away was expensive. If something makes you lose track of time, take it seriously.

03

Don’t forget where you came from.

The older I get, the more I understand that relationships are everything. To friends, to family, and to the people who believed in you before you had anything to show for it. The people I’ve loved have shaped me more than any degree or job ever could. The people you choose to pay attention to and surround yourself by are the architecture of your life. Everything else is furniture. Canada shaped who I am, and the relationships I have there are the reason I know I will one day be back.

One thing to takeaway

Will is the Co-founder and COO of Miniswap. Backed by Y Combinator, Miniswap is building a more efficient marketplace for the global tabletop gaming community. He stepped away from law school to launch the company alongside co-founder Zak Singh, following a career as a strategic advisor to CEOs at Bridgewater Associates and Pfizer. An alumnus of McGill and Cambridge, Will is now applying high-level operational experience to solve the friction in the hobbyist market.

That’s all 55, in their own words.

This is a snapshot, not a running directory. I put it together once and I’m leaving it as it is.

If you want the next thing I write, subscribe below.

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• Asurion (A): Two Stanford MBAs and a Towing Company (with Garth Saloner, 2026)

• Asurion (B): A New Name and A Bigger Game (with Garth Saloner, 2026)

• Social Alpha: Building Markets Where Markets Fail (with William Barnett, 2026)

• The Human Side of Scaling: Stella & Dot (with Graham Weaver, 2026)

• Keep Rowing: Sami Inkinen and Virta Health (with Garth Saloner, 2025)

This is a growing list.

Our definition of ambition is not ambitious enough.

Ambition (noun) — An ardent desire for rank, fame, or power.

— Merriam-Webster

This definition, and others like it, is accurate only for ambition without principles. It describes a raw desire for status, a pursuit of power for its own sake, devoid of constraints and driven by pure want.

When ambition is defined solely by what we take from the world, stating a massive goal out loud—“I want to build a billion-dollar company” or “I want to transform this industry”—gets heard as selfish, arrogant, or power-hungry.

To avoid that judgment, we often keep our heads down, stay out of the noise, and work in silence.

But working in silence carries a penalty: if we don’t say the goal out loud, people can’t help us. The right partners, capital, and teammates can’t find us. When talented people working on critical problems—in housing, healthcare, or climate—stay hidden, progress in those areas slows.

We need a standard that allows us to state big goals without being dismissed as self-serving.

Fortunately, I’ve observed a different framework in action: a standard that is deeply principled, built for the long run, and massive in scope. It quietly drives some of the world’s most enduring success stories.

If you’ve ever felt like your ambition needed permission, here’s the standard that gives it to you:

Unapologetic Ambition (noun) — The pursuit of meaningful goals guided by uncompromising principles.

— Not Sorry

When we know what we won’t compromise, we can pursue everything else without apology. Principles create permission.

Engineers ask for the promotions and salaries they’re worth. Founders say “billion-dollar company” in the first meeting. Athletes state their drive to make the top roster without burying it under false modesty.

We stop shrinking. We ask for what we’ve earned, state our grandest visions, and step forward to lead.

To see what this looks like in practice, I asked dozens of leaders to define their own “not sorry” statements by answering two questions:

Neil Cawse • Geotab

Building a global telematics giant from outside the venture ecosystem

Operating out of Oakville, Ontario, Neil transformed an entire industry by turning proprietary black boxes into open, transparent data systems. He built Geotab into a $1 billion ARR company processing 100 billion daily data points from millions of vehicles—without a cent of venture capital—ultimately beating Silicon Valley’s hyper-funded giants for a $314 million government contract.

“I’m not sorry for bringing ruthless transparency to an industry built on black boxes.”

The Principles: Do the right thing for the long run. Check your ego at the door. Measure, reflect, and improve.

By discarding VC money, Neil protected his long-term values from short-term growth pressures. He built an empire on transparency, refusing shortcuts that compromise long-term trust. He is proof that checking your ego isn’t a soft skill, but a defensive moat.

Mike Wessinger • PointClickCare

Scaling a $1B software powerhouse on pure customer trust

Based in Mississauga, Ontario, Mike transformed healthcare records when the industry still relied on paper and fax machines. He scaled PointClickCare to $1 billion in ARR entirely on month-to-month contracts, choosing to earn his customers’ trust every single day instead of locking them into annual deals like everyone else.

“I’m not sorry for building a powerhouse from Canada — or for earning trust instead of locking it in.”

The Principles: Over-index on customer delight, not fundraising. Know the difference between a lifestyle business and a category killer. Build a genuine support network.

By discarding traditional lock-ins, Mike turned a structural vulnerability into a company superpower. He built a powerhouse on trust earned daily, not legal traps. He is proof that self-imposed constraints become competitive advantages.

Kristin O’Neill • Team Canada & NY Sirens

Dominating professional women’s hockey on the world stage

Representing Team Canada on the ice, Kristin is a powerhouse forward dominating on the world stage. When the pandemic cancelled her senior collegiate season, she trained for the Olympics in her apartment using a hockey broomstick weighted down with cement blocks, ultimately scoring Canada’s first-ever shorthanded goal in an Olympic gold medal game.

“I’m not sorry for never giving up on my dreams — or for refusing to make excuses when circumstances got hard.”

The Principles: Kindness—make people feel heard and valued. Courage—say the dream out loud. Process over outcome—let preparation create confidence.

By discarding any room for excuses, Kristin let her character dictate her grueling work ethic when the world paused. She built an elite career on preparation, refusing to wait for perfect conditions to play big. She is proof that intensity and kindness are not mutually exclusive—and that preparation creates confidence when conditions are imperfect.

What Are You Not Sorry For?

We have enough vanity lists. This is a home for people whose principles make their ambition entirely defensible: built from Canada, open to the world, with no age limits, no pay-to-play, and no waiting for next year’s class or edition.

Name what you want. Know what guides you.

Then go pursue it without apology.

It was January 2004 when Neil Cawse’s phone rang in his Oakville office.

“Neil. Nothing’s working.”

His brother Clive was calling from Orkin’s headquarters in Georgia.

Clive was there to demonstrate Geotab, Neil’s tracking system, to one of North America’s largest pest control companies. The company’s fleet manager was on his way in, expecting to see 3,500 service vans glowing on a live map, each one tracked in real time by a small black box under the dashboard.

Instead, he was staring at an empty screen.

For years, Neil had been trying to convince fleet managers that GPS tracking wasn’t surveillance or science fiction. That a device the size of a deck of cards could turn invisible, roaming trucks into a grid of actionable data. Orkin was the client that could change everything. Win Orkin, and Geotab would have instant credibility.

Neil and his brother Alan had spent two weeks rebuilding the backend to handle a client this size. They’d stress-tested every query and every load scenario, convinced they’d finally nailed it.

Clive was about to deliver the biggest pitch of their lives with a blank map, and Neil knew exactly which line of code had broken.

“Tell him to grab a coffee,” Neil said, keeping his voice calm.

He had ten minutes.

Behind the story

I interviewed Neil Cawse in person, brining the lens of a Stanford GSB case writer to unpack his personal journey and the strategic choices behind Geotab’s rise.

Read the full story below, or listen to our conversation on Apple Podcasts, Spotify, or YouTube

Hot Dogs, Star Trek, and One Thing His Mother Said

Neil Cawse grew up in Johannesburg with two younger brothers, Clive and Alan, and a younger sister, Lindy, in a household where “[e]verything ended up being a competition,” Neil said. “Who was better at school, who could run the fastest, who could eat their hot dogs the quickest—you name it.”

When Neil was around thirteen or fourteen, his mother said something meant to encourage one of his younger brothers, who was struggling in school. “You may be smarter,” she told Neil, “but your brother will be more successful than you. He’s always making money as an entrepreneur.”

She does not remember saying it, which is one of the small dangers of parenting. A sentence that disappears for the adult can lodge permanently in the child.

“It was like, no, I’m never gonna let that happen,” Neil said. “And it’s a silly thing. It really is silly, but in the back of your mind it sticks.”

Neil made a promise to himself that when he finished school, he would start a company. He didn’t know what kind, but he knew that if entrepreneurship was going to be the family event, he intended to compete.

At eighteen, Neil enrolled at the University of the Witwatersrand in Johannesburg, known as Wits, and considered three possible paths: medicine, actuarial science, and engineering.

Medicine ended at a museum exhibit with preserved fetuses, which revealed Neil’s horrible phobia of blood.

Actuarial science ended even faster. He walked into his first lecture and took in the room. Everyone was staring at the floor and there was little apparent diversity among the students.

“Yeah, not doing that,” he said.

That left engineering. His father wanted him to study civil. Neil secretly wanted computer science. Wits didn’t offer computer engineering, so electrical became the compromise. It was close enough to computers that Neil could live with it, traditional enough that his father didn’t object.

To pay his way through university, Neil took a sponsoring company’s scholarship that would have to be paid back through years of work. The work turned out to be in sales, which he hated. But later, he understood what it had taught him: in those rooms, the best technical answer mattered less than whether anyone believed you.

When Neil finished university, he had saved enough to start a company. A university friend named Ken agreed to join him. Ken’s wife, an actuary, would support them while they got started. Neil’s parents let him keep living at home. They would spend nothing, save every cent, and build a Microsoft consulting shop with almost no overhead.

They called it Vircom. Neil’s younger brother Alan became the first hire, leaving a job at a bank for the uncertain promise of his older brother’s startup. Clive joined later. They took on the kinds of projects established firms either ignored or couldn’t move quickly enough to handle: prototypes, proof-of-concepts, and odd Microsoft South Africa assignments that seemed too small to be prestigious.

Then, one became too important to refuse.

In 1994, South Africa was preparing for its first democratic election after apartheid, and the Independent Electoral Commission needed someone to manage the database behind the vote count. Microsoft recommended Vircom. The job was urgent, messy, and risky enough that the bigger firms weren’t interested, so it landed with two twenty-four-year-old brothers and their laptops.

The Shoe Cupboard

For weeks before the election, Neil and Ken worked around the clock in what Neil describes as a shoe cupboard in downtown Johannesburg. Black South Africans were voting for the first time. Neil and Ken’s job was to take vote counts streaming in from around the country, add them up using Microsoft’s database software, and send live percentages out to the media.

Neil was working the late shift. Ken had finished his twelve hours and gone home. Neil opened a spreadsheet and copied in some values from the system, just to double-check that everything was coming through correctly.

“I looked at the percentage, then at the outputs, then at the percentage again,” Neil said. “And I realized this crazy bug in my stored procedure—I wasn’t adding up all the numbers in every case.”

The percentages going out to news organizations across the country were wrong.

“Goosebumps,” Neil said. “I ran out, tried to find my boss. I said, ‘Listen, this is going on. I made a mistake. This is a problem.’”

Neil’s boss disappeared. Twenty minutes passed. Neil sat there watching the clock, watching the bad numbers continue flowing outward, watching a technical error become more dangerous by the minute. Nobody came back.

“Every minute that goes by, these numbers are trending in the wrong direction,” Neil said. “If I don’t change it, it’s going to get out of hand. I’m making an executive decision. The twenty-four-year-old kid is making an executive decision to fix this.”

So he opened the code and made the change. Alone in that cramped room, with no one watching and no one checking his work, Neil corrected the bug. He had no idea whether he’d just made things better or catastrophically worse.

About half an hour later, people started emerging from offices Neil hadn’t even realized existed. Hundreds of them moving through the building. His boss still hadn’t returned. Then came the instruction that everyone was being sent home, immediately, in the middle of the election count.

Neil got in his car and drove back to his parents’ house.

He walked in and started to speak. “Mom, Dad—”

“Have you heard?” his mother said.

“Mom, I need to tell you—”

“No, have you heard? It’s all over the news. They’re saying there’s been fraud in the election. A hack.”

Neil went cold.

The sudden movement in the numbers had triggered alarms. Election monitors running validation models saw the percentages shift too quickly. They assumed someone had hacked the system. What Neil knew, sitting in his parents’ living room watching the news, was that the crisis everyone was panicking about wasn’t a hack at all. It was his bug. And his fix.

He explained everything to his parents that night. He went to bed not knowing what would happen next.

The election continued. Despite the chaos and concerns about irregularities, international observers and the Independent Electoral Commission worked through the challenges of managing South Africa’s first fully democratic vote. The election ran for four days, from April 26 to 29, 1994. More than 19 million South Africans voted. Nelson Mandela, who had spent 27 years in prison for his opposition to apartheid, won the presidency and was inaugurated on May 10 as the country’s first Black president. The system held.

Neil took something from that night that would shape everything he built afterward. At Wits, he had studied control systems and the endless feedback loop they required. Measure what is happening, adjust, and measure again. The election had shown him what happens when that loop breaks—and what happens when you have the data to fix it. A single bug in the code triggered a national crisis during one of the most important moments in his country’s history, and the only way through was accurate data and the ability to act on it immediately.

Geotab would become the company version of that lesson.

Beers and GPS

Over the next several years, Vircom grew. The three Cawse brothers built a reputation for taking on Microsoft projects other firms either couldn’t handle or couldn’t move fast enough to win. They were profitable, disciplined, and increasingly successful.

By the late 1990s, Vircom had become something of substance. Another idea was forming in the background, helped along by Neil’s mother, a car alarm company, and a few Friday afternoon beers.

Neil’s mother worked at Sanji Electronics, an aftermarket car alarm business run by Larry Khan. In South Africa at the time, car alarms weren’t a luxury but a necessity. Security was a real problem, and alarms were often added after the vehicle was sold.

“Larry bribed me with beers on Friday afternoons to fix his PC,” Neil said. “Great guy. I’d get everything working, and we’d chat over beers.”

One Friday, Larry turned the conversation to GPS. The U.S. government had recently made civilian GPS dramatically more accurate, turning it from a military-rooted technology into something commercially useful. For the first time, anyone could know exactly where something was, anywhere in the world, in real time.

“That was like, whoa,” Neil said. “What could we do with that? How cool would that be?”

To Neil, who had spent his childhood reverse-engineering Star Trek, this wasn’t small. GPS meant you could know where something was without waiting for someone to tell you.

The most obvious application was vehicles. Companies owned cars, trucks, vans, and service fleets that moved through the world all day, generating information nobody was capturing. Information like where they went, how long they stopped, how they were driven, or whether a driver was telling the truth about what happened between leaving the depot and coming back.

Larry and Neil decided to find out if businesses would pay to see their vehicles in real time. They formed a joint venture between Vircom and Sanji Electronics. Vircom would build the software, Sanji would handle the hardware. But before there were customers, revenue, or much of a product, Neil had to sit across from a seasoned group CEO and explain why the twenty-five-year-old software kid deserved half the company.

Neil wanted fifty-fifty.

From the other side of the table, that sounded ridiculous. Sanji had the hardware background, the manufacturing relationships, the tenure. Neil had code, conviction, and his mother listening from the next office.

“I’m like, do you not understand how important software is?” Neil said. “Software is running the world. This is changing.”

The debate went in circles. Neil wouldn’t budge.

“I remember the group CEO eventually getting pretty frustrated with this twenty-five-year-old,” Neil said. “He’s like, ‘Okay, I’ve done whatever I can,’ and he kind of storms out. Mom was listening in the other office.”

Paul and Larry stayed in the room. The device needed both pieces to work—hardware to collect the signal, software to make it useful. One without the other was worthless.

“At the end of the day, they went, ‘Okay, that sounds okay,’” Neil said. “’We’ll do fifty-fifty and see how it goes.’”

They called the company Geotab (Larry was the marketing genius).

For a while, Geotab wasn’t the main event but a side project, small and speculative, while Vircom paid the bills.

Then, in 1999, Dimension Data, one of South Africa’s largest IT services companies, made an unsolicited offer for Vircom. Neil turned it down.

The offer landed inside a much bigger personal decision. Neil and his then-girlfriend Tammy wanted to get married and have children, but they didn’t want to raise those children in South Africa. Suddenly, selling Vircom was no longer just a financial decision.

So Neil did what any young engineer would do when making an emotional decision of enormous personal consequence: he built a model.

The Country Chosen by Spreadsheet

Neil analyzed every English-speaking country he and Tammy could reasonably move to. He looked at immigration data, including how many people moved to Australia and how many came back. He interviewed people who had left South Africa. He pulled statistics on healthcare, education, literacy, GDP growth, infant mortality, and gun violence.

The report pointed toward Canada, with the United States close behind.

“We looked at Canada as being on the doorstep of the US,” Neil said. “Access to the largest market in the world.”

In addition to proximity, Canada offered a safe and stable place to raise a family. Ontario’s schools helped, too. Later, that talent base would become part of Geotab’s advantage.

On paper, Canada won. But Neil wasn’t moving alone.

He invited the family over for a barbecue.

Parents, siblings, spouses. The people whose lives would be upended if the spreadsheet was right, gathered in the backyard. Neil was close with his family, and the idea of leaving them behind didn’t sit right.

“Tammy and I want to get married. We’re going to leave, we’re going to sell the business,” Neil told them. “Can we all make a pact we’ll go to the same place? Here’s the report. Tell me what you think.”

It was an enormous ask. Leave Johannesburg, the only home they’d known, and move to a country they’d barely thought about, based largely on a spreadsheet built by the eldest son. Classic Neil, turning an emotional, life-altering decision into something the family could examine, debate, and decide.

They didn’t say yes on the spot. They made a trip to Canada first, to see if the place matched the numbers. When they came back to Johannesburg, the decision was made.

Neil and his partner Ken put Vircom on the sales block and, eight months after the Dimension Data offer, sold the company for roughly $10 million each, including an earnout. After taxes and immigration costs, he netted around $8 million.

A side project over beers had become the thing he carried across the ocean.

The Market That Didn’t Exist

Geotab came to Canada almost as an extra piece of luggage.

Once he was in Canada, Neil reached back out to the partners in the Geotab joint venture. The business was still tiny, barely more than an idea, but Neil wanted to give them the chance to come along.

“I said, you know, you can put in some money and we’ll get it going,” Neil said. “And they declined.”

Vircom’s new owner didn’t want Geotab. It was too small, barely worth anything. The South African joint venture partners passed on coming to Canada. So Neil started Geotab fresh, this time entirely his own.

“It was a good way to give the family a livelihood,” Neil said.

Left to his own curiosity, Neil might have gone somewhere else entirely. He had nearly gone to MIT to study artificial intelligence.

“Kids—Ethan came along,” Neil said. “So that was canceled.”

Instead of MIT, Neil got Oakville, a few early employees, and a vehicle-tracking product that required a lot of explaining. He put in $250,000, then another $250,000. Revenue was beginning to come in, but the company was still small enough that every decision felt close to his own bank account.

At one point, Neil sat down with the team.

“Guys, how are we doing here?” he asked. “I don’t have infinite money. I could maybe put in another $500,000 if we need to. How do you feel about things?”

The team looked at the numbers, looked at the early traction, and made the call.

“No, no, look, we’re feeling pretty good,” they told him. “We’ve got momentum. It’s going well. We think we should be okay.”

“And we never looked back from there,” Neil said.

But momentum was relative. For years, Geotab kept selling into a world that still found the whole idea strange. The technology worked, so that wasn’t the problem. The problem was that in 2001, putting a tracking device in a company vehicle sounded less like fleet management and more like surveillance. (The original giant eyeball logo didn’t help.)

Neil would pitch fleet managers and hear the same response: “I don’t track vehicles. That’s terrible. My employees would never accept that.”

Most companies would have hired salespeople, opened offices, pushed harder. Neil knew better. The market was not ready, and spending ahead of it would not make it arrive faster. Geotab had to survive long enough for the market to catch up.

“We tried to measure our performance in terms of profitability per person,” Neil said. “Which is a stupid way to do it. Basically trying to keep headcount to a minimum.”

Unorthodox, maybe, but it forced clarity. If Geotab was going to stay small, it had to know exactly what belonged inside the company and what didn’t.

“We were not good at marketing and sales,” Neil said. “I knew nothing about how to sell a product across the US and Canada. I didn’t know anything about hardware manufacturing, even setting up an office and running an office.”

So Geotab focused on the software, the engineering, and the systems that made the platform work. Manufacturing, hardware, sales, marketing, even office space all got outsourced.

“Always ask yourself the question,” Neil said. “What is core to you? Don’t be greedy.”

But if Geotab wasn’t going to hire salespeople, how would it reach customers? Neil did what he often did when facing a problem he didn’t fully understand. He found someone who could figure it out. In this case, that was his sister Lindy and her husband Stephan, whom he paid to build a North American marketing plan for a couple of thousand dollars.

The report pointed to resellers.

Geotab didn’t have the money, the footprint, or the credibility to sell directly into fleets across the United States and Canada. But resellers already had the relationships, local knowledge, and installation capacity Geotab lacked.

Geotab would build the product. Resellers would get paid for every customer they brought in. The goal was to find people who believed in the product enough to bet their own time on it.

The first reseller Neil signed wouldn’t even agree to represent the product without a $5,000 upfront payment, on top of the commission he’d earn on every sale.

It wasn’t exactly a vote of confidence. “We literally had to give away the first one and hand-hold it,” Neil said. “But once you have a good reference, it just becomes so much easier to get your next sale. The first one is always the hardest one.”

That first sale led to a second, the second to a third, and slowly, the reseller network that would eventually scale Geotab across North America began to take shape.

Then came the call that would test whether any of it actually worked.

The First Big Break

Two weeks before Clive stood in Orkin’s office staring at an empty screen, Neil was on the phone with Orkin’s fleet manager.

Through one of Geotab’s resellers in Georgia, Neil and Alan had landed a call with Orkin. Founded in 1901, Orkin had become one of the largest pest control companies in North America, with a fleet of 3,500 service vans making house calls across the country every single day. Those white vans with the red Orkin Man logo were everywhere—in subdivisions, office parks, apartment complexes. If you lived in America, you’d seen one.

For Geotab, Orkin represented more than revenue. It was a fleet that never stopped moving, with technicians running routes from early morning to late afternoon, hitting dozens of stops a day. The operational complexity was exactly what telematics was built for: tracking arrival times, optimizing routes, verifying service calls, monitoring driver behavior across thousands of miles. If Geotab could handle Orkin, it could handle anyone.

Everything was going well on the call with the fleet manager until he asked Neil about the database.

“We’ve had a lot of trouble with Microsoft Access-based systems,” said the fleet manager. “Is your product based on Access?”

Neil paused. If he said yes, the fleet manager might hang up. If he lied, Clive would show up in two weeks and they’d find out immediately.

“It currently is,” Neil said. “But why?”

The fleet manager explained that Access crashed under load and corrupted data in ways that made people stop trusting the technology. If Geotab wanted Orkin’s business, it needed to run on SQL Server.

Neil knew the migration made sense long-term. The question was whether it could happen in two weeks.

“We’re working on it,” Neil said.

The fleet manager gave them the deadline. Demo it on SQL Server in two weeks, and Orkin would give them the business.

“It was literally day and night,” Neil said. “Alan and I were sweating blood to get this thing done.”

They migrated Geotab off Access and onto SQL Server, tearing apart the database, rewriting queries, testing what they could. The version they sent Clive was buggy, but it was what they had. Then Neil made one last change that morning before Clive’s demo.

That change broke everything.

Clive arrived at Orkin, started the system, and called Neil. Nothing was working.

Neil realized what he’d done and had ten minutes to fix it while Clive bought time. When the fleet manager came back, the map loaded and vehicles appeared across Georgia.

The fleet manager tested it for twenty minutes, then said they’d be in touch.

A few days later, Orkin called back. They were moving forward.

For a company that had been selling ten, maybe twenty vehicles at a time, and sometimes waited months between deals, Orkin was the proof point Geotab needed. Reference calls became easier. Skeptical fleet managers started returning emails.

“They put us on the map,” Neil said. “Everybody in America knew Orkin. As soon as you say you’ve got them as a customer, doors open.”

But a marquee customer wasn’t a market.

Around 2010, the world started catching up. Digital maps were normal. Smartphones meant everyone was already being tracked. Cameras were everywhere. The privacy objections didn’t disappear, but they stopped being the first thing fleet managers said.

The market was coming. Geotab was growing. Then the rules changed.

Double Six

On December 18, 2017, the Electronic Logging Device mandate reached its first major compliance deadline in the United States. Commercial truck drivers who had long recorded their hours on paper now had to track them electronically.

After more than a decade of Neil trying to convince fleets to connect their vehicles, the government had forced everyone’s hand.

“I didn’t appreciate the importance of that ELD mandate,” Neil said. “We talked about it, said it’d be important because everyone leaves things to the last minute. But I didn’t fully appreciate how big it would be.”

Resellers were flooded with calls. Installation schedules backed up for months. Support lines lit up. Fleet managers who had spent years resisting tracking were now scrambling to connect vehicles that had never been connected before.

During the ELD period, Geotab grew around eighty percent a year, the fastest stretch in the company’s history. The strange Canadian box was no longer strange. In many cases, it was mandatory.

Geotab had survived by matching spending to demand, but the ELD rush flipped that discipline inside out. The company now had to build capacity before customers went elsewhere.

“The longer you play, eventually you’re going to get double six. And when you get double six, you need to go big.”

So Geotab went bigger. It scaled manufacturing, expanded the reseller network, hired more people, and built the infrastructure to handle the flood of data coming off vehicles.

Revenue surged. The company’s owners were mostly family and early employees, people who had lived through the years when Geotab was small, strange, and far from certain. After the ELD wave, Neil wanted them to be rewarded for their work. In 2018, Geotab paid out roughly $100 million in dividends.

Winston Park Drive vs. Sand Hill Road

Around 2018, a different kind of competitor emerged.

Samsara had launched in 2015, founded by Sanjit Biswas and John Bicket, who had built Meraki and sold it to Cisco for $1.2 billion. Geotab had faced incumbents before—Verizon, Teletrac, others. But Samsara was different. They had technical founders, a modern product, and venture-backed speed. In 2018 alone, Samsara raised $150 million across two rounds, reaching a reported $3.6 billion valuation by December of that year.

Neil watched it happen and recalibrated. He’d just paid out roughly $100 million in dividends—a reward for years of patience. But watching Samsara raise $150 million in a single year made him realize the market wasn’t going to wait for Geotab to decide when to reinvest.

“I can categorically say that was my biggest mistake today,” Neil said. “Yes, we got some money out of the business, but that was never what this was about. That money should have been reinvested. We should have been building video technology and a whole bunch of other areas. I think the world of Samsara would look very different today.”

After that, the money stayed in the business. Geotab now spends roughly $200 million a year on research and development.

“The tech business is hard,” Neil said. “You’re on a bit of a treadmill. You have to make your product better all the time.”

Neil still didn’t want venture capital or the loss of control that came with it, but he understood what competing against Samsara required. Geotab would have to be disciplined about where it invested and how it executed.

The test came in 2022.

The United States Postal Service put out a procurement for one of the largest civilian fleets in the world. Over 230,000 vehicles, including more than 140,000 Long Life Vehicles originally deployed in the 1980s. The contract was worth up to $314 million over nine years.

USPS needed telematics that could work on everything from 1987 Chevrolet S-10s to modern electric vans, across thousands of depots running different routes with different operational needs. The older vehicles presented a particular challenge. They didn’t have the standardized diagnostic ports that came in newer cars. Tracking them required a custom cable and device that could plug into systems never designed to share data.

Geotab had spent years developing and refining their solution across various vehicle types and generations of automotive technology. Samsara didn’t yet have this capability. While the team committed to building it within six months, they couldn’t provide the Postal Service with technical diagrams or a concrete development roadmap.

In November 2022, USPS announced its decision. Geotab had won.

Samsara filed a protest with the U.S. Court of Federal Claims, arguing the Postal Service had improperly evaluated their proposal. In May 2023, the court denied Samsara’s request for a preliminary injunction, and USPS proceeded with the contract.

Then, in January 2024, the court found an error in how USPS had evaluated Samsara’s approach. The Postal Service was ordered to reevaluate both proposals and, if necessary, make a new award decision.

USPS reconvened its evaluation team. The conclusion was the same. Samsara still hadn’t provided sufficient detail on how they’d build the solution, what it would look like, or how it would integrate with their existing system. Geotab’s technical score remained significantly higher.

On January 18, 2024, USPS reaffirmed the award to Geotab.

Twenty years of patient, disciplined work had won the contract. But in technology, winning once doesn’t mean winning twice. The next test was already forming.

The Next Game

The side project that arrived in Canada over beers twenty-five years ago is no longer a side project.

Geotab now generates more than $1 billion in annual revenue and more than $125 million in operating profit, all of it reinvested in the company. It employs 3,500 people and serves more than 100,000 customers on every continent, including Antarctica. The platform processes more than 100 billion data points every day from 6 million connected vehicles.

Neil built it without raising a single dollar of venture capital. He still owns roughly two-thirds of it. His brothers, Clive and Alan, along with a few hundred employees, own the rest.

He made bets others wouldn’t, saw opportunities before they were obvious, and stayed true to the principle he learned in engineering: measure what is happening, change the input, and measure again.

But the game changes when you become the incumbent.

When Geotab was small and the market didn’t exist yet, Neil could afford to be patient. He could wait for companies to understand why tracking mattered. He could survive on discipline and low costs while the world caught up.

Now Geotab is what competitors are trying to disrupt. And the next technology shift—artificial intelligence—is moving faster than anything Neil has seen. For twenty-five years, the question was whether companies would connect their vehicles. Now it’s what those 100 billion daily data points can actually do, and whether Geotab moves fast enough or gets outmaneuvered by someone younger and faster.

“This is the most profound and important thing that’s happened in my lifetime,” Neil said. “And that includes everything—PC revolution, SaaS, GPS, all of that stuff. If I do not get this right, there will not be a Geotab. The company will be out of business, and nobody will be employed.”

Twenty-five years in, Neil still doesn’t know which bets will pay off. He just knows what happens when you stop making them.

The dice came up double six once. He’s betting they will again.

Neil’s Not Sorry

From Neil Cawse

I’m not sorry for ruthless transparency.

Being honest is not the same as being cruel. It means being straight with people early, while there is still time to help them get better. If someone is doing the wrong thing and you avoid the uncomfortable conversation, you are not protecting them. You are letting the problem grow until it becomes much harder to fix.

Three winning principles

01

Do the right thing for the long run.

Never compromise on what matters long term: your customers, your people, your family, your health, or your technology. Do not take the quick buck. Do not take the shortcut. Build for the long run as much as you can.

02

Check your ego at the door.

The worst, most powerful evil is to believe that you are somehow special, that you’re always right, or that you can’t be questioned. The more successful you become, the easier it is to fall into this trap. The more successful Geotab becomes, and the bigger we grow, the more important it is for me to keep reminding myself of this point. Surround yourself with people who can tell you the truth, and listen when they do.

03

Measure, reflect, and improve.

You cannot manage what you do not measure. Build feedback loops into everything: your work, your company, your relationships, your health. Look at what is happening, understand it, change the input, and measure again.

One thing to takeaway

A couple months ago, Ben Clayton reached out asking how he could help make Canada the place he wants to build. We planned to connect, but before we ever spoke, he sent me this note:

“I contacted the CEO of Float, had a call with him yesterday and am working on an article.”

That’s Not Sorry in action. Ben saw what he wanted to build, did the research, and made it happen.

I’m thrilled to run his piece on Rob Khazzam, who built Float, a Toronto fintech now serving 6,000+ Canadian businesses, the exact same way.

Onto winning.

By Ben Clayton

I am the biggest obstacle to creating the next great Canadian success story. So are you.

I believed that building something great meant eventually moving to the United States. Bigger market, more capital, more talent density. That’s just what serious entrepreneurs do.

Then I spoke with Rob Khazzam.

Rob is the co-founder and CEO of Float, a company aspiring to build Canada's most intelligent business finance platform. He taught me three things that changed how I see entrepreneurship in Canada:

1. The longer you wait, the harder it becomes

2. Ideas mean nothing; execution is everything

3. Canada is the right place, right now

Let me explain.

The longer you wait, the harder it becomes

Rob took the “safe” path. Western Ivey undergrad, then Private Equity on Bay Street, Canada’s equivalent of Wall Street. By conventional metrics, he was successful.

“For the last two years of my time in Private Equity, I was unhappy and unsatisfied,” Rob told me.

Leaving felt impossible. Startups sound attractive until you’re facing a pay cut, an unclear path forward, and questions from family about why you’d walk away from such a “great career.” For Canadians, the US often offers higher salaries and a favourable exchange rate. When it’s that easy to make more money south of the border, why take the risk to build something here?

“I felt a cultural aversion to risk-taking, to being aggressive, being ambitious,” Rob said.

That version of Rob is gone. When I speak with him today, his demeanour is battle-ready like a modern-day gladiator preparing for combat, except his battle is against outdated bookkeeping. And unlike a gladiator, he had just put his kid down for a nap.

The evolution from risk-averse professional to founder didn’t happen overnight. After five years in Private Equity, Rob realized the risk he’d worried about was largely imaginary. A mentor asked him one question: “What’s the worst that could happen? You find another job?”

Turns out, he did just that.

Rob joined Uber in 2014, back when the company was still fighting regulatory battles, like operation SLOG, around the world. He joined their International Launch team and spent time in Eastern Europe, helping expand from 66 cities at the start of 2014 to 266 by year’s end.

“I found the ownership intoxicating,” he said.

Over five years, Rob learned what building at scale looked like. By the end of his tenure, he was managing a $1B profit and loss statement in Canada. He’d settled into another comfortable role, itching to scratch that entrepreneurial itch yet again. And his mentor’s question rang through his brain once again: what’s the worst that could happen?

In late 2020 and early 2021, he began exploring ideas to build something more ambitious for Canada. Through extensive networking, he met Griffin Keglevich and Ruslan Nikolaev, then computer science students at the University of Waterloo, who had already been building together and experimenting with early ideas around modernizing business finance. They had encountered the same frustrating problem while interning at Shopify and Uber: the dreaded employee expense report.

Rob recalls, “I didn’t know what to expect when I met them. Our first meeting was meant to be an hour and ended up running more than three.” The three quickly bonded over a shared belief that business finance was far too complicated, and that embedding payments and financial services directly into software could deliver 10x better experiences for Canadian companies.

“I was blown away by how sharp and determined they were,” Rob said. “I went home and told my then girlfriend, now wife: this is it. This is the problem space and team I’ve been looking for.”

Shortly thereafter, in the spring of 2021, Float was born.

If Rob could change one thing, he would have started sooner. By the time you’re approaching thirty, many people have mortgages, obligations. The golden handcuffs of a stable career start to feel comfortable. A mortgage doesn’t care how many pre-IPO stock options you have.

“The vast majority of young people take the least amount of risk early in their career, when it’s actually the time they can afford to take the most,” Rob said. Looking back on leaving finance, he put it simply: “It would have been a lot easier at 24 than it was at 28.”

Of course, Rob at 24 wasn’t Rob at 28. He didn’t have the PE experience, the network, or the business judgment that came from watching deals up close. Would 24-year-old Rob have built Float? Probably not.

But here’s what Rob learned: there’s never a perfect time. You’ll always have a reason to wait. At 24, you don’t have experience. At 28, you have a mortgage. At 35, you have kids in school. At 45, you’re thinking about retirement savings.

The question isn’t whether 24-year-old you could build the same company 28-year-old you can build. The question is the same one Jeff Bezos uses in his risk minimization framework: At the end of my life, will I regret not having done this?

Rob wishes he’d started at 24 not because he would have built Float then, but because he would have built something. And that something would have taught him lessons that took years in corporate to learn.

The perfect timing doesn’t exist. Waiting for it only guarantees you’ll never start.

Ideas mean nothing; execution is everything

Remember the last time you submitted an expense report? The receipt dated June 30th, but your credit card statement showed July 1st? Your finance team makes you wait a month, then schedules a 30-minute meeting to sort it out while you’re still carrying a $500 charge on your personal card.

Float eliminates those problems by automating what used to take finance teams days to complete. Corporate cards, expense management, and bill payments, all built for Canadian businesses.

“It was a ‘duh’ product. We never struggled for product-market fit,” Rob told me.

The hard is often not the idea, but actually building the business.

Rob’s differentiator, he says, is that he does things when other people don’t.

“A lot of what I thought about business building was wrong. Insights are easy, but getting stuff done is the hard part.”

He learned this from watching another Canadian success story: Shopify. CEO Tobi Lütke once spoke about hiring on a podcast. As Shopify grew, impressive developers applied for jobs, but hiring didn’t get easier. Lütke realized the challenge wasn’t finding skilled workers, but rather finding people who would take full ownership.

“The hardest thing is not intelligence. It’s courage,” Rob said.

At Float, courage means shipping fast. The team measures themselves on output, not hours. They don’t wait for perfect. They build, learn, and iterate.

“I’m not sorry for having high expectations. I’m not sorry for wanting to be the best. I’m not sorry for demanding excellence from myself and from my team,” Rob said.

Canada is the right place, right now

Yes, the US market is bigger. Yes, US salaries are often higher. But here’s what Rob and his co-founders discovered when they nearly started Float in the United States.

“We had been diluted into thinking that in Canada, we can’t have better things, and things always come to Canada late and watered-down,” Rob said.

So they looked at the numbers.

Canada has over a million small and medium-sized businesses employing over 5 million people. A $10 monthly subscription on just 10% of that population is a $60M annual recurring revenue business.

“Our addressable market has proven to be so much larger than we originally predicted,” Rob said. “Many Canadian businesses are 20 years behind the technology curve.”

Float found a big market, hungry customers, and competitors who don’t believe the market is worth building in.

What about talent?

Canadian schools like the University of Waterloo regularly produce more founders in prestigious Silicon Valley accelerators like Y Combinator than many Ivy League schools. They’re among the most highly represented institutions at big tech companies in San Francisco. You can’t walk two blocks there without bumping into someone who has spilled a Tim Horton’s Double Double on a Go Train.

The exodus of Canadian talent to the US, ”Brain Drain,” as it’s commonly called, is real. But it’s not the whole story. And it’s reversible.

The inflection point is here. Canada is reducing barriers to interprovincial trade. Tax policy is shifting to favor business investment. The infrastructure for building great companies exists.

We just need entrepreneurs.

What Now

If you’re considering a move to Silicon Valley, run the numbers first. Could your business work in Canada?

If you’re an investor, back Canadian founders building for the Canadian market. Float proved the returns are there.

If you’re choosing between that $200k offer in San Francisco and a startup in Toronto, remember Rob’s wisdom around there never being a perfect time to take a startup leap.

And if you have a mortgage and kids? You don’t have to quit your job tomorrow. Start building something on the side. Test your idea. Talk to customers. The risk of waiting is greater than the risk of starting.

I’m writing this as much for myself as for you.

Canadians are known for being polite. But it’s time to stop apologizing and start building.

The longer we wait, the harder it becomes.

Give me a call in five years. If I haven’t taken my own advice by then, I better have a good reason.

Rob’s Not Sorry

Written by Rob Khazzam

Three Winning Principles I Live By

1. Where there’s a will, there’s a way.

   1. Most things that look impossible are just unsolved.

   2. The job of a founder is to refuse the default constraints and keep pushing until a path forward is found.

   3. Resourcefulness beats resources almost every time.

2. Winning is a conscious choice.

   1. You will encounter failure constantly; it is inevitable in life and your career.

   2. What matters is whether you learn fast, adjust, and keep going.

   3. The people and teams that ultimately win are the ones that simply refuse to stop.

3. Courage is rare, bet on yourself.

   1. Intelligence is abundant. Courage is not.

   2. The willingness to take risks, speak plainly, and pursue ambitious ideas when others doubt you is what creates progress in the world.

One thing to takeaway

• Stop being passive and go build something. The world is not built by people who are smarter than everyone else, it is built by people who take action. If you care about Canada’s future, start something and keep going.

  ---

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In the month since Prime Minister Carney’s Davos address, I’ve been asked the same question seventeen times: What’s different this time?

The answer is simple: this time, we’re not sorry.

Yesterday afternoon in San Francisco, I sat on my couch watching Team Canada dismantle France in the Olympic preliminaries. For an hour, I listened to an American broadcast. The commentators were using words like masterclass and dominance. When Sidney Crosby became Canada’s all-time Olympic scoring leader in a 10-2 blowout, the announcers called it like they saw it: world-class.

It felt right, and I felt proud.

I felt that same surge during Carney’s address at Davos last month. I was in a room with friends from New York, London, Paris, and Mumbai. They all came up to me to say the same thing: “Wow, you must be proud to be Canadian right now.”

In those moments, the world sees us as we are. We are peers. We are winners. We are leaders.

Here’s what I’ve come to realize: excellence is universal, but influence is distributed. Sidney Crosby didn’t suddenly become a better player when he stepped onto Olympic ice. Nor did Mark Carney become a better economist when he stepped onto the Davos stage. The talent was always there. What changed was the platform. The Olympics and Davos are global distribution engines. They turn excellence into influence.

I write cases at Stanford on some of the world’s best founders. Part of my mission is bringing more Canadian builders into that classroom, because the Stanford classroom works the same way. When the next generation of leaders studies Canadian founders alongside their peers, Canada becomes part of the standard.

The next question is obvious: how do we build that kind of stage at home?

The Patek Paradox

I often describe Canada as the Patek Philippe of nations. We are Quiet Luxury.

In watchmaking, the “movement” refers to the internal mechanism, the masterpiece of engineering that powers everything. In a Patek Philippe, that movement is refined. Subtle. You have to hold it to your ear to hear it.

We have perfected that kind of movement: exceptional, precise, quietly brilliant. Look at turbopuffer in Ottawa. Founded by Simon Hørup Eskildsen, the team has quietly rebuilt the economics of AI, making vector search 100x more scalable for companies like Anthropic, Cursor, and Notion. They are the "movement" inside some of the world's best software.

A Patek Philippe can afford to be a secret known only to those in the know. A nation can't. If we stay quiet, we'll only attract the people who already know us, and lose everyone else to the louder signal.

Creating Our Own Gravity

When excellence stays quiet, we miss what Stripe co-founder Patrick Collison calls a “Schelling Point.”

Think about the Collison brothers. They are Irish to their core. Stripe became a Silicon Valley icon because they followed the signal to the place where smart, optimistic people naturally congregate, the place where “everyone” agrees the world-changing conversations are happening.

Silicon Valley built the loudest signal. When a PhD in Waterloo looks for a blueprint for global ambition, that signal pulls them south. We are training the world’s best pilots but giving them the G7’s smallest fleet: despite producing 5% of the world’s top AI researchers, Canada holds just 0.7% of global AI compute capacity.

We can build our own signal. We are entering a new era of strategic autonomy. We lead the world in two of the most critical technologies of the next century: agriculture and electricity.

We have gold in the ground and gold in the grid. From the prairies, Morad Al-Katib (known as the “lentil king”) turned the humble lentil into a multi-billion dollar global empire that feeds millions across continents. Meanwhile, our mastery of electricity grid management can become the secret weapon of the AI revolution. You cannot run a world-class AI lab without the smart grid precision we have perfected.

The advantages are real and storytelling is how we make them visible.

The Compounding Power of Storytelling

Sitting in both rooms, studying excellence in the Valley and caring deeply about what is being built back home, I see a critical gap: distribution.

When Mike Wessinger’s story was published in Not Sorry earlier this month, founders wrote that they decided to incorporate in Canada because they saw a path to winning from home. One story can create hundreds of small shifts. As Charlie Munger said:

“The first rule of compounding is to never interrupt it unnecessarily.”

In nation-building, storytelling is the compounding agent. Every time we celebrate a win, we accelerate our own growth. One success story is interesting. Ten is a trend. A hundred becomes gravity.

The playbook already exists. When Estonia decided to become synonymous with digital government, they told that story relentlessly on global stages. Now, for a country of 1.3 million people, they are the automatic choice.

Storytelling creates attention, and attention is what makes capital move and policy follow. When a 23-year-old in Hamilton sees ten paths at home instead of one, the talent retention math changes. When an ambitious founder in Bangalore thinks about where to build their next breakthrough, Canada becomes the obvious answer.

The “Not Sorry” Strategy

Not Sorry is designed to be a megaphone: a platform that turns isolated wins into gravitational force. Our mission this year is to profile dozens of winners, telling stories that work in two directions at once.

At Home: Proving the path exists. When builders see Morad Al-Katib turn lentils into a global empire from Saskatchewan, or Neil Cawse (Geotab) and Vitaly Pecherskiy (StackAdapt) scale to billions from Ontario, they realize you don’t have to leave to win.

Everywhere: Proving our values travel. When the world studies Garrett Camp (Uber) , Stewart Butterfield (Slack), and Michelle Zatlyn (CloudFlare), they see that kindness and ambition are unmatched when combined. Take Zatlyn: a Prince Albert, Saskatchewan native who co-founded the security and performance infrastructure that now powers nearly 20% of the entire internet.

Together, these stories create pattern recognition. Just as Estonia became the automatic choice for digital government, Canada can own the categories where we choose to lead, whether agriculture technology, grid infrastructure, or something else entirely.

Success looks like this: when the best builder in Canada realizes they don’t have to leave to be world-class, and the best builder in Bangalore realizes they should move to Canada to join the standard.

To Winning

What’s different this time? We’re not sorry.

We have the best hockey team, the best values, and the foundation to lead the world in the technologies that define the next century.

We've perfected the movement and now we're building the stage. When we do, respect becomes gravity and the world will come here to build.

We are here. We are world-class. And we are not sorry.

To winning (together),
Bryan

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Hold on to your wheelchairs. This one’s a ride.

Mike Wessinger is the Executive Chairman of PointClickCare, one of North America’s leading health tech companies, driven by one simple mission: to help providers deliver exceptional care. Before moving to the Chairman role, he spent 25 years in the trenches as CEO, taking a “non-sexy” idea and turning it into a global standard. Now, he’s helping guide the next generation of Canadian builders as the Co-Chair of C100.

Mike and I share a deep passion for entrepreneurship, and particularly for highlighting massive Canadian wins. I love Mike’s story because it is the ultimate proof that you can build and scale a leading company: almost one billion dollars in Annual Recurring Revenue (ARR) from Mississauga, Ontario. (Yeah, that’s right, Sauga! Imagine that.)

More than anything, Mike is a phenomenal storyteller who is completely down-to-earth and practices exactly what he preaches. He has every reason to be on a high horse, but he isn’t. He’s a mentor to many, always looking for the next way to give back, and I’m grateful to be able to tell his story.

One thing before we dive in.

Mike’s story is not only exceptional, but also timely. The “Silver Tsunami” is here. In Canada alone, the 85‑plus population has already doubled since 2001 to more than 860,000 people, and is projected to nearly triple again to about 2.5 million by the mid‑2040s, even as younger age groups grow much more slowly.

With that, onto winning.

Nursing Homes to Nine Figures

A blizzard swallowed Highway 401 whole. Inside a freezing Mississauga office, Mike Wessinger sat alone, twenty-seven and broke, placing his bet on the industry no one his age ever thought about: nursing homes.

He was still staring at the whiteout when the door crashed open behind him.

Dave Wessinger, Mike’s younger brother, stumbled through with snow covering his coat and ice on his toque.

Dave wasn't supposed to be there. He was supposed to be managing IT for a chain of long-term care facilities. The kind of stable job with a pension plan and benefits package you don't abandon when you've got a newborn at home and a fresh mortgage strangling your bank account.

Without announcing himself, Dave dropped his snow-covered coat and started fixing broken computers, putting his computer science degree to work. For ten minutes, the only sounds were the clicking of keys and a radiator struggling to heat the room. Finally, Dave surveyed the secondhand furniture, the chaos of a one-man operation held together by duct tape and delusion.

“I could see myself working here,” he said.

Mike’s stomach dropped. He’d been hawking software for two years and could hardly afford instant ramen. He grabbed his ledger and ran the numbers twice, praying the math could work.

“I can match your current salary,” Mike said, his mouth forming words his brain screamed were insane. “But if you’re not pulling your weight in six months, I’ll fire you.”

“Done,” Dave replied.

Dave pulled out his phone. Now came the hard part: telling his wife he was torching his stable career for his brother’s longshot software company.

“Hey. You know my brother, Mike?” A pause that stretched. “Yeah, I’m gonna work with him.”

Mike watched his brother’s face shift as, somehow, miraculously, his sister-in-law gave her blessing through the phone.

The brothers shook hands while the storm raged outside.

It was February 12, 1997. PointClickCare was born.

Asphalt, Asbestos, and Ambition

Long before the blizzard of ‘97, the Wessinger household was its own kind of storm. Four brothers arrived within five and a half years, creating what Mike called “proper chaos.” The dynamic was tight and relentlessly competitive, the kind of environment where you learned early that if you wanted something, you needed to move fast and make your case before someone else beat you to it.

While Dave earned the label of “the smart one,” as Mike puts it, Mike became known as the restless kid. His teachers wrote him off as a bad student, though that assessment never quite captured the truth. Mike wasn’t incapable of academic work. He simply couldn’t sit still in a system built for memorization when his brain demanded action and immediate feedback. “I’ve probably got ADHD,” Mike said with a laugh.

At Western University, he treated his education like an experiment in minimum viable effort. “I found it boring,” he told me. “I would go to the minimal number of classes I needed to and study the minimal amount. I scrambled on that...I guess I just wanted to see if I could pull it off.” He did, crossing the stage with his commerce and economics degree. But the real education was happening elsewhere.

Mike spent his university years collecting what he called “every awful job you could ever imagine.” He shoveled cement in a roof tile factory in the summer heat. He cleared asbestos from factory vents.

The job that changed everything was on the factory floor. Mike spent months watching a machine drop metal springs into boxes. The same motion, over and over, eight hours a day. The people around him had been doing this work for decades.

“I was miserable,” Mike recalled. “Standing there watching springs drop into boxes, I thought, I can’t do this for twenty years. I can’t do this for another year.”

The answer arrived during university when Mike stumbled into selling Cutco knives door to door. The work revealed something four years of formal education had failed to uncover. Cutco operated as a pure meritocracy. If you put in the effort, you saw the results.

“I realized I felt like an entrepreneur because you got the returns for the effort you put in,” Mike explained. “I realized I had the power of persuasion...There’s some real glory in sales.”

By the time Mike graduated from Western, he had developed three crucial insights about himself. First, he was a practical learner who needed immersion rather than theory. Second, he had a genuine talent for persuasion. Third, he would do whatever it took to avoid watching another spring drop into a box.

What he didn’t have was a clear map forward. To find his actual path, Mike had to move back home and get on the train.

The GO Train MBA

Mike graduated from Western and moved back into his parents’ house in Oakville. He was in his early twenties, broke, and working a full-commission sales job that paid him only when he closed deals. Every morning for a year, he joined the stream of commuters heading toward the 7:45 a.m. train to Union Station. His father sat beside him.

To the outside world, Mike’s dad was a government economist who handled international marketing for Ontario, moving sewage treatment plants and highway projects around the globe. Born in Nazi Germany in 1942, he had arrived in Canada at thirteen, learned a new language, and entered government service in an era when smart people with economics degrees saw public sector work as a legitimate way to change the world. To Mike, he was the first person who showed him how to actually think.

Mike was hitting walls everywhere in his early sales jobs. He would land meetings that seemed promising; lose deals he thought were certain, struggle with prospects who said one thing and did another. On the forty-five-minute Go Train ride into Toronto, he would dump these frustrations on his father.

This pattern repeated for a year. Mike would describe a problem, his father would see the underlying structure, and Mike would go back armed with insight that turned a stalled deal into a signed contract. “I would give him a couple of random pieces of the puzzle, not even a corner piece,” Mike told me. “And he would paint me the whole picture. He’d say, ‘Oh, here’s what’s happening. There’s this beautiful landscape and there’s mountains in the back.’ I’m like, how did you get all that?”

“I feel like I got the full MBA, riding on the GO train from Oakville to Toronto my first year out of school,” Mike said. The education was faster and more practical than anything he could have gotten in a classroom. His father was teaching him pattern recognition: the ability to see the mountain in the fog, to understand what was actually happening beneath the surface of what people said and did.

Each morning, by the time the train pulled into Union Station, Mike was less salesman and more strategist. The hustle from the factories, the persuasion from Cutco, the pattern recognition from his father: the pieces were coming together. Mike could see opportunities others missed.

He just needed a market where the patterns were completely broken. As it turned out, he didn't have to look far. His mother, a CPA who worked for a chain that owned and managed distressed LTC facilities, was already standing in the middle of the perfect mess. Through her contacts, all four Wessinger boys had found themselves working in and around the same overlooked industry.

Mike just didn’t know yet that this obscure, low-margin world would become his mountain.

The ‘I’ to Get the ‘R’

Mike didn’t wake up one morning with a burning desire to revolutionize geriatric care. In the early 90s, nursing homes were the last place a self-proclaimed “adrenaline junkie” in his twenties would look for a career.

“I didn’t pick the industry,” Mike told me. “It just happened to be where my mother had contacts.”

Mike spent months walking through fluorescent-lit hallways and cramped administrative offices, developing a feel for the operators who ran these places. Some facilities were faith-based organizations. Others were family businesses, often the largest employer in town, operated by owners who had inherited both the mission and the razor-thin margins.

Mike saw the same scene play out over and over. An administrator would show him a quote for a new billing system and the number at the bottom was around a hundred thousand dollars.

“We clear about two percent on a good year,” one administrator told him. “I’d have to write this check and pray it pays off in three years, maybe four. But I don’t have an IT guy to maintain it. I don’t have the staff to learn it. So I’m not going to do it.”

The administrator wasn’t stupid or resistant to change. He was simply trapped by math that didn’t work.

Mike saw the same pattern everywhere: one to two percent margins, hundred-thousand-dollar server quotes, no IT staff. Most operators walked away.

“They didn’t have the ‘I’ to get the ‘R’ on their ROI,” Mike said.

As Mike spent more time in these facilities, the operators began changing his perspective on what constituted an opportunity.

“Just because you’re passionate about it, there’s ten people who want to do every job, so they can underpay you and overwork you,” he explained. “But you go to somewhere where it’s a little less sexy and it doesn’t attract the hordes to get into it; there can be a great business in there.”

Mike’s initial indifference was giving way to conviction.

“I got a passion for it,” he told me. “These are great people. We can help them.”

Mike had found his mountain, hidden in plain sight while everyone else chased glory in sexier markets. He just needed someone willing to climb it with him.

On February 12, 1997, during a blizzard that shut down Highway 401, that person walked through the door.

Betting on the Jockeys

Mike tried to raise venture capital (VC) in 2001. The meetings did not go well.

The pitch was straightforward: PointClickCare would host nursing home software on centralized servers, deliver it over the internet, and charge customers a monthly subscription. No upfront license fees, no expensive hardware installations, no IT staff required.

"Let me get this straight," Mike recalls one investor saying. "You're gonna put healthcare records on the internet and customers are gonna pay you forever? Don't let the door hit you in the ass on the way out."

The VCs had just survived the dot-com crash. PointClickCare was asking them to believe in a business model that did not exist yet, serving a market nobody cared about. Mike and Dave needed to find money somewhere else.

“We’ve got to find people who are going to blindly bet on the jockeys,” Mike said.

The jockeys were Mike and Dave. The people willing to bet on them went by the names of aunt and uncle and friend and coach. People who'd known Mike since he was fourteen, otherwise known as his Billy Idol era.

“For some of them, it was their life savings,” Mike recalled. “This is money you can’t afford to lose. I better get it right.”

Between 2001 and 2002, PointClickCare raised roughly $600,000 CAD in friends and family money. More importantly, it came from people who were not betting on the business model. They were betting that Mike and Dave would figure it out.

What they were building did not have a name yet. “Salesforce was not a household name,” Mike said. “Nobody could spell SaaS. No one’s talking about the cloud. We’re just trying to solve for a market problem.”

Mike eliminated the last barrier by refusing to ask for multi-year contracts. “If you don’t like us in 30 days, kick us out.” It was a game changer. Administrators who had been paralyzed by risk suddenly had nothing to lose. Deals that would have stalled for months closed in weeks.

Years later, Mike would coach other founders stuck in the same trap. “You’re an unknown commodity with a disruptive model, and you’re asking them to commit to three years,” he’d tell them. “You’ll never get customers if you’re asking them to take all the risk.”

When founders shifted to shorter terms, deals closed.

The thirty-day model became a forceful function. To this day, PointClickCare largely operates on month-to-month contracts while competitors lock customers into multi-year agreements. “We were forced to do it because they could have left us at any time,” Mike said.

For the next four years, PointClickCare reinvested every dollar and stayed profitable.

By 2005, they were profitable, growing, and building a reputation with small and mid-sized chains.

Then one of the largest nursing home chains in America started calling.

Crossing the Chasm

The true test of a platform is how it holds up when a giant steps onto the scale.

In 2005, Mike’s phone rang. On the other end was one of the largest nursing home chains in the United States: over four hundred homes across thirty-six states. PointClickCare had fifty people.

“We knew this would be high-profile, either in a good way or a bad way,” Mike told me. “If it blew up, everybody would know it.”

Rather than try to oversell them, Mike did the opposite. He told them exactly why they shouldn’t hire him.

“We are not ready for you yet. We are ready for thirty-home chains, not four hundred-home chains. If you expect this to work out of the box, you’ll blow our brains out.”

Honesty worked. The chain had dealt with enough vendors who promised the world and delivered nothing. They agreed to work with PointClickCare as an early adopter.

Shortly after, a second major chain sent PointClickCare a three hundred page Request for Proposal (RFP). Mike read through the document and realized it was written to favour one of their competitors. The project was literally named after the competitor.

Mike declined to respond.

Eight months later, the chain called back, upset that PointClickCare had ignored their request. A dozen other vendors had responded, but none could deliver what the chain needed.

Would PointClickCare respond to a smaller RFP? No. Would they at least come to do a demo? That, Mike agreed to do.

Mike laid out the same terms. Both organizations would coordinate their priorities, because if they pulled PointClickCare in conflicting directions, they would rip the company apart.

“You’re the only ones who said no to the RFP,” the executives told him. “You’re the only ones who were being straight with us.”

Both chains signed.

Suddenly, Mike and Dave were caught between two titans. PointClickCare doubled its headcount over eight months, hiring so fast it couldn’t even onboard people properly.

“It took us to our knees,” Mike recalled. “Every Monday morning, people were standing at the door. I’d ask, ‘Who’s your boss?’ They’d say, ‘Andy.’ I’d tell them, ‘He’s not here yet. Find a computer in a box over there, find a desk, and get set up.’”

What almost broke them wasn’t one crisis, but the cash constrained nature of an early subscription business. The chains paid as they brought facilities online, which meant revenue trickled in while expenses exploded. They were funding the growth of two giants on a month-to-month budget.

Mike went to one of the Chief Information Officers (CIOs) with a proposal.

“If you pay me for two years in advance, I will put one hundred percent towards R&D.”

It was an ask that required trust PointClickCare hadn’t yet fully earned. But PointClickCare had built enough trust through eight years of brutal honesty and desperately needed cash.

The CIO came back with approval.

It was a make-or-break moment. If they failed, the cloud experiment would be dead. If they succeeded, they would become the default winner in the market.

PointClickCare executed. The two chains went live, facility by facility, state by state. The software worked.

The other top ten nursing home chains had been watching the entire time, calling the early adopters and asking how it was going, banking on PointClickCare failing spectacularly. The answer kept coming back the same: the software was working; the early adopters were happy.

The market flipped. Nobody had wanted to be first to take the risk on a small Canadian vendor with an unconventional model, but nobody wanted to be last either. The remaining large chains started calling.

PointClickCare had crossed the chasm, meaning it had gone from having to prove itself to every customer to customers assuming it was the best choice.

Crawling Through a Ditch With a Knife

PointClickCare had crossed the chasm with the large chains, but Mike quickly realized he had not entered one American market. He had entered fifty.

Healthcare in the U.S. is regulated state by state, each with its own billing requirements, licensing rules, and compliance frameworks. In the early days, PointClickCare tried to take customers wherever they could find them. A facility in Nevada. One in Rhode Island. Another in Pennsylvania, then Ohio, then Minnesota.

The approach was exhausting.

“We were trying to localize and create products for every state simultaneously,” Mike said. “We almost ran out of money. We can’t fight on all these fronts.”

Mike and Dave made a decision that would define their expansion strategy for the next five years. They would stop chasing opportunities across the country and start building market density one state at a time.

“I call it crawling through a ditch with a knife in your teeth,” Mike told me. “Every new market was as hard as hard gets. You had to put everything you had in order to get that first ten percent market share.”

The strategy was methodical. PointClickCare would enter a state and build relationships with every accounting firm that worked with nursing homes, find the high-profile consultants, show up at state trade shows, and learn who held influence. Getting the product right for each state’s regulatory requirements was only half the battle. The real advantage came from building density. Staff in nursing homes hopped between facilities constantly, and a nurse who loved PointClickCare at one home became Mike’s best salesperson when she moved to the facility across the street.

The grind was identical in every state.

“From ten to twenty-five percent market share, we were in the mix,” Mike said. “We always got invited. Before that, you had to beg just to get them to listen to you.”

After twenty-five percent, PointClickCare became the default consideration. After fifty percent, the game was over.

“Once we hit fifty percent market share in a state, we were taking orders,” Mike said. “How many beds? When do you want to start?”

Mike developed a philosophy about market selection that ran counter to everything venture capitalists wanted to hear.

“VCs want to hear about this huge TAM,” (total addressable market) Mike said. “I don’t care about your ten-billion-dollar TAM. I care about your fifty-million-dollar target market.”

The distinction mattered. A massive total addressable market meant nothing if you could not dominate a specific geography with enough density to create momentum.

By 2009, PointClickCare was a massive success by any Canadian standard. It was profitable, growing forty percent a year. It had built a world-class business entirely on its own terms, without venture capital, without sacrificing control, without doing unnatural things to hit arbitrary growth targets.

Then Mike hired a Chief Financial Officer (CFO), and the questions started changing.

Lifestyle or Powerhouse

In late 2009, Mike hired his first “real” CFO. PointClickCare had people handling the books before, but they were accountants and bookkeepers. This was different. The new CFO had run finance for companies at PointClickCare’s scale and brought a vocabulary that was somewhat foreign to Mike.

A few weeks into the job, the CFO sat down with Mike and said something that sounded important.

“Your capital is constraining the business.”

Mike stared at him. “I don’t know what that even means.”

The CFO tried to explain, but the concept did not land. Mike had spent his entire career avoiding the venture capital fundraising cycle. He had watched too many entrepreneurs introduce themselves by their funding round rather than what their company actually did.

“Every entrepreneur I’d meet would be like, ‘Oh yeah, we’re a Series A company,’” Mike said. “I’m like, that tells me nothing. Where do you add value to the world? I never got caught up in that fundraising cycle.”

But the CFO’s comment stuck with Mike. Around the same time, a venture capitalist showed Mike a model about how raising money could allow him to take some chips off the table while accelerating growth. The idea of de-risking personally while growing the company faster sounded interesting in a way Mike had not considered.

Then Mike attended a conference that an investor had organized. Frank Slootman, then CEO of ServiceNow, was speaking to a room full of SaaS CEOs. He asked a simple question.

“How many of you are growing your SaaS business to break even?”

Mike’s hand went up fast, along with a couple other CEOs. Growing profitably while bootstrapped? Damn right!

Slootman’s face said it all.

“You’ve got a company that’s growing thirty to forty percent a year, your gross margins are over eighty percent, you’ve probably got one hundred and ten percent retention rates, and you could grow faster. You choose not to, because you’re worried about an artificial line called profitability. You’re being irresponsible.”

Mike sat there processing what he had just heard.

“I went, ‘No, I’m not being irresponsible.’ I thought I was being responsible. But the reality is, I could have grown faster, and I chose not to, because I didn’t want to raise capital.”

And then it clicked. That was what the CFO had been trying to tell him. They were capital constraining the business.

Mike went back to Mississauga and started thinking about how PointClickCare actually made decisions. The annual budget cycle always started the same way. Mike would look at his brother Dave and ask what he wanted for the next year. Dave would say he wanted a cottage and a wake boat. Mike would say he wanted the same things. They would figure out what those cost, determine the revenue they needed to generate, and build the budget from there.

“That’s the definition of building a lifestyle company,” Mike realized. “I looked at him and I go, ‘Do we want to build a lifestyle company, or do we want to build a powerhouse?”

They were still relatively young. They had poured their hearts into PointClickCare for over a decade. They had proven the model worked, proven they could compete, and proven they could win. The question was whether they wanted to find out what the company was really capable of.

“Let’s see what this guy is really made of,” Mike said. “Let’s go raise money and see if we can build a powerhouse.”

In 2011, PointClickCare ran a formal fundraising process. Fifty interested parties. Twenty management presentations. Thirteen term sheets.

They raised fifty million dollars. Half went to the company. The other half went to the founders and early shareholders that took a risk on Mike and Dave.

“If it doesn’t work out, we can still be drinking Bordeaux,” Mike said.

The decision to raise capital was not about needing money to survive. PointClickCare was profitable and growing. It was about making a conscious choice between two different versions of success.

To lifestyle, or to powerhouse, that was the question.

Mike and Dave chose the powerhouse.

The Silver Tsunami

PointClickCare now generates almost one billion dollars in annual revenue and employs over two thousand people, with Dave running operations as CEO and Mike serving as Executive Chair of the Board of Directors.

The scrappy team of fifty that could have broken while crossing the chasm has become a critical part of North American long-term care. PointClickCare’s care collaboration network connects over thirty thousand long-term care providers and three thousand hospitals across the continent, ensuring that when a senior moves from hospital to nursing home to home care, their medical data moves with them.

The moment Mike and Dave have been building toward has arrived.

The first Baby Boomers turn eighty this year. Facilities face a crisis that makes everything that came before look manageable. The cost to deliver care has climbed to one hundred thirty thousand dollars per resident per year, while government and insurance reimbursements cover seventy-five thousand. The math that trapped administrators decades ago has gotten worse, not better.

There are not enough nurses even if facilities could afford them. The gap between what care costs and what society is willing to pay keeps widening.

PointClickCare has shifted from record-keeping to outcome-optimization, using predictive analytics and artificial intelligence to help chronically short-staffed facilities triage patients before crises occur. The platform can identify a resident at risk of falling three days before it happens, flag a urinary tract infection before it becomes sepsis, predict which patients will be readmitted to the hospital within thirty days. The industry cannot solve this by hiring more people because there are no more people to hire. Technology has to fill the gap.

Mike spends much of his time now as co-chair of C100, helping build the next generation of Canadian tech companies. When he talks to young founders, he tells them the same thing his father taught him on the GO train: pick the market where you can see patterns others miss, build density before anyone else understands why it matters, and be willing to crawl through ditches while everyone else chases glory somewhere easier.

On February 12, 1997, Mike Wessinger shook hands with his brother in a freezing Mississauga office during a blizzard that shut down Highway 401. He was in his late twenties, broke, and betting everything on an industry nobody his age thought about. He had no venture capital, no clear business model, and no idea that the company name they picked that day would still be on the platform serving millions of people three decades later.

The silver tsunami has arrived.

PointClickCare is ready to meet the wave.

Mike’s Not Sorry

Written by Mike Wessinger

Three winning principles:

1. Lifestyle vs category killer is a decision. Nothing is wrong with either but your actions will be very different depending on what you choose. Know it’s a choice.

2. Don’t over index in fundraising. Over index on your customer and customer delight. Make sure you know where you add value to the world and be the best at it!

3. Develop a strong support network. This can include investors, team members and leaders of similar companies that are 4-16 quarters ahead of you.

One thing to takeaway:

• We built a billion-dollar company from Mississauga. So can you.

That’s all for today. Let’s go build powerhouses!

To winning,
Bryan

Not Sorry exists to Champion Canadian ambition. Subscribe for more stories.

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Hello friends,

We are in for a treat today!

I sat down with professional hockey player, Kristin O’Neill, a relentless two-way force and the kind of person who makes everyone around her better. This week, she got the call every small-town Ontario kid dreams about: Team Canada, Milan 2026 (watch the video; it’s top-shelf)! She’s doing it as the PWHL catches fire, with attendance up 52.5% year-over-year.

Not Sorry is for anyone who cares about winning the right way: whether you're building a company, leading a team, or trying to become the person you said you'd be. Ambition spreads through story.

In the words of Tyrion Lannister (not Canadian, but gold):

“What unites people? Armies? Gold? Flags? No. It’s stories. There’s nothing in the world more powerful than a good story.”

Kristin's story is one of those. Ambition that never quit.

So with that, onto winning.

The Work No One Sees

“LET’S GO!”

Kristin O’Neill read the text on a plane home from her Hawaii vacation and had no idea what it meant. The text was from Micah Zandee-Hart, Kristin’s old Cornell co-captain and now the captain of the New York Sirens.

It was June 24, 2025: draft night. Kristin had texting Wi-Fi and nothing else, so news arrived in fragments from teammates: who got drafted, who got traded. Then the feed went dead. Long enough that she did what everyone does on a plane: blame the connection.

Then another message came through from Zandee-Hart:

“You have no idea how happy I am to be your teammate again.”

Kristin stared at it, confused. She still hadn’t heard anything official.

“Micah, what’s happening? I don’t know what you’re talking about.”

Zandee-Hart didn’t know that Kristin didn’t know. So a friend, trying to celebrate, broke the news mid-flight: you’ve been traded from Montreal to New York.

The follow-up came moments later: “I’m so sorry to be the one to tell you.”

It didn’t sink in until the wheels hit the tarmac in Montreal. That familiar thud, the cabin lights, people reaching for their bags.

Kristin was home. Except she wasn’t.

The Queen Elizabeth Way (QEW)

On Saturday mornings in Oakville, the O’Neill house ran on a familiar drill: four girls and four hockey bags, two parents loading the trunk until it finally shut and then opening it again because someone had forgotten their helmet. They would pile into the car and hit the road (QEW), with coffee in the cupholders, gear in the back, and a weekend that was already spoken for.

“My family and I basically spent our weekends at arenas,” Kristin told me. “It was tournaments, just back-to-back games. The volume was very high.”

At home, the dynamic was exactly what you would expect from four sisters packed into one orbit: It was chaotic. The middle two bickered, and the oldest led. Everyone followed her lead. Kristin, the youngest, observed.

She spent years seeing the game before she ever had to play it, sitting through her sisters’ shifts and learning what got rewarded and what didn’t. She learned the difference between effort and drifting and the difference between being in the play and being near it. Then she stepped onto the ice and surprised everyone, including her parents.

“When it came to hockey, I got on the ice and I knew,” she said. “My parents were like, ‘Where did this come from?’ But then you think about it, I’d just been quietly watching my sisters for years.”

The same pattern showed up outside the rink. Kristin remembers home videos of learning to ride a bike, her parents whispering behind the camera because the other girls hadn’t picked it up that fast. She had watched the wobble and the falls three times already. When it was her turn, she rode.

The weekends had their own small rituals. Tim Hortons, obviously. “Oh my gosh, Tim Hortons was definitely involved in a lot of my pregame…when I was a kid,” she said. She remembers the drive as fondly as the games: “Singing in the car…I have such good memories of singing in the car with my parents”.

And she remembers the kid moments, the ones that are not in any highlight reel but are in every childhood: The lobby, the vending machines, the bargaining. “I’d always ask for quarters, for the gumball machines,” she said.

Weekdays were the same discipline, only tighter. Practice before school. School. Cross-country or track. Hockey at night. Homework wherever it could fit. “It was just on repeat every single day,” she said. She loved it.

Summers used to break the pattern. “Every summer, I would go to my cottage all summer long,” Kristin said. It was a tennis town, so that is what people did, long days on the courts, variety for her body, space in her calendar.

Then hockey got more competitive and the summers got shorter. She started turning down other sports, started off-ice training, started making decisions based on where hockey could take her.

She was serious about track and field too, good enough for the Ontario championships, and she still missed them. “I remember the Ontario championships I had to miss because I had to do an SAT test to go to Cornell,” she said.

That day was a desk under fluorescent lights, filling in bubbles while her competitors ran. It was the unglamorous step that makes everything else possible. "In the moment, I was sad about it," she said. "But at the end of the day, I would make that sacrifice again."

Two Days From the Frozen Four

Cornell took that Oakville volume and turned it into consequence. Kristin arrived and immediately started deciding games, showing up at the exact moment a close night turns into a win. Over four years, she posted 145 points in 125 games, including 81 goals, and left with two records that reveal what mattered when it mattered most: 21 game-winning goals and 10 shorthanded goals.

Leadership followed early. Cornell named her a captain as a sophomore, only the third player in program history to get that letter so soon, and she carried it for three seasons. Rather than see captainship as a reward, she described it as a change in posture. “A switch was flipped,” Kristin told me.

By her senior year, Cornell was number one in the country at 28-2-3, the top seed heading into the NCAA tournament, just two days from its quarterfinal, the Frozen Four, when the season vanished. Kristin and her teammates had been hearing about COVID, but it still felt distant until NCAA basketball was canceled and everything else started falling in line behind it.

The team met and the coach confirmed what the players already knew. Practice was still on the schedule that day, and they went anyway, because nobody wanted their last moment together to be a meeting room. They skated, loosened up, stayed out a little longer than they needed to. At the end, they gathered at centre ice in one tight cluster, and the image that stayed with her was their coach standing alone, watching from a distance.

“It wasn’t a natural reaction,” she said. “But we were kind of just like, we might as well. This is the last time we’re all gonna be on this ice together.”

After that, campus emptied and training stopped looking like training. Kristin stayed at school when COVID first erupted and made do with whatever she could find. The clearest memory from that stretch sounds almost ridiculous, but it tells you everything you need to know about her.

“I think I was bench pressing with a broomstick and cement blocks on either side,” she said with a laugh.

200 Beats a Minute

It was September 18, 2023: draft night. Kristin was sitting with her parents in a room full of players doing their best impression of calm when she noticed she had a line of sight to the teleprompter. The announcer started the sentence, the league took its time with the pause, and she saw her name before the room heard it. She nudged her parents and felt the moment hit her body first.

“My heart just started racing 200 beats a minute,” Kristin said.

Then the announcement followed: “With the first pick in the second round of the inaugural PWHL Draft, Montreal is pleased to select….

Kristin O’Neill!”

She hugged her parents, walked to the stage, shook hands with the coach and the GM, and then got pulled backstage immediately into the part that makes it real. Cameras, lights, questions, a microphone in front of her before she had time to locate the feeling. “They ask you how you’re feeling even though you haven’t had a minute to process your feelings,” she said.

"I really wanted to go to Montreal," Kristin told me later.

She came back out and sat down again, because the draft keeps moving and people you care about are still waiting. You learn quickly that your moment can be true while someone else's is still pending.

The Bell Centre

At the Bell Centre, the first thing Kristin noticed was what she couldn’t do. She came off after a shift, sat down, and tried to use the usual bench rhythm to reset: the quick breath, the quick listen, the small cues that tell you when you’re up again. The fans had consumed all of it.

“It wasn’t until we played at the Bell Centre that I felt… the impact of this league had on people already”, she said. “You couldn’t even hear yourself think.”

During a whistle, Kristin looked up into the stands and registered who was there. Parents leaned forward during play the way they do when they know the next ten seconds matter. Phones came up for faceoffs and went down as soon as the puck moved. Kids pressed close to the glass with that serious, open-mouthed focus that makes you feel watched without feeling judged.

Then, Kristin noticed a detail that she says would have been rare when she was growing up. “You look into the crowd, and there’s not just girls, but little boys too,” she said. “It’s just so normal for these kids now to be watching women’s hockey”. When her line stood, she stood, and she went back over the boards into the noise.

At the dot, the ritual is automatic: tuck the jersey, spin the stick once, drop low. Lower than most players can comfortably get. Her 5'4" frame turns into an advantage, bringing her closer to where the puck will land. She finds her opponent's eyes across the circle and waits. When the ref's hand moves, she's already won.

In the playoffs, the same city gave her a different test. On May 11, 2025, at Place Bell, Montreal played a game that began at 7 p.m. and kept going deep into overtime.

The game narrows in those stretches. You stop thinking in systems and start thinking in the smallest things you can control: one clean change, one faceoff, one shift without a mistake. The simplest plays become harder as legs fade and hands lose precision. What stayed with Kristin wasn't the exhaustion or the overtime goals, but the ever-full stands. The game was the longest in PWHL history: "The 7 p.m. game that went to, I don't know, 2 a.m.," Kristin said. "Hardly anyone left." Montreal won.

Once you play in buildings like that, first loud enough to erase your internal voice and then late enough to test everyone’s patience, the league stops feeling fragile. It also stops feeling sentimental, because the same machine that can fill a building and keep it full past midnight is the machine that makes business decisions the next morning.

Family Business

A couple days after Kristin learned she’d been traded on her flight home from Hawaii, the official call came.

“It definitely did hit me that you have to look at it more of a business,” Kristin said.

What Kristin was holding at the same time was the season she had just lived, because a team is not an abstract idea when you’re inside it; it’s the same room every day, the same faces at the same stalls, the same lift, the same bus, the same postgame meals, and the same losses that follow you into the next morning’s practice. That closeness produces its own language, because it has to.

“We are family, and we love each other, but also we are family playing for business,” Kristin said, reflecting on the contrast between those two ideas.

She didn’t argue with the premise. She named the trade-off, because the players had spent years pushing for a league that was real, and real leagues do not only bring crowds and standards; they bring decisions that can change your life.

“This is what we wanted…we wanted it to be professional like this”.

New York was where that professionalism showed up in her daily role. The Sirens were “definitely a more youthful team,” she said, and the youth changed her place in the room immediately.

“I’m showing other people the ropes,” she said, like back in her Cornell days. She was excited to be part of it.

Then, as she was settling into that new room, Team Canada called.

6:00 P.M.

Team Canada had booked Kristin for ten minutes on January 8, 2026, at 6 p.m., one of thirty calls scheduled back to back.

She’d known about this call for a week, and the days leading up to it had felt longer than any training block she could remember. That day, Kristin went to practice and tried to move slowly through the rest of the day so she wouldn’t spend the final hour sitting still and staring at a clock.

By the time the Team Canada call came, Kristin was at her dining table with her laptop open. Ryan, Kristin’s partner, was home, but she had banished him to the bedroom because she didn’t want an audience for whatever was about to happen.

At six, she clicked into the Zoom.

There was the loading screen, the brief lag, and then the grid of faces came into focus.

“All their faces were smiling, ear to ear,” she said.

She knew before anyone spoke. The relief arrived like a physical release, the kind that makes you exhale without meaning to, and she sat there trying to hold her posture steady while her mind ran ahead to the one fact that mattered.

Assistant coach, Kori Cheverie, said “Congratulations,” and after that Kristin remembers very little. “I think I kind of stopped listening after that,” she said.

Then the head coach, Troy Ryan, spoke, and his voice cracked.

He started tearing up while he talked, and the call changed. The emotion spread across the screen until it wasn’t just him crying. “Eventually everyone was crying,” she said, and then there was a pause where nobody could find the next sentence because everyone was sniffling and trying to pull themselves together.

When Kristin hung up, she walked straight to the bedroom, opened the door, and Ryan didn’t need an explanation. The couple shared a long embrace, and only then did Kristin start calling her family, adding person after person until the FaceTime thread turned into a small reunion.

Later, Kristin told me that she had rehearsed that exact sequence during workouts she hated, using it as a way to keep going when she didn’t want to, because she could picture the moment she would finally get to make those calls.

And call she did. That little girl from Oakville had made it.

Kristin’s Not Sorry

I’m not sorry for never giving up on my dreams.

Three winning principles I live by:

1. Kindness: make people feel heard and valued

   Nothing big is built alone. Teammates, coaches, and mentors invest in you when they feel respected, not used. People forget the details, but they remember how you made them feel. Kindness builds trust, and trust is what holds teams together.

2. Courage: say the dream out loud

   I started saying “Team Canada” when I was a kid. It sounded impossible, but my family and coaches didn’t laugh; they asked what the next step was. Saying the goal out loud forces you to take it seriously, and it helps the people around you help you. If you won’t name it, you won’t chase it.

3. Process over outcome: let preparation create confidence

   I can’t control selection. I can control my habits: training, recovery, film, and the small details every day. When you focus on what you can control and do it consistently, confidence builds. On game day, you know you’re ready.

One thing to take away:

When confidence is hard to find, remember the “rule of thirds”.

That’s all for today. Let’s go do the work no one sees!

To winning,
Bryan

Not Sorry exists to Champion Canadian ambition. Subscribe for more stories.

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Hello friends,

What a week. Between the capture of Nicolás Maduro and the military rhetoric surrounding Greenland, this week has felt (to put it mildly) unsettled.

Earlier this week, a Globe piece by Thomas Homer-Dixon and Adam Gordon drew attention for a simple reason: It articulated a fear many have been feeling but few have named.

The authors argue that under the newly unveiled “Trump Corollary” to the Monroe Doctrine, Washington no longer treats Canada as an “irrelevancy,” but as a strategic asset to be secured.

“With its oil, minerals and water, Canada is a vital resource hinterland in the U.S.’s part of the map.”

Homer-Dixon and Gordon conclude that if Canada wants to stay independent, we can no longer outsource our security or technology to foreign giants. We need homegrown systems.

I’m not a geopolitical expert. But I am a fan of builders.

If the authors are right, some of the most important work in the country is happening in the unglamorous corners of defence tech.

Today marks the launch of Not Sorry For Winning: our weekly series celebrating Canadians absolutely crushing it on the world stage.

Not Sorry for Winning is designed to be fun. Because when the world feels heavy, we get to choose where we put our attention, and right now, the good deserves it.

Think of it like tuning in for the Jays, but instead of baseball, it’s Canadians dominating their fields. Let’s see if we can get 18.5 million.

First up: Defence Tech. (If the authors’ analysis is correct, this space is more critical than ever).

Let’s tuck in.

Quote of the week

“Canada is free and freedom is its nationality.” — Sir Wilfrid Laurier

Song of the week

“Northwest Passage” — Stan Rogers (the Hamilton GOAT)

Ok, onto winning!

(1) North Vector Dynamics, Calgary, AB | Paul Ziadé, CEO
Counter-drone systems and hypersonic propulsion.

North Vector Dynamics is trying to solve a very simple modern problem: drones are cheap, and the places we care about aren’t.

A small drone in the wrong place can shut down an airport, stalk critical infrastructure, or turn a public event into a security incident. And the annoying part is the mismatch: the drone might cost a couple thousand bucks, but the response can cost a fortune if you don’t have the right tools.

That’s where North Vector comes in. They build counter-drone (counter-UAS) systems: the practical job of detecting, tracking, and stopping drones that shouldn’t be there. They emerged from stealth in 2025 pitching made-in-Canada solutions to this exact problem.

They’re also playing in a completely different league of “future air”: North Vector secured a four-year, $4.2M contract with Canada’s defence R&D organization (DRDC) for work tied to propulsion and hypersonic technologies (meaning Mach 5+, about five times the speed of sound)!

From Paul:

We’re not sorry for being a pure defence company. “Dual-use” is real, but it’s too often a euphemism used to soften or sanitize what is ultimately a serious responsibility. As nations take sovereignty more seriously, we must be unapologetic about the most fundamental enabler of that sovereignty: a strong, capable, and innovative domestic defence industry – and we’re proud to build it.

The fastest way to help is to make introductions to defence founders in the US, Europe, Australia and other friendly countries who are building exciting technologies. We are always open to exploring interesting collaborations.

(2) CCX Technologies, Ottawa, ON | Chris Bartlett, President
Secure networks for aircraft and defence.

Everyone understands cybersecurity in the place we live: phones, laptops, bank accounts. You click the wrong link, it’s a mess. Now take that same idea and move it to a place where “restart it” isn’t an option: an aircraft.

Modern aircraft have digital systems that talk to each other: avionics, communications, maintenance systems, and sometimes connectivity to the outside world. That’s great for efficiency, but it also means you need to take cyber really seriously.

That’s what CCX Technologies builds: onboard cybersecurity (hardware and software) that lives on the aircraft and watches the aircraft’s internal network.

I love this story because it’s classic Canada: quiet, unglamorous, extremely important. The stuff that keeps complicated machines honest, so the rest of us can fly (defence and commercial) and never have to think about it.

(3) Dominion Dynamics, Ottawa, ON | Eliot Pence, CEO
Sovereign Arctic surveillance.

Dominion Dynamics is trying to solve a very simple Canadian problem: Canada is gigantic, the North is remote, and it’s surprisingly hard to know what’s happening up there in real time.

Their idea is to build a “single picture” of the Arctic by bringing together existing sensors (satellites, drones, maritime data, and other off-the-shelf tools) from land, sea, air, and space. Instead of each sensor living in its own silo, Dominion wants it all to flow into one Canadian-controlled system so decision-makers can see what’s happening quickly and clearly.

They launched publicly in October 2025 with $4M in pre-seed funding, backed exclusively by Canadian investors. They’ve also partnered with the Arctic Training Centre to test in extreme conditions.

From Eliot:

We’re not sorry for building a defence prime in Canada — and insisting that control, ownership, and IP matter. The Arctic is becoming a front-line theatre, and Canada can’t outsource its awareness, autonomy, or security stack to foreign primes forever. We believe this country can invent, integrate, and export world-class defence platforms again — and we’re proving it by building AI-native systems designed for the hardest operating environment on earth.

The fastest way to help is find builders who want to do the most meaningful work of their careers — engineers, product leaders, and operators who believe Canada should control the technologies that protect it. And help tell the story: share what Canadian defence companies are actually building, challenge the idea that the only path to scale is to sell early to a foreign acquirer, and amplify the teams choosing to build here, for the long haul.

(4) Cellula Robotics, Burnaby, BC | Eric Jackson, President and CTO
Long-range autonomous underwater robots.

Canada has the longest coastline in the world, and it’s hard to keep an eye on it.

If you’ve never thought about underwater robots (AUVs), you’re not alone. The simple problem is: the ocean doesn’t have outlets. When the robot runs out of power, the mission ends. And if the mission ends quickly, you’re usually paying for the expensive part: the ship and crew needed to launch it, keep tabs on it, and bring it home.

Cellula builds underwater robots designed to stay out for a long time. Their flagship, Guardian, is listed at 45+ days underwater and up to 5,000 kilometres on a hydrogen fuel cell. Basically Vancouver to Halifax, except underwater!

And that matters. If the robot can stay out for weeks, you don’t need a ship hovering nearby the entire time. More coastline and Arctic water covered, for a lot less money.

(5) Kraken Robotics, Mount Pearl, NL | Greg Reid, President and CEO
High-resolution subsea intelligence.

If you’ve ever tried to look into the ocean, you know the feeling: you can see a bit… and then it turns into murk. Now imagine you’re trying to do that at the bottom of the ocean, where it’s dark, cold, and the water is full of noise. You can’t use a camera. So you “see” with sound (sonar).

Kraken Robotics builds sonar that makes those underwater pictures sharp enough to be useful, instead of “is that a fish?” Their synthetic aperture sonar is designed to produce 3 cm × 3 cm resolution in real time, which is an absurd level of detail underwater. In a major naval exercise (REPMUS 2025), Kraken said its sonar clearly showed mine-like objects and even subsea cables as small as 5 cm in diameter.

If you’re wondering why any normal person should care: clearer sonar helps you find hazards, clear old explosives, and protect the underwater cables that basically run the internet. And the story behind it is very Newfoundland. Founder Karl Kenny passed away in February 2025. Today, Kraken supports customers in more than 30 countries.

Have a great weekend everyone!

To winning,

Bryan

Thanks for reading Not Sorry! Subscribe for the founders winning now, the playbooks of giants, and other fun stuff. If a piece isn’t useful or interesting, tell me. It’ll help me make the next one better.

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Welcome to 2026.

I’m grateful you’re here.

Not Sorry's mission is to make Canada impossible to ignore. Writing is how we get there.

Today I’m sharing a persuasive writing playbook, inspired by what I learned from Glenn Kramon (longtime NYT editor) while at Stanford. Use it on every email, pitch, and note. Write so people say yes.

Not Sorry spotlights builders across fintech, defence, and everything in between. Each comes with one clear ask: a hire, a pilot, an intro.

Many of you have asked how to help. Here’s how:

Be the reason a founder gets a yes by Friday. If you can help with the ask, say yes. If you can’t, forward it to the person who can.

And here’s my one New Year’s ask: Send Not Sorry to five people. If five is a lot, two is fantastic.

The friend who stayed in Waterloo. The expat who still orders double-doubles. The Montrealer in New York with a Habs jersey in the closet (we all know one).

The bigger we get, the more doors we open.

Margaret Atwood put it best: “A word after a word after a word is power.”

Let's use ours. 🇨🇦

Stop Apologizing for Having a Point

I used to write like my job depended on sounding “professional.”

From McGill to McKinsey, I leaned on the “Corporate Buffer.” I’d clear my throat for three paragraphs, hide behind words like alignment or synergy, and hope the reader would guess what I actually wanted.

It was polite. It was professional. But it failed to respect the reader’s time.

At Stanford, I studied “Winning Writing” with Glenn Kramon, a longtime New York Times editor. He gave Andrew Ross Sorkin his first shot, years before DealBook. Sorkin later wrote 1929, one of my favourite reads in 2025.

Glenn is a human lie detector for bad prose. He can hear one sentence and tell you exactly where your thinking starts to wobble.

He taught me this: don’t make people decode you. Say what you want, say why, and make the next step easy.

Inspired by Glenn, here is my playbook for clarity, so you can ask cleanly, lead warmly, and get to yes faster.

This is how we make Canada impossible to ignore.

1. The Result is the Only Metric

Before we type a single character, we have to answer the “Not Sorry” question: What result do I want?

Not “what do I want to say.” Not “what is my update.”

What do we want the reader to do when they finish?

• Approve the $100M project?

• Grant 15 minutes to a founder from Vancouver?

• Take a shot on a product pilot?

If you don’t know the result, neither will the person you’re writing to. Hold off until you do.

2. B.L.U.F. (Bottom Line Up Front)

Glenn borrows this from the military. In a world of 3-second attention spans, you have to win—or otherwise risk losing—your audience immediately.

Stop “clearing your throat.”

The Sorry Way:

Hey! Just wanted to circle back on this. I know you're probably super busy, but I'd love to grab 15 minutes if you have time to chat about how we might be able to help with your workflow. No pressure at all—just thought it could be valuable. Let me know!

The Not Sorry Way:

You mentioned your team spends 10 hours a week on manual reporting. We automate that. Want a demo Tuesday at 2pm?

Lead with the point. If someone only reads the first two lines on their phone, they should still know exactly what you want.

3. The “Seasoning Rule” for Jargon

This rule is blunt: Enough flavour to make it work, not so much you kill the dish.

We say utilize when we mean use. We say commence when we mean start. We say streamline the process when we mean accelerate.

Say it to a friend, then write it exactly like you said it. If you wouldn’t say “I’m incentivizing my VP of Sales to implement an expansion plan” over coffee, don’t write it in a memo.

4. Cold Outreach: One in a Million vs. One of a Million

Glenn always says:

Be one in a million, not one of a million.

Canada is done being the “farm team” for global talent. When you reach out to the Nadellas, Carneys, or Andreessens of the world, don't start with "I hope you are well." Doing so reads like “one of a million” spam.

To be “one in a million,” try three things:

• Start with what they don’t know: Give them an insight about their own business or a trend they haven’t seen.

• Pick a lane: Don’t send a CV. Tell a story that shows us in motion.

• The Small Ask: Don’t ask to “pick their brain.” Ask for a 10-minute reaction to a specific thesis.

Example:

Don’t write: “I’d love to pick your brain about AI strategy.”

Write: “You mentioned in your 2023 letter that compute is the new oil. I’m seeing a $40M gap in Canada’s inference capacity. Can I send you a 2-pager on how we’re filling it?”

Now you’ve given your busy reader a reason to care, and you’ve made it easy to say yes.

5. Feedback is Not “What’s Wrong”

This is the soul of leadership. Glenn (via Tom Friedman) says there are two kinds of critics: those who want you to fail, and those who want you to succeed. People can smell the difference a mile away.

The “Not Sorry” Feedback Loop:

• Praise liberally. Say what you like, then say what you would like.

• Be constructive. Don’t write “This is boring.” Write “This would be stronger if we led with the project’s ROI.”

• Use the “We”: We’re building this together. “We should have invested” becomes “Should we have invested?” It’s a conversation, not a command.

6. Save Yourself (The Epilogue)

Glenn ended “Winning Writing” with a plea: Save yourself. Save yourself from becoming a shrivelled version of who you are. In business, we often trade our identity for a “corporate voice.” We become dependent on the approval of people who aren’t even in the arena.

To live large, write small.

Retain your own identity: If you're from Hamilton, say Hamilton. If you went to McGill, say McGill (not the Harvard of Canada).

Be for something: As Ken Burns told Glenn, “Do not lose your enthusiasm.”

Scatter Joy: The best writing leaves the reader feeling like they are the cleverest person in the room, not you.

The Not Sorry Writing Checklist

Words move people. If we're going to make Canada impossible to ignore, we need to write like we mean it—clear, warm, and impossible to miss.

Here’s the checklist:

• BLUF: Is the point at the top?

• The Cut: Can I delete 30% of this? (Usually, yes).

• The Human Factor: Would I say this back home, or is this corporate jargon?

• The Ask: Is it small, clear, and actionable?

Writing is a muscle. Practice it every day. I’ve kept a journal for years to keep the blade sharp, and I’m still learning.

Here's your homework: Open your last five emails that didn't get answered. Pick the most important one. Rewrite it using the checklist above. Send it again. See what happens.

Write with clarity. Lead with confidence.

Let's make Canada impossible to ignore.

Bryan

If a piece isn’t useful, tell me. It’ll help me make the next one better.

When Geoffrey Hinton won the Nobel Prize in 2024 for inventing the brain of AI, he used half his speech to warn everyone not to screw it up. The guy built the thing that runs the modern world and mostly seemed worried we’d set it on fire.

That’s so Canadian, it’s beautiful. Frankly, it’s our super power. It’s what makes people trust us and want to do business with us, again, and again.

Though sometimes, we forget you can be polite and relentless at the same time.

We have titans in our backyard. Geotab in Oakville tracks over 5 million vehicles worldwide. PointClickCare in Mississauga runs the health network for over 30,000 organizations. These are empires. And most of us couldn’t name them at gunpoint.

We whisper about our wins like we're embarrassed they happened. Somewhere along the way, being polite turned into being sorry. Sorry for our success, sorry for taking up space, sorry for building empires that actually matter.

2025 felt different: Tax incentives that actually reward builders who ship, Waabi putting self-driving trucks on real highways, Cohere building arguably the most secure AI on earth. The momentum stopped whispering and started yelling.

I started Not Sorry to make Canada impossible to ignore.

This is home for the builders who stayed, the ones who left but still check the score, and anyone tired of the betting against us.

2025 was the year we got loud. 2026 is the year we stop being sorry about it.

2025: The Year Canada Got Loud

1. The Spreadsheet That Rewrote the North

There’s a guy named Bruce (there’s always a Bruce). He runs a manufacturing company. He’s sitting in a boardroom on the 15th floor of Brookfield Place, staring at a spreadsheet that’s about to decide where he builds his next factory.

For ten years, that spreadsheet pointed south. The U.S. had better tax math. But that had changed:

• The Success Tax (METR): This is the “Friction Tax” on investment. In 2024, Canada was at 15.6%. In 2025, the Productivity Super-Deduction slashed our rate to 13.2%. We are now the lowest in the G7.

• The “Time Tax” (Day 1 Write-Offs): Before 2025, if Bruce bought a $100M building full of robots, he had to write it off over 20 years. In November 2025, the rule changed: Write it off on Day 1.

Bruce ran the numbers again. Hamilton, Ontario won. Bruce is building here because the math finally makes sense. We stopped being modest about wanting to win and built a tax structure that makes Canada the obvious choice.

2. Speed Became Strategy

Canada decided to move fast.

On December 18, 2025, Canada and Ontario signed a deal: one project, one review, one decision. We backed it with $213.8 million for a Major Projects Office (MPO) led by former Trans Mountain CEO Dawn Farrell. Her job is to get nation-building projects approved in 24 months, not 20 years.

The office named the targets: $116 billion in projects like the Ring of Fire mining roads and LNG Canada Phase 2. Because every year we wait is a year someone else builds it first.

3. The Money Rules We Rewrote

If you've ever tried to build fintech in Canada, you know the problem: innovation required permission slips from people who already owned the playground.

In 2025, the infrastructure finally caught up:

• The Stablecoin Act: This took digital money out of the shadows. The Bank of Canada set the bar: if your stablecoin isn’t 1:1 backed by high-quality liquid assets, it isn’t money.

• Open Banking: With the Consumer-Driven Banking framework, if a customer wants to share their financial data with your app, the bank has to let them. No more gatekeeping.

For builders, if you follow the regulations, you can build. You don't need a bank to say yes first. We're not sorry for getting serious about fintech. The world is watching, and Canada made its move.

4. Compute as Infrastructure

Our AI minds are among the best in the world, but we’ve been renting the “factories” from U.S. cloud providers. In 2025, we stopped renting. We treated compute like a highway or a power grid: publicly funded, Canadian-owned, and sovereign.

• The $2.9 Billion Stack: After the November 2025 Fall Statement added a fresh $925.6M investment, our Sovereign AI Compute Strategy is now a $2.9B powerhouse.

• The SCIP is Live: The Sovereign Compute Infrastructure Program (SCIP) has moved past “planning.” Construction on the national supercomputing backbone is officially underway to ensure the world’s largest AI models are trained on Canadian soil.

• The Access Fund: As of this fall, the $300M AI Compute Access Fund is fully operational. Canadian startups no longer have to beg for credits from AWS in Virginia. They are scaling on subsidized, high-performance Canadian capacity right now.

Canadian AI scales here now. We are officially done being the farm team.

5. Minerals Became Strategy

We stopped just mining the Canadian Shield and started owning it. Stockpiling minerals. Financing projects. Controlling supply chains our allies actually need. We're not sorry for going big on critical minerals. We're owning what we've got.

As an aside, the Shield is a massive 8-million-square-kilometre storehouse of ancient rock that forms the core of North America. It is one of the world's richest areas for mineral ores, containing vast deposits of nickel, gold, copper, and the specialized materials that power the modern world.

We launched the Critical Minerals Production Alliance to fast-track $6.4B in projects. But the real “Not Sorry” move was the $2B Sovereign Fund. It can do what a government department can’t: equity investments and offtake agreements. We activated the Defence Production Act to stockpile these minerals, signaling to our allies that if you want a secure supply chain, you come to the North.

So…Let’s Go!

That was just the start. There’s more:

• The Energy Moat: Clean Electricity Credits are forging an unbeatable grid that makes our industrial power the cheapest and cleanest in the G7.

• The R&D Turbocharger: SR&ED was doubled to $6M meaning your research spend is now backstopped by a 35% refundable credit.

• The Deep Tech Anchor: A $334M Quantum-AI defense push to ensure our most sensitive breakthroughs stay on Canadian soil.

• The New Industrial Heartland: Alberta carbon hubs are pulling CO2 from the sky, while Ontario and Quebec battery giants (like the 90GWh PowerCo plant) are gearing up to power North America’s electric century.

Spreadsheets don’t lie (well, the ones I’m talking about). The builders who left for Palo Alto and New York a decade ago are staring at the numbers and seeing the same thing:

Canada is not playing around.

And look, we haven't solved everything. Housing is still broken. The productivity gap is real. We're still losing homegrown companies to foreign buyers. But something shifted in 2025, and for the first time in a long time, it feels like we're playing to win.

Hinton proved you can invent the future from a porch in Toronto and still care enough to warn the world not to burn it down. He proved you can be the undisputed best on earth and stay a decent human being.

That is the “Polite” part. It’s our soul. It’s non-negotiable.

But for too long, we used that decency as an excuse to stay small. We treated our genius like a secret.

Not anymore.

We’re adding the “Relentless” part now. The part where we stop whispering about our wins and start building the empires our geniuses made possible. The part where we realize you can hold the door open for someone and still take their market share.

2025 was the year we got loud about what we’re building.

2026 is the year we stop being sorry for winning.

Let’s go!

If a piece isn't useful, tell me. It’ll help me make the next one better.

The first time I felt Canada’s innovation problem in my bones, I was in a glass-walled conference room off Sand Hill Road. A venture partner—nice suit, nicer smile—was praising Canadian talent. Our engineers. Our labs. Our papers. Then came the shrug, the one you can hear across the room: “You’re great at making the thing. We’re great at owning the thing.”

I flew home with that condescension stuck to my ribs like damp fog off the lake.

On December 9th 2025, in Montréal, Industry Minister Mélanie Joly made that line harder to deliver with a straight face. She announced $1.7 billion for the Global Impact+ Research Talent Initiative—100 research chairs at up to $1 million a year each, plus 900 early-career researchers building teams around them in AI, quantum, biotech, climate tech. This isn’t the old penny-ante NSERC grants averaging $47,000, barely enough to keep the lights on while American NSF labs get $200,000+ starting cheques. This is real firepower.

Celebrate it. And then don’t confuse fuel with a destination.

Canada doesn’t have a research problem.

We have a commercialization problem. I’m saying that as someone who used to find where organizations create value and someone else captures it. Canada’s leakage is ownership.

The proof is brutal. IRPP researchers tracked U.S. patents with at least one Canadian inventor and found the share transferred to foreign firms on the date of issue more than doubled over two decades—from 18 percent to 45 percent. On the date of issue. Not years later after some acquisition. The ink dries, the deed changes hands.

We pay for the training camp, buy the gear, hire the coaches—and our best players sign with the Yankees on draft day.

Here’s the story that still stings. On June 12, 2017, Aidan Gomez—then 23, University of Toronto alum, Google intern—co-authored “Attention Is All You Need”. That PDF birthed the transformer architecture, the mathematical engine underneath ChatGPT, Google search, every chip Nvidia sells. That paper became the foundation of a multi-trillion-dollar industry built and owned almost entirely outside Canada.

Canada helped train the mind that wrote the blueprint. Gomez came home and built Cohere, now worth $7 billion. Geoffrey Hinton won the Nobel for neural nets from the same labs. But the value? Mostly scaled abroad.

Pride doesn’t pay doctors.

The Chain We Pretend Not to See

Here’s the chain: Ideas leave. Companies follow. Headquarters move. Tax revenue disappears. And that missing money? It shows up as longer wait times, understaffed operating rooms, MRI machines that Thunder Bay can’t afford.

You can’t run a first-world healthcare system on someone else’s tax base. Not forever. The OECD projects Canada dead last in G7 GDP per capita growth to 2060. When high-value companies get built and owned elsewhere, we lose the boring, essential capacity to fund the things that keep a country livable.

Bringing world-class researchers is essential. But if we don’t change the ownership structure underneath, we’re just training a bigger diaspora.

Two Fixes. Not Twenty.

So while Joly’s $1.7 billion is still warm on the press release, here are two fixes.

First: change the default. When public money funds the research, Canada should get first crack at owning or licensing the IP. Not case-by-case negotiations. Not maybe-someday partnerships. Standard terms that anchor commercialization here. Will some multinationals balk? Let them. If the research is good enough—and it is—they’ll come anyway. They need the talent more than we need their validation.

Second: build the people who build companies. We don’t just need researchers—we need the operators who know how to scale. Use government purchasing power to create domestic customers for Canadian innovation. Make it easier for Canadian expats who’ve scaled firms abroad to move home and do it here. Reward companies that keep headquarters and IP in Canada.

The partner in that conference room wasn’t wrong. Their system is built to capture value. Ours creates it, then acts surprised when someone else collects the cheque.

We’ve Been Renting Out Our Future

But Joly’s bet just changed the equation. We have the fuel. Now we need to stop leaking it—and start building the engine that keeps the value here.

I don’t want my kids growing up in a country that invents the world’s next transformer and rents it back at retail. I don’t want the next generation of Canadian founders flying home with that same condescension stuck to their ribs.

That’s why I’m building for Canada. Not out of nostalgia. Out of refusal to let another generation rent back what we invented.

We’ve been renting out our future. It’s time to own it.