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

Andrew Lockhead

Andrew Lockhead portrait

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.

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 take away

You don’t need to be in Silicon Valley to build something massive but you do need to think like you are. Especially as Canadians, where we tend to play things a bit safer than we should. The opportunity is there, the constraint is usually mindset.

Andrew Lockhead portrait