I’m Rob Woodbridge.
I’ve been starting, running, and occasionally saving companies for over 30 years. I was a GM at Lyft as it entered Canada. I was CEO of a fitness tech company. I founded UNTETHER.tv and spent 8 years interviewing founders who were smarter than me. I’ve sat on boards, advised startups, and been the guy in the room when things went sideways.
Now I’m co-founder and COO of Trexity, a same-day delivery company operating in six (and growing) Canadian cities (and expanding). We’ve done over 2 million deliveries. I’ve personally done more of them than I’d like to admit.
I write about what actually happens when you try to build something — the operations, the psychology, the decisions that seem obvious in hindsight but weren’t at the time.
If you’re new here, these will give you a feel for how I think:
On the emotional reality of founding a company
I’ve Actually Spent My Last Penny The unglamorous part of entrepreneurship — being broke, staying broke, and the stranger who saved my business with an act of faith.
The Founders Bluff Why founders hide from the truth, and what it costs them when they do.
On running operations
The Secret to Scaling is Stopping We were on the road doing deliveries when we realized we’d built a trap. The side quests that feel productive are often the ones holding you back.
A Simple Price to Pay Our “fair and honest” pricing model was killing our business. The moment you have to explain how your pricing works, you’ve lost.
On focus and decisions
10X Forces You to Stop Bullshitting Yourself When you’re trying to double revenue, every initiative looks promising. 10X thinking kills that delusion immediately.
The Fast No There’s nothing better than a fast “no.” It’s a gift — sometimes as valuable as a yes.
On building teams
Hiring is Lazy Most hiring can and should be delayed. More people too early means things that should get automated simply don’t.
On what’s next
AI is Just Another Layer, Not the Destination Remember when everyone scrambled for a “mobile strategy”? AI is following the same path — and will disappear into the background the same way.
If any of that resonates, pick a topic and go deeper: