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. CEO of a fitness tech company. Founded UNTETHER.tv and spent 8 years interviewing founders who were smarter than me. 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 Canadian cities. We’ve done over 2 million deliveries. I’ve personally done more of them than I’d like to admit.

I’m writing a book called LOSER: A Book About Winning Wrong. It’s about what founders actually lose, whether they succeed or fail. This blog is where I work out the ideas.

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If you’re new here, these will give you a feel for how I think:

On the emotional reality of founding a company

→ Deferral — The startup equation nobody talks about. You defer everything to build. Then you either fail and lose it all, or succeed and become the thing you left.

→ You’re Broke. Stop Acting Like You’re Not. — The unglamorous part of entrepreneurship. Being broke, staying broke, and what happens when you stop pretending.

On running operations

→ Every Merchant We Rushed to Launch, We Launched Twice — We were so desperate for growth that we skipped the work. Then we did it all again.

→ Set the Pace — The speed you run at determines everything. Most founders run too fast for their teams to follow.

On building teams

→ Hiring is Lazy — Most hiring is a patch for broken processes. Fix the system before you add people.

→ I Hired Smart People and Trained Them to Stop Thinking — The one you hired for their expertise stopped bringing ideas. You didn’t yell. You didn’t shut anyone down. But you trained them to stop thinking anyway.

On focus and decisions

→ Chasing Everything Means Catching Nothing — Every founder thinks they can run five priorities at once. They can’t.