Rob Woodbridge
Founder. Operator. Writing a book about what founders actually lose.
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Heroes Can't Scale
Our CEO became the lead sales person. Our CPO codes features himself. I've done deliveries when we were underwater. …
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We've Run Five Offsites. Here's What We Got Wrong
It took us five offsites to figure it out. Too much agenda. No strategy before. Momentum that evaporates the day you …
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I Asked for a Bowl Once
I asked a hotel staff member for a larger bowl. He brought me one. The next morning it was already at my seat. Every …
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Deferral
Founders defer pay, vacations, health, family, friendships. Everything. In the hopes it eventually works out. But the …
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Hiring is lazy
We hired a team to manage routes, assign bonuses, and call couriers. It worked so well that leadership had no idea. We …
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Chasing Everything Means Catching Nothing
Growth is slow, so we chase the next opportunity. But growth is slow because we never commit long enough to see if the …
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Every Merchant We Rushed to Launch, We Launched Twice
We wanted a merchant live in two weeks. Their team wasn't ready, so we built around them. They launched. It broke. Now …
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You're Broke. Stop Acting Like You're Not.
I've been at zero. Put my own money in to cover payroll. So I know the mistake most founders make when they get there: …
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We Finished Our 2026 Plan Two Weeks Ago. It's Already Wrong. Here's Why That's Fine.
Two weeks ago, I shared our 2026 plan. Six Canadian cities. Clear targets. The next day, an enterprise customer asked us …
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Don't nickel and dime
Team members. Investors. Advisors. The Board. Everyone suggests ways to squeeze more from existing customers. …