Rob Woodbridge
Founder. Operator. Writing a book about what founders actually lose.
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Slack is the Only Tool Where Losing Information is a Feature
Slack isn't broken. It's doing exactly what it was designed to do: let information disappear. The problem is you're …
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I Hired Smart People and Trained Them to Stop Thinking
The one you hired for their expertise stopped bringing ideas. The one who used to push back now just waits for …
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You're Not Busy. You're Just Doing AI's Job.
Everyone's worried about AI taking jobs. They're asking the wrong question. Most of what we call work — synthesis, …
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I Haven't Written a Line of Code in 25 Years. I Just Built 6 Apps.
I haven't touched code in 25 years. I just built six production apps that replaced subscriptions, cut hours of weekly …
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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 …