Rob Woodbridge
Founder. Operator. Writing a book about what founders actually lose.
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I Gave Him My Options to Keep Him
I paid the ransom out of my own pocket. He cashed it at the exit.
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You Owe Us $22,000 and You Want Me to Care About Today's Delivery
Big logos don't pay faster. They just make you wait quieter.
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What Do You Think, Rob?
The most dangerous question in a startup is the one that skips the person who owns the answer.
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Side Quests Are Tantamount to Suicide
The thing that kills your company is rarely the competition. It's the brilliant idea you decided to run on the side.
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Nobody Decided This Was Your Job
Authority in a startup doesn't get assigned. It gets assumed. And nobody goes back.
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You Hired Them Into a Job, Not Into a Fight
The first fifteen people joined a fight. Everyone after that joined a company.
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We Already Know What's Changing. You Don't.
The gap between what leadership knows and what the team knows is always wider than founders think.
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Nobody Knows If We Know What We're Doing
I have done this enough times to know the pattern. I still cannot explain it.
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The Moat Isn't the Code
Three years ago investors wouldn't take the meeting. Now they're chasing. The asset didn't change. Their lens did.
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The Permission to Spend
He made the right call for the wrong night, and the reason he made it was that nobody told him which night he was in.