Rob Woodbridge
Founder. Operator. Writing a book about what founders actually lose.
-
Compound Loss
Pay yourself last is the most romanticized startup advice ever given. It's also the dumbest financial decision you'll …
-
The Kill/Keep Decision
We launched a consumer delivery app. 1,500 downloads, 100+ deliveries in 45 days. Not bad, not good enough. The hard …
-
We Wrote the Offsite Playbook. Then It Failed Anyway.
I wrote the offsite playbook. Then I watched it fail anyway. Turns out alignment is a word we use to feel good, not a …
-
The Craft Gap
Startups demand speed, and speed creates debt. Not just technical debt but craft debt: the gap between people who do …
-
Defeat in Detail: The Only Way to Beat the Giants
Every startup that tries to out-resource Amazon, DoorDash, or Uber loses. The only way to win is to fight battles the …
-
The Promises You Keep Breaking
A founder confession about the promises we make to our best people and don't keep. After five years of saying "soon" and …
-
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 …
-
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 …
-
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, …
-
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 …