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Jason Cohen from WP Engine dropped a truth bomb: they spent time and money fixing what they thought was “poor...
If you think you’re too old to start... you’re wrong.
Business failure rates:
30 year old owner: 11.1%
45 year old owner: 9.6%
60 year old owner: 8.2%
Everyone worships the 22‑year-old hoodie founder, but the numbers say your crow’s feet are actually a competitive advantage. As you...
3 things I notice in CEOs who scale past $10M:
1. They hire for culture > skill
I once had to let go of our best designer at AppSumo. Flawless work but everything took 4x longer than it should. She couldn’t align with our "ship fast" culture. Hire a ship dirty designer and speed of learning went up. CVR closely followed.
2. They’re ruthless with their time
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Most founders get stuck between hustle mode and actual CEO mode. The business grows, but their calendar, stress, and decision-making...
Own the parking lot.
I saw a guy outside the biggest, nicest house in my neighborhood, so I said hi and asked what he does for a living. Turned out to be a good business lesson.
He told me he used to own a bunch of restaurants in Austin. Then he said, almost like it was boring, that he never really made money on the restaurants. He made his money on the parking lots.
What? Excuse me!
...
Most people hustle to own the flashy restaurant. Smart people quietly buy the boring parking lot. One gets press, stress,...
It's not sexy to say, but most of AI transformation has nothing to do with AI.
There are 10 steps in the sequence of making an internal process or external product AI-native.
Only 1 step is AI, and ironically, the other 9 steps are the far harder part.
Step 1: Identify the problem
- find the manual process worth automating. turn your brain off autopilot & turn on your "suck meter". ...
Everyone wants the magical AI button. But if you skip the boring groundwork, that button does nothing. These 9 non-AI...
Bezos had the 2-pizza rule:
Never have a meeting that can’t be fed by 2 pizzas
I never understood this rule because I could eat a pizza by myself
I have the 2-car rule:
...
Everyone loves the romantic “founder stage” of a company: small team, fast decisions, zero meetings about meetings. But there’s a...