Become An Entrepreneur That Can't Lose

Dear Lee,

You've done things with money that would make most people's stomachs turn. Bet more than you could afford to lose on the strength of a hunch, and barely paused to think about what happens if it goes wrong. To you it never felt reckless. It felt normal. If it went wrong, you'd deal with it then.

That's not nothing. That appetite for risk is exactly what let you launch in the first place. If you weren't wired this way, none of it would exist yet.

But there's a difference between having that appetite and knowing how to survive it.

You can only lose the game of entrepreneurship one way. By being taken out of it for good.

Keep a working brain, a body that can do the work, a small amount of cash and a connection to the internet, and you can rebuild from a total collapse. So the real question was never how to avoid risk. It's how to take it and still be standing afterwards.

Nassim Nicholas Taleb has a word for this. Antifragile.

• Fragile things break under stress.
• Robust things survive stress without changing.
• Antifragile things get stronger because of it.

Think about a muscle. You tear it apart at the gym, on purpose, and the body doesn't just repair the damage. It rebuilds stronger than before. That's the model. Not avoiding the stress. Using it.

Put everything on red at the roulette wheel and one bad spin ends the game completely. That's not risk-taking. That's fragility wearing a confident face.

You are not your business. You are the engine that creates businesses. Protect the engine.

Financial. Your life has to survive if the business doesn't. Keep your own lifestyle low-leverage. Fund the bold bets with excess, never with survival money. Don't let your rent depend on product-market fit.

People. If everything breaks the moment you go offline, you don't have a business. You have a job with no off switch. Build slack into the team, and hand over real responsibility before you think they're ready for it, so the whole thing doesn't stall the second you're not in the room.

Process. What starts manual either gets automated or gets killed. Test the messy version first, but the moment something works more than once, turn it into a system you never have to think about again.

Look at your business today. If you disappeared for a month, what breaks first?

That's the piece that isn't antifragile yet.

Go and fix it.

Lee