How to Bet Your Life

I'm standing on an abandoned bridge one hundred feet above a stream in the lush rainforest of Costa Rica. Suddenly, I had doubts. It was a great idea when we plan it in the serenity of the hostel. But up there, with the bungee cord tied up around my ankles, the view is a bit wobbly. The theoretical has just become the very real.

That exact feeling is what most people encounter when they're contemplating quitting their corporate job to join an early stage startup.

Startups are hot and everyone wants a piece. A 13-person startup can be sold for a billion dollars. Even hollywood is getting in on the action. Bono is a VC and Ashton is an angel. That's enough to make dreamers out of everyone. But what if suddenly you're offered a chance to join an early stage startup? Are you willing to give up your position in a nice, stable, established corporation for one in a hectic, never-enough-sleep, constantly-dying startup? 

Corporate jobs, especially in high-tech, is nice and cushy. If you're good, you're likely making six-figures in your mid-20s. Not a lot of responsibilities as long as you get your shit done. There will be a smattering of trips, lots of weekend parties, and plenty of time to socialize, get a hobby, or start a family. Now imagine throwing away (or I call it, de-prioritizing) all that for least for a few years. Work-life balance is a nice concept and I try to achieve it when I can, but often reality gets in the way. If you think that sounds bad, then you're not ready.

You're not ready because you're not ready to bet your life. That's what it's like living inside a startup. That's right. You don't work at a startup. You live in it. In poker, you won't double up unless you go all-in; bet all your chips on one hand. This is same in a startup. You go all-in, but you bet with your life. Everything else in your life will take second priority. And just like poker, you shouldn't go all-in unless you're sure that you have the best cards. You should only join a startup if you truly believe in its potential. And as in poker, even with pocket aces, you can still lose. That's why it's called a bet.

A line from the hip-hop preacher that I love:

To achieve success, you have to be ready, at any time, to sacrifice who you are for who you want to be.

There are only two ways to make this kind of bet. The ballsy way and the poor way.

Jeff Bezos did it the ballsy way. He asked himself what he would regret more, doing it or not doing it. And it helps that he's a crazy bastard, intensely driven and cooly logical. I did it the poor way. I bet everything when I had very little to bet with (I was poor). I had no lifestyle to lose, no debt to pay back and no savings to miss. With nothing to lose, I had everything to gain.

I jumped from that bridge in Costa Rica. That was months after I had already gone all-in with my life and sold my first company. After that, bungee jumping seemed too trivial for any second thoughts.