Want To Win? Learn to Hate Losing


As I'm writing this, I'm sitting in a casino hotel room having come back up from losing a ton of money in just a couple hours. I feel like crap. If you were my friend I'd call you right now and whine for an hour.

But there's nothing I can do about it. My friends are all downstairs having a great time. Some are winning, some are losing. Nobody wants to hear my freaking sob story, and at this point, I'm the cooler. So I'm upstairs pounding away at my keyboard in hopes of turning this rage into something useful for you.

Consider this a very expensive article. But you deserve it.

I definitely don't have a gambling problem. In fact, I have the opposite of a gambling problem. I have risk aversion. I love numbers and I play the odds. I count cards in blackjack. I play the pass line and the come line in craps. I never touch roulette, slot machines, or basically anything else in the casino where there's a big house edge.

When I'm winning, I'm on top of the world, and I walk away up almost every time. When I'm down, which usually happens when I start losing right away and can't get even, I hate myself, I blame myself, and when my pre-determined stake for that session is gone, I walk away and go upstairs to sulk for a few hours.

I love to play poker. Specifically, I love tournament no-limit Texas Hold ‘Em. I play conservatively, but I bluff when I think everyone thinks I'm playing too conservatively. To me, poker isn't gambling. It's a game of skill with money involved.

The most I'll lose in a night of poker is 20 to 30 bucks, which is more than enough of a down payment on the fun I have and the endless, monotonous conversations that will take place later that only true poker-heads can enjoy. We use terms like “trips” and “boats” and “river” and “inside.” It's slightly hipper than stamp collecting. But I like people who like poker.

Oh, I still hate losing at poker. It ruins my night and most of the next day.

I have a love/hate relationship with the stock market. I started investing on my own during the crash of 2008/2009. I bought Ford at $4 and sold it at $12. I bought Wynn at $30 and sold it at $50, then bought it again at $70 and sold it for $200. But since those crazy days I'm mostly in cash, and I hate that.

For all I know the stock market is indeed gambling. I have no idea what moves most stocks up and down these days. It isn't fundamentals and it isn't potential. It's some oddball combination of external market forces (Greece, the Fed, energy, China) and plain old-fashioned hip factor (Tesla, Shake Shack, even Apple).

So I'm scared. I'm scared because I don't know what the risk is and thus, I don't know how to mitigate it and I don't have a plan B.

But. If I were to tell you that I was going to quit a steady job at a company that was about to go public and that I was going to start my own company with 2-year-old twins at home and a wife who was three months pregnant, you'd think I was nuts, right?

That's BASE jump type stuff.

And if I then told you I would later shelve that business, which was doing over $1 million in revenue per year, to help lift off a startup that was going to teach computers how to write stories, you'd probably say that was equally, if not more, insane.

But that's what I did.

In both of those situations, the odds for failure were startlingly high, but I knew what would make those ventures succeed and what would make them fail. I didn't know how to get from point A to point B at the time, but I knew it was up to me (and in the latter case, me and a guy I really trusted).

That's. Not. Risk. Tolerance.

I don't know how venture capitalists do it. I don't know how they can put up a chunk of their funds to fuel an idea that they have little control over. And I know some VCs are more hands-on and meddly than others, but still, they're not the ones with the vision. At most, they get a little bit of influence into how that vision plays out.

This is why investors are so reliant on the caliber of the founding team as a key metric of their decision criteria. But the trait that they look for in these founders shouldn't be risk tolerance. Risk tolerance doesn't mean shit.

What they should really be looking for is those people who hate losing.

I would contend that I'm one of the most competitive people on this planet, and that no one hates losing more than me. Not LeBron James, not Bill Belichick, no one. I hate losing with the heat of a thousand suns. I hate losing at ping pong. I hate losing at craps. I hate losing in business. I hate it so much that I do everything in my power to put the odds in my favor as far as they will stretch.

If I'm going to teach robots how to write, I'm going to make damn sure they know how to write, and that they know how to write in a way that will make people want to buy what they write, then buy the technology that allows them to write, then buy the company that creates the technology that allows them to write.

I get zero happiness from anything less.

This is what makes solid founders tick. It's not the ignorance to jump off the side of a building. It's the years of training and the hours of safety check before they leap. It's the fact that they hate losing so much, they'll do whatever it takes to avoid it. But when it happens, they also know how to recover.

And with that said, I'm going back downstairs.