Blog Post

Card Shark

For the past five years I’ve made my living playing poker. It’s been a lot of fun, and even more profitable than I had hoped for when I first took the leap. I’ve travelled around the country and met all sorts of interesting people. I’ve even had a “best-selling book”: published. And best of all, I’ve done it all without ever having to set an alarm clock.

But a lot has changed for me in that time. I’ve grown up, bought a house and a dog, and even got engaged (we get married in about 3 weeks). My 27th birthday is right around the corner, so while I’m still young, that youthful feeling is fleeting. And as I’ve grown older I’ve begun to look for something more fulfilling to spend my time on. I’m still not quite ready for the alarm clock, but I have developed a desire to build something tangible, something people will like. That’s why I’m in the process of launching a startup.

The question I’m facing (and the theme that will tie together my columns here) is whether my poker experience will be a blessing or a curse as I transition into life in the “real world”. Playing cards for a living is definitely the sort of experience that changes you in numerous ways, many of which you could never have guessed beforehand. Some changes are undoubtedly for the better, some for the worse. And some depend on the situation. The intersection of professional gambling and business would seem to fall largely in that unknown grey area, and that’s what I will be exploring here.

So far my poker experience has been a blessing as far as the startup goes. The first time it really came into play was during our “interview with the folks at YCombinator”: When I got to their offices in Mountain View I had a good feeling. I sensed a vibe from the other interviewees that was pure apprehension. It was not unlike sitting at a poker table with people who’ve never been there before.

Five years ago, I would have been nervous in that situation too. I’m not even sure I could have gone through with it. I was just that type of person. For instance, once when I was in middle school I won a chance to walk with Tom Purtzer at the NEC World Series of Golf during a shootout event (which, for those who’ve never attended, is part of the festivities that go on in the few days before the tournament begins) and nearly had a panic attack. I almost gave my spot to one of the hundreds of other dejected kids who’d entered in the drawing and were milling about, watching the lucky ones who’d been called, and probably wishing all sorts of unspeakable horrors upon us. Luckily for Mr. Purtzer I called my dad, who calmed me down and told me that I needed to have my head checked if I didn’t do it. He went on to win that year (Purtzer that is, not my dad) and it was pretty much the highlight of his career. You’re welcome Tom.

But with professional poker comes pressure on a level that few people ever experience. When I first started playing, the lowest stakes available were enough to win or lose what I made in a week working at Sam’s Club. When you’re working a retail job and trying to pay for college, that sort of thing can be pretty stressful. I was a fast learner so it wasn’t long before I was winning more than I lost, but even then the swings could be pretty brutal.

As I improved and moved up through the poker world the pressure only became greater. I got to the point where I would regularly win or lose more in a day than many people make in six months. I’ve been the chipleader in a tournament with an $80 million plus prize pool and have had ESPN’s cameras filming me for hours on end. I’ve had to remain focused despite the throng of onlookers and the knowledge that any blunder might end up on national television, doomed to be forever repeated in bars across the country in between episodes of SportsCenter.

And worst of all, I made a brief foray into the publishing industry. If you think there are sharks at a poker table, try negotiating a literary contract. In poker I was often a big fish in a small pond, in the literary world I was a small fish flopping around on dry land. In the middle of a freeway.
So a fifteen minute interview with the folks at YCombinator was easy. At the end Paul even remarked that everyone else he had talked to was nervous, their hands shaking and their voices quivering. Everyone but “the poker player” as he told some of the alumni who’d been there that day.

In Jesse May’s seminal Shut Up and Deal (the one book I recommend even to people who have no knowledge of or interest in poker) the protagonist, Mickey Finn, is asked by a lower-stakes player what the difference between the big games and the little ones is. Mickey tells him “the color of the chips”. The inquisitor thinks Mickey is just being a jerk, but he isn’t. As you move up through the games you realize that nothing really changes, except the chips go from being red to green, and if you’re really good maybe to black. They’re worth more at the end of the night, but they perform the same function, and the game doesn’t really change no matter what color they are.

And so it goes with talking to people. Talking to Paul Graham is no different than talking to any other stranger who might be interested in hearing my idea. The stakes are maybe a bit higher, and when talking to a VC they will be higher still, but the game is the same.
So when our interview was done, I told them that I wished it were an hour. I meant it too. Luckily they accepted us (I just got out to Cambridge this weekend) so we’ll get to make up for lost time.

5 Responses to “Card Shark”

  1. It is good to find there is a poker player even at this places, here! Your story on your poker experience is very inspirational and shed quite some light on how it must’ve been like playing poker for a living.

  2. koolmoe


    A successful poker player gets paid for exploiting his opponents’ weaknesses, much the same as a successful entreprenuer gets paid for exploiting his competitors’ weaknesses.

    Also, it is fairly common for a successful player to stake an up-and-coming player in order to generate some residual income. The relationship between staker and stakee are strikingly similar to that of a VC and a startup.

    Finally, a well played bluff isn’t that uncommon in the startup arena.}

  3. I’ve spent a fair amount of time at a poker table, too – I’m sure it pales in comparison to the author’s experience, but it was long enough to notice how it can affect your thinking. Two things to look out for in your thinking 1) life outside the poker table isn’t usually a zero-sum game, and treating negotiations, weather with VCs or partners, as if they were could lead to some novel results 2) getting paid at poker is, in essence, getting paid for lying. A constant search for angles, setups, or worse can, again, lead to some less than optimal results.}

  4. carleen

    Funny, and good to know J.R., only I had to look it up: *card·sharp* Pronunciation: -“shärp
    Variant(s): or card·sharp·er Noun: *”a person who habitually _cheats_ at cards”*

    Naturally, and using the vernacular known so well to those of us who don’t own a deck, I took “card shark” to mean “expert.” Anyway, ’tis my choice in headline, not Matt’s, so any error is mine, too. But heh, thanks for playing!}