MattMaroon.com

I’ve read a few articles lately about startup founders advising other people whether not to start up themselves (usually not) and it’s given me a sense of déjà vu. Back when I was a B-list professional poker player I got a lot of inquiries from people I didn’t know asking me if they should go pro. A lot of other pros who were asked that question said no every time. And they weren’t really wrong to do so, because if you’re asking someone you don’t even know that question, no is at least 75% likely to be the correct answer.

It’s not a very helpful one though. I realized early that people aren’t really asking you if they should go pro. They’ll make their decision regardless what you tell them, and if they got far enough along in the process to start asking, the smart money was that they were going to do it in the near future. I’d bet that the majority of them did, even though almost all of them were told not to.

So instead of just giving them a flat out no, I asked them a bunch of questions. Do you have kids to support? How much do you need to make each month to make ends meet? Do you have enough saved up to break even for three months (or six if you’re playing live) and still have a bankroll left? What’s your win rate and sample size? Yada yada yada.

My goal was to help them at least realize that going pro means a hell of a lot more than just quitting your job and gambling all the time. And it even means a lot more than just being good at poker, because something like 30% of people are winning players, but only a tiny fraction of them could successfully do it for a living. Success as a professional is more about bankroll management than poker skill, and avoiding going broke is a lot harder to do well than beating a $10/$20 game.

A lot of people probably ignored everything I told them anyway, just as they would had I said no (or yes for that matter, since they were going to anyway, though they’d blame me if it went badly for them). But I know I saved a few people from a lot of agony, and ended up encouraging a few who went on to have success with it. By not advising them one way or another, but rather giving them more information, I helped anyone who I could, and I at least didn’t hurt the rest.

I think startups are much the same as poker. People often ask if they should do one, but they’re not really looking for a yes or no answer. Most of them are just thinking out loud or looking for confirmation of the decision they’ve already made (or, if you say no, someone to tell “I told you so” after their IPO) but many are looking for information to help them come to their own conclusion. So you try to help the ones who might actually consider what you say and make their own informed choice, and assume the rest will ignore you anyway. Just saying no is definitely more convenient for me, but I don’t mind taking a few seconds to help someone.

Just like poker, startups can be a great way to go, you just have to be prepared and know what you’re getting into. If you’re used to steady, professional employment it’s a big change. You’re jumping out of the hot tub and into a frozen, stormy ocean. While other people might just advise staying dry, I try to give them a metaphorical wet suit and a life raft.