Why Every Startup Founder Should Play Poker (1 of 3)

In this series, I’m want to persuade startup founders (all startup founders) that playing poker is not just something you could do but rather that poker is something that you should do. I know — a bold claim.

In this first post, I intend to clear the air and set the record straight about just what poker really is and its power to build relationships — i.e., an unparalleled opportunity for you to find the help you need for your startup.

The second post will explain why poker is not only a fun and powerful way to build relationships but also an opportunity for improving your decision-making skill in a way that directly improves your skill at building companies — i.e., poker is “wax on, wax off” for startup founders.

Finally, for those inclined, the third post will provide a startup founders roadmap to poker.

Let’s get started!

Poker has a dark reputation as a devil’s playground, a vice, only for criminals, degenerates and ne’er-do-wells… and men. Cigar smoking, cursing, cheating, drunkenness, and gambling addiction are all part of poker’s infamy.

If you’ve never played poker, then I’d be willing to wager that your opinion of poker is informed by at least some of these disgraces. Before I started playing poker with other founders and investors in 2006, my view of the game included most of these stereotypes. I wasn’t even sure if it was legal.

But I learned that these stereotypes — all of them — are misplaced, i.e., none of these disgraces are inherent in poker. The truth about poker is:

  • It’s fun.
  • It’s a game of skill.
  • Women are awesome at it. (This is so important!)
  • Alcohol, tobacco, cursing and weapons are not required.
  • Math and psychology are far more important than bluffing and keeping an ace up your sleeve.

I also learned that the game of poker can be slow, almost boring. The majority of the time you spend at a poker table is waiting for your next hand to start. If you’re playing well you may only play three to five hands an hour, while you fold five times as many hands.

Perhaps unexpectedly, this ‘boring’ pace is part of what makes poker a beautiful game for startup founders — it gives everyone at the table plenty of opportunity to get to know each other. What happens during all that boring time is what makes poker the ultimate “un-networking” activity.

When I say “un-networking”, I’m not just trying to be clever. The truth is that traditional networking is in most instances a massive waste of time for a serious, venture scale founder. Starting and growing a venture scale company is hard… very, very hard. There is literally not enough hours in a day to do everything that a founders need to take care of. Spending an evening searching for a valuable conversation while dodging service providers in a noisy, crowded room has a negative expected value for a founder. For sure.

But surely a founder needs to build her network, right? Certainly. In difficult and risky business of building a company, success will likely require that founders find help from others — advice, insight, introductions, investment, partnerships, etc. Help of this kind is critically valuable.

In my 20-ish years experience as a serial founder, mentor and advisor, it is my observation that this kind of help most often comes from the people a founder already knows. This is why a strong network is so important for a founder.

Of course, great help can come from many sources, but I have seen over and over again that the best of that help will come from other founders. The reason is simple: no one else understands what it takes to build a company better that someone else who has built a company. And because founders share a unique experience, founders are often more willing and able to help. This is why it is so important that a founders network with chock full of relationships with other founders.

But why, you may ask, is poker such a good way to build a valuable founder network? Here’s why?

Besides the natural chit chat among peers, it’s the excitement of occasional big pots, bad beats, and the good-natured trash talking in the game that creates shared experiences and inflection points from which real relationships are forged. It’s hard to imagine playing friendly poker with someone a couple times and not becoming trusted friends.

It’s not a secret that many tech founders are not natural networkers. Over many years of startup networking, what I see as the most common behaviors for founders are A) congregating with people they already know and feel comfortable with, and B) standing in the corner with a beer in hand waiting for someone to come up and ask them what they do. Neither is a productive use of a founder’s valuable time.

Poker gives everyone a simple, shared task to perform that makes everyone feel comfortable, making conversations natural and easy. How simple is poker? It takes about 15 minutes to learn enough about poker to start playing the game with others. Your skills won’t match up, but if you find the right game and commit to paying attention and continuing to learn, then your nascent skills won’t matter much. More on this later.

For that 15 minute investment, you’ll be ready to sit down with eight or so other founders and investors and start playing poker — a much more valuable use of time than going to an open networking event with 100 “startup community members.” It’s unlikely that there would even be eight other venture-scale founders or investors at such an event and the chances of actually meeting one of those eight and building a relationship with any of them would be vanishingly small. But you’ll have no problem finding a full contingent of service providers, ‘wantrepreneurs’, gadflies and curiosity seekers. Again, not a great use of time for a busy founder.

One of my favorite aspects of poker is its strong leveling effect — all the various strata that keep us in our respective boxes disappear. The billion-dollar VC fund guy and the multi-exit founder have no inherent advantage over the bootstrapper and the two gals in a garage (as long as the stakes are reasonable for everyone at the table.)

At a poker table, all that matters is the cards you get and how you play the game. Neither your gender nor your race grant you any advantage or disadvantage whatsoever. This creates a relationship dynamic that is almost never seen anywhere else in the startup ecosystem, where gender, race, wealth, and celebrity are virtually meaningless.

All of these elements of poker combined make it a uniquely valuable use of time for a founder looking to build a network, for a founder to find help for their startup and, importantly, for a founder to find other founders they can help.

If you were a poker naysayer before reading this post, I hope that you now see poker as the powerful mechanism it is for building relationships, especially among founders. In case that is not enough to convince you that you should find some founders to play poker with, in the next post I will explain how poker can actually make you a better founder. Pro tip: if you haven’t already seen the classic 1985 movie, “Karate Kid”, I highly recommend you watch it before reading the next post.

Chronic Technology Entrepreneur, Dad to Twin Daughters, Mentor @Techstars, Philosophy Grad, Poker Instigator

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