8 startup lessons I learned from playing poker

I learned to play poker almost a decade ago through a Seattle startup connector called Startup Haven that connects founders with education, opportunities and (most importantly) each other. Through this journey that began in 2008, I have learned that there are a lot of similarities between the startup world and the game of poker. I have even found myself making references to poker moves in my role as a founder and CEO.

Through this journey, I have learned that there are a lot of similarities between the world of startups and the game of poker.  I often find myself making references to poker game moves a lot.  For example, do I fold or raise on the consumer side of our business? Do I double down or raise when it comes to employees? I even know to play aggressively when I see a possible win on the other end.  

​The photo below is a photo of me winning my very first poker game (out of 50-ish people) in January of this year.  Crazy.  BTW, if you are a startup founder, I definitely recommend checking out Startup Haven and playing the Poker 2.0 games.  Super fun.  You don't have to know how to play poker to go.  

​8 startup lessons from poker

Last week, we had Phil Gordon in to play with us. Phil Gordon is a professional poker player who has placed multiple times in the World Series of Poker – a big deal. He’s been a commentator on poker games, designed digital poker games, and written several best sellers on poker. But more importantly, Phil is also an entrepreneur.

Before we started playing, Phil took some time to share some insights that would inspire us founders at the table: eight startup lessons we can learn from poker:

1. Be aggressive. Don’t just mimic competitors. That’s the opposite of innovating and leading. Take control of the betting. Generally, when it comes to people on the team (employees), I like to bet in favor of a person. Give someone the upper hand of what you can afford to compensate them with, especially in equity.
   
2. If you can’t be aggressive, fold. Folding is the next best option if you don’t have a hand worth betting on or raising. Calling says, “I don’t know if I have the best hand,” which is something you should never do. Winners make money because people call too much. In business, once you see that data is pointing in a different direction, stop playing “calls.” It might mean you don’t have product-market fit. Just pause and reassess the game. Don’t keep playing.
   
3. Have patience. Wait before you identify a profitable opportunity. Then wait some more. Don’t throw money here and there or you’ll run out if it.
   
4. Choose your ambitions. Be selective of what you go after. Then, once you choose what you want, go for it. Be the person who raises the stakes.
   
5. Have courage. You may know the right play, but it takes courage to act on it. Have courage and conviction, and aim for success.
   
6. Be resilient. Bad things are going to happen. A bad poker player will take the bad beat then instantly spew the rest of their chips. But it’s the bounce back that will define you and the way investors think about you. You can’t teach resilience. You either have it or you don’t.
   
7. Assume the game will be hard. Just like the game of poker, starting up is not easy. We had to pivot in May 2015, and I had to make some heart-wrenching decisions that involved letting go of my team and rebuilding it from scratch. But we were able to figure out a way to rebuild a different kind of team and continue to make progress.
   
8. Be observant. Look for tells. Tells are signs that give away the strength of a person’s hand. In the startup world, this means navigating to the spot competitors have overlooked and taking ownership of it. Always look for the one little tell or weakness in your industry, then be aggressive. Work your game and don’t be afraid to ask the better players for help. Take them up on their expertise, and always work to improve your own game.

​If you were to relate your startup journey to a poker tournament, where would you be right now? What does your hand look like? Are you being aggressive or not? 

If you’re to take any entrepreneurial lesson from poker, it’s to be real. Don’t talk yourself into playing if you don’t know that you have the best hand. How you get to the end does matter. Don’t sell yourself short by running out of fuel earlier than you want.

 I got a photo with Phil.  Neither of us won the poker game in February 2017.  :)
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--Arry
PS This article was originally posted here.