4 Lessons for Entrepreneurial Success From Professional Poker

Founders need more than just a little persistence. Their primary role involves resolving issues and putting out fires right and left, taking a breather, and then doing it all again—despite the wounds to ego and mental and emotional fatigue.

Poker is a lot like that, too.

Most people don’t have the stomach or patience for this kind of persistence. When you play poker, you play the long game. Success doesn’t happen overnight; you have to make decisions on the basis of incomplete information. If you don’t stick to winning strategies that give you an edge, you’re sunk. Still, it can be tough to hold onto your endgame strategies when they produce short-term losses.

What I learned during my years playing professional poker has given me distinct advantages in business that college courses simply couldn’t. Making decisions hunkered behind a handful of playing cards, I developed tenacity and motivation. I also found out just how tough it is to keep calm with chaos swirling all around you.

Related: 7 Ways to Persist When Everything in You Wants to Give Up

A Poker State of Mind

Overcoming small failures on the road to “the big win” is par for the course in both business and competitive poker. Here are four lessons I’ve learned as a professional poker player and a founder/CEO. Apply them liberally to your own entrepreneurship.

1. Stick to your principles.

Even when you feel pressured to abandon them. Be resilient and dig your heels in to defy those naysayers who don’t share your vision.

I played mostly cash games, for example, but one year, I decided to try out for big tournaments, including the infamous World Series of Poker Main Event in Las Vegas. After playing in several of these events, I was out $2,000 and psychologically and emotionally crippled by tens of thousands more dollars in would-be winnings. Analyzing my play, though, I realized those “near misses” indicated my overall strategy was working. So I tried my hand again, won, and proceeded to win two out of the next three satellite events I played, which I cashed in.

Similarly, my organization’s tech-platform build initially killed our services margins, strained our profits and losses, and ate up my time and focus. When early versions of our tech (which uses data to develop effective marketing strategies across all channels and funnel stages to drive growth for our customers) weren’t strategist-friendly, resulting in more work for everyone, I asked the same questions I had after my poker losses: Why risk more, especially when the emotional toll hasn’t even reached its peak?

Because I had my sights set on executing a sound strategy and achieving grander vision.

 

Holding tight to that long-term vision of what we wanted the future to look like, we reached the other side stronger, bolder and more focused.

 

While Ladder is successful today, it won’t surprise you to hear that a lot of people told me to stop building our technology early on. Looking at the short-term snapshot, their arguments were based on sound principles: We were bleeding all over the place. However, holding tight to that long-term vision of what we wanted the future to look like, we reached the other side stronger, bolder and more focused.

2. Be open to pivoting on those principles.

But only when you have new information that contradicts previously held assumptions.

Poker is a game of data analysis. You’re constantly presented with new information as you play, whether it’s the cards on the table, the ones in your hand or the opponents sitting across from you. Every second brings something new. The dealer pulls two aces in the flop. An opponent raises and doubles the pot. Another shows his tell—a scratch of the nose or an adjustment of a hat.

Related: Do You Have Adaptability?

Each of these actions, and every bit of data you gather along the way, requires a rapid re-evaluation of your strategy. What worked so far may not work on your next hand. The best poker players pivot their approaches on the basis of these insights to tackle the challenge with a new strategy—one that learns not just from the actions of opponents or the cards on the table, but also from the successes of their prior strategies.

Sometimes, it’s good to pivot, but you have to know when. Listen to trusted colleagues with an open mind in order to increase your listening skills and decrease knee-jerk decision-making. It’s tough to hear frank suggestions, but treat them as opportunities to better your company. Ladder, for example, started out operating on a weekly sprint cycle—every week, creating, testing, learning from three new growth experiments, and evolving our strategy. It was a well-oiled machine for a time, but all machines eventually need a little TLC. When we moved to a service-delivery model in 2016, our team realized weekly sprints were no longer viable.

The overly intense pace had become a pain point. After some serious soul-searching, I determined we had to move to a monthly sprint. Since then, we’ve seen better client relationships and lowered stress. It was the right time to pivot; if I hadn’t been willing to change, we never would have gotten to this better place.

3. Accept defeats, and move on.

In business, you’ll have lots of them. Play enough poker, and you’ll find out winning growth curves aren’t linear—they’re rough and jagged. You lose sometimes. If you recover from those losses with new knowledge about why things happened, it makes you stronger and better positioned to win the long game.

When I placed second at my first satellite event, for example, I hadn’t made a mistake; I lost in a coin-flip situation with a 50/50 chance. At the age of 23, I felt like an all-expenses-paid trip to the Bahamas and an opportunity to compete for millions of dollars had been snatched from my fingertips. Despite those setbacks, I played three more tourneys and lost each time.

Instinctually, I wanted to stop. Then, objectivity shook me—hard. As I said earlier, my overall strategy clearly gave me a winning edge. I just had to stay focused. When I tried my hand several more times, I won, again and again and again.

Related: 8 Daily Habits to Build Resiliency

 

What if I’d given up before having my post-meltdown epiphany? Cynicism has no place in battles or in business.

 

What if I’d given up before having my post-meltdown epiphany? Cynicism has no place in battles or in business; unfortunate events can and will happen. It’s what you do next that matters.

In the last quarter of 2016, for instance, we had a sales meltdown of our European monthly recurring revenue that brought it to virtually zero dollars, uprooting our forecast model. Then, in the first quarter of 2017, a full third of our monthly recurring revenue cliff-dived due to renewing contracts. It was the equivalent of that meteor that wiped out T. rex and his buddies.

Despite this painful pill, we soldiered on. And guess what? Our growth graph looks pretty sweet as I write, with a 100 percent uptick in the past six months, proving that the outcome can’t always be predicted by what appear to be catastrophic individual events.

4. Don’t let randomness fool you.

A streak of amazing wins tempts you to believe you’re infallible. This trick the mind plays on you leaves you vulnerable to adopting losing strategies.

You’re rarely the only cause when things go poorly, but it’s even more important to remember: You’re not the single cause when things go well, either. Without analyzing areas of potential improvement, you’re opening yourself up to possible losses.

Simultaneously, attack your worries. Your job is to be two steps ahead of competitors, and the only way to do that is to defeat anxiety. Admit it exists, and then cage it. Don’t use it as an excuse to become a jerk. Worry has no place in the startup world; it can only turn partnerships sour.

For a long time, our business was unfundable, without the classic model or product most investors want. Not being taken seriously by the investment community really hurt. I never wanted to pivot as much as I did then, but that would have meant changing our road map and ditching our technology altogether. Instead, I went back to work in the trenches, and the pain and worry subsided. I stopped focusing on becoming something we weren’t and doubled down on doing what we were good at.

When I took our sales back on after a hiatus, we immediately saw an amazing streak of wins. I could puff out my chest and say my selling prowess was the reason, but the truth is more complicated. My sales were also driven by my marketing team’s ability to get great leads, which came through continuously improving our sales process and material on every level. I’m not one to bask in the sun of perceived success. My years of professional poker made me wary of the allure of the “obvious” answer.

Do you have to compete in national and international poker tour events to succeed in the corporate world? Of course not. You just have to listen to people who have been there and done that, then springboard off their hard-won lessons to accomplish your own goals.

Still, I have to be honest: It never hurts to have a good poker face.

Related: 5 Traits of Naturally Resilient People

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Jon Brody

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