How playing poker can make you a better CEO

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It's not hard to find similarities between running a startup and playing a high-stakes poker game on a green baize-covered table. Business and poker both require you to assess risk, analyze your competition, be aggressive, control your emotions, and--of course--know when to hold and when to fold.

Entrepreneurs who are poker aficionados say the game has helped them run their companies more effectively.

"Poker is a perfect microcosm for business," says Geoff Woo, co-founder of Nootrobox, a San Francisco startup that makes cognitive supplements. "It's a great way to train your assessment and decision-making with incomplete information."

As a Stanford student from 2007 to 2011, Woo used to spend his weekend nights playing poker online (before the 2011 ban in the U.S.) or live at Lucky Chances casino in South San Francisco. While never a serious player--his biggest win was $1,000--he was a student of the game's strategy and its uncanny applicability for entrepreneurs.

Poker is an overly "simplified" game version of running a startup, Woo says. "Everything you have is uncertain, and you need confidence in what you know and what your assets are," he says. The game has helped him be more decisive in a fast-paced, high-stakes environment, without all the information he'd like to have before making a decision.

Woo says he was too afraid to be aggressive in poker at first. But once he started to bluff, reraise a player's bet, and call out an opponent's bluff, he started to perform better. He brought that aggressive confidence to his startup.

"In the business version [of bluffing], you're believing in this crazy weird idea and making a big bet--that's what running a startup is all about," Woo says. "When you do and you're running the table, people respond."

Woo isn't the only startup founder who says poker has helped his CEO game. In submissions to Inc.'s 30 Under 30 contest, a number of applicants like Woo noted that poker has made them a better leader.

Tom Popomaronis, founder of OpiaTalk, a Baltimore startup that makes promotional coupons for e-commerce companies, was an avid online poker player from 2003 until 2009. Popomaronis, who made $45,000 in poker earnings, says his card sharp days gave him a crash course in how to be a better listener, which helps him be a better CEO.

"Poker forced me to listen to the opponent's verbal and nonverbal cues--is his hand moving, is he looking at me, can you see his pulse beating in the side of his neck, is he sweating?" Popomaronis says. "Over time you improve your read on people."

At OpiaTalk, Popomaronis says he uses his poker skills to solve problems by being aware of minute details while speaking with employees, investors, and customers. The game has also taught him to harness and redirect emotion "so you can continue moving forward without jeopardizing yourself and/or your team," he says.

The last time Popomaronis played was at the World Series of Poker circuit in Baltimore in August 2015, where he ranked seventh after almost 10 hours and took home $1,262. At one point, Popomaronis was down to 200 chips; he had 10,000 at the beginning of the tournament. He ended up coming back to finish in the top 10, but it required patience to hold onto those chips and wait to find the right hand to go all in with.

"You have to wait and wait," he says. "All entrepreneurs have been in this position, we've all had only 200 'chips' left and had to figure out how and when to double up, how to get to 400, then 800 and beyond. That happens with startup life all the time. You need to have the ability to rise back up after being knocked down."

(Shortly before this article was published, Popomaronis said he made the difficult decision to shut down OpiaTalk's operations due to lack of funding. "The 'folding' analogy is quite fitting," he said. Popomaronis is now the interim president of RateMyTeachers.)

Suneera Madhani, the founder of Orlando, Florida, startup FattMerchant, a provider of flat-rate credit card processing, says poker has helped her manage being the only woman in the room as a fintech startup CEO.

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"I've never sat at a table and thought gender was a reason I couldn't play," Madhani says. "I apply the same philosophy to FattMerchant today."

Madhani, who has been playing poker for 10 years, says she is usually the only woman at the table. The same goes for when she meets with investors. Over the past 18 months, Madhani has grown her startup from zero to 24 employees, raised over $2 million in venture capital, and created a competitive product in the saturated market of merchant services.

Madhani says FattMerchant closed a $1.3 million Series A round shortly after it raised its seed round, all the while, she says, she was seven months pregnant.

"I had to address my pregnancy, explain my plan for when the baby arrives, tell investors how I won't abandon the business for my child," she says. "I never thought of gender as a reason to hold me back nor have I ever felt I didn't belong somewhere although it was male-dominated."

The biggest lesson poker has taught her? Winning is less about the hand you have and more about sticking to your process--a calm, cool, and collected process that never wavers, Madhani says.

"You have to understand who you're competing against, analyze your competition, and know what decisions they'll be making based on their position," Madhani says. "Poker, like business, is a game of strategy. It's a game to be won. If you follow that process, the odds will be in your favor."

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