Poker, like entrepreneurship, is a game of skill, luck, and risk. You need to be willing to make bold moves, keep an eye on the competition, and develop a winning strategy in order for your efforts to pay off. Similarly, entrepreneurship is a high stakes game where you're gambling big and the odds are against you. But just like the game, a smart and motivated player can often come home with a huge jackpot.

Given the similarities between poker and starting your own company, it should come as no surprise that poker pros are drawn to the entrepreneurial lifestyle. Here are the stories of how three poker pros used their skills, daring attitudes, and even winnings from the game to build companies:

How a Winning Hand of Poker Became Funding

Former World Series of Poker champion David Daneshgar and two friends, Farbod Shoraka and Gregg Weisstein, started the company BloomNation in 2011. They hoped to make their online flower company a big success, but funding the initial development was a tricky proposition. After putting their personal finances together, they were still looking for ways to kickstart the company.

Thankfully, their luck was just beginning. The three friends discovered a nearby poker tournament where the first prize was more than $25,000. This would certainly be a big enough nest egg to get the next phase of the company up and running. The three founders decided together to take the risk, and 2008 World Series of Poker bracelet winner Daneshgar threw his hat into the ring.

"I thought we had lost," said Gregg Weisstein, co-founder of BloomNation. "David looked so composed and his opponent was filled with emotion. So I went up to him and asked what had happened. He looked me straight in the eye and said three words that would forever change the direction of this company: 'It's flower time!'"

As an entrepreneur, you have to learn how to bet on yourself. It's what Daneshgar and his co-founders did the moment they entered the championship that changed their lives. It's what any entrepreneur who is successful will have to do at some point in their career. One day, there will be a big risk you need to take, and so take the leap and trust in your abilities.

How Poker Taught One Entrepreneur to Hustle

Online poker professional Travis Biziorek stumbled upon his company almost by accident. The idea dawned on Biziorek when he was applying for law school and needed friends to edit his work. Out of this experience, online editing company Kibin was born, and soon Biziorek's poker skills came into play in a major way.

According to Biziorek, Kibin was born more of necessity. His personality wasn't the right fit for the 9-to-5 corporate gigs. He held about five good jobs out of college, leaving each one as corporate ennui took hold. After the risk and drama of playing professional poker, settling down into a cubicle was never in the cards for Biziorek. Instead, he decided to deal himself another exciting hand by starting his own company.

Biziorek used the same hustle in the poker world in his startup efforts. He raised money for Kibin and even got his company into 500startups.

"You don't become a professional or even a good poker player overnight, just like you're not going to immediately be good at fundraising," Biziorek said. "Just like you wouldn't head to the World Series of Poker without having played some smaller circuit events, you aren't going to attack your most sought after investor when you're still analyzing and honing your presenting skills."

He worked hard, slowly built his skills, and never took shortcuts. And the payout for him, personally and professionally, has been sweet. Plus, no more cubicles!

How One Poker Player Turned Entrepreneur Learned About Risk and Bootstrapping

When Andrew Seidman's company Digital Reach was founded in 2011, he was already a well-established poker player, so he knew a thing or two about risk. In fact, Seidman had even released a book on poker called Easy Game, currently in its third edition. He knew there was no magic bullet to find funding for his startup, and that bootstrapping was the best way to grow.

"From the beginning, I never wanted to raise money until I had significant traction," Seidman said. "Otherwise, raising money too often occurs on poor terms for the entrepreneur."

Often in poker, Seidman would see the players most focused on money bottom out far more quickly than those just looking to learn more about the game. As a poker player in college, he hadn't burned through his winnings as soon as he hit the jackpot. Instead he reinvested his money back into his poker career, allowing him to rise up the ladder. This bootstrapping strategy worked for poker in the same way as it's worked for his business, which has been able to grow organically and become profitable.

"I'd say that my poker skills were mostly useful for identifying areas of positive expectation and making calculated decisions without being overly risk-averse," Seidman said. "This allowed us to expand Digital Reach somewhat more rapidly--we felt comfortable making big bets on employees that we thought were winners or products that we thought would grow our business. Not all of those bets worked out, but I'm sure that we are farther along today than we would've been had we been risk-averse."

In business, as in the world of gaming, you need to be willing to take risks, hustle to get gain traction, and trust in your skills if you want your company to hit the jackpot.

What do you think? What poker lessons can be applied to running a company? Share in the comments!

Published on: Dec 4, 2014