Playing blackjack helps in business, according to Allego CEO Yuchun Lee.

He would know because he was part of the infamous MIT blackjack team that inspired the 2008 Kevin Spacey movie "21."

"Blackjack has really strengthened me over the years, to go through the ups and downs of business," Lee told Business Insider.

Lee has the track record to back it up. He took his first startup, a marketing software maker Unica, public in 2005, before selling it to IBM for about $500 million in 2010.

After spending a few years as an IBM executive, Lee has launched another startup called Allego in 2013, which provides a sales learning platform service for companies.

"You may not win all the time, but you increase your odds a lot if you find something you love to do," Lee said. "And over the long run, you’re going to win."

Blackjack prodigy

Lee wasn't part of the blackjack team while he was a student at MIT in the 90s. It was only after he graduated and started running Unica that he joined it.

Regardless, Lee has fond memories of the team, in which he spent nearly 6 years flying to Vegas almost every weekend. He says the team doubled its money every year, racking up "millions of millions" in cash. It was a well-organized group that paid taxes every year, too.

But he points out it was important to keep the blackjack separate from his business. "Even though there were 5 employees at Unica that were on the team, and we did practice after office hours together — we never mixed the two bank accounts," he said.

View photos Blackjack Hippodrome Casino Bet More

"Emotional fortitude"

Despite the firewall between his blackjack life and CEO life, Lee says he did apply a lot of the basic principles he's learned from playing the game to business.

One of them is building the "stomach" to survive the swings in a business cycle. Lee says he went through 4 recessions and 3 wars during his 18 years running Unica, and part of the success has to do with having that "emotional fortitude."

"If you ever want to experience volatility, many ups and downs emotionally, there’s nothing better than joining a professional blackjack team where you can win or lose so much money just by the sheer randomness of the game," Lee said. "It's taught me to have conviction in what you do."

Another takeaway is to enjoy the "David versus Goliath sort of feeling" as a startup. Just as his small blackjack team went up against the house at the casino, you have to learn how to succeed when the odds are against you as a startup, he says.

It's one reason why he bootstrapped both of his startups, and didn't take any VC money early on. He believes you become "less discriminatory" when it comes to spending money and allocating resources if you have too much money in the early stages.

"Not having money is a strong incentive to help you make the best decision possible," he said.

Fixing a broken system

View photos Allego CEO Yuchun Lee More

Lee hopes to apply the same principles in his latest startup, Allego.

Launched in 2013, Allego offers a hosting platform for corporate training videos. It doesn't produce the actual videos, but makes it easy for companies to create and share videos that help train sales people. It also makes it easy for managers to give quizzes, and feedback, while collecting real-time data on each sales rep. Lee describes it as a "corporate YouTube," only with more interaction and business content.

Story continues