Yuchun Lee, the son of a Taiwanese ship captain, earned concurrent bachelor's and master's degrees (in electrical engineering and computer science) at MIT and founded his second company while on the school's notorious blackjack team. After that company--Unica--sold for half a billion dollars, he co-founded the Needham, Massachusetts-based online training company Allego, using skills he picked up at school and casinos. --As told to Zachary Lipez

Risky business

I was on an MIT blackjack team for six years. The camaraderie on that team is pretty phenomenal. The money you make is phenomenal as well. You can win or lose thousands of dollars in five minutes. So I've learned to have a very healthy relationship with risk. I was running Unica while I was doing blackjack. I'd work all week, fly Friday evening to Vegas, play all weekend, come home on a redeye, and go back to work. Unica's applications helped companies automate their marketing. We pretty much exhausted all the wrong answers one could run into--that set of scars really helped me later. We went public in 2005. IBM bought us in 2010.

Training brains

One of the biggest challenges in the world is that everybody tries to do a good job at work, but they're going through some antiquated training process that's just not equipping people to be good at what they do. The better way to learn is to look at how the brain works. Human beings don't do well sitting in a classroom, getting crammed with 20 hours of information. They learn if you give them bite-size chunks of knowledge and repeat them over time, or if you embed the skills they need to learn in a game and they compete against one another.

A simple solution

We started Allego in 2013. My co-founder, Mark Magnacca, was a trainer for finance people. He was using iPads and iPhones to record people pitching and then emailing the files to their managers and asking for feedback. But when you email five or 10 three-minute videos, you can crash servers. Mark asked me to consult on that problem. I said, "Are you sure you don't want to build a software company? That would solve this once and for all." He said, "I don't know anything about software." And I told him, "Well, I do."