The MIT blackjack prodigy who inspired the movie '21' tells his employees to make mistakes every day
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But Lee has quietly carved out a successful tech career over the past two decades, taking his first startup, a marketing software maker Unica, public in 2005, before selling it to IBM for about $500 million in 2010.
Now he's running Allego, a sales education startup that he describes as a "corporate YouTube" for the vast number of training videos available on its platform.
Lee likes to apply some of the learnings from his blackjack playing days to actual business. One of them, as he told in an interview with the NYTimes' Adam Bryant, is about making mistakes. He said:
"We tell people you've got to love your mistake. If you go through a whole day without making a mistake, you just wasted a whole day because you probably haven't pushed yourself.
So we try to train and tell every employee that if you can truly embrace your mistake, and not feel this visceral defensive reaction when someone tells you that you did something wrong, you're going to go so much further than anybody else. You need to see mistakes as opportunities to improve."
Lee further elaborated his thinking in a previous interview with Business Insider, describing this mental toughness as "emotional fortitude." He said blackjack takes you through all kinds of emotional volatility, as you can lose a ton of money in one mistake, and it actually teaches you how to become stronger and a better decision-maker.
"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. It's taught me to have conviction in what you do," Lee told us.
You can read the full New York Times interview here>>