Former MIT Blackjack Shark Whose Team Won Millions From Casinos Is Now Investing In Tons Of Startups

[This article originally appeared in Business Insider]

When Semyon Dukach was a student at MIT, he ran the best-performing Blackjack team the school has ever had. On a typical weekend, Dukach and his team of 60 students could win up to $150,000 by using a legal, card-counting system they created at MIT. They were so good, the group amassed more than $4 million and were often threatened or banned by casino managers.

“The [casinos] comped us to high heaven at first, then chased us out with occasional threats and faxed our pics around to other places,” Dukach said in an early interview with Gambling Planet. “We made a few million over a few years, but it was with a lot of people.”

Dukach, who has now invested in and founded a bunch of tech companies, considers that Blackjack team his first startup.

“It was a company, we paid taxes,” he tells Business Insider. But in the late 1990s, he became bothered that he wasn’t doing anything other than making money.

“Aside from proving I was smarter than a few people across the table from me, and aside from the money I won, I wasn’t being productive in society,” Dukach says. After a short stint in real estate, Dukach turned his attention to tech companies and took part in the dot-com boom.

His first startup was funded with $50,000 and ended up selling for $35 million in cash and stock in 2000. His second startup failed. He has since founded a few more companies with varying levels of success and failure.

For the past few years, he’s enjoyed angel investing. “Startups were more interesting than Blackjack — more fulfilling, and more enjoyable,” he recently told BetaBoston’s Kyle Alspach. His portfolio includes 75 companies.

Now, he’s been named managing director of Techstars in Boston, a prominent startup accelerator program that was founded by David Cohen in Boulder, Colorado. The opportunity came after Dukach found himself investing in a number of Techstars companies.

“As an investor/adviser, you make a small difference,” Dukach told BetaBoston. “But in Techstars, 90 percent of the teams get a big impact.”

“Techstars’ primary goal, like it was with my own angel investing, is to help entrepreneurs,” Dukach tells Business Insider. “My own personal impact as an angel investor is limited. I don’t spend that much time with any one startup. I’m just one guy. At Techstars, there are over 100 really amazing mentors and high-quality [founders]. The companies are not the same going in to Techstars as they are going out.”