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Season 03 / Episode 02

Playing the Odds with Semyon Dukach

Leaving your home country isn’t easy. Overcoming a language barrier is hard too. Being socially isolated isn’t what most people would pick for themselves, especially while growing up. But it was overcoming all those challenges that gave Semyon Dukach the grit and willpower to reach what he wanted, like joining the infamous MIT blackjack team, founding and selling his software firm, and driving returns as an angel and VC investor. Today as the managing partner at One Way Ventures, he’s betting on other immigrants to have the same determination that brought his success.

“You have to learn a new language. Learn a new culture. Build a network from scratch without having had one already. You’re more likely to figure out how to navigate the confusing environment where these bigger company executives are making deals to exclude startups. But you’re okay with that, because you already have been in a place where people are excluding you and you found the way in.”

There are parts of Semyon Dukach’s life that sound like they’re straight out of a Hollywood movie. Like when his family fled the Soviet Union with barely more than the clothes on their backs. Or when he joined the MIT Blackjack team and made millions beating the casinos at their own game. Or when he sold his software company just before the DotCom bubble burst of 2000. And from his years as an angel and venture investor, he’s had a supporting role in hundreds of founding stories. But when he was in the middle of those experiences, they didn’t feel like a Hollywood blockbuster. They felt like hard work, day after day, often unjust and unfair. But it’s the lessons learned and character built in those hard times, high stakes, and difficult decisions that ultimately produced his success. Today Semyon leads One Way Ventures, focused on finding and investing in immigrant founders just like he was — determined, hungry, and ready for the challenge.

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