Why being a Techstars chief beats being a blackjack whiz: a chat with Semyon Dukach

Techstars Boston director Semyon Dukach (photo by Kyle Alspach)
Techstars Boston director Semyon Dukach (photo by Kyle Alspach)

Semyon Dukach will probably always be most famous for his blackjack-related exploits as a young man studying at MIT. He was the main figure in a bestselling Ben Mezrich book (“Busting Vegas“), after all.

But Dukach, the brand new head of the Techstars Boston startup accelerator, doesn’t envy that younger version of himself. He made loads of money through a novel — and legal — system he invented for winning at blackjack. But as he told me during an interview Thursday, he now sees blackjack success as “pointless.”

“You have money, and that’s all you have,” he said.

It didn’t take long, Dukach said, to realize that “startups were more interesting than blackjack — more fulfilling, and more enjoyable.”

Since giving up blackjack in 1996 — he says he hasn’t played for meaningful stakes ever since — Dukach has gone the entrepreneurial and then investor route. He founded a series of companies, one of which went public, email delivery provider SMTP. Dukach then became a full-time angel investor three years ago.

In that role he became a frequent backer of Techstars Boston startups, including investing into seven of the 14 startups in the spring 2013 program. Dukach said he’s found a greater passion for serving as an advisor to young startups than he ever did at the blackjack table, or even as an entrepreneur. As an angel investor, he said, “I found myself.”

Dukach says he’s currently an investor in 75 different startups.

He sees Techstars — a three-month program focused on developing startups into real companies — as a chance to magnify the help he can provide to startups.

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

Here are a few other topics Dukach shared about during our hour-long conversation.

Why Dukach couldn’t have gotten into Techstars. “I was starting companies to make money. I never had that passion for customers.”

Why Techstars works. “In this environment, you’re forced to discover the best business.”

Katie Rae’s impact. “Katie was literally a parental figure … Often she told (the founders) things that were hard to hear, that were highly critical — and they listened to her.” (Rae and co-leader Reed Sturtevant concluded their final Techstars Boston session with the Demo Day on Tuesday.)

Upcoming programs. “We will do them every nine months. This last one was late because of the move (from Cambridge to Boston). We’ll do four programs over three years.” The next program begins Aug. 11.

Kyle Alspach has worked in journalism in Massachusetts since 2005 and was one of the original staff writers at BetaBoston.
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