ask him what’s the difference between blackjack and Techstars:
Blackjack was about maximizing the amount of cash—“taking money from people, using our heads,” he says. “I think that was a waste of my time. It was not worth the years I devoted to it.”
Now, as an angel investor and incoming Techstars Boston head, he gets to work on behalf of the entrepreneurs, he says. “I went from a place where you care about others the least—we hated the casinos—to the other extreme where you care about people the most.”
That might sound like lip service from a lot of investors. They care about entrepreneurs, but ultimately they have to serve their own masters, namely the limited partners in their funds. But Dukach has been on the record before saying that his loyalty is to people, not to institutions (more on that below).
He also likes to promote “troublemaking,” via an annual $10,000 cash award that he has given out for two years. The most recent one went to Nadezhda Tolokonnikova, the formerly imprisoned Pussy Riot member. Dukach gave her the prize in February, in a backstage dressing room at an Amnesty International benefit concert in New York that included Madonna and Yoko Ono as speakers.
Like a lot of outsiders, Dukach originally thought Techstars companies do well because of the rigorous selection process. But after becoming a Techstars mentor and then going full-time, he has come around to a fuller appreciation of what goes on in the bootcamp. “The whole program is as intense as I am,” he says. “A lot of the companies aren’t that strong coming in, but they get super-strong going out.”
He says he’s been learning the ropes from Rae over the past few months, working very closely with the current startup class. “I have a hell of a lot to learn,” he says.
“You get this feeling in a class that everyone is in the same boat,” Dukach says. “People go through hell and high water. Companies really get thrown around, and often they change direction, they question things, they get broken down and built up again. They become vulnerable, and they express doubts and fears. And people get very open to each other. In that environment, you can make an advisory impact. There’s a lot of trust. It’s extremely fulfilling to be a mentor. It’s super high-impact.”
And that seems to be why he’s joining Techstars instead of staying independent. “In the angel investing I’m doing, I finally discovered something I want to do forever,” he says. “It makes me happy, it’s what I’m best at. At Techstars you can’t do it alone. I get to draw on the best mentors in Boston. It’s a huge multiplier of my time.”
He stresses that he sees himself as primarily advocating for entrepreneurs in the program. If he makes money for Techstars and for himself—he became a limited partner in the most recent Techstars Boston fund, which covers the current class—that’s great. But his first priority is the startups.
“I am going to 100 percent work for the entrepreneurs. My loyalty is to the entrepreneurs,” Dukach says. “I believe investors will be well served by that.”
I pressed him a bit more on that point. “Of course my natural instincts are to maximize my own rewards, but I’ve learned to suppress them,” he says. “I make myself push in the direction of how can I help them. It comes down to empathy and love. The relationships are personal. I bond with these people and I care about them.” The best investors, he says, “give, give, give, and good things come back. I know if I do the best thing for the companies, and only for the companies, the value is going to come.”
Still, he hasn’t expressed a high opinion of the venture-capital world in general. Is that a liability when it comes to promoting VC investments in Techstars companies—or any of his companies, for that matter?
Fair question, he says. “I have close relationships with angels, but not as much with VCs. I’m intending to grow that network. It’s a critical part of the ecosystem. But the way to get VCs to be more and more excited about the program is not to hang out with them and play golf with them. It’s to make the teams more awesome. I’ll reach out to the VCs, but my attention is on the teams.” (In any case, my observation is that VC outsiders sometimes become effective VCs.)
One more thing to keep an eye on is Dukach’s global connections. “I have reasonably strong networks in eastern Europe,” he says. That might mean more recruitment of international companies to Boston—a trend we’re already seeing around town.
Local entrepreneurs have strong advice for Dukach. “Katie and Reed brought experience in entrepreneurship, product development, and early-stage investing,” says Jennifer Lum, an angel investor and co-founder of Adelphic Mobile. “The next Techstars director must be able to provide hands-on coaching and maintain the highly engaged support network that has been built over the past four years.”
Lum points out that Techstars has helped Boston’s tech community “rally around the participating teams.” To keep it going, she says, “it’s important that the next director continue to foster a high level of community engagement to help the teams develop their products, grow their businesses, and raise capital.”
