Born and raised in Moscow, Russia, I came to the U.S. with my family as a 10-year-old kid in 1979. I have always had an interest in technology, so I studied computer science at Columbia University and co-authored work on virtual worlds at IBM Research in 1988. After taking a year to hitchhike through Southeast Asia, I went on to grad school at MIT, where in 1992 I authored the Simple Network Payment Protocol, which was one of the earliest ways to transfer money on the Internet. Shortly after, I joined the MIT blackjack team and spent several years with my teammates feeling smug about being able to beat casinos around the world out of a few million dollars before finally realizing that it’s not as much of a challenge as it might seem.

Since then I have played key roles in several startups, learning a great deal from the successful ones and even more from the ones that failed.

I founded and ran Fast Engines, an enterprise software solution to speed up Web apps using the FastCGI protocol. I also Vert, a company that produced bright outdoor displays on top of cabs with location-specific video ads. In 2001, I was a lead angel investor and interim CEO at AccuRev, which developed version control software.

In exchange for some AccuRev stock, I acquired SMTP.com, a bootstrapped email delivery provider. I served as board chairman and managed the startup on an as-needed basis.

In 2006 I founded GottaFlirt.com, a dating game that failed to reach critical mass after spending $500,000 in angel money. In 2008 I also co-founded PDFFiller.com, which allows PDF files to be filled online, and served as a board director.

In 2012 I decided to leave my position as CEO of SMTP and focus full time on my angel investing activities and mentoring young entrepreneurs. During my time as an angel investor, I have made over 100 investments, including early investments in Quanergy, SMTP.com, and Wanderu.

In 2012, I also started giving out a Troublemaker Award. The award seeks out young women and men from around the globe who demonstrate outstanding commitment to a cause that is bending norms and breaking rules for the greater good.

In 2014 I became the Managing Director of Techstars (Boston), where I sourced, invested, and nurtured over 50 startups. Some of the alumni from my time there include LovePop, Fam, RocketBook, Mavrck, ThriveHive, AdmitHub, Spoiler Alert, and Tive.

It was during my time at Techstars that I met my current Managing Partner, Eveline Buchatskiy, who is an immigrant from Brazil and a former Director of the Techstars Boston program. We decided that we wanted to start a venture fund with a mission, and supporting immigrant founders was one we were both eager to get behind.

In 2017 we left Techstars and founded One Way Ventures, and we are currently investing our first fund.

In my free time, I love to spend time with my wife, Natasha, and my six kids (Dagny, Miranda, Zoe, Uliana, Elio, and Milan). I kitesurf and run whenever possible, but I sold my helicopter to quit while I’m ahead.