I am angel investor and a serial entrepreneur, passionate about helping young entrepreneurs realize their most daring dreams.

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. The company started with $50,000 in angel money in 1997 and was sold in 2000 with dozens of Fortune 500 customers for $35 million in cash and stock.

I co-founded but was not involved in the daily operations of Vert, a company that produced bright outdoor displays on top of cabs with location-specific video ads. The startup raised over $5 million in venture capital but failed after the ad market collapsed.

At AccuRev, which developed version control software, I was a lead angel investor and interim CEO in 2001. The company raised some venture capital money and is now profitable, with more than 600 enterprise customers.

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. Today the company has more than 10,000 customers worldwide after 40 consecutive quarters of growth. It went public without a bank in 2011 and began to pay substantial dividends in 2012.

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 board director. The company has been profitable and is growing fast, with tens of thousands of happy users.

For a complete list of companies I have invested in and mentored, see the My StartUps page.

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. My goal is to support and guide young, ambitious people from all walks of life who are motivated to create companies that can make a positive impact on our world.

In addition to my angel and entrepreneurial activities I support some causes, including the Carter Center and my own Troublemaker Award. I also serve as a judge for the Lemelson / MIT student inventiveness prize, as well as for Mass Challenge.

I love to spend time with my wife, Natasha, and my five kids (Dagny, Miranda, Zoe, Uliana, and Elio). I windsurf whenever possible and ride my bike through red lights, but I sold my helicopter to quit while I'm ahead.