SecondMarket: Don't build a Homer-mobile

Bambi Francisco Roizen · May 26, 2010 · Short URL:

Founder and CEO Barry Silbert's lessons learned: Find the right partners; roll the dice

If you've spoken to enough entrepreneurs, you'll begin to realize that a good number of them iterate drastically over their original product. In fact, it's often the case that the "right" product and "right" business model is vastly different from the original product or assumptions. For Barry Silbert, founder and CEO of SecondMarket, a leading trading platform for illiquid shares, his entrepreneurial journey was no different.  

"One of the biggest mistakes we made early on was the first platform we built," he said, in this segment of Lessons Learned. "What we built was a Homer-mobile." Barry was referring to Homer Simpson's dream car, outfitted with unnecessary bells and whistles. The lesson? "Build from a base, from a core user base," said Barry.

It takes an entrepreneur to move forward, charge ahead and iterate. And, that's exactly what he did. In fact, SecondMarket shut down one platform and moved to another. "It was that dramatic.”

Other pieces of advice from Barry include:

1) Don't do it alone. Find someone with complementary skills.

2) Find investors who can be mentors. Barry refers to Larry Lenihan of FirstMark Capital as just that. FirstMark is one of the investors in SecondMarket's Series A round.

3) Roll the dice and take risks. "It's OK to make mistakes – entrepreneurs are risk-takers at heart," said Barry.
While entrepreneurs will always be dread failure, it's inevitable. Not all the decisions will be the right ones. It's moving on from those mistakes that count. 



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Bambi Francisco Roizen

Founder and CEO of Vator, a media and research firm for entrepreneurs and investors; Managing Director of Vator Health Fund; Co-Founder of Invent Health; Author and award-winning journalist.

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SecondMarket is the marketplace for alternative investments. It has become the online destination for accessing market data, building your investor network and transacting in assets such as private company stock, structured products, public equity and bankruptcy claims. SecondMarket centralizes and simplifies secondary market activity by connecting buyers and sellers, and providing world-class market and operations expertise. Since 2004, SecondMarket has brought together more than 75,000 individuals and institutions and completed billions of dollars in alternative investment transactions. SecondMarket is a registered broker-dealer and member of FINRA, MSRB and SIPC. For more information, please visit


Barry Silbert

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