VC’s Lament: the ones that got away

May 18, 2010

Vic Gundotra, Vice President of engineering at Google (R) and Omar Hamoui, founder and CEO of AdMob converse during the "Mobile: Where's The Money Going?" panel at the Fortune Tech Brainstorm 2009 in Pasadena, California July 23, 2009. REUTERS/Fred Prouser
Whether it’s passing up on a ticket to Woodstock or not buying Apple stock at $80 a share in January 2009, everybody has regrets.

So what do VCs regret?

We asked the panel of three money-men gathered for the VC Panel at the Reuters Technology Summit for their biggest laments when it comes to the deals they let get away.

“For me the one that comes to mind is AdMob,” said Khosla Ventures partner David Weiden, referring to the mobile advertising firm that Google announced plans to acquire for $750 million in November.

“I talked to Omar (Hamoui, AdMob’s founder and CEO) when he was one employee and spent a bunch of time with him early on and then we didn’t end up doing the investment together and I absolutely regret that,” he said.

Of course, with the Google acquisition now being held up by regulators, AdMob could end up remaining independent after all.

Accel Partner’s Richard Wong did take a chance on AdMob, with Wong now sitting on the company’s board of directors. Wong’s biggest regret has to do with Siri, a maker of voice-activated smartphone software for handling personal tasks that was recently acquired by Apple for an undisclosed sum.

“I remember looking at it, you have a clean shot at it…you just have to have the conviction to do it,” said Wong, who cited worries about how the application would get customers and compete against the likes of Google as issues that gave him cold feet.

Chris Moore, a partner at Redpoint Ventures had an early look at LinkedIn, the Internet social network for professionals that now counts more than 65 million users.

“I remember thinking about how useful this app was to me at the early stages, and not being able to squint to see the business model,” said Moore, who recalls telling LinkedIn co-founder Reed Hoffman that a deal wouldn’t happen.

“In hindsight the utility of the application and the focus is just enormous,” said Moore.

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[...] But consider the alternative — not investing in a winner… [...]

[...] But consider the alternative — not investing in a winner… [...]

[...] But consider the alternative — not investing in a winner… [...]