Summary:

Aydin Senkut, an early employee at Google, was the company’s first product manager, then its first head of international sales. He’s has now been an angel investor for four-and-a-half years and recently closed a fund of about $40 million at Felicis Ventures.

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In any ranking of angel investors (including this one from BusinessWeek), Aydin Senkut would undoubtedly place near the top. An early employee at Google — he joined when there were just 30 employees and became the company’s first product manager, then its first head of international sales — Senkut has now been an angel investor for four-and-a-half years and recently closed a fund of about $40 million at Felicis Ventures. His portfolio includes companies such as Aardvark (acquired by Google), Disqus, Imageshack, Justin.tv, Mint (acquired by Intuit), Posterous, Powerset (acquired by Microsoft), Tapulous (acquired by Disney), and YuMe.

Om spoke with Senkut recently about how Google has changed since he joined, and what the startup and venture capital landscape looks like. Among other things, the angel investor said that the search company changed dramatically even in the time he was there, going from just 30 people to more than 3,000 by the time he left. (It now has more than 20,000.) The early generation of Google staffers, Senkut says, “tend to be more on the humble side, which I think is a real important value that all investors should have.” He also says that the exciting thing about the early days at the company was “it was a blank slate… we could see the changes happening before our eyes,” including an early demo of what became Gmail, which creator Paul Buchheit (who left to start FriendFeed, later acquired by Facebook) demonstrated one day to Marissa Meyer.

“Those days were special,” says Senkut. Google founders Larry Page and Sergey Brin said “anything that can’t be done with a team of three people in three months shouldn’t be done. Those were the good old days.” Now, he says, “the stakes are much higher,” since the company is competing in a completely different landscape, and has “many more administrative layers.” In many ways, the angel investor says, “it was a miracle that Google could keep its culture for as long as it did.” Senkut warns his former employer to make sure it wasn’t smothering its talented staffers in multiple layers of bureaucracy:

Google has to really watch out as far as the talent they have internally and really keep empowering them and not necessarily losing them in multiple layers of administration and management.

Senkut says in the interview that while it’s good to see so many angel investors pursing the startup market, not all of them will likely survive:

“I believe in the power of the marketplace,” he says. “At the end of the day we are all judged by concrete achievements, be that the number of exits, number of companies created, exit multiples and so on.”

When it comes to Felicis Ventures’s own track record, Senkut says that 16 of the company’s investments have been acquired, and others are growing strongly. He says the VC industry is going through its own form of “Darwinism,” and not everyone will remain standing once the current phase is over.

The angel investor also says he sees great opportunities in several major investment areas, including education (where Senkut has investments such as Inkling, which is developing interactive textbooks for the iPad), health care and energy conservation. “I know there will be great companies created in these areas,” he says. Senkut also says he is focusing his portfolio on mobile, e-commerce and enterprise applications, especially mobile, which is “like the early days of the internet.” E-commerce is also “a huge opportunity,” he says, and companies that can tie online behavior to offline commerce will have found “the holy grail.”

Video produced and edited by Chris Albrecht.

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