Serial entrepreneur Mike Cassidy sells Ruba to Google

Mike Cassidy has scored multiple hits as a serial entrepreneur. His latest coup is selling his online travel site Ruba to Google today, according to a Ruba blog post.

Terms of the deal haven’t been disclosed. Cassidy himself tweeted the news, saying “Now I’m a Googler. Very excited!” On Monday, Ruba’s team will move into the Google headquarters.

Ruba is just 15 months old. It has created a visual travel site and community with a focus on guides, photos, maps and interactive tour listings — all for improving the online travel research experience. Google will integrate Ruba into its iGoogle personalized information service.

Cassidy scored big with other company exits in the past, including Xfire, Direct Hit and Stylus.

But there’s an interesting personal connection here. Cassidy’s last startup was Xfire, an instant messenger system for gamers that MTV Networks bought for $110 million. Cassidy’s co-founder and head of marketing there was David Lawee. Lawee is now vice president of corporate development at Google in charge of mergers and acquisitions, and he’s buying his old boss’s new company. How’s that for an inner circle in Silicon Valley?

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  1. [...] Raise smaller rounds. Cassidy recommends raising smaller amounts of VC funding, because they can propel you quickly to the next step in your business, with minimal dilution. You can raise money later at higher multiples. The results speak for themselves: He sold Stylus Innovation for $13 million after he and his founders put a total of $1,500 into the company to start with — a near 10,000 times return, he notes. With Direct Hit, he took about $1.3M in funding in his first round, and produced $532M the eventual exit in a year and a half to AskJeeves. With Xfire, he raised $1M, and sold it to MTV/Viacom for $110 within two years. With Ruba, he raised a first round, and Google bought the company within two years after he launched it, but he isn’t saying for how much. [...]

  2. [...] Raise smaller rounds. Cassidy recommends raising smaller amounts of VC funding, because they can propel you quickly to the next step in your business, with minimal dilution. You can raise money later at higher multiples. The results speak for themselves: He sold Stylus Innovation for $13 million after he and his founders put a total of $1,500 into the company to start with — a near 10,000 times return, he notes. With Direct Hit, he took about $1.3M in funding in his first round, and produced $532M the eventual exit in a year and a half to AskJeeves. With Xfire, he raised $1M, and sold it to MTV/Viacom for $110 within two years. With Ruba, he raised a first round, and Google bought the company within two years after he launched it, but he isn’t saying for how much. [...]