For StumbleUpon and some of its investors, this isn't their first time at the rodeo. Founded in 2001 by some scrappy Canadians, the company moved to San Francisco and scored $1.5 million from investors in 2005. Those investors included Ram Shriram (Sherpalo Ventures) and First Round Capital.
In 2007, eBay purchased StumbleUpon for $75 million in cash. For early investors like Shriram, that was a nice payout.
Many questioned eBay's decision to purchase StumbleUpon -- the move never made much sense. In April 2009, StumbleUpon's founders bought the company back from eBay for a reported $29 million. The beauty of the buyback? Some of the investors -- including Sherpalo Ventures -- were the same investors in the pre-eBay days.
Now StumbleUpon has closed a second round of funding.
As it was in 2007, the content discovery space is now hot again. StumbleUpon is unique in that it has continued to grow its user base -- 14 million members and counting -- while also maintaining a presence in areas like mobile and video.
The founders of Foursquare are often praised for creating Dodgeball, selling the service to Google and then basically creating the same service all over again. From where I'm sitting, StumbleUpon and its long-time investors scored and even bigger coup. Create innovative web company. Sell said company for large chunk of cash. Buy company back for less than 50% of sales price. Raise additional funding for "new" company. Rinse. Repeat.