With Lightbank, Groupon founders spread their wings as Chicago’s angels

Where I’ve Been, developers of a Facebook application that lets friends discuss travel plans, today announced it has secured Series A funding — its first formal round — for $750,000. While the size of the round is smaller than an angel round of $1 million raised in 2008, the investors are interesting: They’re Groupon founders Eric Lefkofsky and Brad Keywell, through their recently launched investment fund Lightbank.
Lefkofsky told VentureBeat he and Keywell that they both remain active in their own early-stage startup, Groupon, which provides subscribers a daily coupon with large savings and has reportedly raised funding at a valuation of more than $1 billion. (Groupon hasn’t yet commented on the rumors of funding.) With the amount of time and effort that goes into running a startup, and the pressures of investors hoping for a return, it’s suprising that they have launched another venture that focuses on investing in other startups.
When asked how he plans to manage working with various start-ups, Groupon cofounder Eric Lefkofsky told VentureBeat that with over 3,000 employees across the technology companies he and Brad have invested in, and the growth and maturation those companies have seen, they feel comfortable launching and investing in additional technology startups.
There’s more to come. Lightbank plans to invest as much as $10 million annually in technology companies. This includes startups that need financing that range from $100,000 to $1 million. It will be interesting to see how much time and energy they give to these other startups. Where I’ve Been is the first Lightbank investment based in Chicago, also Groupon’s hoem turf.
Where I’ve Been hopes to use the new funds to expand its more than 9 million registered users, who use the service to map out where they’ve been, where they want to go, or even if they are just heading to a restaurant on a Friday night. A back-end software leverages an interactive map and allows users share their profiles and travels with their social networks. There’s buzz about the company: The popular application was even rumored to have been bought by travel recommendation company TripAdvisor for $3 million, but the claim was eventually revealed to be untrue.
There are other connections to Lefkofsky and Keywell’s portfolio at play here: Rob Solomon, Groupon’s new president and COO, sits on the Where I’ve Been advisory board, according to the company’s announcement. Solomon was a former partner at Technology Crossover Ventures, a Palo Alto-based venture capital firm, as well as former president and CEO of travel search engine SideStep and a senior vice president at Yahoo.
Companies: Groupon, Lightbank, Where I’ve Been
People: Brad Keywell, Eric Lefkofsky, Rob Solomon