Co-founder Ken Lerer is former AOL exec VP

The sale of the Huffington Post is a homecoming of sorts for one of the site’s co-founders.

Kenneth Lerer was once a top communications executive at AOL in the late 1990s and went on to be an exec veep at AOL Time Warner after the merger. Naturally, Lerer is banking on the union of Huffington Post and AOL to be a better fit than the famously disastrous AOL-TW marriage.

Lerer said bringing Huffington Post into AOL’s tent will put AOL CEO Tim Armstrong’s plan to reinvent the company as a major content provider “on a much faster footing.” Lerer will serve as an adviser at AOL. “This allows him to bulk up much more quickly,” he said of Armstrong’s plans.

After Lerer sold the PR firm he helped found, Robinson Lerer & Montgomery, he joined one of his clients, AOL, and worked closely with then-AOL prez Bob Pittman. When Pittman left AOL Time Warner in 2002, Lerer departed shortly thereafter.

Lerer went on to form his own angel investment firm, Lerer Ventures. A big Democratic fundraiser, Lerer partnered with Arianna Huffington in 2005 to launch Huffington Post with an initial $1 million investment. Subsequently, funding rounds topped $35 million.

“Kenny has always had a great sense for new opportunities in media and the skills to execute them,” said Pittman, now chairman of media and entertainment platforms at radio giant Clear Channel and head of his own investment firm, Pilot Group. “He broke new ground with Huffington Post, and this deal is validation of his and Arianna’s game-changing vision.”

Lerer’s myriad of investments include text messaging company GroupMe, online payment firm Group Commerce and Popdust, a TMZ-like site for the music biz. Lerer Ventures invested in 33 companies in 2010, but Lerer said he expects to make fewer investments this year. His entrepreneurial spirit has been passed on to the next generation. Lerer’s son, Ben, is a founder of the regional recommendation website for young guys, Thrillist, in which Lerer Ventures was an early investor.

When asked how the Huffington Post deal ranks in terms of his track record with investing, Lerer chuckled and said: “Pretty good.”

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