From Mudslinger to Maverick! The Transformation of Kenneth Lerer

Just trust me. It’s Kenneth Lerer’s favorite line, and the 58-year-old general partner at Lerer Ventures and co-founder of the

Just trust me. It’s Kenneth Lerer’s favorite line, and the 58-year-old general partner at Lerer Ventures and co-founder of the Huffington Post–“Kenny,” as he’s known to friends–employs it convincingly. Huffington Post senior editor Katharine Zaleski, one of the site’s first employees and the home page editor until May of 2009, recalls the early days of the site, when it wouldn’t be unusual to receive 20 phone calls a day from Mr. Lerer regarding the headline of the top story. “He was the kind of boss who would make you do something, or you’d put it up and say, ‘This is crazy, this headline makes no sense,'” and then he’d say, “Trust me, just trust me.’ And then, oh my God, it would be a huge hit.”

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Mr. Lerer made headlines himself on Feb. 7, when it was announced that he and Arianna Huffington were selling their monster news site to AOL for $315 million. It’s crazy; it makes no sense–and it’s a huge hit for Mr. Lerer. But there’s very little emphasis on his role in the coverage of the story. He’s often eclipsed by his brash, charismatic co-founder, in part because he intentionally shuns the spotlight with the vigor of someone who’s done something wrong on reality television (he declined to comment for this piece). His name rarely appears amid the speculation about exactly how much money Ms. Huffington made from the sale of the site, despite the fact that the two started it together after raising and contributing around $1.5 million, split fifty-fifty. And he likes it that way.

But he may not be able to stay out of the spotlight for long. Even as he offloaded the Huffington Post to AOL, Mr. Lerer also made an acquisition–Huffington Post’s CEO, Eric Hippeau, a former partner at Softbank and an effective rainmaker who could turn Mr. Lerer’s fledgling seed-stage fund into a powerhouse venture capital player. Mr. Hippeau knows the business and has deftly made the transition from operator to financier before (he was the CEO and chairman of Ziff-Davis from 1993 to 2000 before joining the large venture fund), so it’s not a new path for him. But it’s relatively new for Mr. Lerer, who, prior to the Huffington Post, was a high-powered PR executive accustomed to navigating the political structures of large, established companies. He has no formal finance experience, and the Huffington Post was his first real entrepreneurial venture. His fund is tiny, consisting of three partners: Mr. Lerer; his 28-year-old son, Ben (the CEO of and the manager of Lerer Ventures); and Ben’s pal Jordan Cooper (a venture partner who’s also the CEO of Hyperpublic). How can he be a serious contender in the venture space? Should we just trust him?

On the upside, so to speak, it’s one endeavor that doesnt have a press release in mind.

“Kenny had and has no discernible public ego–and I have a Geiger counter for public egos,” said formal mayoral candidate and a longtime friend of Mr. Lerer’s, Mark Green. “But he also has an enormous private pride in pulling off things well.”

After a stint in politics, where he met Mr. Green, and a few years covering the beat for New York magazine, Mr. Lerer entered the public-relations world, first with Warner-Amex, and eventually founding the firm Robinson Lake and Lerer in 1986, where he gained attention as the flack for embattled junk bond trader Michael Milken. His image as PR Guy was solidified by a passage in James Stewart’s 1989 Den of Thieves that described Mr. Lerer’s interactions with the reporters of the major papers. “Lerer would call these reporters frequently, working the phones as he played Nintendo in his office, or calling from his car, planting story ideas worked up by members of his staff,” Mr. Stewart wrote. “Occasionally he dribbled bits of ‘exclusive’ information to his current favorites. Lerer once called it ‘breast-feeding’ the reporters.”

“Lerer was doing less of the story-by-story push-back and more of a softer sell, trying to sell Milken’s human side,” said John Riley of Newsday, who covered the Milken trial during that period. No one was buying that Mr. Milken had a human side, and the former junk bond king went to jail, but Mr. Lerer had already developed a reputation for taking the long view in damage control. He began working with MTV in the Beavis and Butt-Head era on retainer for when, as then-MTV CEO Tom Freston put it, “someone would blow up a dog with a firecracker and try to blame it on us.”

He became close with future-AOL President Bob Pittman, and continued working publicity through the ’90s until Mr. Pittman convinced him to abandon a Microsoft account to join him at AOL for PR work. Mr. Lerer did damage control at AOL– notably working on one of the “America Offline” connection crises, when the company became so swamped with users that none could sign on–and eventually became a senior vice president, one with a reputation for dispensing withering criticism. “He never did it with a smile,” said a former Time Warner executive who worked with Mr. Lerer in that period. “There were probably people who were a little more in-your-face, but they did it with a smile. He never did.”

Then again, Mr. Lerer is not really a smiler. He’s not the sort of clichéd media macher who needs to fully occupy any conversational space at a party. Which is not to say that he’s not social, though he downplays it. “As a wing man, he was ideal,” says Mr. Green. The two used to double-date, in the ’70s, the women they would go on to marry. He’s been active in the Public Theater and is known to hit the town with jet-setting hotelier André Balazs. Fred Wilson took him out to dinner to celebrate the sale last week. A frequently tanned string-puller with Zelig-like connections and a penchant for put-downs, he’s terse and witty. He looks a bit like a young Al Pacino, but he’s less Michael Corleone than Tom Hagen–the calming force in the room.

The plaintiffs in the lawsuit over the origins of the Huffington Post, recently detailed in Vanity Fair, point to Mr. Lerer’s complete silence during the site’s first major meeting as damning evidence, but it would seem hardly out of character to anyone who knew him at AOL. Even among heated discussions about the merger, which by most accounts Mr. Lerer opposed, former Time Warner CEO Gerry Levin remembers Mr. Lerer as a bastion of collectedness.

“I can remember some pretty intense, highly intense, volatile meetings where there were conflicting points of view, things were really rattling around the table, and I’d look at him and call on him and he was just calm, straightforward, extremely poised while everyone else around the table was losing it,” Mr. Levin said. Mr. Pittman left the company after the merger, followed later by Mr. Lerer, both of them with enough money to retire, and Mr. Lerer eventually became a member of Mr. Pittman’s investment fund, the Pilot Group.

From Mudslinger to Maverick! The Transformation of Kenneth Lerer