Meet the Divisive Figure Behind Yahoo’s New Ad Push

“Yahoo has an opportunity to be a leader again,” Heckman said. “That’s what I’m excited about.”

Heckman landed at Yahoo in May when Yahoo paid $28 million for 5:1, a company founded by Heckman that acted as a buying consortium where premium publishers could theoretically sell their “class 2” inventory at higher prices. It was the third company Heckman headed that resulted in a sale, having run Scout.com, which sold for $60 million to Fox Interactive Media in 2005, and Rivals.com, which sold for $100 million to Yahoo in 2007. Unlike many top ad executives, Heckman has entrepreneurial cred.

“I’ve started a lot of businesses,” said Heckman. “It is really difficult to have a positive exit. It’s tough to raise money, it’s tough to make the really hard decisions. That’s the nature of being a CEO. In my case I’ve always gone up river. Over the last 10 or 15 years of my career, you can point to several companies which I founded that changed the Internet and the media business.”

Heckman is clearly not short on confidence. That should help in convincing top-tier publishers that they should join with Yahoo and its partners. None have publicly declared they will, although Heckman promises “at least 25” will come out by early next year. Digiday canvassed over 20 top Web publishers earlier this month and found no takers.

Therein lies the rub with Heckman, who for all his success has alienated many over the years with his bluster and hard-charging ways. Early in his career, as a young sales executive in Washington state, he was caught up in not one but two college football recruiting scandals, one of which led Heckman to file a suit against the Los Angeles Times for libel. His tenure at Rivals ended with his ouster in 2000. At FIM, he’s credited, and blamed, for the infamous $900 million Google/MySpace deal. He had a short, forgetable stint as a top executive at customized-goods company Zazzle in 2007. In speaking with over a dozen digital media insiders who have dealt with Heckman, Digiday found polarizing opinions of the executive. Assessments of Heckman range from “if anyone can make this deal work it’s Heckman” to “I don’t trust that guy at all.”

“Jim is very smart,” said MediaLink CEO Michael Kassan. “He talks fast and thinks faster, and sometimes that get misinterpreted. But he is the right one for this [portal] alliance. He’s very tenacious and he gets things done.”

There’s a fine line, of course, between tenacious and reckless. Many who’ve worked closely with Heckman concur that he’s a sharp sales executive, albeit one who choses conflict when it’s not always necessary and fudges facts at opportune times.

Take 5:1, the company that brought him to his current position. The original concept for 5:1 was to build an ad system that would let users pick which ads they wanted to see, much like they do on Hulu. Then, as startups often do, 5:1 morphed into an ad technology product that would put more manual ad serving control in the hands of publishers’ ad opps teams. 5:1’s model would again shift — this time as a buying consortium that billed itself as a fulcrum for many premium publishers.

However, several top Web publishers allege that Heckman claimed to have deals signed with publishers that he didn’t, using these phantom deals as leverage to woo other publishers — and close the deal with Yahoo. One publisher described hearing from his own business-development team that 5:1 had called, saying it had signed a contract when that publisher’s top executives already had rejected working with the company. Several other sites say they heard about 5:1 claiming to represent some of their inventory when that wasn’t the case — and some even called Heckman on it directly. That’s critical since much of value 5:1 brought Yahoo was not so much on the tech side but through its relationships.