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Jeff Weiner has been highly successful as the CEO of LinkedIn, but it’s a role he never would have found had he not accidentally ended up at Yahoo.

Weiner, a self-described aspiring media mogul, landed a job early in his career helping to build Warner Brothers Online, he explained during tonight’s PandoMonthly fireside chat. It was one of the first ever digital video entertainment initiatives and he was working under then CEO Terry Semel. Semel and Weiner would later leave to start a private equity company to invest in media assets.

As a former New Yorker living in LA, Weiner was effectively living his dream. Not surprisingly, he had no intention of leaving the company.

It was early 2001 by this point and the dotcom bubble had fully popped. Yahoo was still a dominant Internet company, but it had been badly damaged. Semel was offered the opportunity to come in and take over an ailing online giant.

Weiner wasn’t surprised by the offer, having predicted as much days earlier when his mentor was called to Silicon Valley for a meeting with Yahoo CEO Jerry Yang. But he was surprised that Semel decided to accept.

“I said, ‘you have no idea what you’re getting yourself into,’” Weiner recalls. “This is one of the highest profile companies in one of the highest profile industries, and the whole industry just imploded. This is going to be a very intense turnaround situation – very different from what you’re doing.”

While Semel was a mentor and all around central figure in his business life, Weiner’s first reaction was to wish him well. But Semel was unrelenting, eventually wearing Weiner down on the idea of uprooting his life and joining him in the Valley.

“I said, ‘Well, good luck with that, I’m going to sit tight down here.’” Weiner recalls. “And he said, ‘No, no, no. You’ll come up.’ … He’s almost impossible to say no to, it’s one of the reasons for his success.”

The initial idea was that Weiner and another colleague from his private equity days named Toby Coppel would simply be “Terry’s Guys,” but that idea didn’t fly with Yahoo founder and Chairman Yang. “I don’t know about you guys being Terry’s ‘guys,’ and helping him out and whatever, but that’s not how it works up here,” Weiner recalls Yang saying. “You need full time jobs, you need titles. From now on you run corp-dev.”

Weiner stuck to corp-dev for the better part of a year when Dan Rosensweig was hired to be COO. Like Semel, Weiner describes Rosensweig as being enormously persuasive. Rosensweig spent a year recruiting Weiner from the corp-dev team, or as he called it “doing deals and pushing paper for Terry and Jerry,” to the operations side of the business. Weiner was again unsold, until Rosensweig convinced him that a switch would put him in a better position to eventually lead people and create the change that he aspired to create – specifically around his passion for education reform.

Of course, Yahoo had its struggles during Weiner and Semel’s tenure. But he describes it as, “the most invaluable period of learning in my entire career.”

When he arrived at the company, Weiner found Yahoo to to be full of value. “In terms of the fundamental assets, it wasn’t diminished,” he says. “I think that’s one of the things Terry found so appealing. He could always identify undervalued assets.”

But soon, the company’s greatest strengths became its biggest vulnerabilities. Namely, Yahoo was having so much success across so many different categories – it was No. 1 or No. 2 in almost all categories it competed in – that it was almost impossible to focus or eliminate less valuable departments. Yahoo organized the consumer Web, Weiner says, but it was a strategy that didn’t scale as the Internet matured and competitors became more sophisticated.

It worked for a really long time. But over time, when any industry matures you’re going to get competitors. And when you’re a broad-based, horizontal platform, your competitors are going to specialize in certain verticals, and that’s all they’re going to do. And they’re going to get that vertical right. I don’t know of any company that can compete across every space it’s in if it’s a broad-based horizontal platform, when you have single minded competitors that specialize.

It’s a great observation, but as Weiner points out,

Recognizing that, is probably easier than doing something about it. because you’ve built up the company and because the expectations have grown, and the valuation is based on those expectations. And people joined to be a part of that, not something more narrowly defined. And so it would require both vision and extraordinary courage to say, ‘This is not sustainable. So we’re going to need to get extremely focused and make some really hard decisions about what we’re going to need to do and what we’re not going to do. And it’s going to be painful for some interim period of time, but over the long run we’ll be much more valuable than we otherwise would have been.’ And that’s just really hard. It’s almost impossible.

Weiner eventually left Yahoo, after finding himself feeling like the company needed to do certain things to be successful but couldn’t do them. But, like the decision to first come to Silicon Valley, Semel proved difficult to say no to and it took longer than he expected to exit. Weiner looks back at his time at Yahoo and calls it instrumental to the leader he is today.

“The most valuable lessons I learned were what not to do,” he says. “You learn importance of focus. You learn the importance of culture and values and building great teams. And, you learn personal lessons – I learned how to manage compassionately.”

None of this would have happened without Semel and his legendary persuasiveness. Weiner describes his mentor, saying, “He’s very thoughtful, very generous, he engenders great loyalty, he has great business sensibilities, and a golden gut. There’s just something very endearing and familial about it. You don’t feel as if you’re being manipulated in any way because it’s coming from a good place And he literally thought it will be this great adventure, and it was. It changed my life.”

[photo by Geoffrey Ellis]