Ovitz does Silicon Valley

October 10, 2013, 11:58 AM UTC

Peter Szulczewski is a 31-year-old San Francisco entrepreneur with a promising startup on his hands. It’s a mobile app called Wish, with the catch phrase “Shopping made fun,” that connects the personalized “wishlists” of acquisitive consumers with participating retailers. You want a green polka-dot dress? Wish links you to shopkeepers with matching products. With 15 million registered users, Wish is growing by 50,000 a day.

When Szulczewski (pronounced SHOOL-ches-kee) launched the company in 2011, though, it had an identity problem. The company had an uninspired name, ContextLogic, and its beta website was the forgettable wishwall.me. Wish.com wasn’t available.

Then, last year, Szulczewski was introduced to an unusual adviser: Michael Ovitz, the 66-year-old erstwhile L.A. über-agent. Once known as the most powerful man in Hollywood, Ovitz ruled the town with a gap-toothed smile that belied a taste for blood. But after a series of apparent betrayals and competitive overreaches, he fell from the throne.

Now, in his latest incarnation, the enigmatic Ovitz is trolling about Silicon Valley, making new business buddies and millions of investment bets too. He and Szulczewski hit it off immediately, even if Ovitz — in his cashmere sweaters and Armani blazers — didn’t quite grasp the indigenous dress code. Compared with his glamorous deals for Tom Cruise and Madonna, Ovitz’s advice for Szulczewski was remarkably small-bore. Ovitz saw immediately that the domain name was critical. “I can help with that!” he told Szulczewski, and, with his big swinging Rolodex, within weeks tracked down the owner of wish.com. It was a French subsidiary of Barry Diller’s IAC. Szulczewski handled the actual negotiation — he won’t disclose the price — but Ovitz war-gamed tactics with him beforehand. Szulczewski was impressed. “Michael’s here a lot,” he says. “We’ve learned to use him with laser precision.”

Ovitz has said he just loves associating with the tech stars of tomorrow. But of course he also wants a piece of the action. He’s never overt; his approach is always coy, sometimes made through an intermediary. That’s what’s to be expected of the greatest Hollywood operator of his time. At Wish, Ovitz got his cut, according to Valley investors. (Szulczewski is too polite to confirm that — he’s a big fan of Ovitz.)

There are similar tales of Ovitzian assistance around the Valley as he rises again, this time far removed from the lights of show business. At Andreessen Horowitz, the venture capital firm, Ovitz is an in-house mentor on how to build a full-service operation in the mold of Creative Artists Agency, the Hollywood talent monolith he built and ran from 1975 to 1995. “Michael is the classic kind of entrepreneur that we like up here — he’s highly aggressive, he’s highly disruptive,” says Marc Andreessen, with whom Ovitz has cultivated a relationship since 1999. “Michael’s a very close friend of the firm. He’s a great friend to have.” He’s also an investor in the firm, though AH won’t say for how much. Andreessen introduced Ovitz a while back to Peter Thiel, another VC, a PayPal co-founder, and the chairman of Palantir Technologies, the burgeoning data-analytics company that caters to intelligence agencies like the CIA. “Michael can get us in to see any CEO in the U.S.,” Thiel says. “The Valley has this excessive insularity. But he has cross-sector relationships in New York, L.A., and other places.” Thiel says Ovitz has a preternatural ability to “learn things quickly and then communicate them to the outside world.”

What Thiel means, for example, is that Ovitz helped the nine-year-old Palantir branch out beyond government customers. The company wanted to market its wares to hedge funds and other financial outfits but wasn’t particularly good at it. Despite what engineers believe, “products don’t sell themselves,” Thiel says. Since the dotcom implosion of the late 1990s, he says, too many new companies in the Valley have “retrenched,” de-emphasizing relationships with other businesses and institutions. Consulting Ovitz, whose network Thiel calls “second to none,” has been a way to overcome that inclination. Ovitz is an investor in Palantir.

His tentacles extend elsewhere. At Anki, a consumer-robotics startup, the CEO says Ovitz has advised him during some late nights about “psychological transitions” as his company grows. Ovitz has shown interest in Iconiq Capital, a press-shy private-wealth-management firm whose clients include Facebook’s Mark Zuckerberg. At Formation 8, a flush new VC fund focused on Asia, Ovitz has explained to the three investment partners how to hone their image and brand for Wall Street types. “Michael knows that world too,” says Joe Lonsdale, one of the young Formation 8 partners. “He can show us how to ask them for a favor, but how not to push too hard.” One time Ovitz also suggested to Formation 8 what to name one of its portfolio companies that was in stealth mode. His idea: Stealth. Lonsdale, who met Ovitz through Thiel, was the conduit for Ovitz to Szulczewski.

Ovitz serves as a guru to other prominent people in the tech world, including Tony Bates, the president of Skype, and Brian Chesky, CEO of Airbnb, the home-sharing network. Ovitz coaches them on culture and storytelling. He picks them up when they have bouts of doubt, sometimes inviting them to visit the curated mega-million-dollar collection of contemporary art on display in his 28,000-square-foot home in Beverly Hills. For Bates at Skype, Ovitz even named a special $20 salmon-and-snapper roll at his West L.A. sushi joint Hamasaku after him. “He’s having the time of his life,” says Ron Conway, the inexhaustible angel investor in the Valley who introduced Ovitz to Andreessen.

For all his labors, many folks in the Valley don’t even realize Ovitz is there. One venture capitalist I spoke to asked, “You mean the guy who flamed out years ago?” Another helpfully offered, “I heard he’s got an apartment at the St. Regis in San Francisco” (which he does). But those who are aware of Ovitz’s reinvention in the Valley wonder both why he’s set up an outpost and why the locals have taken to him. That dual psychodrama is as intriguing as the actual work Ovitz is doing.

A lot of fellows nearing 70 — with a net worth of reportedly hundreds of millions of dollars and a 184-foot motor yacht curiously named Illusion — wouldn’t be working so hard. Ovitz has a new girlfriend in Manhattan — Tamara Mellon, co-founder of Jimmy Choo — as well as a range of philanthropic activities to keep him busy. Besides, his emerging prominence in the Valley only risks having the inglorious chapters of his past resuscitated.

For their part in the relationship, the nerds — typically a skeptical, evidence-driven bunch — have been uncharacteristically enchanted by their new ally from the Southland. Says Thiel: “I’ve learned to discount bad things said about people by rivals, and I’m not aware of a single bad thing about Ovitz that wasn’t said by a rival.” Which still leaves an awful lot of “I was Ovitzed” stories to discount. Maybe Thiel missed the one about Ovitz’s attempt in 1997 to make peace with Ron Meyer, his former CAA co-founder and ex-friend. During brunch on a Saturday, Meyer mentioned a parcel in Malibu he was going to buy — only to discover on Monday that Ovitz had bought it out from under him.

Ovitz declined to cooperate with Fortune for this profile — though he made an initial charm offensive — citing a bad back and a view that his new Silicon Valley patrons ought to be the ones commanding the stage. He then encouraged them not to cooperate either. More than a dozen friends and foes alike agreed to be interviewed only on the condition we not use their names. Such is the respect and fear he still inspires. Ovitz wants back in the game, an opportunity to be vindicated. But, haunted by his past, he may not really want anybody asking now, “For the love of Mike, what’s he up to?”

Michael Ovitz has long been a source of polar disagreement. In his long reign in L.A., some loved him, some loathed him. For the clients Ovitz championed, he was a nonpareil negotiator. For the adversaries he vanquished, he was a manipulative scoundrel. The things people say are “probably all true,” says Herbert Allen Jr., a Manhattan investment banker, who adds that all his experiences with Ovitz were good. What nobody challenges is that once upon a time, Ovitz owned Hollywood. Agent, dealmaker, consigliere, power broker — he was the man to see.

Early on, he loved being where the action was, but just off to its side. Following his freshman year of college, he worked part-time as a tour guide at the old Universal Studios. After UCLA, in 1969 he landed the ultimate trainee perch for power: the Machiavellian mailroom at the William Morris Agency. By his own account in a 1997 biography, he was a “brash, inquisitive lunatic.” Others delivered the mail; he made a point to read it, studying contracts and memos while the honchos went out for dinner.

Within eight months he was made an agent in the agency’s TV department. Six years later he bolted with four colleagues to launch CAA. All five partners got matching Jaguars. Over the next two decades CAA became a juggernaut, poaching such icons as Paul Newman and Dustin Hoffman from other agencies. Ovitz made his agency a kind of meta-studio. Whereas other talent agencies represented this actor or that screenwriter, CAA packaged the clients and offered them as a unit, monopolizing talent. Over time, Ovitz transcended the role of agent altogether. In both Sony’s $2.4 billion acquisition of Columbia Pictures and MCA’s $6.6 billion acquisition by Matsushita Electric, he played multinational investment banker. A New Yorker profile in 1991 preposterously suggested that Ovitz might have eyes on the White House. But even with influence, he remained a man of mystery, operating in the wings.

With power, Ovitz made enemies. An NBC executive named Don Ohlmeyer famously called him “the Antichrist,” prompting David Geffen to remark, “Apparently, Don Ohlmeyer thinks more highly of Mike Ovitz than I do.”

Ovitz finally flew too close to the sun when, in 1995, he left the agency he had built to become Michael Eisner’s No. 2 at Disney — a publicly held company with nearly 100 times the revenue of CAA. While he and Eisner had been close friends, their Disney marriage was disastrous. Ovitz the shrewd operator simply couldn’t figure out how to navigate a complex corporate culture.

In 15 months Ovitz was out, though with $140 million in parting gifts. “My biggest problem was that you played the angles too much, exaggerated the truth too far,” Eisner — no teddy bear himself — wrote in his dismissal notice to Ovitz. “And while you were telling me that those dishonest days were over, you were deceiving me.”

In 1999, Ovitz went back to representation — but this time as a manager, rather than as a simple agent, so he could produce content and share in profits. The firm he founded, Artists Management Group, was to be his crowning triumph, but his arrogance had not abated. As the story goes, when he was pursuing another agent in Hollywood, the agent asked why he should switch firms. “Because,” Ovitz reportedly replied, “I have a Picasso and you don’t.”

AMG was a colossal failure — chiefly because financing fell through for its TV division — and a source says Ovitz lost more than $100 million of his own money in the venture. He did not take well to ignominy. Several months after he sold off AMG’s core assets in 2002, he blamed the firm’s collapse on what he called a “gay mafia” led by Geffen. The comment, for which he later apologized, was widely ridiculed. Ovitz retreated into the professional wilderness, devoting his time to investing, serving on boards, collecting art, and philanthropy. Though he surely had enough money left to keep the Picasso and more, his run looked over — much to the glee of his detractors.

When Ovitz in 1999 first got hooked up with Silicon Valley through Ron Conway, Ovitz still had both feet in L.A.; he was just getting AMG started. Yet he was no tech neophyte. Four years before, he and CAA had hatched Tele-TV, an early video-on-demand effort, with a group of regional telephone companies (Howard Stringer left CBS to join as CEO). Costs were out of line, and Tele-TV fizzled, as did a “multimedia lab” joint project of CAA and Intel. But Ovitz’s instincts about the future of digital entertainment were dead-on.

Conway urged Ovitz to dive into the Valley. “I told him that if he wanted to appreciate the excitement that he should come here and experience it,” Conway recalls. After he introduced Ovitz to Andreessen, the two of them bonded. Ovitz was soon on the board of Andreessen’s latest company, Loudcloud. “I went to see him at his house in L.A.,” Andreessen says. “He was one of the first guys outside the tech industry to map through and understand … what was going to happen with interactive TV.”

With the fall of AMG in 2002, Ovitz began spending more time in the Valley. He bought his place at the St. Regis. Today he typically spends most of the week in town, using a desk at Andreessen Horowitz as his base, where he can advise on recruiting, promotion, and business development. A couple of years ago he and Andreessen held a private, hourlong discussion about philosophy in front of investors, entrepreneurs, and friends. With AH’s blessing, the video made its way onto the web. It was vintage Ovitz: smart, smooth, seductive. He spoke of the Valley’s “art of collaboration” in contrast to Hollywood’s “dog-eat-dog” world. Bearing the lessons of “age,” he even gave a nod to his past lapses. “We may have been too competitive,” he said, though adding a convenient qualifier that undercut what he had just seemed to admit: “Human beings always find a way to get upset with other human beings — it sure happens a lot in West L.A.” When a former Ovitz colleague saw the video, he was incredulous. “Can you believe this?” he said to a friend. “Well, I guess he’s convinced Marc Andreessen!”

It is that kind of suspicion that runs deep in those who doubt that the dark lord of Hollywood has changed. “Mike’s the best salesman I’ve ever met,” says an L.A. executive who used to compete with him. “He assumes people won’t check up on him. And the sad part: He’s right 80% of the time.” The irony, of course, is that Ovitz — who’s trying to escape his past — is always saying that “the past is prologue.” That’s the way he contends his CAA experience makes him relevant in Silicon Valley.

Some Valley veterans see that as the empty sales pitch of an impostor. “The naive are buying into a cult of personality,” says one Valley investor. “But what more do you need to know than the Teddy Forstmann story?” That’s the one about how Ovitz not two years ago reportedly tried to wrest control of sports and media company IMG from his friend Forstmann, the private equity pioneer and IMG owner — while Forstmann was dying from brain cancer. (Ovitz declined repeated requests for comment.)

Although Andreessen and others in Ovitz’s new circle acknowledge the skepticism, they have different takes on it. Andreessen is the most dismissive of Ovitz doubters and ascribes Ovitz’s repute more to the peculiarities of Hollywood than to any of his own faults. “We’re used to guys like that here — I mean, Steve Jobs, for God’s sake! Or my career, right?” Andreessen says. “That’s the cultural difference between Silicon Valley and L.A.” Had Intel’s Andy Grove or Netscape’s Jim Clark made his mark in Hollywood, according to Andreessen, he’d have the same kind of bad-boy name as Ovitz.

Peter Szulczewski of Wish says, “I haven’t seen the type of things that people warned me about.” Formation 8’s Lonsdale agrees. “People are naturally more cautious because of his history,” he says. “But he’s demonstrated awesome value in so many tangible ways to different people that they overlook it. And it’s hard to map out what’s true and what isn’t.” Ovitz is a limited partner in Formation 8, with a “small” investment of “under $5 million,” as the firm describes it.

“There’s a disconnect between a lot of the things written about him and kind of the person we’ve gotten to know,” says Boris Sofman, the CEO and co-founder of Anki, who talks almost daily with Ovitz. Sofman says Ovitz has alluded to his own past by counseling Sofman on what happens when you’re successful. “When you lead in your industry,” Ovitz told him, “it’s easy to start getting vilified, and the tide can turn on you quickly and unexpectedly.”

Sofman says Ovitz has no stake in Anki, not even advisory fees. That may merely mean Ovitz hasn’t asked yet. Or, as Sofman suggests, it could be that Ovitz really is in it for more than the money. “One of the things he shared with me is he truly loves working with young people,” says Sofman, who just turned 30.

It may be Ovitz is looking for something more enduring, though harder to attain: personal redemption. Forever beckoning those who seek to slip the bonds of prior failure, the Valley has given countless comers before him new life. Cast out of Hollywood, not quite a player on Wall Street, never a sensation on Madison Avenue — Ovitz must see Silicon Valley as a final chance to become Michael Ovitz again. Maybe the Valley ought to be careful what Ovitz wishes for.

Disclosure: The oldest son of the writer, David A. Kaplan, was an intern at Airbnb last winter.

This story is from the October 28, 2013 issue of Fortune.