Lessons From the VC Who’s Seen It All Before

Jordan, who is 60, savors his alone time in the morning. Office hours are at the nearby venture capital firm Andreessen Horowitz, where he meets with entrepreneurs, listens to pitches, and decides which of these prospects are worthy of the firm’s backing. But in the wee hours, he typically sets out alone. “I have to be an extrovert at work. So to recover, I just walk through the hills,” he says, before making the shocking confession, at least in the type A world of Silicon Valley VCs, that he’s “right on the introvert-extrovert line.” Says Jordan: “It’s the only thing in my day I do that’s solitary. Everything else is meeting after meeting after meeting.”

Fortunately for Jordan and his partners, his enervating face time has proved fruitful. On behalf of Andreessen Horowitz, Jordan invested early in what are now some of the hottest companies in tech, including home-­sharing giant Airbnb, grocery delivery company Instacart, and the hobbyist site ­Pinterest. The firm’s bet on Pinterest alone, one of Jordan’s first after joining the firm in 2011, is worth $1 billion. Jordan’s nonmonetary reward: Earlier this year he became managing partner of the decade-old firm, meaning he’s now responsible for personnel, budgeting, day-to-day operations, and the like, all while continuing to invest and sit on boards. (He’s currently on nine, including still-private Airbnb and Instacart, newly public Pinterest, and high-stakes e-scooter startup Lime.)

Jordan is a bit of an outlier at the epicenter of the global technology industry, a place of titanic egos and triumphs borne of brilliant ideas. He didn’t become a VC, widely acknowledged to be a young person’s game, until he was in his fifties. He’s not a technologist but rather a general-management type, typically second-class citizens in the Valley. And he at least professes to hate being in the spotlight. What he has, in spades, is something that is gaining currency amid the scandals and missteps of the Valley’s behemoths: experience. Says Meg Whitman, Jordan’s boss at Disney and later at eBay: “Investing requires pattern recognition, and Jeff was able to recognize the potential” of the companies he has invested in, thanks to what he had seen earlier in his career, particularly at eBay.

Thanks to these successes, and the battle scars Jordan makes no effort to hide, entrepreneurs young and old now want to learn from him. Pattern recognition can’t necessarily be taught. But getting advice from someone who can see it—especially when that someone didn’t always make the right call or climb to the highest rung on the ladder—is beyond valuable. As for what drives him, well, let’s just say Jordan isn’t above having something to prove, a trait that makes him fit in rather well in Silicon Valley after all.

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Jordan’s first reaction to Airbnb was that it was “the stupidest idea I had ever heard.” It was 2011, and he was at an Allen & Co. tech-investing meeting in Arizona. Brian Chesky, then a relatively unknown entrepreneur, was explaining his business, and Jordan couldn’t help mentally listing the number of risks associated with opening up one’s home to strangers. Then it hit him. Airbnb’s fast growth and online marketplace that matched homeowners with renters reminded him of eBay. It was, he says, “a déjà vu experience.” Having worked in top positions at eBay for seven years, he literally had seen this picture before.

Jordan and Chesky met after the entrepreneur’s talk, and the two discussed network effects, the notion that a product or service becomes increasingly valuable the more people who use it. Chesky was looking for investors, and Jordan was interested in becoming one. He’d grown bored running OpenTable, a restaurant reservation site, when Marc Andreessen and Ben Horowitz asked if he’d be interested in joining their young firm. The duo asked Jordan to name a hot company in the consumer sector. The first to come to mind was Airbnb. He got the job and the deal. Jordan guided the firm’s $60 million investment in Airbnb, a stake that has grown 30-fold at the private company’s last valuation. Chesky chose Jordan over Andreessen to be an Airbnb board member. “From the first time we met, Jeff struck me as somebody I should learn from,” he says.

Days after becoming an Airbnb director, Jordan proved his mettle. An Airbnb renter vandalized a home, jeopardizing the trust critical for a marketplace among strangers. Airbnb needed a system to make homeowners comfortable. Jordan had introduced a program at eBay called Buyer Protection, which helped resolve issues between buyers and sellers. He advised Chesky to create a property damage protection policy called Host Guarantee that would cover loss or damage by renters up to $50,000, a figure that has since grown to $1 million. Since then Jordan has applied his eBay lessons in advising Airbnb in other ways, including international expansion, adding site functionality, and designing new products, a process Jordan calls “adding layers to the cake” and all steps eBay took.

Jordan claims his investing sweet spot is not a company’s earliest stages but rather when he can see some signs of traction. When he encountered Pinterest in 2011, the company had just reached “product-market fit,” a hallowed Silicon Valley cliché for the moment when a nifty idea finds willing customers. “I do best in investing when there’s a little signal to respond to,” Jordan says. Pinterest already had rapid user growth despite limited marketing. Jordan, says Ben Silbermann, Pinterest’s cofounder and CEO, “saw similarities between Pinterest and the early days of eBay, which had aspects of commerce as well as aspects of community.”

Wisdom and the ability to discern patterns aren’t foolproof, of course, and Jordan found this out the hard way. The same year he invested in Airbnb and Pinterest he also staked an e‑commerce startup called Fab.com. Andreessen Horowitz led the investment round, meaning it put its imprimatur on the deal. It eventually pumped $40 million into the young company. Jordan saw the positive telltale signs of growth: The company’s CEO, Jason Goldberg, said at the time his company was generating $100,000 in online sales per day.

Fab would eventually reach a valuation of almost $1 billion, and then it began to falter. It expanded prematurely into international markets and spent too heavily on marketing. “Cake-layering” and otherwise leveraging a growing user base didn’t work for Fab, and the company sold its assets in 2015 for $15 million.

Jordan, who calls the Fab experience “painful as hell,” feared for his job. He recalls that three other VCs who backed Fab exited their firms soon after. “Boom. Boom. Boom,” he says, forming a finger pistol and loudly firing three bullets. Jordan remembers walking into Andreessen’s office to ask, “Anything I should know?” Andreessen’s response: “Are we still in Airbnb? Are we still in Pinterest? Okay, you can stay.”

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Smooth Operator

After stints at Boston Consulting Group and Stanford Business School, Jordan logged 20 years running com­panies before he started investing in them. He tried retiring once, but leisure time didn’t suit him. Here are some key stops along the way.

The Walt Disney Co.

(1990–1998)
CFO of The Disney Stores Worldwide

He ultimately was responsible for strategy, finance, and business development for Disney’s retail arm (including the store above), which accounted for about $1 billion in revenue: “This was my first taste of being in an operating business.”

eBay, North America

(1999–2006)
Senior Vice President and General Manager

Jordan oversaw eBay’s early growth into one of the Internet’s biggest commerce brands. (That’s him holding the “a.”) After eBay bought PayPal, he helped the payments company increase revenue by 39% year over year.

OpenTable

(2007–2011)
President and CEO

He led the online reservation company through its initial public offering in 2009 at the height of the financial crisis. On its first trading day, the company’s stock price popped nearly 60%. It increased more than threefold during his tenure.

Andreessen Horowitz

(2011–Present)
Managing Partner

Jordan credits his operating experience for investing early in some of Silicon Valley’s hottest tech companies. They include Airbnb (whose founders are pictured here), Pinterest, Instacart, Lime, Lookout, OfferUp, Accolade, and Wonderschool.

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Jordan has known real setbacks in his professional and personal life. He grew up in the Philadelphia area, the middle of three children. His father, who worked as a pharmaceutical executive, died of cancer when Jordan was 15. His mother, a homemaker until then, eventually became the family’s sole provider and found a job as an executive assistant. There was enough money for tuition at Amherst College in Massachusetts but not, says Jordan, for living expenses. So he took jobs as a cook at campus restaurants and throughout his summer breaks. (He remains an enthusiastic cook.)

After college, Jordan worked briefly for the insurer Cigna, where a boss spotted his ambition and recommended business school. He was accepted at Stanford, where he told the admissions director he couldn’t afford to go. She told him, “You can’t afford not to.” He made it work through a combination of financial aid and student loans. After Stanford and three years at Boston Consulting Group, he joined the venerable strategy group at Disney, where his boss was Meg Whitman.

Despite working for one of the most iconic brands in the country, Jordan answered the siren call of the budding dotcom sector, becoming CEO of online DVD seller Reel.com in 1998. The company was a dud. “That was my huge career failure,” says Jordan. “I mean, it was just a terrible business, and I wanted it to be something that it wasn’t.” He was supposed to take the company public but quit after six months to rejoin Whitman, who was now CEO of eBay.

eBay was tiny when Jordan joined as general manager for North America in 1999. Six years later, the unit had 6,000 people. As a key member of Whitman’s leadership team, Jordan championed the $1.5 billion acquisition of PayPal in 2002. The deal was controversial internally because eBay already owned a payments company called Billpoint. “It was clear Billpoint was an abject failure,” Jordan says. He favored PayPal because eBay users favored it. Jordan later became president of PayPal, and at a time eBay was riding high, he was considered a potential successor to Whitman. But she passed over Jordan and hired John Donahoe, the top executive at Bain & Co., where Whitman had once worked. Jordan, who says he took himself out of the running for the eBay CEO job long before Donahoe entered the picture, quit. And for the first time in his adult life he was out of work.

He considered retirement. “I biked every single mountain path like 50 times, and then when I started doing them for the second time, I said, ‘Okay, it’s time to get a job,’ ” he says. Nine months after leaving eBay, he became CEO of OpenTable, a job his eBay fans considered beneath him. One investor thought it was “such a waste having him at the head of that teeny little-ass business,” Jordan says he was told. Nevertheless, he took OpenTable public and stayed for four years, eventually becoming as restless as a CEO as he’d been as a retiree. “I had started advising companies on the side because I was having fun doing that,” he says. That’s when Andreessen and Horowitz called.

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There’s a framed ­Chicago Bulls jersey above a plaque on the wall of Jordan’s Sand Hill Road office that reads:

JORDAN
A true leader.
A role model for other players.
Never steals the limelight.
Understands the need for teamwork.
Never lets adversity get him down.
Always practices excellence on the court.
And we’re not talking about Michael.
Good luck, Jeff.

“That was my going-away present from Disney,” he says. And then he shows his other business trophies: framed charts and graphs from his time at eBay and PayPal. “I joined eBay in 1999,” he says, pointing to the chart. “They did $3 billion in gross merchandise volume the first year I ran it,” referring to eBay’s preferred metric for total commerce conducted on its platform. By the time he left, that number had grown to $19 billion.

Not counting Reel.com, a mistake, and OpenTable, a modest success by the outsize standards of Silicon Valley, Jordan always has played supporting roles. As an executive at Disney and eBay, he had helped contribute to the success of high-profile CEOs like Michael Eisner and Meg Whitman. His name will never be on the door at Andreessen Horowitz.

But he has another measure of success beyond the wealth he accumulated at eBay, OpenTable, and his early wins at ­Andreessen ­Horowitz. He calls it his “scorecard,” otherwise known as a ­personal track record. “My biggest issue is that I don’t like to talk about myself,” he says, while simultaneously noting that he consistently ranks higher than anyone else at Andreessen Horowitz on industry investing lists, a humblebrag of the first order. Indeed, Jordan ranks No. 5 on the most recent CB Insights list of top VCs, a ranking known as more of a quantitative measurement than a popularity contest.

Jordan even wins praise from competitors. “It looks to me that Jeff’s behind some of the firm’s most iconic investments,” says Benchmark’s Bill Gurley. (The two have been allies as well as rivals; Gurley was an OpenTable investor when Jordan ran the company.)

Asked why he’s still at it—­digging through company reports, serving on boards, meeting with so many people when he could be off on his own on the trail, Jordan leans forward and says, “It keeps me young.” Later in the day, Jordan joins six Stanford Business School students for lunch to discuss his career and offer advice about theirs. Immediately after finishing his meal and shaking hands with everyone, he’s off to Seattle for a board meeting of OfferUp, an e-commerce company. Prominent VCs at competing firms have recently opted to scale back their investments. Not Jordan, who has re-upped as a partner in Andreessen Horowitz’s newest fund. “I’ll be doing this for a while,” he says.

A version of this article appears in the July 2019 issue of Fortune with the headline “The VC Who’s Seen It All Before.”

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