growing user base didn’t work
for Fab, and the company sold its
assets in 2015 for $15 million.
Jordan, who calls the Fab ex-
perience “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.”
J
ORDAN HAS KNOWN real
setbacks in his profes-
sional and personal life.
He grew up in the Phila-
delphia area, the middle of three
children. His father, who worked
as a pharmaceutical executive,
died of cancer when Jordan was
- His mother, a homemaker
until then, eventually became
the family’s sole provider and
found a job as an executive as-
sistant. 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 ambi-
tion and recommended busi-
ness 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 champi-
oned 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 fail-
ure,” Jordan says. He favored Pay-
Pal 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 by
hiring John Donahoe, the top
executive at Bain & Co., where
Whitman had once worked. Jor-
dan, who says he took himself out
of the running for the eBay CEO
job, 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
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