You Only Have to Be Right Once

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First published by Portfolio / Penguin, a member of Penguin Group (USA) LLC, 2014

Copyright © 2014 by Forbes Media LLC

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Most of the selections in this book have appeared in issues of
Forbes
magazine.

Photograph credits

1
,
2
,
3
,
4
: Forbes Media LLC

5
: Elon Musk by Kristoffer Tripplaar / Alamy

6
: Christian Peacock

7
: Michele Clement

8
: Walter Smith

9
,
10
,
11
: © Eric Millette

12
: Don Feria / Getty Images

13
: © MGPI / MichaelGrecco.com

14
: Ethan Pines / Copyright © 2014 Ethan Pines

15
: Jamel Toppin

16
: Gabriela Hasbun

ISBN 978-0-698-18568-5

Introduction

W
edged into a corner, Sean Parker sported the removed look of someone at a crowded party where they don't know many people. Which, at a media soiree at New York's clubby Monkey Bar on October 4, 2011, happened to be the case. Given that two weeks prior, Parker became the first person to adorn the cover of
Forbes
magazine since I returned as the editor, it seemed right to introduce myself.

“I know exactly who you are,” Parker responded, quickly parrying with a short history of my personal background,
Forbes
's position in the marketplace, and my stated goals for the magazine. He then explained his (typical) obsessiveness with a soliloquy that can be summed up in two words:
Thank you
.

It's not that the
Forbes
cover had been a valentine: It revealed the polymath who had helped shape Napster, Facebook, and Spotify with all his quirks and faults. But until that story—viewed more than 700,000 times online and by millions more who saw the print magazine version—the world equated him with the villainous character portrayed by Justin Timberlake in David Fincher's movie
The Social Network.
Even Mark Zuckerberg conceded the movie did Parker factual injustice. Reduced to an evil-businessman caricature, Parker had barricaded himself in LA's Peninsula Hotel for two months, where he'd gained thirty pounds.

His twenty-two-year-old fiancée had helped him ditch the depression, and the weight. And so Parker stood before me, himself again, as a brash actor in a story that has only a little to do with Facebook and feels one hundred times bigger: how a handful of young digital swashbucklers shrugged off the Great Recession to transform how industries operate and fortunes get made.

The day after my conversation with Parker, Steve Jobs passed away. Jobs had epitomized the
old
new guard, one of a trinity of tech entrepreneurs—with Bill Gates and Michael Dell—who two generations earlier, while themselves in their twenties, proved the disruptive power of technology. Now Jobs was dead. Gates had become a full-time philanthropist. And Dell's company, as with Apple and Microsoft, was viewed by this new generation as the bloated prey rather than the hungry predator.

This narrative isn't new. The first half century of the American computer age has seen perennial waves of the young taking on the old. During my first go-around at
Forbes
, just out of college in the early nineties, I chronicled tech-savvy Generation X, which valued entrepreneurship over the corporate ladder and fueled the original dotcom boom and bust, carving out a handful of huge winners, notably Google and eBay, in the process.

In this round, however, the underlying drivers have accelerated exponentially. This new model of Young Turk isn't merely comfortable with technology—he can't remember a world without the Internet. Accordingly, he's no longer content merely conquering the technology space—
every
industry is now the technology space, whether hotels or music or transportation. And thus ripe for pillaging.

Then there's the cash. History will determine whether this proves to be yet another financial bubble—when a five-year-old taxi-sharing app, Uber, raises venture money at a $17 billion valuation, it's hard to bet against that. But what's undeniable is that we're witnessing the most prodigious wealth machine in human history. Zuckerberg, worth some $30 billion on his thirtieth birthday, may be the poster boy for this new breed, but he's far from an outlier. Almost a dozen Americans, ineligible by dint of age to serve as president, became self-made billionaires over the past five years. What's more, no one in this cohort finds that particularly unusual—they pretty much feel
entitled
to it.

Youth, meanwhile, has officially ceased to be a disadvantage, upending pretty much the entirety of civilized history. Previously, whether you were a blacksmith or a lawyer, wisdom and experience rendered you more valuable as years went on. No longer. For the past twenty years, if your computer broke, you'd prefer that the twenty-five-year-old fix it rather than the fifty-five-year-old. For ten years, venture capitalists favored young “digital natives” over industry veterans, as long as the former got paired with an operational “adult.” We've now skipped the adult requirement. The kids are fully running the show.

And unlike the hedge fund managers of the previous decade, who were rightly perceived to have conjured their billions without actually creating anything (other than the complicated financial structures that wound up collapsing everything else), no one resents them for it. Quite the contrary, they glide across the country in their chartered Gulfstreams like folk heroes.

The white hats stem from the perception of meritocracy. The high stakes put a premium on ideas and technical execution, rather than connections and salesmanship. As you turn the pages of this book, there's a far higher correlation between financial success and a stint as a teen hacker than having daddy's name on a building at Harvard. The engineers have trumped the salesmen. Sexism remains embedded in the coder-boy set (it's not by choice that this book is chock-a-block with guys; very few women have launched major tech-enabled start-ups). But just ask Jan Koum or Pejman Nozad or Daniel Ek—the American Dream has never been more vivid. The only nepotism, as best as I can tell, comes from being the catalyst's roommate, buddy, or frat brother. (In the 2010s, there's no sweeter title than “co-founder.”) It's hard to resent someone when you had the same shot at the brass ring.

To me, however, the ultimate commonality across all these chapters, the one that lets them reap adulation, boils down to individualism. The post-meltdown recovery has proven among the most tepid in national history, especially the job market. Where others see a paralysis-inducing world, these guys see a gold rush, and they
take action
. They'd all rather regret the things they did than what they didn't do. Jobs and Gates and Dell made dropping out acceptable; among this group, it's cool, a badge of honor. (Snapchat's Evan Spiegel dropped out of Stanford in the middle of a class, a month before graduation . . . on principle.)

Failure is an acceptable option. There's hardly anyone in this book who hasn't tasted it. Venture capitalists, in fact, view failure as an asset, and fund based on whether you've had the good fortune to make mistakes on someone else's dime. The entire VC ecosystem is based on flops: the idea that a one-in-ten success ratio is fine, as long as that success is a blockbuster.
You only have to be right once.
The greatest successes come when people aren't afraid to fail—a decidedly American outlook that explains why almost every innovation of the Internet era has sprung from this country.

Credit belongs to the
Forbes
writers and researchers who brought forward—and home—this endless parade of digital robber barons: George Anders, Victoria Barrett, Jeff Bercovici, Steve Bertoni, Abram Brown, J. J. Colao, Hannah Elliott, David Ewalt, Tomio Geron, Andy Greenberg, Ryan Mac, Parmy Olson, and Eric Savitz. This book, to a large degree, is yours. Thanks at Penguin's Portfolio imprint go to Adrian Zackheim, Natalie Horbachevsky, and Will Weisser, who instantly grasped the power and importance of what we'd assembled, and scrambled with the speed of a start-up to get this to market. At
Forbes,
two people deserve a special call-out: Lewis D'Vorkin,
Forbes
's chief product officer, whose return to
Forbes
four years ago brought a refocus on chronicling people-based entrepreneurial capitalism—he set the stage for the stories that infuse this book; and Bruce Upbin, who as managing editor oversees
Forbes
's technology coverage—he was at the genesis of almost all of these profiles.

For the past three years, my job has provided the perfect perch to see the waves swell, as
Forbes
, scorekeepers of capitalism, emerged as the preferred venue to introduce (or reintroduce) yourself to the world. The large majority of these chapters were born from
Forbes
magazine features, and the majority of those were cover stories. The facts in every chapter have been updated, resulting in an accurate snapshot of what was going on as we went to press in the summer of 2014. I ordered them in roughly sequential order, based on when the companies began taking off. Even across just three years of profiles, while the core traits remain consistent, you'll see the numbers swell ever-larger.

Which brings us back to my party pal Sean Parker. The most famous line attributed to him in
The Social Network
, of course, was his advice to Zuckerberg on their first meeting:
A million dollars isn't cool. You know what's cool? A billion dollars.
It was, he told me, complete Hollywood fiction. He never said it. And even if he had, as you progress though these chapters, you'll recognize a second level of folly. In the land of the young tech elite, a billion isn't cool anymore. Ten billion is.

—Randall Lane, August 2014

@RandallLane