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Book Summary: You Only Have to Be Right Once – The Unprecedented Rise of the Instant Tech Billionaires

This comprehensive collection of profiles features Silicon Valley’s newest and most influential tech entrepreneurs and provides you with an inside look at the habits, philosophies, and ideas that helped them take the world by storm. In this summary, you’ll explore the lives of four major figures who created companies that are reshaping the world and how they achieved their super-entrepreneur status by betting big on major ideas.

Based on Forbes magazine interviews with some of Silicon Valley’s most successful tech entrepreneurs, You Only Have to be Right Once outlines how today’s tech wunderkinds achieved their successes.

Discover insider secrets to entrepreneurship from the tech giants shaping the world.


  • Are curious about the unbelievable success found in the tech world
  • Want to find out about the new breed of billionaires
  • Wonder how super-entrepreneurs create their empires

Did you know that Airbnb started out as an inflatable mattress and WhatsApp as an online address book with the ability to share status updates?

Book Summary: You Only Have to Be Right Once - The Unprecedented Rise of the Instant Tech Billionaires

Over the last few years, a few entrepreneurs have struck it big, very big. In a relatively short space of time, the people behind success stories like Dropbox, Airbnb and WhatsApp have taken an initial simple idea and made it into businesses worth billions.

This book summary describe the journey that many of these tech billionaires have taken. Based on interviews with Forbes, they teach you that in the modern digital world the possibilities from simply having a good idea are endless.

In this summary of You Only Have to Be Right Once by Randall Lane,In this book summary you’ll discover:

  • how one entrepreneur got into Silicon Valley through selling carpets;
  • why the genius behind Tumblr didn’t want to run his own business; and
  • which innovative product began life as a disposable camera strapped to an arm.


The disruptive power of technology is changing the world one invention at a time, and the new tech billionaires who populate Silicon Valley are leading the way. With unprecedented genius and massive amounts of venture capital, these superentrepreneurs come from all walks of life but share one crucial quality: They each discovered that, to make it big in the tech world, you only have to be right once.

In the digital age, innovative platforms and software that change the way people live are being invented every day, and it only takes one incredible idea to create an international phenomenon. The keys are knowing when to keep working on your vision and how to launch your venture before someone else thinks of it.

Thanks to rapid global development, technology isn’t an isolated market anymore. Every market is now a tech market — from medicine to housing to transportation. Tech startups are changing the face of every industry imaginable and making their founders and investors enormously wealthy in the process.

In this summary, you’ll examine in-depth profiles of four of the world’s most successful entrepreneurs: Elon Musk, creator of Tesla and SpaceX; Jack Dorsey, creator of Twitter and Square; Alex Karp, creator of Palantir; and Jan Koum, creator of WhatsApp. These innovators of the internet era prove that the American Dream is alive and well. They also show that, in the age of technology, it only takes one successful idea to catapult you to phenomenal levels of wealth and achievement.

Elon Musk (Tesla & SpaceX)

You’ve probably heard of Elon Musk’s two pioneering startups: Tesla, which focuses on renewable energy across multiple sectors, and SpaceX, which aims to privatize space travel and exploration. But even if you’re not familiar with Tesla or SpaceX, you might know him by the other wildly successful companies he was involved with: eBay and PayPal.

Musk, the inspiration for the popular Iron Man character of the Marvel Cinematic Universe, has been called the greatest entrepreneur of the 21st century, and for good reason. Musk dreams big, works tirelessly, attempts to tackle some of the world’s greatest problems, and makes his career of disrupting some of the most outdated industries on the planet — energy and automobiles.

Only a visionary could attempt such lofty goals, and few people have the grit to endure the enormous pressures he’s faced to protect his companies. Known for his tenacity and ingenuity, Musk has successfully led his companies in creating technologies that are on the cutting edge of modern human history.

In Musk’s world, Hollywood and Silicon Valley converge, each providing inspiration for the other. Musk, a father to five boys, spends most of his time working on his ideas himself, with his background in engineering and his insatiable curiosity propelling him toward new inventions. One of his key traits is his honesty. He gives brutally honest feedback on business operations and designs and expects to receive the same in return.

Together, these qualities — authentic curiosity, brilliant imagination, unparalleled vision, and rigorous honesty — have contributed to Musk’s outrageous success. They’ve enabled him to weather the storms that have rocked the tech world in recent years and propelled him to the highest levels of business success.

Jack Dorsey (Twitter & Square)

Jack Dorsey made history (and billions of dollars) by founding two of the world’s most exciting tech companies almost simultaneously. In his case, he’s been right — really right — about the potential of an idea not just once, but twice. This earned Dorsey a reputation as one of Silicon Valley’s major game-changers.

Twitter, one of the most popular and ubiquitous social media platforms of the digital age, began with a simple idea: What would it look like if the internet could send and receive text messages? This idea turned out to be powerful and transformative, disrupting traditional news cycles and forms of communication. Dorsey and three friends created what would become one of the most visited sites on the web within months of its launch, and eventually, it would become the internet’s ultimate promotional platform, news disseminator, and communications tool. Today, major corporations, news organizations, and world leaders break stories and interact directly with the public via Twitter — which is currently valued at nearly $40 billion.

Square, Dorsey’s lesser-known enterprise, was created to help small businesses accept credit card payments without incurring outrageous fees. While Square hasn’t quite reached the same heights of success as Twitter, it has significantly altered the landscape of traditional payment platforms and democratized access to online financial services. Today, two million small businesses use it regularly.

The way Dorsey allocates his time is crucial to his success. He uses everyday activities like running, walking, and traveling to their fullest, so he can concentrate on structuring his thoughts. One of his favorite things to do is let his mind wander while he wanders around his offices or unexplored parts of town. This is how he mentally tucks into the process of unpacking his next great project.

Alex Karp (Palantir)

Palantir isn’t a household name — but it should be. Considering the wealth of intimate knowledge it has likely collected about you, Palantir could aptly be called Big Brother. But despite the breadth of information it has collected, it remains one of the most mysterious companies in the tech world.

Palantir’s data-mining capabilities are second-to-none, which might explain how it won early funding from the CIA and other government groups. And while advocates of transparency and civil liberties might decry its purposes and uses (it purports to help the government track terrorists and detect corporate hacking attempts), there’s no denying that its advanced, custom programs can perform incredibly complex calculations instantaneously. It’s truly one of the most powerful tech innovations to emerge from the past decade.

Alex Karp, the company’s founder, holds a doctoral degree in social theory and is acutely aware of both the profound benefits and dark drawbacks to creating a product that’s developed around poking into people’s private worlds. The competing tensions of privacy and security influence his approach to how his business operates, but it can be hard to balance them equally when most of the company’s contracts come from government surveillance agencies.

Nevertheless, Karp’s incredibly successful idea has catapulted him to the top of the tech world and landed him a spot on the burgeoning list of Silicon Valley billionaires. With his uncanny ability to translate complex ideas into simple terms and his dream of building a platform that enables humans to analyze vast sums of data, Karp has maintained a steady focus on nurturing a major idea. That idea has changed how governments, corporations, and investigators map out the secrets and intricacies of the modern world. Few people are aware of the vast scope of Palantir’s growing reach and resources, but there are few people beyond the scope of Palantir’s ever-multiplying data points.

Jan Koum (WhatsApp)

In 2014, Facebook acquired the messaging platform WhatsApp, which facilitates the conversations of over half a billion people worldwide, for the tidy sum of $19 billion. Jan Koum, WhatsApp’s unlikely founder, became the recipient of much of that sum. In a nod to his unconventional background, Koum used the moment to distinguish himself from many of the Silicon Valley elites populating the startup offices around him. As a poetic gesture, he signed the deal against the door of the welfare office where he used to go as a teenager.

Jan Koum’s story follows the quintessential trajectory of the classic American Dream. He led a rags-to-riches existence, culminating in one of the greatest tech deals of the century. Born in Ukraine, Koum emigrated to the U.S. as a teen, living on government checks with his cancer-stricken mother until she died a few years later.

Koum’s one big idea was to create an indispensable social utility for mass communication — an idea that would materialize in the form of WhatsApp. The company became an almost overnight success, with nearly half of its users returning daily and hundreds of millions of people using it to connect with loved ones locally and around the globe. In addition to its text, video, and picture-sending capabilities, WhatsApp also provides voice calling — all with the added benefit of encrypting your conversations.

It’s no wonder people all over the world rely on it for their communication needs and equally unsurprising that Facebook purchased it for such a massive sum. And although the app has already erased $33 billion in text message revenue from mobile service providers around the globe, they promise even more disruptive moves in the future. Their goal is for the service to reach half the people on planet earth in the next few years.

To understand how Koum transformed WhatsApp into what it is today, you must first understand the environment that shaped him. Before coming to America, his family lived in poverty in Kiev. Hot water and electricity were rationed, and there was limited access to hospitals and schools. Although there was a beauty to the family’s rural life, danger clouded their days: His parents avoided talking on the phone because they knew it was likely being tapped by government officials. Raised with this looming concern for privacy, Koum internalized the desire to talk freely and communicate without the ear of the state listening in.

Years later, after designing networking infrastructure at Yahoo, Koum found a way to give that desire wings. He created the code for WhatsApp, incorporated his business in California, and began writing the code that would allow his app to connect with any phone number in the world. His messaging service expanded exponentially when people realized that it allowed them to connect with friends anywhere around the globe at the touch of a button, all with encryption built in — for free. There was nothing else like it.

Regarding his success, Koum, an intensely private individual, says that all he ever wanted was to do one important thing and do it well.

Many tech-billionaires achieved their success by boldly pursuing a dream.

If you want to be successful in life, what’s the best path to take? Here’s the conventional answer to that question: work hard at school and then find a mentor to help you along your career — which you should pursue at a slow and steady pace.

Although this approach probably sounds familiar, most of today’s mega-successful young entrepreneurs — the tech-billionaires — followed a different path. For them, success was all about boldly pursuing a dream and ignoring what society expected of them.

Let’s look at one example: when he was just 23-years-old, Evan Spiegel, the co-founder of Snapchat, turned down Facebook’s offer to buy his company for $3 billion. Although it’s too early to tell whether his decision was wise, we can still learn from Spiegel’s stratospheric path to success.

Like many other successful entrepreneurs, Spiegel learned how to get his own way at a young age. When his high-powered lawyer parents split up, Spiegel used it to his advantage: his dad refused to buy him a BMW, so Spiegel moved in with his mother. It wasn’t long before his dad caved and bought him the car.

There’s another similarity between Spiegel and his entrepreneurial peers: that he dropped out of college to pursue his startup. He and Snapchat co-founder Bobby Murphy came up with the idea for their app while they were still in college, but struggled to get the concept to take off. Although their parents pestered them to look for “proper jobs,” the duo stayed true to their dream.

And finally, they received an investment from a venture capitalist. Spiegel promptly quit college (weeks ahead of graduation) and started on Snapchat day and night.

And of course, you know how this story ends: Spiegel’s efforts paid off and Snapchat became one of the world’s most popular apps — so popular that Facebook offered to buy it for $3 billion.

Plenty of outsiders have broken into the closed world of Silicon Valley.

After hearing that last story, you might be wondering, “Hmmm. Was Evan Spiegel really an outsider who achieved success solely through hard-work and boldness? After all, weren’t his parents high-powered lawyers? Didn’t he go to Stanford?”

Although there’s some truth to that objection, plenty of tech-billionaires come from different backgrounds. Here are two stories about mega-successful entrepreneurs who came into the tech industry as complete outsiders.

First we have Pejman Nozad. Born in Iran, Nozad’s family fled to Germany when he was a boy. Later, he made a bold move to San Francisco with just $700 in his pocket. Although he didn’t speak English, he soon learned the language and found a way to survive by doing odd jobs.

Eventually, without having prior experience, he started working as a salesman at a carpet store. He turned out to be a great salesman and an even better networker. Through his sparkling conversational skills and personal warmth, Nozad built up relationships with many of the businessmen and tech leaders who came to the store. And eventually, he leveraged these connections to start the investment fund Amidzad, which invested early in successful companies like Dropbox — earning over $100 million in the process.

Our second story centers around Adi Tatarko, who co-owns Houzz, a home-design community worth $2 billion.

Tatarko is one of the few women who achieved great success in the tech industry despite the overwhelming gender bias in Silicon Valley. (Consider that 43 percent of the 150 biggest companies in the Valley don’t have a single woman on the Board of Directors!)

How did she manage to cut through the sexism? Well, it had a lot to do with sheer energy: Tatarko can work nonstop. And for motivation, she looks up to her grandmother, who worked as a designer when fashion was still a male-dominated industry.

Tech entrepreneurs get to the top with a little help from their friends.

Whenever we read about the latest wildly successful tech wunderkind, we’re tempted to think, “Wow—he must be a genius to accomplish so much at his age!” Not to detract from anyone’s well-earned success, but it’s important to remember that all of these people had lots of help along the way.

To that end, let’s look at the story of Tumblr. Today, the wildly successful social network is a top tech enterprise, yet, founder David Karp never planned for it to be a business. He was just happy to have the tool for his personal use.

Luckily, he had a mentor. Entrepreneur Fred Seibert recognized Tumblr’s vast potential for success, and managed to persuade Karp (pretty much against his own will) to turn his product into a business.

At first, Karp hated being a manager and overseeing the expansion of his company. But he persevered and Tumblr flourished. Eventually, the company’s success attracted Yahoo!, and the tech giant bought Karp’s blogging platform for $1.1 billion. So, thanks to Seibert’s advice, Karp turned his small idea into a major success.

Here’s another story about mentorship in the tech world. It concerns Palmer Luckey, the creator of the Oculus Rift virtual reality (VR) headset. It’s important to note that VR is a notoriously tricky field, and that many have tried and failed in this area — including games giant Nintendo, whose 1996 foray into VR was so disastrous that it literally gave players a headache when they used it.

Nevertheless, Luckey ventured forth. And luckily, he had the help of VR pioneer Mark Bolars, who shared his trailblazing research with Luckey for free. Luckey also had the help of video game programmer John Carmack, who demoed Oculus Rift to the games industry.

All this assistance paid off: Facebook eventually bought the company for $2 billion.

So now that we’ve seen a few tech-billionaire origin stories, let’s delve deeper into what it takes to turn a great idea into a phenomenal success.

Many billion-dollar companies have created simple solutions to small, everyday problems.

What does it take to come up with a great idea? Surely it’s a matter of thinking long and hard about life’s great problems.

Well actually, no — not at all. To be successful, you don’t have to come up with a formula for cold fusion or design a perpetual motion machine. Rather, success often lies in simplicity, in solving a small, everyday problem.

This was the case for Nick Woodman. After his first business idea failed, Woodman took some time off to surf in Indonesia and Australia. When he wanted to record some of his surfing adventures, he faced a problem: how was going to take pictures while riding the waves?

He came up with an incredibly simple solution and strapped a disposable camera to his wrist. When he told his friend about his DIY creation, his friend urged him to take his simple idea to the next level.

Woodman eventually created a wearable camera with durable casing, so that it would be impact resistant and waterproof. This tool developed into GoPro and Woodman went on to sell $1 billion worth of cameras.

Next, we have the story of Jack Dorsey. Dorsey is best known for his world-changing product, Twitter, but he also has a $1 billion stake in a payment processing company called Square.

Square was inspired by a real-life problem: Dorsey’s friend, a glassblower, lost a $2,500 sale because he didn’t have the tools to process a credit card payment.

Dorsey set out to find a solution, and ended up creating a very cheap smart-phone-based terminal that would allow small businesses to accept credit cards.

It was a very straightforward solution, and it was also Dorsey’s second billion-dollar idea.

Challenging established companies and business models can lead to success.

If you want to rise to the top, you’re bound to upset a few people along the way. And tech-billionaires aren’t scared to.

Consider Aaron Levie, the founder of Box, a company which allows you to share and edit files and documents on any device.

Before we dive into his story, it’s important to note that for years, the computer software industry was dominated by four main companies: Microsoft, SAP, Oracle and IBM. Their dominance didn’t lead to a lot of innovation in the tech industry: Since there was so little competition, clients paid high fees for tech services and upgrades; and furthermore, the quality was often not the highest. Even today, these companies lack many adequate products for the mobile and tablet markets.

For startups like Box, this presents an opportunity. The Box app allows people to share, open and edit files on any device. This kind of software has traditionally been Microsoft’s domain, but the tech giant has been slow to adapt its Office Suite for mobile. And what’s more, Box offers a free basic service without requiring users to pay for upgrades.

The company’s nimble, efficient approach has proven to be a huge success: By 2013, Box had $124 million in revenues and even traditional powers were clamoring for a partnership.

But for startups, success isn’t always about challenging established leaders. For companies like Airbnb, it’s about creating entirely new ways of doing business.

Faced with a market completely dominated by hotels and guesthouses, founder Brian Chesky thought outside of the box and developed a whole new model for hospitality. Airbnb allows people to connect online to find private lodging while traveling.

Although the company’s share of the hotel market is still small (Airbnb has $100 million of a $1 billion industry), established companies have taken note. Airbnb poses such a threat to the traditional way of doing business that the hotel industry is counting on government regulation to curb the company’s growth.

For tech entrepreneurs, persistence and the ability to overcome failure are crucial to success.

In the case of any challenging, competitive venture, success is largely a matter of persistence.

And the story of Dropbox founder Drew Houston epitomizes this lesson. When he was just 14 years old, Houston already knew what he wanted to do. When a teacher asked his classmates what they wanted to be when they grew up, his hand shot up: “I want to run a computer company,” he said.

From that point forth, he never gave up pursuing that dream. As a high school student, Houston started working as a beta tester for an online game. The company spotted his talent and hired him as a network programmer. Later in college, Houston worked for five more tech startups.

And then one day, Dropbox was born: Houston needed to pull up a few files, but realized they were on another computer. He started working on his idea right away, developing the basic technology which would allow him to synchronize files over the Internet.

Five years later, Houston has a $600 million stake in his $4 billion company — and he’s made his childhood dream come true.

Of course, many aspiring entrepreneurs experience failure on their path to success. This was the case for Sean Parker, the former president of Facebook and founder of Napster.

Parker’s path was riddled with failure. For example, while he was president of Facebook, police found cocaine in a house that was rented under his name. Although the incident led him to resign from the social network, Parker didn’t give up.

He went to Spotify, the super-successful music streaming service which was then in its early days. Parker helped secure deals with major record labels like Universal and played an instrumental role in Spotify’s social network integration. As you can see, Parker didn’t let obstacles hold him back.

Successful entrepreneurs are prepared to tweak their products to develop what the users want.

It’s easy to feel protective of a company you’ve started, but resisting change will get you nowhere. The most successful companies know how to be flexible and respond to what their customers want.

Kevin Systrom, co-founder of Instagram, exemplifies this principle. Today, Instagram is an incredibly successful photo-sharing network, which was recently purchased by Facebook for $1 billion. But when it first started, Instagram was a very different kind of company.

Systrom and his co-founder first created Instagram as a combination of Foursquare, which allows users to “check-in” their location, and a photo-sharing service. This concept fell short: the overall product was slow and cumbersome, and people didn’t respond to the check-in feature.

But then, while they were vacationing in Mexico, Systrom had an idea. Why not add filters to the photography feature? These filters would allow users to add instant nostalgia or poignancy to everyday pictures. Within a month of introducing the filters, Instagram’s user base grew to one million.

Facebook’s other recent purchase, WhatsApp (which was purchased in 2014 for $19 billion), is another great example of a flexible startup.

Jan Koum, the brainchild behind Whatsapp, was a poor immigrant from the Ukraine. He and co-founder Brian Acton originally launched their company as an address book for the iPhone which allowed users to update their status (e.g. “at the gym,” “battery low”).

Although the initial idea didn’t win over users, things changed when Joum and Acton combined the concept with Apple’s new “push notification” feature. Now every time you updated your status, all your WhatsApp contacts would get a notification about it.

Remarkably, people started using the app in a completely different way than originally intended, as an instant messaging service. WhatsApp quickly changed its focus, and its user base grew to 480 million before it was acquired by Facebook in 2014.

We’ve learned a lot about how tech-billionaires achieved their fortunes. And now in the final book summary, we’ll look how they’ve managed to maintain their success.

Maintaining success is never easy; successful entrepreneurs will always face competition from other companies.

So now that we’ve learned about how a few tech-billionaires managed to turn simple ideas into billion-dollar companies, it’s time to find out what it takes to maintain that level of success. Because for tech wunderkinds, it’s not enough to stop at the billion-dollar valuation.

This is especially true because the giant established companies — the ones which were challenged by the upstart entrepreneurs discussed in this book summary — are always trying to reclaim their market dominance.

Consider Palmer Luckey’s story. (We’ve already talked about how Luckey was able to turn his design for a virtual reality device into a company, Oculus Rift, which sold to Facebook for $2 billion.)

Despite his immense success, Luckey (who still runs Oculus Rift, even after the sale to Facebook) still faces a challenge in keeping his company at the top of the market.

There are plenty of competitors encroaching on his turf: For one, electronic giant Sony is developing its own VR headset for its latest console, Playstation 4.

Amazon is also rumored to be entering the market. The e-commerce company may be planning to create VR shopping malls. So instead of just looking at a photograph of an item, these “malls” would allow you to virtually pick up a product, look at it in detail and even try it out.

Because of competitors like Amazon and Sony, for Luckey the work never stops. He must constantly seek out new ways to stay ahead of the competition.

And that’s exactly why he used the money from the sale of Oculus to purchase other companies that might allow him to improve his product. Among his purchases were RakNet, an open source game networking engine (which allows people to create and share their own games), and Carbon Design Group, a product design studio.


The internet age is giving rise to tech billionaires by the dozens, not only in Silicon Valley but around the globe. Although episodes of failure and years of wandering sometimes characterize these innovators’ lives before they make it big, what they all have in common is their ability to find the one big idea that changes not only their lives, but the lives of millions of people around the globe.

The four figures profiled in this summary are only a handful of the 15 or so whose lives, ambitions, and successes are featured in the full-length book You Only Have to Be Right Once. Each of these 15 game changers came from disparate backgrounds and walked diverse paths before founding the companies that are shaping modern human life. There’s no proven formula for becoming a tech billionaire, but it certainly takes courage, grit, and instinct to take a brilliant idea and grow it into a platform that transforms the course of humanity.

The key message:

In today’s age of rapid technological innovation, there are plenty of opportunities for success. And as we can see from the stories of today’s top tech billionaires, all you need is one great idea — and the courage and the determination to bring it to fruition.

About the author

Randall Lane is an editor at Forbes magazine and co-founder of 1997 Adweek startup of the year winner, P.O.V. Lane also launched Doubledown Media and is the author of The Zeroes: My Misadventures in the Decade Wall Street Went Insane.

RANDALL LANE is the editor of Forbes and the author of The Zeroes: My Misadventures in the Decade Wall Street Went Insane.

Since 1917, FORBES has provided leaders with strategic insight and information. The largest business magazine in the world, Forbes has 6.1 million readers in the United States and more than thirty international editions.


Business Biographies, Business and Money, Finance, Venture Capital, Computers and Technology Industry, Company Business Profiles, Business Technology Innovation, Company Histories, Entrepreneurship, Self Help

Table of Contents

Introduction vii
Chapter 1 Sean Parker, Facebook: Master of Disruption 1
Chapter 2 Drew Houston, Dropbox: No More Hot Pockets 17
Chapter 3 Elon Musk, Tesla Motors and SpaceX: Inside the Mind of Iron Man 29
Chapter 4 Kevin Systrom, Instagram: No Revenues? No Revenue Model? No Problem! 41
Chapter 5 Daniel Ek, Spotify: Hacking the Music Industry 55
Chapter 6 Aaron Levie, Box: The Man Who Would Be Gates 69
Chapter 7 Jack Dorsey, Twitter, Square: Jack of All Trades 81
Chapter 8 David Karp, Tumblr: The $1 Billion Art Project 93
Chapter 9 Nick Woodman, GoPro: Chasing the Thrillionaire 107
Chapter 10 Brian Chesky, Airbnb: The Sharing Economy’s Broker 119
Chapter 11 Alex Karp, Palantir: Meet Big Brother 127
Chapter 12 Pejman Nozad, Angel Investor: Silicon Valley’s Cinderella 143
Chapter 13 Evan Spiegel, Snapchat: The $3 Billion Bet 155
Chapter 14 Palmer Luckey, Oculus VR: Virtual Reality, Tangible Fortune 171
Chapter 15 Adi Tatarko, Houzz: Breaking into the Boy’s Club 183
Chapter 16 Jan Koum, WhatsApp: The Face of the American Dream 193


The ultimate insider look at the newest titans of tech—and what you can learn from their success

In 2007, twenty-one-year old David Karp launched Tumblr, a simple micro-blogging platform, on a whim. By 2012, it had become one of the top ten online destinations, drawing 170 million visitors. By 2013, Yahoo had acquired Tumblr for over $1 billion. Just like that, a kid who hadn’t even earned his high school diploma was worth over a quarter billion dollars. And he’s not the only one…

* * * * *

Silicon Valley’s newest billionaires represent a unique and unconventional breed of entrepreneur: young, bold, and taking the world by storm with their extreme speed, insatiable hunger, and progressive leadership. They are all turning just one brilliant insight or hook into money at a rate never before seen in human history—creating companies that, even with no revenue, garner insane valuations.

With unique insider access to the world’s most influential and wealthy entrepreneurs, Forbes has dug in to find what these superentrepreneurs say about their own success. This book, introduced, edited, and updated by Forbes editor Randall Lane, is the first comprehensive look at who these instant tech billion­aires are and how they achieved their quick wins. With sixteen illuminating pieces, we get behind-the-scenes examinations of the founders of Tesla, Spotify, Airbnb, Tumblr, Twitter, and more, including:

ELON MUSK: The billionaire founder of Paypal, electric carmaker Tesla, and private space company SpaceX. His extreme ambition is matched by his preternatural engineering mind; no wonder he was the model for Robert Downey Jr.’s portrayal of Iron Man.

EVAN SPIEGEL: In 2013, the twenty-three year-old founder of Snapchat declined a $3 billion cash offer from Mark Zuckerberg. Today, Snapchat is valued at $16 billion. The story of Snapchat’s origin is even wilder than Facebook’s, but Spiegel’s ability to parlay infamy and popularity into revenue is still up in the air.

ALEX KARP: An eccentric philosopher with almost no tech background turned a Peter Thiel–backed venture, Palantir, into a data-mining champion, with clients like the NSA, the FBI, and the CIA. Amid heated privacy concerns, Karp continues to grow Palantir like crazy, to over $1.5 billion in funding and an estimated $1 billion in contracts in 2014.

You Only Have to Be Right Once is the definitive collection of everything we can learn from these incredible game changers and what their next moves spell for the future of business.


From “You Only Have to Be Right Once”
Wedged into a corner, Sean Parker sported the removed look of someone at a crowded party who doesn’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 since I returned as the editor, it seemed right to introduce myself.
It’s not that the “Forbes” cover had been a valentine: it revealed the polymath who had helped shape Napster, Facebook and Spotify for all his quirks and faults. But until that story, the world equated him with the villainous character portrayed by Justin Timberlake in David Fincher’s movie” The Social Network.” Now Parker stood before me as a brash actor in a story that has only a little to do with Facebook and feels a 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. This narrative isn’t new.
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 the pillaging.

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“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 summary 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



The evolution of the Internet, from unfettered hacker toy to unlimited wealth machine, comes embodied in one Sean Parker. As the teenage cofounder of Napster, the music piracy site that nearly crippled the recording industry, he gained notoriety, even as he flirted with bankruptcy and jail. As the twentysomething president of Facebook, entrusted with giving Mark Zuckerberg some adult supervision, he cemented his digital bad boy reputation, even as he made himself a few billion dollars. But when Steven Bertoni tried to track down the mercurial Parker in 2011, he found proof of the adage about wealth’s ability to buy happiness. Parker, recovering from surgery and a freshly branded villain of the tech world, courtesy of David Fincher’s movie The Social Network, devolved into a hermit, holing up in the Peninsula Hotel in Los Angeles for two months, a digital Howard Hughes. When he emerged, he invited Bertoni for what was supposed to be a relatively brief sit-down in his new $20 million townhouse in New York’s Greenwich Village. That meeting turned into a meticulously chosen sushi dinner, and after two bottles of expensive sake, a trip to the West Coast, via rented Gulfstream, where Parker pinballed around various interests. His passion at the time: Airtime, a video-sharing service that he zealously kept under wraps—and eventually flopped. No big deal. This is a guy adept at identifying problems, and at peace if not every solution works out. He also backed Spotify, a legal reincarnation of Napster—by 2014, it was valued at more than $4 billion.

Pointed toward his eighteen-acre compound in Marin County, Sean Parker ripped through the night fog on the Golden Gate Bridge in a stealthy Audi S6 that masks a Lamborghini engine, one pale hand on the wheel, the other toggling through thousands of songs uploaded on the car’s sound system.

Facebook’s former president had endured a typically busy day. Over the last ten hours he’d interviewed two potential VPs for his new video startup, answered hours’ worth of e-mails about the music platform he was backing, Spotify, and met with a potential CEO for his Facebook charity app, Causes. He had also booked bands and wrangled vendors for his engagement party, scheduled in New Jersey the same night Hurricane Irene hammered the Northeast (with Lenny Kravitz grounded in North Carolina, he eventually subbed in the Cold War Kids). Later, he broke from work to dine with Jack Dorsey, the chief of Facebook rival Twitter and payment service Square. After dinner, at the restaurant bar, he interviewed another potential boss for Causes. By the time he dropped me off at my hotel, it was 11:30 p.m. Parker’s day was about half done.

For the next six hours Parker fired off e-mails, then turned to his private Facebook page. The previous afternoon—or earlier the same day, if you’re on Parker’s body clock—the world had learned that Steve Jobs resigned from Apple. Around 6:00 a.m., Parker posted this Schopenhauer quote: “We can come to look upon the deaths of our enemies with as much regret as we feel for those of our friends, namely, when we miss their existence as witnesses to our success.” It immediately leaked. Gossip site Gawker accused him of dancing on Jobs’s grave. He e-mailed Gawker that the quote was a tribute to Jobs—his longtime idol and more recent rival (iTunes versus Spotify). Just before 7:00 a.m. he went to bed.

Four hours later he was up, ready to do it all again.

Flighty, manic, and unpredictable, Parker grates on investors—he’s been jettisoned from the three companies he helped create, soon after they lifted off. “He’s seen as an unknown quantity, and VCs love for things to be very much in control,” said Facebook cofounder Dustin Moskovitz. But VCs also love big ideas, and Parker has those in spades—LinkedIn founder Reid Hoffman calls him a “big-ass visionary.” And in terms of boardroom scheming, he’s nothing like his fictional portrayal in The Social Network. “The movie needed an antagonist, but that’s not what he was,” said former Facebook growth chief Chamath Palihapitiya. “He’s really the exact opposite of his portrayal in the film.”

Boiled down, Sean Parker is a human accelerant, an idea catalyst who, when combined with the right people, has fueled some of the most disruptive companies of the last two decades. At just nineteen he blew up the record industry as the cofounder of the music-sharing site Napster. Two years later his address book service, Plaxo, demonstrated the potency of digital propagation, something he took a step further as the twenty-four-year-old president of Facebook, helping the social network become the most important Internet company since, well, maybe ever. Yes, all three companies eventually bounced him, but not before, by thirty-one, he tucked away enough equity to boast a fortune of more than $2 billion. And he was just getting started.

By 2011 he was out to upend music distribution again, bringing the Swedish music platform Spotify to America—and masterminding how the service would work with Facebook’s music efforts. He was also hunting new startups as general partner at venture firm Founders Fund and reuniting with Napster’s Shawn Fanning to create Airtime, a live video site.

Parker’s personal network is astounding, a combination of foresight and fate. Starting as a teenager, when he interned for Mark Pincus (now Zynga’s chairman) Parker has teamed, in one way or another, with the men who now control the modern Internet: Mark Zuckerberg, Mike Moritz, Peter Thiel, Reid Hoffman, Yuri Milner, Dustin Moskovitz, Adam D’Angelo, Daniel Ek, Ron Conway, Ram Shriram, and Jim Breyer.

“He can see things most people won’t be able to see for a year or two,” said Palihapitiya. As Shervin Pishevar of Menlo Ventures describes it: “Parker has access to trends and signals that are invisible to many people. For him it’s like hearing a dog whistle.” Parker didn’t disagree: “I find a lot of things relevant that aren’t necessarily relevant to the world when I’m thinking about them.” Parker is drawn to big, universal problems and spends years looking for them. “Most of us kind of agree on the thrust of history. The key is to understand how we get there,” said the young billionaire as he rolled his desk chair closer to me in the office of his recently purchased $20 million Manhattan townhouse. “The transition strategies are more important than understanding what the outcome state will be.”

By focusing on problem selection, rather than rushing out an innovation no one wants, like so many trigger-happy entrepreneurs, Parker put himself in position for the string of blockbusters that his critics blithely attribute to sequential luck. Napster was the transition between CDs and MP3s after the Internet made it possible to strip content from its container. Facebook was a vehicle to create a reliable identity in an anonymous online world. Spotify is an attempt to fix the very music industry that Napster helped break a decade before.

“He thinks about where he perceives the world to be going,” explained Spotify founder Daniel Ek. “If he doesn’t think there is a company that will win, then he builds it himself.”

This deep investigative thinking bleeds into everything else in his life. Ask Parker about the genesis of his former company Plaxo, and he starts with theories of how real viruses spread across populations. Before he shares the name of his favorite sushi restaurant—prior to one dinner we had in New York, he called five to find out which chef was cutting the fish that night—he discusses rice density and the ideal geometric shape for sushi cuts (trapezoids). Question this audiophile about the best brand of headphones and you first learn how sound waves are registered by our tympanic membranes. As the expression goes, ask him for the time, and he’ll tell you how to build a watch.

“We talked for what I originally scheduled for an hour, ended up being three hours,” Reid Hoffman recalled about their first meeting back in 2002. Jack Dorsey had the same experience: “It’s rare to find someone who can have those kinds of conversations. . . . I appreciate any conversation where I can walk away questioning myself and my ideas.”

Thus, Parker’s life becomes impervious to time, a subject friends and business partners acknowledge with a defeated laugh. Peter Thiel calls it Parker’s “absence of dramatic punctuality.” Ek manages Parker by telling him there’s a meeting at 11:00 a.m. and informing others it starts at 1:00 p.m. There’s even a name in Silicon Valley for this phenomenon: Sean Standard Time.

“Making people wait and not fulfilling all your obligations feels bad. I probably feel worse about it than people realize, but I don’t do it with malice,” said Parker. When focused on a task, he blocks everything else out and works himself into a trance. The outside world fades; time slips away. “It requires a lot of rescheduling, but I try to focus on things that are the highest value and get those done perfectly.”

Parker’s definition of “done perfectly” is extreme. On the afternoon of his Forbes cover shoot, Parker summoned three full racks of Italian suits. Twenty dress shirts—still in their wrappings—waited on the wicker couch in his Greenwich Village townhouse. Rows of eyeglasses and sunglasses blanketed the coffee table, piles of suspenders and ties filled chairs, a shoe store’s worth of wingtips, loafers, and boots lined the wall. The shoot was scheduled for 4:00 p.m. Sean emerged at 5:30 p.m., flanked by a proper entourage: a clothes stylist, hairstylist, makeup artist, assistant, publicist, tailor, and his fiancée (now his wife), Alexandra Lenas.

During the shoot Parker changed his wardrobe more often than a Las Vegas headliner. He switched from streamlined suits to three-piece numbers to casual cardigans over designer jeans. He obsessed over the spacing of suspenders and triple-checked that the red in his skinny tie matched the red in his hipster eyeglasses. At one point he broke for a snack. Ten minutes later he was in the kitchen, dressed in a dark Christian Dior suit, whisking a bowl of homemade ranch dip. He was trying to lose weight and was eating only vegetables. The ranch dressing on hand was too runny, so he added sour cream to firm it up. His assistant (one of three) coaxed him back in front of the camera. After hundreds of photos in four locations around the house, the shoot was finished, at 2:00 a.m.—perfect, calibrated Sean Standard Time.

Two nights later I arrived at his house at 11:00 p.m. A chartered G450 was scheduled to fly to San Francisco from Teterboro, New Jersey—wheels up at midnight, sharp. Parker was out meeting Spotify’s Ek. When midnight hit and there was still no Parker, I got a little nervous. Everyone else yawned. Parker strutted in at 2:00 a.m. He still had to pack and shower. At 3:30 a.m. a Cadillac Escalade was loaded with luggage and takeout fried chicken from Blue Ribbon, a late-night, New York chefs’ hangout, and across the Hudson we went.

We took off at 4:00 a.m., a half hour before FAA fatigue laws would have grounded the pilots. When I awoke to a view of the California desert outside the plane window, Parker was sitting across from me, snacking on a piece of fried chicken, his veggie-only diet already over. “Did you sleep well?”

We landed in San Francisco at 9:00 a.m., where yet another Escalade ferried us to Marin County. Everyone parted ways to sleep for a few more hours before Parker, eager to meet with colleagues and pitch potential hires, began a sprint through San Francisco and Silicon Valley.

• • •

PARKER’S PATH TO SILICON Valley began the day his father, Bruce, formerly the chief scientist at the National Oceanic and Atmospheric Administration, taught him how to program on an Atari 800. He was in second grade. By high school Parker was hacking into companies and universities (alias: dob, which he chose for its aesthetic symmetry). When he was fifteen, his hacking caught the attention of the FBI, earning him community service. At sixteen he won the Virginia state computer science fair for developing an early Web crawler and was recruited by the CIA. Instead he interned for Mark Pincus’s D.C. startup, FreeLoader, and then UUNET, an early Internet service provider. “I wasn’t going to school,” he said. “I was technically in a co-op program but in truth was just going to work.” Parker made $80,000 his senior year, enough to convince his parents to let him put off college and join Shawn Fanning, a teenager he’d met on a dial-up bulletin board, to start a music-sharing site, which became Napster in 1999.

Parker never did make it to college, but Napster provided an education all its own. “I kind of refer to it as Napster University—it was a crash course in intellectual property law, corporate finance, entrepreneurship, and law school,” said Parker. “Some of the e-mails I wrote when I was just a kid who didn’t know what he was doing are apparently in [law school] textbooks.” Those e-mails, which admitted Napster customers were likely stealing music, would end up as evidence in copyright lawsuits that would eventually shutter Napster. But by that time Parker had already been exiled by management and was living in a North Carolina beach house. “I didn’t understand at the time that when someone asks you to take an extended vacation that’s basically a prelude to firing you.”

While at Napster, Parker met angel investor Ron Conway, who was funding another company in the startup’s building in Santa Clara. Conway has backed every Parker production since.

On our first night in San Francisco, Parker and I visited Conway on the porch of his house overlooking Richardson Bay. We drank Brunello and nibbled on prosciutto. “We’ve gone through hell together,” said Conway, who backed Google, PayPal, Twitter, and FourSquare, among others.

Napster was less a company than an all-hours circus, a strange tangle of people who thought they had joined a renegade social movement rather than a startup. “So much of what I learned at Napster was learning what not to do,” said Parker, as Conway scribbled on a notepad. Conway had learned the hard way to listen to Parker. “When Sean became president of Facebook, he called me and said, ‘You have to look at this company.’ The killer is that I could have been Peter Thiel,” said Conway, referring to Thiel’s investment in Facebook, which made him a billionaire. “But I said, ‘You have to clean up the issues at Plaxo, so don’t introduce me to this Facebook thing.’” He sipped his wine, shook his head and laughed: “These are painful memories.”

Plaxo was Parker’s first attempt at creating a real company—an online service that aimed to keep your address book up to date. It sounds boring compared to Napster and Facebook, but Plaxo was an early social networking tool and a pioneer of the types of viral tricks that helped grow LinkedIn, Zynga, and Facebook. “Plaxo is like the indie band that the public doesn’t know but was really influential with other musicians,” said Parker.

Once you downloaded Plaxo, the program would mine your address book and e-mail every contact with a message, coaxing them to sign up for the service. When the next person signed up, the software would pirate the new address book and spread further. Within a short time millions of e-mail accounts had been hit with Plaxo pitches. “In some ways, Plaxo is the company I’m most proud of because it was the company that wreaked the most havoc on the world,” said Parker. Those experiences later changed the history of Facebook.

There are diverging stories about Parker’s swift exile from Plaxo. His take is that Ram Shriram, a former Google board member recruited to help manage the company, conspired to throw him out and strip him of his stock. “Ram Shriram played this very vindictive game not only to force me out of the company but force me out broke, penniless, impoverished, and with no options.”

Shriram would not speak about this, but cofounders Todd Masonis and Cameron Ring shared a different story: that Parker was essential in creating the company strategy and raising money but grew bored with the daily grind of running it. Masonis claimed that Parker was often absent, and when he was around, he was distracting: “It was the sort of thing where he doesn’t come to work, but then maybe if he does it’s at 11:00 p.m., but it’s not to do a bunch of work, it’s because he’s bringing a bunch of girls back to the office because he can show them he’s a startup founder.”

Whatever the motivation, Parker’s removal was messy. He insisted that investors had hired a private eye to build a case. There were allegations of misconduct and drug use—claims that went unproven. “It happened poorly; we should have done a better job being up front about it and doing it ourselves,” said Ring. “But looking back, it was the right decision for us and for Sean.”

Parker was on his own, isolated from his cofounders and close friends. “I felt a complete loss of faith in humanity, impending doom, a sense that I couldn’t trust anybody,” said Parker. He thought of suing but knew the battle could drag on for years. So he let it go. After all, he had already discovered a new company with potential to get really big.

• • •

WHEN PARKER WAS FIRST shown Facebook by a friend’s girlfriend (not through a one-night stand, as depicted in Aaron Sorkin’s screenplay) he was already a social networking veteran, both because of Plaxo and, more directly, as an advisor to Friendster, the ill-fated Facebook forerunner he stumbled across when reporters asked him if it was connected to the similar-sounding Napster. He knew the larger college market was ripe for its own social network—there were several small sites functioning at individual universities—and Facebook, which had already leapt off Harvard’s campus, gave him a play. He wrote to Facebook’s generic e-mail address and later met Zuckerberg and Eduardo Saverin over a Chinese dinner in Manhattan in the spring of 2004.

A few weeks later, by chance, he ran into Zuckerberg and crew on the streets of Palo Alto and shortly moved into Dustin Moskovitz’s room at the rented Facebook house. “It’s the only thing the movie got kind of close to right,” deadpanned Adam D’Angelo, Facebook’s early technology chief, whom I met at the Palo Alto headquarters of his company, question-and-answer site Quora.

Just twenty-four, Parker was Facebook’s business veteran. He helped the college-aged Facebook founders network around Silicon Valley, set up routers, and meet benevolent investors like Thiel, Hoffman, and Pincus.

“Sean was pivotal in helping Facebook transform from a college project into a real company,” Mark Zuckerberg said in an e-mail. “Perhaps more importantly, Sean helped ensure that anyone interested in investing in Facebook would not only buy into a company, but also a mission and vision of making the world more open through sharing.”

D’Angelo credited Parker for recognizing that design was as vital as engineering. “Our first employee [at Quora] was a designer, and we knew to do that because we saw how important that was at Facebook.” Together with Aaron Sittig, an early Napster friend who would become Facebook’s key architect, Parker helped drive Facebook’s minimalist look. He was adamant that the site should have a continuous flow and that tasks like adding friends be as frictionless as possible. “We wanted it to be like a telephone service,” said Sittig. “Something that really fades into the background.” Later Parker helped push Facebook’s photo-sharing function. It would be one of his last acts as Facebook’s president.

In August 2005, Parker was questioned in North Carolina after cops found cocaine in a beach house rented under his name. He was never arrested or charged, but the incident swiftly kick-started his downfall at Facebook.

Because of agreements, the principals can’t discuss how or why he was ousted. The Team Parker take was that Accel Partners resented him because he forced the VC to invest in Facebook at a then-high $100 million valuation (Accel has since invested in Spotify, and its star Jim Breyer now says Parker had “exceptional insight”). Parker had many supporters, and the cocaine controversy caused a rift between the founders and the investors. In the end, Parker decided it was best for Facebook if he resigned. He had been pushed out of his third company in five years. He moved to New York in the fall of 2005, crashing with Grateful Dead lyricist John Perry Barlow, a friend from the Napster days.

Although no longer on the Facebook payroll, Parker continued to advise Zuckerberg on strategy and to recruit key executives like Chamath Palihapitiya. Sittig said he still helped with the site’s design and was a strong outside influence in the development of Facebook’s “share” platform, which allowed users to upload news articles, video, and other third-party content. Still, likely Parker’s greatest contribution to Facebook was his creation of a corporate structure—based on his Plaxo experience—that gave Zuckerberg complete and permanent control of the company he founded.

Parker’s plan fortified Zuckerberg with supervoting shares that resisted dilution during fundraising and armed him with enough board seats to stay in power for as long as he wanted. “Sean was pretty material in setting up the company in a way that Mark retained as much control as he does, both in being able to get high-valuation, low-dilution financing but also in terms of the board structure itself and details of control,” said Facebook cofounder Dustin Moskovitz. “He’d been coming off the Plaxo mess and was sensitive to that.”