About the Book
About the Author
Title Page
Author’s Note
Prologue: Initial Public Offering
Part I: An Evan Spiegel Production
1. Rush
2. Future Freshman
3. Million-Dollar Idea
4. The Other Startup
5. Lawsuit Possible
6. The Fight
7. Snapchat
8. Sexting
9. Betrayal
10. A Not-So-Innocent Toy
11. Poked
12. Reggie’s Return
13. The Phenomenon
14. Stories
15. How to Turn Down Three Billion Dollars
16. Happy New Year!
Part II: Toys are Preludes to Serious Ideas
17. Hangover
18. The More Personal Computer
19. Snapchat Everywhere
20. Goodbye Reggie
21. Snapchat Live!
22. “We Need to Make Money”
23. Blank Space
24. Discover
25. Major Key
26. Keeping Secrets
27. Evan’s Empire
28. The Road to IPO
29. The New TV
30. Discover Falters
31. Fear and Loathing in Menlo Park
32. Snap Inc.
33. Spectacles
Picture Section
Works Cited


From a college dream to billionaires: how Snapchat redefined communication

When he was just twenty-three years old, Evan Spiegel and his Snapchat co-founder stunned the world by turning down a three-billion-dollar offer from Facebook. How could an app teenagers use to text dirty photos dream of more? Was this hubris, or genius?

A fellow Stanford undergrad and fraternity brother of the founders, Billy Gallagher takes us inside the rise of one of Silicon Valley’s hottest start-ups. His thrilling account offers a wild ride from the parties and drama of the early days, through the challenges of transitioning from a playful app to one of the tech industry’s pre-eminent public companies. In the tradition of great business narratives, How to Turn Down a Billion Dollars offers the definitive account of a supremely ambitious company striving to remake the future of entertainment.


BILLY GALLAGHER is an MBA candidate at Stanford’s Graduate School of Business. He has worked in venture capital and as a writer at TechCrunch, which he joined as a Stanford sophomore, writing a profile of a popular startup on campus: Snapchat. Billy wrote over a dozen exclusive pieces on Snapchat. His writing has also appeared in the New York Times and Playboy.

Title page for How to Turn Down a Billion Dollars: The Snapchat Story

To my mom, Eileen. Thank you.


I first interviewed Snapchat cofounder and CEO Evan Spiegel over six years ago, as Snapchat was just gaining traction and Evan and I were both still undergraduates at Stanford University. I have been following the story ever since. Because no one reads book dust jackets, and I occasionally use the first person in this book, let me tell you a bit about myself: I was two years behind Evan Spiegel and Reggie Brown at Stanford University. They were the class of 2012; I was the class of 2014. Bobby Murphy, Snapchat’s other cofounder, was the class of 2010. Most of the principals in this book, especially the early Snapchat team, went to Stanford between 2010 and 2013.

While at Stanford, I joined the same fraternity that Evan, Reggie, and Bobby were members of, although they had all left the fraternity by the time I joined (more on this later). I was the editor in chief of the school newspaper and a writer for one of the major tech blogs, TechCrunch. I interviewed Evan several times for TechCrunch during Snapchat’s early days in 2012; however, he stopped granting me interviews in 2013 when I covered ousted cofounder Reggie Brown’s lawsuit against Snapchat. After I graduated from Stanford, I worked on the investing team at Khosla Ventures, a prominent Silicon Valley venture capital firm (though not a Snapchat investor).

This book is based on nearly two hundred interviews, thousands of pages of court documents, and hundreds of articles. I personally visited (and in some instances lived at) many of the locations in this book; I reviewed primary characters’ emails, text messages, internal Snapchat documents, calendar appointments, and more. Evan, Bobby, and Snapchat, alas, declined many requests for interviews for this book, which is of course their prerogative. Why didn’t they want a book written about them? You’d obviously have to ask them, but I suspect the answer is a mix of a company culture that is very protective of its secrets and the fact that they were working long days during most of the period of writing this book, fending off significant challenges from competitors and driving the innovations necessary to keep Snapchat relevant in advance of taking the company public. You will find more on both in the pages that follow.

As often as possible, I have let the principals share this story through their own words, in speeches, emails, interviews, or other forms. In a few instances, I have made minor edits to these texts to correct misspellings or grammatical errors. Most quotes in this book are from recorded interviews, lawsuit documents, emails, text messages, and other permanent records; others are based on what multiple sources said another person said at the time. Beyond the permanent records, this book is necessarily based on anonymous sourcing. It simply wasn’t possible to do it any other way. I needed to get the unbiased truth from sources, and since the principal characters chose not to participate and asked employees and friends not to participate, those who spoke to me risked their livelihoods, significant amounts of money, and relationships, both professional and personal. Many of these sources only agreed to speak under the condition of anonymity. I have not shared the names of anyone who spoke on the record for fear that doing so might help expose, by process of elimination, those who chose to remain anonymous.

I would caution readers not to assume that just because I have written about a person’s thoughts or actions that that person is the direct source. People typically share their thoughts and feelings with friends and colleagues, especially during times of high stress and notability, which many of the events in this book were. There are often discrepancies between sources’ memories, as they have different recollections and versions of the truth. I have done my best to triangulate on the truth from witnesses’ memories and other documents. In some cases, I have had to use my best judgment as to what happened based on the information available. I have changed some minor characters’ names and personal details to both protect sources and private citizens who have nothing to do with our main story.

Other excellent reporters have worked hard to crack Snapchat’s tough shell. I have included a works cited list detailing the articles I have referenced. I am particularly indebted to the excellent work of Josh Constine, Jordan Crook, Alyson Shontell, Mike Isaac, Austin Carr, and Kurt Wagner.

I do not claim that this is an impartial account. This is one version of the Snapchat story, undeniably colored by my experiences and those of my many sources. If Evan has his way, there will be many books written about Snapchat and Evan Spiegel.

It has been a significant challenge to write about a medium as visual as Snapchat, especially knowing that many readers have never used the app. I urge you to download Snapchat if you haven’t and try it out as you read this book. At the very least, you’ll understand what those damn teenagers are doing.


Initial Public Offering

March 2, 2017

Smiling in their navy blue suits, Evan Spiegel and Bobby Murphy stood next to New York Stock Exchange president Thomas Farley on a balcony at the exchange. A large yellow screen with the black letters snap inc., the parent company of the hit app Snapchat, hung behind them. The company’s logo shined on seemingly every screen in the building. In a few short moments, Snap would go public on the New York Stock Exchange.

Farley turned and took a selfie using Snapchat as Evan and Bobby smiled and looked out at the crowd. Evan’s fiancée, supermodel Miranda Kerr, stood on the floor of the stock exchange, as did early Snapchat employees Dena Gallucci and Nick Bell and Snap chief strategy officer Imran Khan. Bobby and Evan pressed a button together and a bell rang out loudly, signaling the opening of the day’s trading. The assembled throng of Snap employees, friends, and reporters cheered. Farley encouraged the crowd to cheer louder. Evan, in a white shirt and gold tie, and Bobby, with a blue shirt and darker blue tie, smiled at the crowd, then turned and shared a moment. Bobby patted Evan on the back in celebration as Farley turned and shook hands with them each in turn. This was actually happening.

$SNAP was priced at $17 a share, but it opened at a much loftier $24. Snapchat CFO Drew Vollero watched the stock jump and exclaimed, “That’s crazy!”

After Snap began trading, Evan, Bobby, Kerr, and Khan headed over to the fourth-floor equities trading desk at Goldman Sachs on 200 West Street. When Snap’s stock jumped up to $24 right out of the gate, the Goldman trading floor broke out in jubilant cheers. The stock closed at $24.48, up 44 percent, with a closing market cap of $34 billion, on par with Marriott and Target. By the end of the day, Evan and Bobby were worth more than $6 and $5 billion, respectively.

Never before had so much economic value been created by a consumer product, used by millions of people daily, that was still so misunderstood.

As Snapchat rose from a silly photo-sharing app with a bad reputation for sexting to one of the hottest startups in the world, it became an increasingly common topic of conversation, particularly in the media. But it was little understood. A 2016 New Yorker cartoon depicted a man whose head had exploded, leaving behind his corpse holding his phone with Snapchat on it; in the caption a coroner explained to a cop, “Looks like another case of someone over forty trying to understand Snapchat.” In a 2015 New York Times article, “Campaign Coverage via Snapchat Could Shake Up the 2016 Elections,” the writer, commenting on Snapchat’s seriousness as a platform, still referred to Snapchat as “a company known for enabling teenagers in various states of undress to send disappearing selfies to each other.” Another New York Times writer said, “The user interface and design looks like the cross between a weird Japanese animation and a 1980s sitcom.”

Evan occasionally tried to control the narrative surrounding Snapchat. In June 2015, he posted a video on YouTube titled “What is Snapchat?” In the video, Evan is wearing his usual white v-neck t-shirt, sitting in what looks like a windowless room. He spends four minutes awkwardly using slides written on a pad of paper to discuss the history of social media and how to use Snapchat. The video did not do much to clear up the perplexity surrounding the app.

But Evan has also embraced opaqueness at Snapchat. The app is designed for existing users rather than new ones; this helped early growth at Snapchat as users showed friends how to use all of the app’s features in person. Confusion also lets Snapchat work in private, building hardware, computer-vision software capable of analyzing Snapchat pictures, and other moonshot projects that are key to the company’s future. This attitude, combined with Snapchat’s youth-focused design, has led outsiders to question how serious the company is.

As Snapchat set out on its IPO roadshow, Evan, Bobby, and the team found themselves pitching the company to potential investors far outside Snapchat’s core demographic. There is a generational divide that Snapchat illuminates. As with many new social apps, Snapchat’s user base skews very young. Some of this is inherently age based—young people tend to experiment more and have wider social circles. But a lot has to do with what age you were when you initially joined Facebook or Myspace. Older people who arrived to Facebook in its more constant state don’t understand the appeal of Snapchat. Indeed, it was easier for me to write this book than teach my mom how to use Snapchat.

So what is Snapchat? To fully understand the company, you have to understand Evan Spiegel and how the thinks. Evan and Snapchat are inseparable. So we must go back to the beginning and examine how Evan approached his previous ventures, how Snapchat was created, and the environment it was born into. We will look at how the Snapchat team approached problems when they were a scrappy underdog with few resources and how that approach changed over time as their assets grew exponentially. By understanding the company’s challenges and decisions, we can explore how the tech world’s most creative product minds are approaching the future of communication.

As eventful as Snapchat’s story has been to date, the company still has far to go to carry out Evan’s grand ambitions. The night before the IPO, Evan emailed Snap’s two thousand employees, noting that the IPO was merely a milestone and that the company had much left to accomplish. The next day, three thousand miles from the New York Stock Exchange, employees at Snapchat’s headquarters in Venice, California, celebrated with doughnuts and champagne before returning to work.

One notable figure was missing from the celebrations: the guy who came up with the idea behind Snapchat.

Part I




April 2010 Stanford, CA

SAM LEANED AGAINST the shopping cart, forearms bulging as he pushed with all his strength, picking up his pace from a trot to an all-out sprint. On most days, he used his athleticism to play wide receiver for Stanford’s football team. Tonight, he was using that same athleticism to push his friend Stuart in a shopping cart because they were freshman boys trying to get the older guys’ attention at fraternity rush.

Pushing Stuart off a makeshift ramp designed for frat bros to tricycle over seemed like a good way to make an impression. It was working. As they rounded the corner of Kappa Sigma’s parking lot, several fraternity brothers standing on the concrete steps and sidewalk realized that these freshmen weren’t using the normal Target-bought tricycles.

Where the hell did they get a shopping cart? one of the guys thought as he joined his brothers and started cheering as Sam steered the cart around the turn of the parking lot.

Stuart, a thin, goofy kid with his dark brown hair in a bowl cut, sat in the cart, looking diminutive next to his friend Sam and wondering why he’d thought this was a good idea. The Jack Daniels had initially calmed his nerves, but Sam was pushing him pretty damn fast. He didn’t have time to rethink things.

Sam whipped the cart around the corner of the parking lot, its wheels rattling over bits of broken beer bottles. The parking lot’s lone light cast a faint orange glow over the scene. The cart went up on two wheels as it turned; Stuart almost fell out, but Sam grabbed it and slammed it back down.

Steadying the cart, Sam sprinted toward the hastily constructed ramp and threw the cart forward into the warm California night.

The plywood ramp sagged atop its cinder block supports. Rather than soaring gloriously into the air as the boys had intended, the cart slid right off the end, its old wheels digging straight into the asphalt with a harsh screech. The cart violently ejected its cargo—Stuart flew through the air and tumbled end over end against the hard asphalt.

The onlookers paused.

Rolling over, Stuart rose gingerly. He turned and looked back at the group watching him and triumphantly raised his fists in the air over his head, like a snowboarder who had just won Olympic gold.

The older brothers exploded into hollering and cheering. This kid was getting a bid.fn1

Evan Spiegel smiled and sipped his beer from a red Solo cup, watching the chaos from the crowd. Tall and lanky, Evan had brown hair that he kept short and styled up across his sharp, angular face. He was often seen partying on campus in a tank top and shorts. As a sophomore rush chairman, Evan held the keys to the kingdom for these potential newcomers. All around him, nervous freshman engaged in the same small talk with active brothers: Where are you from? What freshman dorm are you in? Did you play any sports in high school? How’s freshman year going?

All told, there must have been more than a hundred people there, milling about between the makeshift tricycle track in the parking lot and the fraternity house. The freshmen had come sporting a variety of attire, from the East Coasters in polos to Southern Californians in tank tops, most trying too hard to look cool and casual at the same time. All the brothers were wearing yellow t-shirts for rush; the front depicted Curious George passed out next to a tipped-over bottle of ether. The lower right side of the back showed a small anchor with the fraternity’s letters, KΣ, on each side—it was Evan’s signature. The anchor was his way of saying, “This is an Evan Spiegel production.”

Evan was born on June 4, 1990, to a pair of highly successful lawyers. His mother, Melissa Thomas, graduated from Harvard Law School and practiced tax law as a partner at a prominent Los Angeles firm before resigning to become a stay-at-home mother when Evan was young. His father, John Spiegel, graduated from Stanford and Yale Law School and became a partner at Munger, Tolles & Olson, an elite firm started by Berkshire Hathaway’s Charlie Munger. His clients included Warner Bros. and Sergey Brin.

Evan and his two younger sisters, Lauren and Caroline, grew up in Pacific Palisades, an upper-class neighborhood bordering Santa Monica in western Los Angeles. John had the kids volunteer and help build homes in poor areas of Mexico. When Evan was in high school, Melissa and John divorced after nearly twenty years of marriage. Evan chose to live with his father in a four-million-dollar house in Pacific Palisades, just blocks from his childhood home where his mother still lives. John let young Evan decorate the new home with the help of Greg Grande, the set designer from Friends. Evan decked out his room with a custom white leather king-size bed, Venetian plaster, floating bookshelves, two designer desk chairs, custom closets, and, of course, a brand new computer.

From kindergarten through senior year of high school, Evan attended Crossroads, an elite, coed private school in Santa Monica known for its progressive attitudes. Tuition at Crossroads runs north of $22,000 a year, and seemingly rises annually. Students address teachers by their first names, and classrooms are named after important historical figures, like Albert Einstein and George Mead, rather than numbered. The school devotes as significant a chunk of time to math and history as to Human Development, a curriculum meant to teach students maturity, tolerance, and confidence. Crossroads emphasizes creativity, personal communication, well-being, mental health, and the liberal arts. The school focuses on the arts much more than athletics; some of the school’s varsity games have fewer than a dozen spectators.fn2

In 2005, when Evan was a high school freshman, Vanity Fair ran an exhaustive feature about the school titled “School for Cool.”fn3 The school, named for Robert Frost’s poem “The Road Not Taken,” unsurprisingly attracts a large contingent of Hollywood types, counting among its alumni Emily and Zooey Deschanel, Gwyneth Paltrow, Jack Black, Kate Hudson, Jonah Hill, Michael Bay, Maya Rudolph, and Spencer Pratt. And that’s just the alumni—the parents of students fill out another page or two of who’s who A-listers. Actor Denzel Washington once served as the assistant eighth grade basketball coach, screenwriter Robert Towne spoke in a film class, and cellist Yo-Yo Ma talked shop with the school’s chamber orchestra.

Evan was attracted to technology early on, building his first computer in sixth grade and experimenting with Photoshop in the Crossroads computer lab. He would later describe the computer teacher, Dan, as his best friend.

Evan dove into journalism as well, writing for the school newspaper, Crossfire. One journalism class required students to sell a certain amount of advertising for Crossfire as part of their grade. Evan walked around the neighborhood asking local businesses to buy ads; once he had exceeded his sales goals, he helped coach his peers on how to pitch businesses and ask adults for money.

By high school, the group of 20 students Evan had started with in kindergarten had grown to around 120. Charming, charismatic, and smart, Evan threw parties at his dad’s house that were “notorious” in his words. Evan’s outsized personality could rub people the wrong way at times, but his energy, organizing skills, and enthusiasm made him an exceptional party thrower. He possessed a bravado that could be frustrating and off-putting but was great for convincing everyone that the night’s party was going to be the greatest of all time.

Obsessed with the energy drink Red Bull and the lifestyle the brand cultivated, Evan talked his way into an internship at the company as a senior in high school. The job involved throwing parties and other events sponsored by Red Bull. Clarence Carter, the head of the company’s security team, would give Evan advice that would stand him well in the years to come: pay attention to who helps you clean up after the party. Later recalling the story, Evan said, “When everyone is tired and the night is over, who stays and helps out? Because those are your true friends. Those are the hard workers, the people that believe that working hard is the right thing to do.”

In the fall of 2008, Evan burst onto the campus scene at Stanford. Known as “The Farm” because Leland and Jane Stanford founded the school on their old Palo Alto farm, Stanford has an idyllic 8,000-acre campus in northern California, just south of San Francisco. He lived on the top floor of Donner, a three-story all-freshman dorm. Evan quickly became friends with the guy who lived right across the hall from him, Reggie Brown. Evan could not possibly have imagined it at the time, but meeting Reggie would become one of the most important things he did at Stanford.

Reggie was born on January 17, 1990, in Isle of Palms, an affluent coastal town just outside of Charleston, South Carolina. Reggie had a masterful way of making people feel welcome and comfortable around him, like he was genuinely interested in getting to know you. He could come across as a goofball at first, as he smoked and drank and made lowbrow jokes, but he was deeply intelligent and creative. Reggie knew from the day he got to Stanford that he wanted to be an English major and focus on writing. Reggie was a beefy, good-looking kid with shaggy blonde hair that was typically tucked under a backward cap. A wide, silly smile usually brightened his face. His Southern manners set him apart in Northern California, as he would frequently address professors and friends’ parents more formally.

Evan and Reggie spent a lot of time partying together. The group in Donner was unusually social that year, not least because the two fast friends frequently threw parties in their dorm. This was not common for freshmen because it was frowned upon. These gatherings were typically lubricated by handles of vodka and Red Bull Evan had shipped to him, as he was still working for the company as a brand manager, giving out free samples.

Most freshmen did not have a car and were adjusting to life without their parents. Evan drove a Cadillac Escalade and thrived in his new environment. In addition to his ever-growing group of friends he met through his and Reggie’s parties, he started dating a pre-med student named Lily, and they were soon attached at the hip.

Lily was a steady, positive influence on him. She was a very patient, understanding girlfriend and put up with some of his absurdity because the good times—from fraternity parties to adventures for just the two of them to a spring break trip to Cabo San Lucas in Mexico—were so much fun.

Throughout the year, Evan designed and printed tank tops for his Donner crew. He had befriended the owner of a printing shop and was able to negotiate discounted prices and short turnarounds on orders. Evan created a tank top mimicking the Stanford athletes’ Nike gear. The shirts said stanford across the chest, but instead of a team sport underneath “Stanford,” it read hustling. In the spring, a friend tossed out the idea for a “Sun’s Out, Guns Out” tank top; later that day, Evan emailed the dorm a Google doc to collect people’s orders and sizes, and by Friday everyone who paid him could rock their shirt.

By the time spring quarter arrived, Evan’s reputation had grown—he was the kid from LA who liked to throw parties. Most of his Donner crew joined a fraternity or sorority that spring. Reggie, Evan, and their friend Will rushed the Kappa Sigma fraternity.

The Kappa Sigma brothers had a work-hard/play-hard ethos; they prided themselves on being able to excel on campus while drinking and throwing ridiculous theme parties. The leaders of the house typically did very well academically and balanced sports teams and other extra-curricular commitments with heavy drinking binges. The Stanford Flip-side, the school’s beloved Onion wannabe, summed up the culture best with an article titled, “Kid Vomiting in Stall Next to You to Run Fortune 500 Company Someday.” In April 2009, Evan, Reggie, and Will were awoken in Donner by Kappa Sigma brothers, offering them Natty Lights and little manila bid cards—invitations to join the fraternity. They were in.

Evan and Reggie took widely divergent routes through the fraternity pledging process. Most of the new members went with the flow during pledging and did what the older brothers told them to do. Evan constantly questioned: Why do we do it this way? Why are we letting other people tell us what to do? Why can’t we go do this? Reggie, on the other hand, simply couldn’t be bothered to show up or take pledging seriously. During the process, the older brothers frequently wrote out the pledges’ names on a big whiteboard and gave them points for tasks well done, events they showed up to, and generally how much they were liked by the active members. Reggie was always at or near the bottom of the list.

While he didn’t put any effort into the setting up, cleaning up, or planning of parties, Reggie excelled at one part of the process: the parties themselves. All pledges were given tasks: one had to carry a lunch-box around to classes, another had to roller blade around campus, and a third had to wear a bike helmet to every party. All received nicknames as well: Reggie earned the nickname Blue Suit, given every year to the pledge who parties the hardest. He was handed down a baby blue men’s suit that was rarely, if ever, washed. He had to wear it to every party, adding more layers of liquor stains to its illustrious history.

Evan moved into the Kappa Sig house his sophomore year and was assigned a room in the Mid, so named because it was located right in the middle of the house, where the bedrooms met the kitchen, lounge, and chapter room to form a T. Five pledges lived in two small bedrooms, with a larger common room connecting them in the middle.

Choosing to live in the Mid meant committing to a quarterfn4 where keg stands would take precedence over classes. Mid residents who wanted to get homework done had to escape the fraternity for the library. And it was difficult to get to bed before two o’clock in the morning most nights, as fraternity brothers would drink and party or smoke and play Super Smash Bros. on a beat-up N64 in the middle room. In the larger common room of the Mid, Evan and his friends would throw regular weeknight parties, inviting everyone they knew.

Evan had a private text group with a bunch of the girls in his year to which he’d regularly send mass texts like, “Raging tonight at Kappa Sig, be there.” Almost inevitably, Evan’s Thursday-night parties would explode into all-campus events. Sorority girls, overeager freshmen, and jaded-but-drunk seniors alike would wander over and cram into the Mid to slam back Natty Lights, take pulls from plastic handles of bottom-shelf vodka, and forget that they had class the next morning. During these parties, Evan was in his element. He could often be found sitting on top of a speaker DJing in a tank top, gauging the mood of the crowd, and making sure everyone was having a blast. He even came close to getting LMFAO, a hip-hop duo best known for their “Party Rock Anthem” hit, to come play at one of the fraternity’s parties.

Fraternity life posed a continual challenge for Evan—he always wanted to take things to the next level. Instead of planning mere parties, he constantly increased their vision and scale until they became planned events with specially built props and specifically designed tank tops. “Spiegel, we can’t do that” became the most common phrase uttered at house meetings. Evan would type up ridiculous event descriptions for emails and Facebook invites, describing parties in the most absurd, dramatic ways.

Evan was elected a social chair and quickly went way over budget. As Stanford’s football team embarked on their first winning campaign in nine years and the busy student body started to pay attention to the games, Evan pushed to make tailgates into bigger spectacles. For every home game, he would cart his own enormous speakers down to the dirt parking lot next to Stanford Stadium. The Kappa Sig brothers invited every girl they knew and threw a full-on frat party in the parking lot. Evan worked the crowd with ease, greeting people left and right with a thin, wide smile on his face. When his head wasn’t thrown back laughing, he was typically drinking from his red Solo cup or gesticulating with his long, gangly arms to make a point. The tailgates kept growing, week after week, riding the unstoppable waves of the football team’s success and Evan’s party-throwing acumen.

In addition to obsessing over his parties looking a certain way, Evan had already begun to think about his future. Evan decided to study product design, to learn how to look at the things he used in his daily life and see how he could make them better and cooler. David Kelley, the head of Stanford’s famed design school, took Evan on as his advisee. One thing was clear; as he frequently put it, “I’m not going to work for someone else.” And this gave him freedom from the heavy grind of Stanford. Nobody would ever see his résumé or grades, so he took classes for what he actually wanted to learn.

Evan was actually unique on a campus where most of the bright sheep were only unique in their own minds.

During his sophomore year, a family friend introduced Evan to Peter Wendell, the founder of venture capital firm Sierra Ventures. Wendell had been teaching a class for second-year MBA students, Entrepreneurship and Venture Capital, at Stanford’s business school for over twenty years. Stanford MBA students take the class hoping to learn how to start their own businesses. Wendell let Evan sit in on the class and put his visitor’s chair right next to the guest speakers. A thrilled Evan sat on the edge of his seat next to prominent venture capitalists and entrepreneurs like Google’s Eric Schmidt and YouTube’s Chad Hurley. The class poured fuel on the fire of Evan’s desire to found his own company. He learned directly from Silicon Valley superstars who had accomplished exactly what he aimed to do.

From Red Bull to his dorm-room tank-top business to frat parties to Wendell’s class, Evan threw himself into the endeavors that managed to hold his interest. And, typically, these projects were different from what most Stanford students found captivating.

After class one day, Intuit cofounder Scott Cook told Wendell he was impressed by the intelligence and reasoning of Evan’s response. Wendell replied, “Well, you will be surprised to know he isn’t an MBA student. He is an undergraduate who is auditing this class.” Wendell introduced Cook to Spiegel, who promptly begged to work with Cook. Cook let Spiegel join him on a small Intuit project called txtWeb, which aimed to make available online information accessible via SMS messages in India. The txtWeb team consisted of Cook, Spiegel, and an engineer. Evan didn’t work there very long, but he learned how much he could accomplish with a small team—and how much he wanted to work for himself, where he could call the strategic shots.

One day, Evan had coffee with Peter Wendell and talked to him about his experiences working for Cook and his desire to get involved with startups. “Being your own boss is great,” Peter told him. “There’s no boss more kind, more generous than yourself.”


If you made a country out of all the companies founded by Stanford alumni, it would have a GDP of roughly $2.7 trillion, putting it in the neighborhood of the tenth largest economy in the world. Companies started by Stanford alumni include Google, Yahoo, Cisco Systems, Sun Microsystems, eBay, Netflix, Electronic Arts, Intuit, Fairchild Semiconductor, LinkedIn, and E*Trade. Many were started by undergraduates and graduate students while still on campus. Like the cast of Saturday Night Live, the greats who have gone on to massive career success are remembered, but everyone still keeps a watchful eye on the newcomers to see who might be the next big thing.

With a $17 billion endowment, Stanford has the resources to provide students an incredible education inside the classroom, with accomplished scholars ranging from Nobel Prize winners to former secretaries of state teaching undergraduates. The Silicon Valley ecosystem ensures that students have ample opportunity outside the classroom as well. Mark Zuckerberg gives a guest lecture in the introductory computer science class. Twitter and Square founder Jack Dorsey spoke on campus to convince students to join his companies. The guest speaker lineups at the myriad entrepreneurship and technology-related classes each quarter rival those of multithousand-dollar business conferences. Even geographically, Stanford is smack in the middle of Silicon Valley. Facebook sits just north of the school. Apple is a little farther south. Google is to the east. And just west, right next to campus, is Sand Hill Road, the Wall Street of venture capital.

Silicon Valley has always had an influence on Stanford, and vice versa. But starting in the late 2000s, tech started to dominate the university. In the fall of 2010, as Evan began his junior year, I arrived on campus as a freshman. Coming from the East Coast, I knew that Stanford and Silicon Valley were closely linked and that tech companies were a big deal out there on the West Coast. I just didn’t realize how big. One of the guys in my freshman dorm made a new social networking app that he was trying to get this tech blog called TechCrunch to write about. My friends and I went to see The Social Network in Mountain View, right next to Google’s campus. You never expect one of your friends to start a billion-dollar company. But watching The Social Network, we all had a strong feeling: This could happen again. Here.

It wasn’t just the nerds starting companies, either. Even fraternity guys and sorority girls had ideas for apps and companies. Perhaps especially them—the Greek system naturally drew out the more social students, who mixed that outgoing nature with the brains and work ethic that got them into Stanford into a potent recipe for creating popular consumer companies. Instagram cofounder Kevin Systrom was a member of Sigma Nu a couple of years before Evan, Reggie, and Bobby arrived on campus. Other high-profile companies like Chubbies, a men’s shorts and lifestyle brand, and Robinhood, a stock-trading app that would eventually be valued north of $1 billion, would be founded from the fraternities’ members in the years to come. The founder of Hewlett-Packard was a brother in Kappa Sig at Stanford as well, but that was many years ago.

Most of the ideas people pitched sounded idiotic. And there was a definite fatigue that set in among students who were sick of hearing so many classmates pitching so many apps. But there was nevertheless an energy on campus. People were creating and building.



October 2010

WHEN WE LAST saw him, Stuart was a freshman getting thrown from a shopping cart while trying to join the Kappa Sig fraternity. Six months later, having achieved his goal, he was a sophomore living in the fraternity house. It was a typical Wednesday night, and Stuart was anxious. He was supposed to meet up with some classmates to work on a group project. Instead, he was sitting with two dozen of his fellow pledges in the End, one of the three rooms where new members lived, like a more laid-back version of the Mid. As with the Mid, it was quite cleverly named because it sat at the east end of the house, overlooking a large parking lot.

The main room, a large, fat rectangle with a vaulted ceiling, was furnished with couches and low tables; the sophomores had set up a big projector and would watch movies on the room’s largest wall. They’d managed to jam one desk into a corner for when someone had to work but didn’t want to make the trek to the library. Other guys in the house would come through the room to smoke weed and cigarettes off the balcony. Two smaller rooms, which connected to the main room on either side, were filled with two bunk beds and dressers in one room and three bunk beds and dressers in the other. Sometimes the guy sleeping in the top bunk would drunkenly roll off and crash onto the floor, causing the other inhabitants to run in and check on him.

The pledges were awaiting the arrival of Evan Spiegel. Stuart wasn’t the only one who was anxious about what fate awaited them. Evan had spearheaded a number of rollouts that fall—these involved active members rolling pledges out of bed in the middle of the night to perform various drinking stunts. Evan’s rollouts were feared because they featured complicated tasks and lots of booze. The practice had become an increasingly vital part of the house shenanigans, as the fraternity had been placed on a year-long probation, banning them from throwing any of Evan’s precious parties.

But Evan wasn’t focused on rollouts tonight. As he entered the End, he excitedly addressed the group, telling them about a new startup he was working on.

“It’s going to be this platform where kids in high school can go on and learn about all these different universities,” he told them, his face lighting up with enthusiasm. “They can put in their credentials, then the system will give suggestions on what schools they should apply to.”

The iPhone had only reached its third generation, the iPhone 3GS, and mobile app development was not ubiquitous, so students and entrepreneurs at the time would still think to build a website first and foremost. Evan explained that he and Bobby Murphy, one of the brothers who had graduated the previous spring, had been working on the website throughout the summer. The problem, Evan said, was that the way high school students searched for college information was tedious, slow, and inefficient. They had to look at every school’s website individually. He and Bobby had designed a site that would solve that problem. Future Freshman would aggregate information on most of the country’s colleges and universities; the site offered ancillary material like videos of college counselors talking about life on campus. Parents and guidance counselors would pay a monthly subscription fee to access the database. It was a potential goldmine.

Unfortunately, someone had to do the work of aggregating all of that data, which involved manually pulling it from college websites and inputting it into Future Freshman. That’s where the pledges came in. They’d each have to dig up a whole host of information on the colleges like population, location, Greek Life: Yes/No, and much more and add it to a shared Google spreadsheet.

Wrapping up his short pitch, Evan handed each pledge a slip of paper with 25 colleges on it, and told them get to work. Then he turned and exited the room.

“Fuck this,” Stuart blurted out.

Some of them argued that they should just get up and leave immediately. Evan was totally abusing the pledging process—it wasn’t the sophomores’ job to get his startup off the ground by doing mind-numbing data entry. They had their own homework and student groups to deal with. Cole had soccer practice early the next morning. Chris had rehearsal for his a cappella group. Sam was trying to get into Harvard Law School. Jeremy was struggling with the pre-med core classes. Others argued that alternative pledging events would suck more.

The room was split—some of the guys were good friends with Evan and looked up to him. His ease with girls, ability to throw great parties, and flair for the absurd bought him significant social capital. Others thought he was an obnoxious clown who spent too much time and energy on impassioned speeches at house meetings about inconsequential things like party themes.

They huddled around a leftover keg, half of them drinking and bitching about Evan and pledging, the other half drinking while doing the work, all inhaling a scent equal parts stale weed and beer. A few of the guys had come right from the gym, and it really would have been great if they’d found some time to shower. Some of them sat around texting their girlfriends on BlackBerrys or checking to see if anyone had sent anything funny to the fraternity email list. Others typed away diligently, some even buying into Evan’s dream, wondering if Future Freshman would change the way their younger siblings looked at colleges.

The sophomores sat in the crowded End for hours. Evan anxiously checked in on them periodically. In the end, only about a quarter of the work got done. Evan was pissed, but one of the other older brothers pulled him aside and told him to let the pledges go.

A few days after the pledging event, Evan gave a few of the sophomores who had contributed a full tour of the site. They had to admit it looked very professional with its striking background and intertwined “FF” logo. In Evan’s hands, it could be something huge. A few were sufficiently convinced of its promise to keep helping Evan get all the college information into the database. They sat together in the fraternity’s single small study room and entered the data for two or three hours at a time. In a few weeks, Future Freshman was packed with information about colleges across the country.

Evan and Bobby Murphy got ready to launch the site. Bobby was two years older than Evan and had grown up in El Cerrito, California, near Berkeley. His parents were California state employees, one of whom had emigrated from the Philippines. Like Evan and Reggie, he had also been placed on the third floor of Donnerfn1 when he was a freshman in 2006–7. He rushed and joined Kappa Sig with his Donner buddies as well, living in the Mid like Evan. He was almost exactly the same height as Evan, but Bobby’s face was rounder than Evan’s angular facial structure, and he had black hair that he typically styled up and to the side.

When Evan was first learning computer science, he would frequently bound into Bobby’s room at two in the morning, interrupting Bobby’s Starcraft sessions to ask for coding help. While Evan and Bobby were just two years apart in school, Evan’s class had already started to shift from favoring more traditional career paths toward studying computer science and working at startups after graduation; this drift would accelerate in the coming years. Before Future Freshman, Bobby recruited Evan to work with him on a new social network that was a different spin on Google Circles. It went nowhere.

Bobby was quiet, introverted, and unassuming to the point that most of his fraternity brothers didn’t know he was a part of Future Freshman until Evan told them. Bobby was more than happy to let Evan run the show and take meetings with Teach for America, tell customers about the service, and make pledges input data, while Bobby quietly worked on the company’s technical backbone. Evan could sometimes get on his nerves, but they worked well together, and Evan respected Bobby’s opinion.

At the end of the fall quarter, Evan left to spend the winter studying abroad in Cape Town, while Reggie headed off to study for a quarter at Oxford. Evan was pulled toward new ideas and projects in South Africa as Future Freshman found itself battling for mindshare and dollars with well-established companies that had deep pockets and large sales teams.

And there were signs all too close to home that the product wasn’t connecting with its intended users. “Both of [Bobby’s and my] siblings were applying to college at the time and neither of them used it,” Evan later said. “So that was a sign that that was probably not the right way to go.” Eventually, they pulled the plug on Future Freshman. While the outcome was disappointing, Evan learned a valuable lesson: in order to avoid getting destroyed by better-funded competition, his next idea had to be more original.

As if the startup’s failure wasn’t enough, in the middle of the winter quarter of their junior year, while Evan and Reggie were still abroad, the University completed its review of Kappa Sigma’s probation. University administrators said the fraternity had a toxic drinking culture causing incidents that went “beyond shenanigans,” an admonishment that became something of a catch phrase for the group. In order to be reinstated, the members would have to prove that the organization had changed. The fraternity would be kicked out of their house for the 2011–12 school year, Evan and Reggie’s senior year. They would be allowed to stay in the fraternity house through June 2011, but they could not throw any parties.

With rent in Palo Alto exorbitant, 96 percent of undergraduates lived on campus, making it a heavy blow to the fraternity Evan had worked so hard to build up. Several guys questioned whether the fraternity should even go on. A number of the fraternity’s members, focused on their own startup dreams, job prospects, and academic careers, seemed ready to give up on the house. The fraternity’s leadership did a membership review, interviewing every member and weeding out any brothers who were deemed unfit to be a part of the house. Evan and Reggie were picked as two bad apples and kicked out of the fraternity.

Reggie’s expulsion came as no surprise to anyone who’d been paying attention.

He was known principally for getting wasted, breaking things, and leaving a mess in the kitchen. His room, which reeked of weed and tobacco, was filled with cups and plates from the house’s kitchen that he hadn’t bothered to return. He never showed up for house meetings or lent a hand on house cleans or party setups. Although he was very book smart and super friendly to everyone, he was a downright nuisance to live with.

Evan’s case was not so clear-cut—ask ten people why he got kicked out and you’ll get ten different answers. Some say he was a willing scapegoat, volunteering to be kicked out because he knew he wouldn’t have the house for his senior year anyway. Others say he was scapegoated because he had angered younger guys by pushing for parties while the house was on probation. Others say Evan deserved to be kicked out because he didn’t want to fight hard enough get the house back, and he had been taking too cavalier an attitude toward the trouble the fraternity faced.

No matter the reason, Evan was out. Guys in the fraternity blamed him for their house being taken away. Friends who he thought would have his back didn’t.

Bad news came in threes for Evan. He had already lost Future Freshman. He lost the fraternity. Then, his girlfriend Lily told him she’d had enough and dumped him after two-plus years of dating.



Spring Quarter April 2011

REGGIE CAREFULLY RAN his fingers over the blunt, admiring its tightly rolled perfection. It was almost a shame to smoke such a work of art. He leaned back on the couch in his Kimball Hall dorm room as he discussed the weekend’s social events with two of his former fraternity brothers, David and Zach.

Reggie, now in the spring of his junior year, had plateaued—academically and socially.

What’s more, he didn’t seem bothered by it—he didn’t really have any sort of a plan beyond enjoying himself and going to classes. Most students at Stanford throw themselves into academics, student organizations, athletics, and part-time jobs and generally continue their overachieving habits that got them into the school in the first place. Reggie didn’t do much of that. He seemed to many of his friends like a more subdued Van Wilder, just a regular guy who wanted to hang out and have a good time without worrying about the future.

The subject of the conversation moved on to the girls. A dreamy expression appeared on Reggie’s face.

“I wish I could send disappearing photos,” he mused, almost absentmindedly.

David and Zach laughed and agreed that it would be useful if photos disappeared, then turned to who was coming to their party that weekend. Reggie withdrew. He was thinking.

Through the haze of smoke, David and Zach’s chatter faded. Reggie focused on the usefulness of this new idea. A way to send disappearing pictures. He wouldn’t have to worry about sending a hookup a picture of his junk! And girls would be way more likely to send him racy photos if they dis appeared.