Disrupted

by Dan Lyons

  Begin Reading

  Table of Contents

  Newsletters

  Copyright Page

  In accordance with the U.S. Copyright Act of 1976, the scanning, uploading, and electronic sharing of any part of this book without the permission of the publisher constitute unlawful piracy and theft of the author’s intellectual property. If you would like to use material from the book (other than for review purposes), prior written permission must be obtained by contacting the publisher at permissions@hbgusa.com. Thank you for your support of the author’s rights.

  FOR TEAM SHRED: L.S., M.B. & P.B.

  THE BEST PALS EVER

  Author’s Note

  I’ve spent the past decade writing satire about the technology industry—first on a blog, then in a novel, and most recently on a TV show. But nothing I ever dreamed up in those fictional accounts could compare to the ridiculousness I encountered when I took a job at an actual tech company, a software maker called HubSpot. This book is the chronicle of my time at the company, and it’s not satire. Everything in Disrupted really happened. With some individuals I have used real names, but in most cases I have invented pseudonyms and nicknames. Some current and former HubSpotters agreed to be interviewed for the book, but only on condition that our conversations remain off the record. Some people were afraid to talk to me at all. At the time I thought their concerns were silly. But as things turned out, those people may have been right to be afraid.

  Regarding terminology: When I use the term Silicon Valley I do not mean to denote an actual geographic region—the sixty-mile peninsula between San Francisco and San Jose, where the original technology companies were built. Instead, like Hollywood, or Wall Street, Silicon Valley has become a metaphorical name for an industry, one that exists in Los Angeles, Seattle, New York, Boston, and countless other places, as well as the San Francisco Bay Area.

  The term bubble, as I use it, refers not only to the economic bubble in which the valuation of some tech start-ups went crazy but also to the mindset of the people working inside technology companies, the true believers and Kool-Aid drinkers, the people who live inside their own filter bubble, brimming with self-confidence and self-regard, impervious to criticism, immunized against reality, unaware of how ridiculous they appear to the outside world.

  HubSpot, where I worked from April 2013 to December 2014, was part of that bubble. In November 2014, the company floated a successful IPO, and it now has a market value of nearly $2 billion. But this book is about more than HubSpot. This is a story about what it’s like to try to reinvent yourself and start a new career in your fifties, particularly in an industry that is by and large hostile to older workers. It’s a story about how work itself has changed, and how some companies that claim to be “making the world a better place” are in fact doing the opposite.

  Myths and mythmaking are rampant in Silicon Valley. I wrote this book because I wanted to provide a more realistic look at life inside a “unicorn” start-up and to puncture the popular mythology about heroic entrepreneurs. HubSpot’s leaders were not heroes, but rather a pack of sales and marketing charlatans who spun a good story about magical transformational technology and got rich by selling shares in a company that still has never turned a profit.

  At the heart of the book is my own sometimes painful and humbling journey of self-discovery, as I attempted to transform myself from a journalist into a marketing professional at a software start-up. My hope is that my story offers an overdue behind-the-scenes look at life inside a start-up during a period when the tech industry had temporarily lost its mind—and when I, for better or worse, did the same.

  Midway on our life’s journey, I found myself

  In dark woods, the right road lost.

  —Dante Alighieri

  I used to be with it. But then they changed what “it” was.

  Now what I’m with isn’t it, and what’s “it” seems weird and scary to me.

  —Grampa Simpson

  Prologue

  Welcome to the Content Factory

  If you made a movie about a laid-off, sad-sack, fifty-something guy who is given one big chance to start his career over, the opening scene might begin like this: a Monday morning in April, sunny and cool, with a brisk wind blowing off the Charles River in Cambridge, Massachusetts. The man—gray hair, unstylishly cut; horn-rimmed glasses; button-down shirt—pulls his Subaru Outback into a parking garage and, palms a little sweaty, grabs his sensible laptop backpack, and heads to the front door of a gleaming, renovated historic redbrick building. It is April 15, 2013, and that man is me. I’m heading for my first day of work at HubSpot, the first job I’ve ever had that wasn’t in a newsroom.

  HubSpot’s offices occupy several floors of a nineteenth-century furniture factory that has been transformed into the cliché of what the home of a tech start-up should look like: exposed beams, frosted glass, a big atrium, modern art hanging in the lobby. Riding the elevator to the third floor, I feel both nerves and adrenaline. Part of me still can’t believe that I’ve pulled this off. Nine months ago I was unceremoniously dumped from my job at Newsweek magazine in New York. I was terrified that I might never work again. Now I’m about to become a marketing guy at one of the hottest tech start-ups on the East Coast. There is one slight problem: I know nothing about marketing. This didn’t seem like such a big deal when I was going through the interviews and talking these people into hiring me. Now I’m not so sure.

  I reassure myself by remembering that HubSpot seems pretty excited about having me come aboard. Cranium, the chief marketing officer or CMO, wrote an article on the HubSpot blog announcing that he had hired me. Tech blogs wrote up the story of the fifty-two-year-old Newsweek journalist leaving the media business to go work for a software company.

  But when I arrive at HubSpot’s reception desk, something weird happens: Nobody is expecting me. The receptionist, Penny, who could pass for a high school student, has no idea who I am or why I’m here. She frowns and looks me up on her computer: nothing. This seems odd. I wasn’t expecting a brass band and balloons, but I did assume that someone, presumably my boss, would be there to meet me on my first day at work.

  “I’m going to be working for Cranium,” I tell Penny.

  Cranium is a big, hulking, baby-faced guy in his late thirties who once was a college football lineman and still looks the part. In his official HubSpot management team photo, he wears an open-collar oxford shirt and a white T-shirt, like a beefy-faced frat boy. Officially he is the person who hired me, but the decision was made by HubSpot’s co-founders—Brian Halligan, the CEO, and Dharmesh Shah, the chief technology officer. Halligan and Shah didn’t recruit me; I recruited them. I found HubSpot through a job posting on LinkedIn, had two interviews, and finally met with Halligan and Shah, who offered me a job as a “marketing fellow.” The title was unusual, but also pleasing, with a quasi-academic ring to it and an implication that my role would be to serve as a kind of éminence grise at the company. My job description was vague, but I believed I would be writing articles for the HubSpot blog, advising executives on media strategy, writing speeches for the CEO, and attending conferences as a kind of brand evangelist.

  Penny makes some calls. Finally she tells me that Cranium is not in the office today. I check the calendar on my phone and glance through my email to make sure I’ve arrived on the correct day. As far as I can tell, I have.

  “How about Wingman?” I say. Wingman is Cranium’s sidekick, a thirty-one-year-old director of something or other. I’ve met Wingman, and he’s nice enough. I don’t really know what he does, but basically he seems to be a mini-Cranium. Wingman actually looks like Cranium—round-faced, with short hair—and dresses like him, wearing a “business casual” uniform of jeans, sport coat, open-collar oxford shirt and whi
te T-shirt.

  Penny makes some calls. Wingman, too, is nowhere to be found.

  “Maybe you should take a seat,” she says.

  I sit down on an orange couch and gaze up at a big flat-screen TV that shows TED talks on a loop. Orange is the official color of HubSpot, and it’s everywhere: orange walls, orange ductwork, orange desks. HubSpotters wear orange shoes, orange T-shirts, and goofy orange sunglasses. They carry orange journals and write in them with orange pens. They put orange stickers on their laptops. HubSpot’s logo is an orange sprocket, a circle with three little arms sticking out, each with a knob on the end. Sometimes the word HubSpot is rendered with the sprocket where the O should go. I have no idea what the sprocket is meant to convey, nor do I know if anyone realizes that the three arms with bulbous tips look like three little orange dicks. Those orange cocks are all over the place, including on the hoodies, hats, and other pieces of HubSpot apparel and swag that are on display nearby, available for purchase either in person or through the company’s online store, the HubShop.

  I’m still waiting on the couch, and now it’s nine on a Monday morning and HubSpotters are streaming into the office, many wearing HubSpot clothing, like members of a sports team. Most are in their twenties. Attire for the guys skews toward bro-wear—shorts and flip-flops, untucked button-down oxford shirts, backward-facing baseball caps—while the women cultivate a look that a friend of mine calls “New England college girl going on a date,” meaning jeans, boots, sweaters.

  A woman shows up and reports to the reception desk. She’s wearing a suit—here for an interview, no doubt. Penny tells her to take a seat. The woman sits down next to me but then, in a minute, gets scooped up and called to her meeting. Meanwhile, I sit. And sit. Penny looks at me. “I’m still checking,” she says. I smile and tell her it’s no problem. Penny keeps making calls, glancing up at me and then glancing away, trying to figure out what to do with this gray-haired guy who just showed up claiming to be an employee.

  Finally, a few phone calls later, a guy named Zack arrives. He’s sorry that Wingman and Cranium aren’t here today, but he wants to give me a tour around the offices. Zack is in his twenties. He has a friendly smile and gelled hair. He reminds me of the interns at Newsweek, recent college graduates who did background research for the writers. I figure he must be someone’s assistant.

  The building we’re in also houses a venture capital firm and a few other small companies, including Sonos, which makes wireless home stereo equipment. But HubSpot keeps growing, spreading out, and colonizing more of the building. The engineers are on one floor, marketing on another, sales on another. HubSpot has five hundred employees and is hiring like crazy. It has been named one of the best places to work in Boston, with perks like unlimited vacation and Blue Cross health insurance that is fully paid for by the company.

  The offices bear a striking resemblance to the Montessori preschool that my kids attended: lots of bright basic colors, plenty of toys, and a nap room with a hammock and soothing palm tree murals on the wall. The office-as-playground trend started at Google but now has spread like an infection across the tech industry. Work can’t just be work; work has to be fun. HubSpot is divided into “neighborhoods,” each named after a section of Boston: North End, South End, Charlestown. One neighborhood has a set of musical instruments, in case people want to have an impromptu jam session, which Zack says never happens; the instruments just sit there. Every neighborhood has little kitchens, with automatic espresso machines, and lounge areas with couches and chalkboard walls where people have written things like “HubSpot = cool” alongside inspirational messages like “There is a reason we have two ears and one mouth. So that we listen twice as much as we speak.”

  On the ground floor, an enormous conference room doubles as a game room, with the requisite foosball table, Ping-Pong table, indoor shuffleboard, and video games. The cafeteria next door boasts industrial refrigerators stocked with cases of beer, cabinets with bagels and cereal, and, on one wall, a set of glass dispensers that hold an assortment of nuts and candy. It’s called the “candy wall,” and Zack explains that HubSpotters are especially proud of it. The wall is one of the first things they show off to visitors. It’s kind of a symbol of the fun-loving culture that makes HubSpot unique. It’s a young place, with lots of energy. Teams go on outings to play trampoline dodgeball and race go-karts and play laser tag.

  Dogs roam HubSpot’s hallways, because like the kindergarten décor, dogs have become de rigueur for tech start-ups. At noon, Zack tells me, a group of bros meets in the lobby on the second floor to do pushups together. Upstairs there is a place where you can drop off your dry cleaning. Sometimes they bring in massage therapists. On the second floor there are shower rooms, which are intended for bike commuters and people who jog at lunchtime, but also have been used as sex cabins when the Friday happy hour gets out of hand. Later I will learn (from Penny, the receptionist, who is a fantastic source of gossip) that at one point things got so out of hand that management had to send out a memo. “It’s the people from sales,” Penny tells me. “They’re disgusting.”

  Later I also will hear a story about janitors coming in one Saturday morning to find the following things in the first-floor men’s room: a bunch of half-empty beers, a huge pool of vomit, and a pair of thong panties. The janitors were not happy. They get even more distressed when, one morning, a twenty-something guy from the HubSpot marketing department arrives wasted and, for reasons unknown, sets a janitor’s cart on fire.

  Everyone works in vast, open spaces, crammed next to one another like seamstresses in Bangladeshi shirt factories, only instead of being hunched over sewing machines they are hunched over laptops. Nerf gun battles rage, with people firing weapons from behind giant flat-panel monitors, ducking and rolling under desks. Standing desks are the hot new thing for tech companies, and HubSpot has installed them everywhere. People hold standing meetings and even walking meetings, meaning the whole group goes for a walk and the meeting takes place while you’re walking.

  Nobody has an office, not even the CEO. There is a rule about this. Every three months, everyone switches seats, in a corporate version of musical chairs. HubSpot calls this a “seating hack,” and says the point is to remind everyone that change is constant. If you want privacy, you need to book one of the meeting rooms that are strung around the edges of the working spaces. Some meeting rooms are named after Red Sox players, others after “famous marketers”—I take a moment to let that sink in. Some have beanbag chairs instead of actual furniture, and in those rooms people sprawl out, with laptops propped on their knees.

  Sure, it’s kind of kooky, and it all feels a bit forced, as if everybody is working just a little too hard to convince themselves that their job is cool and they’re having fun. But who cares? It’s my first day. I’m excited to be here. I think it’s a hoot. In the past few years I’ve visited dozens of places like this, and I’ve wondered what it would be like to work at one.

  As we make our way around the building Zack tells me a little bit about himself. Just like me, he’s a newcomer to HubSpot. He only joined a month ago. In college he majored in English and wanted to be a sportswriter. But after graduation he decided that journalism seemed too shaky and took a job at Google instead. I tell him he did the right thing. Publications are struggling, and reporters are getting axed in droves, which is why people like me are now showing up in places like this, trying to “reinvent” ourselves by working in PR or marketing. Those jobs supposedly draw on the same set of skills that you develop as a journalist, meaning that you can write and you can work on deadline. And frankly, by the standards of corporate America, you’re cheap.

  Zack thinks it might be helpful if he explains how the marketing department is organized. We go to a conference room and he begins drawing an org chart on the whiteboard. Zack, I will discover, loves to write on whiteboards. At the top of the marketing department he puts Cranium, the chief marketing officer. Below Cranium are Wingman and three other
people. Each of these people has a team or set of teams organized underneath them. On and on Zack goes, creating a tree structure that keeps getting bigger and soon fills the white board. There’s product marketing, web marketing, email marketing, social media marketing, customer marketing, conversion marketing. There are people who do demand generation, others who do customer advocacy. There are people who do sales enablement and lead nurturing. There’s something called the funnel team, and another group called brand and buzz, which oversees the public relations team and runs the annual customer conference.

  Finally, off to one side, is the content team. It comprises the people who write for the blog and another group who write e-books. That’s where I will be working.

  I notice something: On the chart, Zack’s name is located above the content team, right below Wingman. I’m no expert in corporate organization, but based on the arrangement of this chart, I think—or, rather, I fear—that this guy who I thought was some kind of administrative assistant might actually be my boss.

  “Wait a minute,” I say. “I’m confused.”

  I look at Zack.

  “Zack,” I say, “what do you do here? What’s your job?”

  “Oh,” he says, “I run the content team.”

  “So if you run the content team,” I say, in a halting voice, “does that mean that you’re my boss?” I’m trying not to sound alarmed. “Do I work for you?”

  Zack says he doesn’t know if he would actually call himself my boss. Strictly speaking, as he understands it, my official manager will be Wingman. But on a day-to-day basis, well, it’s true that I will be working on the team that Zack manages.

  Fuuuuuuck, is what I say to myself.

  “Okay, cool,” is what I say out loud.

  Zack wants to take me to see where I will be working. I get up, feeling dizzy, and follow him out of the conference room, down a hallway past people who suddenly all seem way too young, like high school kids. They’re everywhere, all over the place. They’re rushing around carrying laptops, sitting in groups in little glass-walled meeting rooms, drawing on whiteboards, looking at PowerPoint presentations on giant monitors, drinking coffee, taking notes. I think I may be having a panic attack. Or an acid flashback. Part of me wants to dash for the door.