The Bozo Explosion

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Approximately 1200 words (including works cited). Proper APA formatting and citation is expected. Feel free to cite any and all course readings, lecture materials, and external sources you may feel are relevant to answering the question. In Chapter 8 of Disrupted, Lyons talks about "The Bozo Explosion" and how it impacts that kinds of people that end up working at HubSpot. These bozos, in Lyons opinion, have a huge impact on company culture. Please briefly summarize Lyons' assessments from that chapter to demonstrate your understanding of the main points he is making, then, in response to his points, offer some specific recommendations for how to fix hiring problems there in the future. Please make sure to discuss how company culture should factor into hiring decisions there.

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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-oneyear-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 white 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 dayto-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 glasswalled 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. Fuck fuck fuck fuck fuck, a little voice inside my head keeps saying as I follow Zack and his gelled hair down the hall, my pulse thrumming in my temples. Nine months ago I was the technology editor of Newsweek. In that job I did not even notice people like Zack, or Wingman, or even Cranium. They are the kind of people whose calls I would not return, whose emails I deleted without opening. Even Halligan and Shah were such small fry that I probably would not have taken time to meet them for coffee, and I certainly would not have written about them. And Zack? Good grief. He’s five years out of college, and his work experience consists of two journalism internships and three years in an entry-level job in a regional Google ad sales office. Zack takes me to a cramped little shoebox of a room, about fifteen feet wide and thirty feet long, where twenty young women are packed into two rows, staring at laptops. This is the content factory. That is literally what they call it. These people are content creators. That is literally what they called themselves. “Hungry for more content? Click here to get some!” is something they write on little boxes that they place next to blog posts, hoping that the promise of “more content” will entice readers to stay on the site. I smile and shake hands and go down the line, past a blur of Ashleys, Amandas, Brittanys, and Courtneys, realizing as I do that I am literally twice the age of these people, in some cases more than twice their age. “So where were you before this?” I ask some of them, who give me a strange look and say, “Uh, college?” I stop asking that question. They’re all women, they’re all white, and they’re all wearing jeans and sporting the same straight, shoulder-length hair. They all seem baffled by my presence. What is this old guy doing here? I smile and realize that I already cannot remember anyone’s name. Next, Zack introduces me to the blog team, the people I will be working most closely with—Marcia, Jan, and Ashley. I’ve read their work already. They say things like totes magotes and awesomesauce, and produce blog articles like “5 Ways to Make Your Landing Pages Awesome,” and “7 Tips to Improve Your Lead Quality.” They write in a folksy style: “Hey, blogging’s hard, right? You don’t have to tell us!! But didya know there’s a remedy for those summer blogging blues? Well, there is, and we’re gonna tell you about it, so read on!” I’m not sure what my relationship to these women will be. I’m not their boss. Zack is. Zack points to an empty desk. “I guess you can sit there,” he says. Instead of a chair, there is a big rubber ball—orange, of course—on a rolling frame. I’m not quite sure what to do. If I ask for a chair, I risk looking like an old fart who doesn’t know how to sit on a bouncy ball or like a prima donna demanding some kind of special treatment. But if I do sit on this thing I’m pretty sure that I will immediately fall off. I imagine myself, age fifty-two, toppling off an orange bouncy ball and onto the floor, as a bunch of young women look on and try not to laugh. Some awkwardness ensues as I ask Zack if it might be possible to find an actual desk chair. We scavenge a chair from a desk in another room. The crisis is averted. Zack goes to his desk and gets to work on whatever it is that Zack does, while I take my seat at my little desk, which is empty save for a new MacBook Air. Is this really it? Is this my job? Will I really go to work every day and sit at this shitty little desk in this shitty little room? Are these people now my colleagues? Will I have to sit in meetings with them and listen to them talk? What exactly is my actual job? Once I finish doing all the first-day paperwork, once I have my picture taken and get my ID badge and set up my parking garage pass, what am I supposed to do? Zack seems to have no idea. He’s so new that he hasn’t even figured out what his job is, let alone mine. I spend the day filling out paperwork and trying not to freak out. Surely, Halligan and Shah would not have hired me and then just stuck me in a room, working for Zack. There must be some kind of mistake. When Cranium gets here, he will sort things out. Then again, is it a bad sign that Cranium made such a big deal out of hiring me and then wasn’t here to meet me on my first day? Stay calm, I tell myself. Take deep breaths. But no matter how hard I try, I can’t block out the sound of that little fuck-fuck-fuck voice, which keeps telling me that I’ve made a very big mistake. Soon I will discover that the little voice is correct. One Beached White Male Nine months earlier, it’s the summer of 2012, and life is good. I’m fifty-one years old, happily settled into married life in a suburb of Boston, with two young kids and a job I love. At Newsweek, I get paid to meet amazing people and write about subjects that fascinate me: fusion energy, education reform, supercomputing, artificial intelligence, robotics, the rising competitiveness of China, the global threat of state-sponsored hacking. To me, Newsweek is more than a company—it’s an institution. And being a magazine writer seems like the very best job in the world. Then one day, without warning, it all just ends. It’s a Friday morning in June. The kids are at school. I’m sitting with my wife, Sasha, at the kitchen table, drinking coffee and going over the plans for our upcoming vacation, a three-week trip to Austria. It’s a bit of a splurge for us, but by using frequent flyer miles and staying in modest hotels we can just about afford it. Our kids—twins, a boy and a girl—are turning seven in a few weeks, and they’re finally old enough to handle an adventure. Sasha has just left her teaching job, because she’s been suffering from chronic migraines and spending too much time in emergency rooms. She needs time off to take care of herself. A few weeks in the Alps seems like a good way to start. We’ll miss her paycheck, and her insurance, which is first-rate, but I can get decent insurance from Newsweek, and in addition to my salary I’ve been making some money on the side by giving speeches. So we’re good. Sasha can quit her job and we can still afford the vacation. It’s all going to be great. That’s what we’re telling each other as we pull up the website for one place where we’ll be staying, a cluster of chalets perched on a hillside in a remote village surrounded by mountains. A local guide takes tourists on day hikes and offers a rock-climbing class for kids. A nearby stable offers trail rides on sturdy little Haflinger horses with shaggy blond manes. We leave in three weeks. My phone beeps. It’s an email from my editor, Abby. She wants to know if I can get on the phone. I go upstairs to my office and call her at the office in New York. I figure Abby wants to give me an update on the tech blog we’re launching. But unfortunately that’s not it at all. “I have some bad news,” she says. “They’re making some cuts. Your job is being eliminated.” I’m not quite sure what to say. On the one hand this should not come as a surprise. Newsweek has been losing money for years. Two years ago the magazine was sold to a new owner, who promised to turn things around. Instead we are losing more money today than we were two years ago. Subscribers and advertisers are drifting away. I suppose some part of me has been expecting this call. Still, I wasn’t expecting to get it today. Abby says it wasn’t her decision to fire me. I ask her whose it was. She says she doesn’t know. But someone, somewhere, has made a decision. Abby is simply the messenger. There’s nothing she can do, and no one to whom I can appeal. This is obvious bullshit. Abby knows who made the decision. I’m betting it was Abby herself. Abby is an old-time Newsweek person. She left the magazine before I joined, but three months ago she was recruited to come back as the executive editor. I was overjoyed when I found out I would be reporting to her. We’re old friends. We’ve known each other for twenty years. As soon as she arrived we started talking about launching a tech blog, which I would run. I figured I would have a year, maybe more, to get the blog off the ground. That’s why I thought my job was secure and why I am now sitting here, staring out my window, feeling as if I have been clubbed over the head. “I think they just want to hire younger people,” Abby says. “They can take your salary and hire five kids right out of college.” “Sure.” I’m not angry. I’m just dumbfounded. “I get it.” From outside comes the roar of a lawnmower. I glance out the window and see that the guys who mow our lawn have arrived in their truck. I make a mental note that this is one small luxury that we now will have to live without, because surely an unemployed man cannot pay someone else to mow his lawn. I’m not even finished getting fired yet and I’m already thinking about ways to save money. Should we get rid of cable TV? Will we stop going out to dinner? Can we still go to Austria? Abby says she really likes me, and this was a really hard phone call for her to make, and she hates to do this because we’ve known each other for so long, and nobody ever wants to call up their friend and tell them this. In a way I actually start to feel bad for her, even though I’m the one getting fired. I tell her I understand. I’m a business reporter, after all. This is the stuff I write about—legacy companies getting disrupted by new technologies, slowly going under, laying off workers. If I were running a magazine that was losing money, I would be looking to cut costs, too. I’d get rid of the expensive old guys and hire a bunch of hungry young kids. It makes sense. I went into this job knowing that it probably wouldn’t last forever. Back in 2008, when I joined, Newsweek veterans were being offered buyouts and early retirement packages. And it wasn’t just Newsweek. Newspapers and magazines were dying out all over the place, disrupted by the Internet. Despite all that, Newsweek was still an amazing place, and even if the magazine only had a few years left in it, I still wanted to work there. Now, on this sunny Friday morning, it’s over. My last day will be in two weeks, Abby says. I will get no severance package, just two weeks of pay and whatever vacation time I’m owed. At the end of two weeks I’ll also lose my health insurance, but the HR people will help me figure out how to set up COBRA to continue my benefits. Some of my colleagues who left when the magazine was sold in 2010 received packages equal to a year ’s salary. I’d expected that if or when I got cut, I’d be given enough severance to provide a cushion. Two weeks seems inordinately harsh. I try to bargain. I ask Abby if they will keep me on for six months while I look for a new job. That will let me save face and make it easier for me to find my next job. Sorry, she tells me, but no. I offer to take a pay cut. That won’t fly either, she says. How about I take a different job, I say. It doesn’t have to be much, but it will keep me on staff, with benefits, while I look for something else. Abby is not having any of it. “Abby, I have kids.” There’s a quaver in my voice. I take a breath. I don’t want to sound panicked. “I’ve got twins. They’re six years old.” She says she’s sorry, she understands, but there’s nothing she can do. I tell her that my wife has just left her teaching job. I’ve just finished sending in the paperwork to move us from Sasha’s insurance to the insurance plan offered by Newsweek. The HR department at Newsweek must be aware of this. That was the “qualifying life event” that enabled us to join the Newsweek health plan outside of the annual open enrollment period. “Look,” I say, “if you can just push back my end date and keep me on for a few months, I’ll at least be able to keep my health insurance, and I promise I’ll get another job and get out of here.” But Abby, my old friend, a woman I’ve known since we were both in our twenties and starting out in the journalism business, says no, she can’t do it. In two weeks I’m done, and that’s that. I hang up the phone, go downstairs, and tell Sasha what just happened. She’s stunned. Wasn’t I just telling her that it was safe for her to quit her job, because my Newsweek job was secure? “I thought Abby was your friend,” Sasha says. “I thought so, too.” Sasha still has the vacation folder with the brochures and plane tickets and hotel and car rental confirmations out on the table. “Maybe we should cancel the trip,” she says. There’s no sense in that, I tell her. Some of the money has already been spent, in deposits that we can’t get back. “We should go,” I say. “We’ll go, and we’ll use the time to think about what we’re going to do next. We can do anything, right? We can start over. We can move someplace new. It’s a fresh start.” I talk about Vermont. We’re always saying how cool it would be to live there. Our friends did that—one day they sold everything and moved to Vermont. They love it! Or there’s Boulder. Or Bozeman. We could live in the Rocky Mountains! We should make a list of the best places to live, rent a Winnebago, visit each one, and then decide. We could spend the whole summer traveling around the country! We could see the Grand Canyon, and Zion, and Yellowstone, and Yosemite. In a way this whole thing is a gift. Because now we have all this free time! When are we ever going to have a chance like this again? Sasha knows that I’m full of shit, and she also knows I’m panicking, because this is what I do when I’m panicking—I talk and talk and talk. But even as I’m reeling through my list of fantasy mountain towns where I can wear plaid shirts and drive a pickup truck and grow a beard, Sasha has arrived at the truth of our situation, which she feels the need to explain to me, as if by speaking the words out loud she might feel more in control of the situation. “Let’s just talk about where we are right now,” she says. She’s working hard to remain calm. “The reality is that I just quit my job, and I can’t get that job back. They’ve already hired someone else. And now you’ve been fired.” “Laid off,” I say, because that sounds better. “Point is, we’re both unemployed, and we have six-year-old twins, and no health insurance, and no income. And we’re about to go on a really expensive vacation.” “Well,” I say, “when you put it like that.” “How else would you put it?” I launch back into my spiel about moving to the mountains, but she cuts me off. None of that is going to happen, and we both know it. We’re not going to spend the summer cruising around the United States in a Winnebago like the Griswolds on some zany adventure. “Look,” I say, “I’ll get another job. I’m going to start hitting the phone today. Right now. I’m going to email everyone I know. I’ve got a bunch of speeches booked, which should keep us going into the fall. And I can pick up some freelance work.” I’m trying to sound confident. But the truth is that I’m fifty-one years old and I have never gone looking for a job before. I’ve always had a job and then moved to a better one. I’ve never had to call my friends and ask them to keep me in mind if they hear of anything. I’ve always been the guy on the other end of that call, and I’ve always felt bad for those friends who were calling me. Sure, I told them, I’ll pass the word around. I’ll keep an eye open. I’m sure you’ll find something. But we all know the reality of our situation. Every year there are fewer jobs in journalism. It’s a game of musical chairs, with a bunch of laid-off old hacks running around and fighting over the few remaining seats. Things are even worse if you’re over fifty. In what now seems like a cruel irony, I learned about this by reading my own magazine. In 2011, Newsweek published a cover story with the attention-grabbing headline THE BEACHED WHITE MALE. The cover depicted a middle-aged white guy in a suit, soaking wet, facedown on a beach at the water ’s edge—maybe not dead, but definitely washed up. The article described a whole generation of once-successful men who, having been laid off during the recession, or “Mancession,” as the magazine dubbed it, were now shuffling around in their bathrobes, stunned, emasculated, psychologically destroyed, humiliated in front of their wives and children, drifting through life like castrated zombies. In the new economy, age fifty was the new sixtyfive. Hit fifty, and your company would find an excuse to fire you, and good luck trying to find another job. As for filing an age discrimination suit: Forget about it. You wouldn’t stand a chance. Even if you won your lawsuit, you’d never work again. I’d read the article when it came out, but it hadn’t bothered me too much. I figured that somehow I was immune to this. Newsweek wasn’t doing well, but as long as the magazine remained in business, surely they would need a technology reporter? Apparently not. Because suddenly, on this lovely sunny day in June, as I sit in my kitchen waiting for my kids to come home from school, wondering if I should tell them what happened and, if so, how best to present the news—right now I am no longer the technology editor of Newsweek. Instead, I am that guy on the cover of Newsweek: facedown on a beach, soaking wet, possibly dead. I am a Beached White Male. I started working in newspapers in 1983, while I was still in college. After graduation I didn’t know what else to do, so I just kept working at newspapers. I thought about law school and business school, but didn’t have the heart for either. Originally I had been headed toward medicine, but I had fallen off the track and it seemed too late to start over. Newspapering didn’t seem like much of a career. It seemed like something to do until you discovered a career, or, as one of my reporter friends, a Brit with a background on Fleet Street, once told me: “It beats working for a living.” At some point I realized that I been working as a reporter long enough that journalism had become my career. It felt almost accidental. In 1987, a friend of mine talked me into joining him at a newspaper aimed at the computer industry called PC Week, which was based in Boston. In those days Boston still had a lot of high-tech companies. I didn’t know anything about computers, but nobody else did, either. The personal computer was still a relatively new thing. We were getting in on the ground floor of what would become a huge new market. In the 1980s Silicon Valley technology companies were boring places where engineers worked in drab office parks writing software or designing semiconductors and circuit boards and network routers. There weren’t any celebrities, other than Steve Jobs at Apple, and even he wasn’t such a big deal back then. In the early 1990s the Internet era began, and Silicon Valley changed. The new companies were flimsy, based on hype and grandiose rhetoric and the promise of making a fortune overnight. The dotcom boom of the late 1990s was followed by the dotcom bust, and then came a period when Silicon Valley felt like a ghost town. Slowly, a new generation of Internet-related companies arose, and while this second boom wasn’t a direct copy of the first one, there were some worrisome similarities, chief among them the fact that none of these companies seemed to be generating a profit. They were all losing money, and some were losing shocking amounts— billions of dollars, in some cases—and nobody seemed to mind. I covered the first dotcom bubble and crash as a reporter at Forbes. Those years have turned out in retrospect to have been a kind of golden age not just for Forbes but for magazines in general. Magazine writers didn’t get rich, but we made a good living, and the perks were amazing. We traveled the world, stayed in first-class hotels, and partied on the Highlander, Malcolm Forbes’s superyacht, with rock stars and heads of state. During my years at Forbes I met my wife, Sasha, and in 2005 we had twins, a boy and a girl. After spending my twenties and thirties bouncing around like a nomad, I settled down in my forties, with a good job and a new family. In 2006 I created a blog called The Secret Diary of Steve Jobs, where I wrote in a persona called Fake Steve Jobs. The idea was to satirize not just Jobs himself but all of Silicon Valley. I wrote the blog anonymously, and the mystery added to its appeal. Pretty soon it was attracting 1.5 million readers a month. The blog depicted Jobs as an insufferable, insecure megalomaniac who had turned himself into the leader of a weird cult based around electronics. Jobs ranted and cursed at the people around him; he went drunk-driving with Bono and smashed into other drivers; he threw scalding tea on his long-suffering assistant; he got into trouble with the Securities and Exchange Commission and lied to investigators; he visited sweatshops in China where children made iPhones and came away feeling that he was the victim. With Sting, he traveled to the Peruvian rain forest, where they tripped on ayahuasca and ended up hugging and sobbing on a mud floor. He and his best friend, Oracle CEO Larry Ellison, drove to the Tenderloin in San Francisco and fired water cannons at transvestite hookers. They made prank phone calls, dialing a local Thai restaurants to order “penis sauce” or calling a hardware store in the Castro section of San Francisco to inquire about black caulk. Eventually I got caught. A reporter at the New York Times figured out who was writing the Fake Steve blog and confronted me, and I came clean. There were profiles about me all over the place, from the New York Times to Der Spiegel in Germany and El Mundo in Spain. Conferences started inviting me to give speeches. Then I got hired at Newsweek, which led to even more speaking engagements, and I was on TV all the time, opining on Fox Business or CNBC or Al Jazeera. I published a Fake Steve novel, sold the rights to a Hollywood production company, and found myself in Los Angeles, developing a cable TV comedy while still working at Newsweek. Then things went south. My cable TV show got killed before it even got off the ground. The Washington Post, which had owned Newsweek since 1961, sold the magazine to a new owner. The new owner merged Newsweek with a website called the Daily Beast, whose brilliant but crazy editor, Tina Brown, became the editor of Newsweek. Most of my colleagues left or got booted out. I hung on, but things were chaotic. People came and went. During the next two years I had a half dozen editors. Sometimes I had no editor at all and just floated around, trying to place stories into the magazine. It was not a happy time, but I kept hoping that things would turn around. In March 2012, that seemed to happen. My old pal Abby was hired back and installed as the executive editor, and I was reporting to her. My job, which had felt precarious under the new ownership, began to feel secure. Finally, I had an ally, a friend in New York who would look out for me. That was a foolish thing to believe. Two When the Ducks Quack Losing my job sends me into a tailspin. On the surface I’m okay, or at least I am trying very hard to pretend to be okay. Inside I feel like I’m barely holding it together, even with daily doses of Ativan. “You’ll land on your feet,” people keep telling me, and I want to believe them, but as time goes by I’m not sure. So far I’ve had a disastrous interview at a big PR firm, with a vice president who invited me down to New York, kept me waiting for an hour, then told me that he didn’t like to hire journalists. At Forbes, an editor who less than a year ago was trying to poach me away from Newsweek now offers me a contract job that pays $32,000 a year and carries no health benefits. At night I lie awake in bed, unable to sleep, secretly afraid that I might never get hired again. That Newsweek story about “beached white males” wasn’t a work of fiction. I know guys my age whose careers are over. They’re in their early fifties and once held senior-level positions, and then got downsized only to discover that no one wants them. Those guys have all been where I am now—freshly out of work, still hopeful, going on interviews. But six months goes by, and then a year, and at some point people stop taking your calls. I’m not there yet. I’ve landed some freelance work, I’m still making money doing speaking gigs, and my lecture agent has promised that he will try to keep me working, but he also has warned me that without the word Newsweek in front of my name those speaking gigs are probably going to dry up. What happens then? Sure, we have savings. But those won’t last forever. For now we’re doing our best to economize. The kids know what’s going on. We don’t talk about it a lot around them, but I have to say something. I don’t know if talking makes things better or worse. I get the sense that they are a bit freaked out, especially my son. He’s a sensitive kid. One night when I’m putting him to bed I recognize something in his eyes that I’ve never seen before—it’s not that he’s scared, it’s that he knows what I’m going through and he feels sorry for me. It’s almost too much to take. “Come here, dude,” I say, and I give him a hug and try to make him laugh, and he does laugh, and I laugh, too, but I’m also trying not to cry. I realize that the way he sees me now is different from the way he saw me before. For the rest of my life I’m going to remember that flash of pity in his eyes. That look is going to haunt me. I need a job. Any job. Soon enough, I get one. This happens in September 2012. It’s not a great job. It’s not even a good one. There are a lot of drawbacks, chief among them that the job will take me away from home, but I don’t hesitate. I jump on it. Suddenly I am the editor-in-chief of a struggling technology news website called ReadWrite, a tiny blog with three full-time employees and a half-dozen woefully underpaid freelancers. ReadWrite is based in San Francisco, which means I fly out on Monday and take a redeye back to Boston on Thursday or Friday. On weeks when I’m not in San Francisco I’m either in New York, where ReadWrite’s parent company is based, or in some other city, making sales calls, trying to get tech companies to buy ads from us. It’s not a lot of fun, but I’m making a paycheck and keeping my eyes open for something better. ReadWrite’s offices are on Townsend Street, in the South of Market neighborhood, where all of the hot tech start-ups are located—Twitter, Uber, Dropbox, Airbnb. While the rest of the country is still licking its wounds from the worst recession in nearly a century, things here are buzzing. Start-ups are everywhere, and they’re all raising money. For a few years after the stock market crash in 2008, it was impossible for companies to pull off initial public offerings of stock. Without IPOs, the venture capital firms that put money into start-ups could not get a return on their investments, so venture funding fell off. But now things are loosening up. In May 2011, LinkedIn, a social network, went public and saw its shares more than double in their first day of trading. Later in 2011 Groupon and Zynga floated the biggest IPOs since Google in 2004. In May 2012 Facebook went public, in the biggest IPO in the history of the tech industry, one that placed a value of more than $100 billion on the social network that Mark Zuckerberg had started on a lark in his Harvard dorm room eight years before. Now everyone is trying to spot the next Facebook, and a new tech frenzy is taking shape. Back on the East Coast, where I spend my weekends, there is a vague sense that maybe things are getting a little bit frothy out in the Bay Area. Here in San Francisco there is no doubt. There’s money everywhere. Any college dropout with a hoodie and a half-baked idea can raise venture funding. Scooter rentals, grilled cheese sandwiches, a company that sends subscribers a box of random dog-related stuff every month—they’re all getting checks. Blue Bottle Coffee, popular among the cool kids in San Francisco, has raised $20 million (and over the next two years will raise $100 million more) and brews coffee using Japanese machines that cost $20,000 each. A cup of joe costs seven bucks. There is always a line. Thanks to all this new disposable income, San Francisco is bubbling with weirdo delights, like twee little shops selling liquid nitrogen ice cream and trendy bakeries making artisanal toast. Every morning, walking to work, I dodge a river of hipsters in skinny jeans and chunky eyewear riding skateboards—grown men! riding skateboards!—while carrying five-dollar cups of coffee to their jobs at companies with names that sound like characters from a TV show for little kids: Kaggle and Clinkle, Vungle and Gangaroo. The place feels a bit too much like it did back in the late 1990s, during the first dotcom bubble. I have the eerie sense that we are about to live through that nightmare all over again. Back then I was a technology reporter at Forbes. I had spent years writing about business and learning the traditional methods by which companies are valued. During the bubble I felt like a sane person who had been thrown into an asylum. The economics of these companies made no sense. Their valuations were completely irrational. I wasn’t the only one pounding the table about this. Yet the stock market kept going up and up. Scammers were getting rich, and I was missing out. It’s a tough thing to be a tech journalist during a tech boom. You spend your days talking to people who don’t seem any smarter than you—some don’t seem very bright at all—and yet they are gazillionaires, while you’re an underpaid hack who can barely pay his bills. I wasn’t sure whether to resent them or envy them. In the end I felt a bit of both. Of course the dotcom bubble finally blew up, and I felt a little bit vindicated and even a bit relieved. Now everything could go back to normal. I figured the dotcom bubble had been a historical anomaly akin to the Dutch tulip mania of the seventeenth century, something we would never see again in our lifetime. Instead another one is taking shape. People my age, who remember the first dotcom bubble, are walking around San Francisco feeling like the character played by Bill Murray in Groundhog Day. We’ve lived through this before. We reckon it will all end in tears, just like the first one did. The young kids running these new companies, however, have almost no memory of the first crash. They were in junior high school when it happened. One day, Aaron Levie, the twenty-six-year-old CEO of Box, a well-funded new tech company, tells me it’s really important to learn from what happened in the 1990s—which is why he has read a bunch of books about that era. To be sure, this bubble is different from the first one. The first bubble was a mania driven by a new technology that captured the imagination of mom-and-pop investors. This new bubble contains the same kind of magical thinking, but with an added twist, courtesy of the Federal Reserve. This time around the problem isn’t just that investors have gone a little bit crazy, but also that money is cheap. That at least is what one venture capital expert tells me. He theorizes that the policy of “quantitative easing” instituted by the Federal Reserve and other central banks after the financial meltdown of 2007 and 2008 is contributing to the stock market boom. By printing more money, the central banks are inflating stock prices. That in turn drives up the value of big pension funds and college endowments. Those organizations thus have more money to put into venture capital funds. As more money flows into venture capital, it becomes easier for start-ups to raise money. The surge of money also causes the valuation of some privately held tech companies to soar. This is an oversimplification, but basically the Federal Reserve is printing money, and a lot of that money is making its way to venture funds and from there into the pockets of a bunch of kids who are building start-ups in San Francisco. As long as the Fed keeps printing money and the stock market keeps going up, the party will continue. There is more money than there are places to put it, so much that instead of entrepreneurs competing to get funded, the venture funds are competing to get into deals—fighting for the chance to give someone their money. There’s more competition than ever before, not just from venture funds but also from start-up “incubators” and “angel investors” who are popping up all over the place. Soon even more money will surge into the Valley from mom-and-pop investors, people who previously were prohibited from investing in start-ups because such investing was deemed too risky. In 2012 Congress passed the JOBS (Jumpstart Our Business Startups) Act, which relaxes the rules on private company investing and allows regular folks to pour money into start-ups, usually by pooling their money into syndicates on websites like AngelList. Silicon Valley companies lobbied for the JOBS Act, arguing it would give ordinary people—doctors, lawyers, retirees—the chance to catch the next Facebook or Google. But some Wall Street veterans are worried: “We are talking about companies that in all likelihood are not going to be winners, being invested in by people who clearly don’t have the expertise and financial smarts of venture capitalists,” former SEC chief accountant Lynn Turner tells Bloomberg, adding that the rule change creates “a real opportunity for scams and fraud and significant losses.” The denizens of Silicon Valley see no such problem. “People are gambling in Vegas and blowing their money. They should have the freedom to angel invest with their money,” is how Jason Calacanis, a Valley entrepreneur and investor who is leading a start-up investment syndicate, puts it. The ranks of new Silicon Valley investors also include Hollywood celebrities and pop stars, the kind of people that Wall Street calls “dumb money.” But in a way it’s all dumb money. Nobody really knows what’s going to work, or which companies are going to succeed. Some investors are just spreading money around everywhere—“spray and pray,” they call it—hoping that somehow, if only through dumb luck, some of their money will land on the next Facebook, and the payoff from that one hit will more than make up for the duds. The biggest risk for venture capitalists is not that they will make a bad bet but that they will miss out on one of the good ones. A lot of the entrepreneurs are just as inexperienced as the investors. Some raise money without even knowing what product or service they will build. Many have never run companies before. Some have never even had jobs before. On top of that, a lot of these new start-up founders are somewhat unsavory people. The old tech industry was run by engineers and MBAs; the new tech industry is populated by young, amoral hustlers, the kind of young guys (and they are almost all guys) who watched The Social Network and its depiction of Mark Zuckerberg as a lying, thieving, backstabbing prick—and left the theater wanting to be just like that guy. Many are fresh out of college, or haven’t even bothered to graduate. Their companies look and feel a lot like frat houses. Twitter, at one point, will literally hold a frat-themed party. In 2012 a new word has entered the Silicon Valley lexicon: brogrammer, which refers to a kind of macho dickhead who chugs from a beer bong and harasses women. Soon come the scandals and lawsuits and criminal cases, with tales of sleazy founders sexually harassing female employees or, in one extreme case, allegedly beating up a girlfriend. These are the people who now run tech companies, who have been entrusted with huge sums of other people’s money. It would be nice to think that when everything falls apart, the only ones who get hurt will be venture capitalists on Sand Hill Road in Menlo Park. But a lot of the money being thrown at these kids originally came from pension funds. The pain, when it comes, will not be confined to Sand Hill Road. Walking around San Francisco, it strikes me that this cannot end well, that the combination of magical thinking, easy money, greedy investors, and amoral founders represents a recipe for disaster. My first response is to feel the same kind of righteous indignation that I felt back in the late 1990s. (Journalists are really good at righteous indignation. It comes naturally to us.) But this time I also feel something else—maybe because I’m older and more pragmatic, or maybe because I now have kids to support, or maybe because I’m still stung by the loss of my Newsweek job and fearful that there is no future in the media business. Maybe it’s because I hate my new boss at ReadWrite, and every day I slog into the office and bang out blog posts only to have her call me from New York and tell me the site isn’t getting enough traffic. I feel like a hamster in a wheel, running and running, getting nowhere. I’m never going to make any money doing this, and meanwhile all around me there are kids in skinny jeans making millions, tens of millions, hundreds of millions of dollars—money for nothing, as Mark Knopfler sang in that old Dire Straits song. This time I start thinking that I should get in on that. I should go get a job at one of these start-ups. Tech companies and VC firms are all poaching journalists to pump out blogs and get them some attention. They’re flush with cash and hiring like crazy. Two of my journalist friends have already made the leap. One is working at Evernote, the other at Flipboard. They both live in San Francisco. I see them all the time. These guys aren’t naïve. They just want to cash in on the madness. Out here, making money is the only thing anyone talks about. Funding rounds, valuations, deal terms, equity percentages, who made what—these are the topics of conversations when I visit friends for dinner in Marin County. The coffee shops are filled with techies who are hunched over laptops and frantically dashing out code, or pitching ideas to investors. Every morning when I’m waiting in line for my fivedollar caffè latte I see these meetings taking place. Sure, this bubble will pop one day, but before that happens a bunch of people are going to make a lot of money. That’s what happened last time—Netscape, which made the first web browser, never really succeeded as a company, yet its cofounder, Jim Clark, reportedly managed to put $2 billion into his pocket—and the same thing is happening now. Zynga and Groupon are losing hundreds of millions of dollars, yet their founders have become billionaires. Finally I have a sort of epiphany. This takes place on a rainy Friday evening in November 2012, in Anchor & Hope, a fancy restaurant on Minna Street, a block away from Market Street, in the part of San Francisco where the financial district and start-up land converge—a spot that is, quite literally, ground zero for the revolution. I’m on my way to the airport. Tonight I’ll be taking a redeye back to Boston, but before I do I’m meeting a friend for a drink. Anchor & Hope is packed with techies and bankers who are spending some of their easily raised money on $200 bottles of Napa Valley Cabernet Sauvignon and oysters sold at $50 per dozen. Tad is an investment banker. He’s sitting at the bar, way in back. He wears black glasses and a gray bespoke suit that probably costs more than I make in a week. Back in the 1990s he made a fortune managing IPOs for tech companies. For the past decade he’s been on the beach, but now he’s back, because the opportunity is so huge that he can’t ignore it. “Do you have any idea how big this is going to be?” he says. “This is going to be huge. It’s going to be way bigger than the last bubble.” Imagine there’s a giant tsunami, way out at sea, he says. Right now you can barely see it, but soon that wave is going to arrive. Some people are going to get wiped out, but some are going to ride the wave and get rich. I ask him if he thinks that start-up valuations are too high. Based on traditional metrics, it seems to me that some of these companies seem way too expensive. “You think these valuations are high today? Wait until you see them a year from now, or two years, or three years. We’re not even near the peak. Before this is over there’s going to be a trillion-dollar transfer of wealth in Silicon Valley.” His bank will make money by helping people move that money around and carving off a little slice as it flows through the pipe. Tad will arrange mergers and acquisitions. He’ll advise start-ups that are raising money, either from private investors or through IPOs. Once again I bring up the issue of valuations and my fear that this can’t be sustained, that we’re going to have another crash. “There’s an old expression on Wall Street,” Tad tells me. “‘When the ducks quack, feed them.’ Have you heard that? Back in the nineties investors wanted to buy anything with the word dotcom at the end of its name. So that’s what we gave them. Our job isn’t to talk people out of buying. Our job is to make what people want. Our job is to feed the ducks. And right now, the ducks are hungry.” Nearby, a cheer goes up as a waiter delivers an enormous, two-tiered tower of seafood, a few hundred dollars’ worth of lobster, oysters, and other shellfish, to a table of twenty-something techies wearing jeans and sneakers and Warby Parker glasses. Tad tells me again about the trillion dollars that is going to change hands. A trillion dollars! It’s the biggest transfer of wealth that has ever occurred. “And I’m here writing about it, instead of getting in on it.” He sips his cabernet sauvignon, and shrugs. “Right.” “I’m in the wrong business,” I say. “That’s true,” he says, in a matter-of-fact voice. It’s time for me to go. There’s an Uber outside, waiting to take me to the airport. We say our goodbyes. Out in the car, driving to the airport, gazing into the dark and watching rain lashing against the windshield, I keep thinking about that trillion dollars. That joke I made about being in the wrong business wasn’t really a joke. It’s the truth. I’m in the wrong business. I’m working in a bad industry where things are only going to get worse. But why? What law says that I have to keep doing what I’m doing, just because this is the only job I’ve ever done? By the time I get to the airport I have made up my mind. The tech market is going crazy again, and this time I’m not going to sit on the sidelines and write about it. I’m going to work at a start-up. I am going to feed the ducks, or surf the tsunami, and maybe I will fall off my surfboard and drown, or maybe, I don’t know, I’ll get eaten by ducks, but to hell with it—I’m going to try. As I see it I have nothing to lose. I hate my job at ReadWrite anyway. Sure, I am fifty-two years old and past the age when you’re supposed to start a new career or go on any adventures. But if I don’t do this now, I might never have the chance again. I might always wonder how things would have turned out if I had just sucked up the courage to make the leap. The trick is to find the right company. Ideally I’d like to join the next Google or Facebook—a rocket ship. Realistically, I just hope to find a company that won’t fizzle out, one that is likely to pull off a successfull initial public stock offering and put a few bucks in my pocket. Pretty soon, I find one. Three What’s a HubSpot? There’s a post on LinkedIn—a software start-up in Cambridge is looking for a “content creator.” The company is called HubSpot. Its offices are six miles from my house in Winchester, Massachusetts, yet I have never heard of the company and have no idea what they make. I pore through their website, which talks about something called inbound marketing, which I’ve also never heard of. All I can tell is that they make software used by marketing departments. I call around to friends who work in venture capital, who tell me that HubSpot is the real deal. The company is a bit of a sleeper. It’s not as well known as companies like Snapchat or Instagram, but it is run by a bunch of guys from MIT and headed for an IPO. Over the past seven years HubSpot has raised $100 million in venture capital, and its investors include some of the best firms in the business. Its business is booming. “Those guys,” one of my VC buddies says, “are going to make a shit ton of money.” I write to the woman who posted the content creator job opening on LinkedIn. She’s anxious to meet. Her name is Sharon. She’s married, in her forties, and has two kids. In January 2013 we meet for lunch at a Thai restaurant in Cambridge, and she brings along Wingman, who runs the company’s content group. Wingman is about thirty years old, has been at HubSpot for just over two years, and before that worked at public relations agencies. He says the job I applied for isn’t right for me, but he has something bigger and more interesting in mind. He’s also concerned about culture fit, which he says is a big deal at HubSpot. They like people who can get along well with others, “the kind of people that I’d like to go have a beer with after work.” I’m not sure I’d want to hang out with Wingman after work, but he seems nice enough. Apparently he feels the same way about me, because a few weeks later they invite me back to meet Cranium, HubSpot’s chief marketing officer. Cranium is a big, affable guy in his late thirties. We meet at HubSpot’s offices and talk over coffee. He has an MBA from the MIT Sloan school and uses the word awesome a lot. We talk about HubSpot’s business model, its path to profitability, and the “stickiness” of its product, meaning how well HubSpot is able to keep customers from switching to a rival software product. Right away, I like Cranium. I can imagine myself working for him and learning from him. The position he has in mind for me, he says, is something called a marketing fellow, which seems to imply that I’m being brought in as a kind of special adviser to the company. The bad part is that it’s not an actual title, like director or vice president, which are the titles you get if you are actually part of the management team. In fact the title marketing fellow implies that you are not really a part of the company; you’re a visitor, a temporary hire, someone who is being kept at arm’s length. I’m too clueless about corporate life to understand that. In my mind, marketing fellow sounds like a cool title. I like it. In the days leading up to this interview with Cranium I have started thinking that HubSpot could be a really good fit for me. I’d be working in the marketing department of a company that makes software for marketing people. Where better to learn about marketing? And marketing seems like a natural next step for me. I could spend two or three years here, become a marketing expert, and then go work for a smaller start-up in a bigger role. HubSpot is small enough that I’ll probably get to wear a lot of different hats. Who knows what I might end up doing? In the next year or two HubSpot will probably have a really hot IPO, and while I won’t get rich on that, I will at least get a little something, and it will be cool to be on the inside of one of those events. Cranium apparently likes me too, so next I get passed up the ladder. Toward the end of February 2012 I go back again and meet HubSpot’s co-founders, Brian Halligan, the CEO, and Dharmesh Shah, the chief technology officer, or CTO. Before the meeting I watch some of their keynote speeches from HubSpot’s annual customer conference, called Inbound. I read Inbound Marketing, the book they coauthored a few years ago, and pore through Shah’s blog and the articles he has published on LinkedIn. We meet in a conference room at HubSpot. They’re both in their forties, which is a relief to me. I don’t want to work at some company run by a twenty-five-year-old boy-king brogrammer and his frat brothers from college. Halligan and Shah met while they were both in grad school at MIT, but I cannot understand how they ever became a team. They could not be more different. Halligan is an extreme extrovert, a classic sales guy. He once sold software for a company in Boston and later worked as a venture capitalist. He is in his late forties and still single, a blustery, hard-partying Boston Irish guy who lives in a luxury condo in the South End, drives a BMW, and has a reputation as a ladies’ man. Shah is married, has kids, and is an extreme introvert who claims he can go weeks without talking to anyone on the phone. He begins his speeches by saying how much he dreads giving speeches, and how he’d much rather stay home and write code. But once on stage he seems to enjoy playing the role of inspirational speaker—a kind of nerd Tony Robbins, overly fond of touchy-feely rhetoric and vapid aphorisms. “Success,” Shah says, striding back and forth across a stage, with his head down, stroking his beard, as if impersonating a professor, “is making those who believed in you look brilliant.” Then he will pause, as if he has just said something incredibly profound and wants to give you a moment to let it sink in. Then he repeats the line, and a ballroom full of marketing people cheer. But when I meet them together it occurs to me that their different personalities are probably why their partnership works. There’s a yin-and-yang quality, like the one between Steve Jobs and Steve Wozniak, the co-founders of Apple. Halligan is the Jobs figure, the corporate visionary, the guy who thinks about sales and marketing. Shah is like Woz, the nerdy software programmer. Shah is wearing scruffy jeans and a rumpled T-shirt, his usual attire. He has dark hair and a dark beard, flecked with gray. Halligan wears jeans, and a sports jacket over a buttondown oxford shirt. His hair is gray, as gray as my own, in fact, and he wears the same kind of chunky horn-rimmed glasses that I do. I take this as a good sign. As with Cranium, I like these guys right away. They’re easy to talk to. It doesn’t feel like an interview. It feels like we’re just having a conversation. Shah, as it turns out, saw me give a speech at a conference a few months ago and really liked it. He says he’d like me to give the same talk at HubSpot’s Inbound conference this year. I tell him I’d be glad to do that. We talk about some of the things that Shah has been writing about on his blog. They ask me about ReadWrite, and I tell them how we are struggling to sell advertising, and how I’ve come to believe that the problem is not our content—the problem is advertising itself. Ads no longer work. But this means the business model upon which the media business is built—create content, put ads next to it—no longer makes sense. The media business now needs to figure out a new way to produce journalism and make money from it, but so far nobody has any good ideas. I mention a new documentary, The Naked Brand, made by a renegade advertising guy in New York, Jeff Rosenblum, who believes the entire advertising business is about to get blown to hell. Halligan’s jaw drops. He just saw the movie and loved it. Everything the guy says in that movie is what he’s been saying for years. It’s why HubSpot exists, he tells me. In their book, Inbound Marketing, Halligan and Shah argue that instead of spending money on traditional marketing, things like buying advertising and cold-calling customers, companies should publish blogs and websites and videos, and use online content to draw customers toward them. The old marketing was outbound, meaning it involved sending messages out into the world. The new marketing is inbound. It’s less expensive and more effective. That’s what HubSpot’s software does. That’s its sales pitch, in a nutshell. Halligan turns to Shah. “Have you seen this movie we’re talking about?” Shah says he hasn’t heard of it. “You gotta see it,” Halligan says. That’s when I play my ace. “You know, I know Jeff Rosenblum. I wrote a story about him for Newsweek. I went to the premiere of that movie in New York. We got to be friends. I can introduce you to him. I think you guys would love each other.” Rosenblum is a hard-partying wild man who went to University of Vermont, the same college that Halligan attended, and competes in Tough Mudder events, the nutso races where people charge through ten-mile obstacle courses straight out of Navy SEAL basic training. Halligan says he’d love the introduction and that maybe we could get Rosenblum to come up to Boston and give a HubTalk, which is what HubSpot calls its speaker series, where interesting people come in and give a quick talk at lunchtime in the big conference room downstairs. I tell Halligan I’m sure that Rosenblum would give a talk. We could probably even set up a showing of The Naked Brand for everyone at HubSpot. Or better yet, we could arrange a big showing in Boston, at a theater, with HubSpot as a sponsor. The ideas are flying. We’re hitting it off! This is going great. Then Halligan says he has another mission for me. “It’s our blog,” he says. “It sucks.” I’ve looked at the blog, and he’s right; it’s awful. But I figure it’s best to be diplomatic. I tell him that I think the blog is pretty good, as corporate blogs go—but Halligan cuts me off. “No, it’s terrible. It used to be better. There were other people running it. But lately, I don’t know. It’s kind of embarrassing.” He turns to Shah. “Do you agree?” Shah agrees. We talk about how a lot of companies, especially tech companies, are hiring journalists and actually producing high-quality news sites. Some of them are doing a really good job, better than what we can do at a place like ReadWrite, if only because they have more resources. Halligan says he wants to produce material that raises awareness of HubSpot and establishes HubSpot as a “thought leader” in the world of marketing. I mention the idea of creating an independent site, sponsored by HubSpot but kept separate from the company. That’s what Adobe, a big software company in California, has done as a way to promote its marketing software. I know the guys who run the Adobe- sponsored site and have talked to them about how they launched it. Halligan and Shah are noncommittal. For now the deal is that I will come on board and find a way to produce better, smarter content that can be put out with the HubSpot brand attached to it. The work I’m doing will exist in a gray area—a mix of journalism, marketing, and propaganda. Halligan and Shah don’t know what this will look like, and neither do I. But it could be an interesting experiment. We shake hands, and I leave the meeting feeling pretty good. Two weeks later, in the middle of March, they make me an offer. The problem is that by the time this happens I also have two other offers, because even while I’ve been talking to HubSpot, I’ve also been interviewing at other places. One offer comes from a media company in New York; I can stay in Boston and write a blog about technology. The other job involves working in the public relations department of a huge Internet company, which wants me to move to Silicon Valley and will pay me more money than I’ve ever imagined I would make. Nevertheless, I’m still leaning toward HubSpot. The media job could be fun at first, but I won’t get to write interesting articles. I’ll be grinding out blog posts and trying to get traffic, just like at ReadWrite and at the Daily Beast, and I’ve had enough of that. The big company in Silicon Valley is tempting, but Sasha isn’t thrilled about moving to California, and a friend of mine who has worked at the company, and knows the people I would work with, has told me she had a less-thangreat experience, and doesn’t recommend going there. Then there’s HubSpot. It’s in Boston, so we don’t have to move, which makes Sasha happy. We don’t have to sell our house and buy a new one, or find a new school for the kids, or make new friends. I like that HubSpot is still a small company. I reckon that at HubSpot I’ll end up doing lots of different jobs. I’ll be more likely to have some influence than I would at some huge corporation with thousands of employees. Also, I like Halligan. He seems smart. I want to work with him. HubSpot also potentially represents more upside, financially. The big company in Silicon Valley is already big. The people who got rich there were the ones who joined fifteen years ago. HubSpot is just starting out. If HubSpot goes public, and if its stock really takes off—if HubSpot becomes the next Microsoft, or Google—I might make some serious money, something I’ve managed to avoid doing over the course of my career as a journalist. “Basically I’m making a bet,” I say to Sasha, after we’ve put the kids to bed and we’re talking about which job I should take. “The only way the HubSpot job is worth taking is if they’re going to go public and have a big IPO.” The deal at a start-up is that you get a lower salary, but you also get a pile of options, which vest over four years. The strike price on my HubSpot options is set at a level that reflects the valuation put on the company’s last private round of funding. If HubSpot goes public at a valuation higher than that, my options will be worth money. If the IPO is a dud, or if the market crashes and HubSpot can’t go public, or if HubSpot fizzles out altogether, then my options will be worthless. To pull off a successful IPO, HubSpot needs to reach $100 million in annual sales. That’s about double what the company did in 2012. What are the odds that they can do it? How savvy are Halligan and Shah? What will investors on Wall Street think of these guys? My sense is that things will go well. Halligan used to work as a venture capitalist, so he thinks like an investor. Shah, before going to grad school at MIT, built a different software company and sold it. Also, from the perspective of Wall Street, HubSpot ticks all the right boxes. It sells to businesses, rather than to consumers. It’s a cloud computing company and uses a business model called software as a service, or SaaS, which means customers don’t install the software on their own computers but instead connect to it over the Internet and pay a monthly subscription fee. Cloud computing is hot right now. The whole tech industry is moving to this model. Investors love it. Over the years Halligan and Shah have come up with a creation myth about the company, which is that while they were in grad school they had a vision for how companies could transform their marketing departments. They came up with the concept that they call inbound marketing, then Dharmesh and a team of engineers wrote a set of software programs based on that concept. Companies that use HubSpot software are able to find new customers, boost their sales, and save money. That’s the pitch. In fact the early days were not quite so tidy. People who were around in those days later tell me that Halligan and Shah considered other things before deciding to make marketing automation software. What’s more, I’ve been told, for the first five years, HubSpot’s product wasn’t very good. It was so bad, in fact, that according to one former engineer HubSpot’s own marketing department couldn’t depend on it and instead used marketing software made by one of HubSpot’s rivals. “The fucking product was a disaster,” the engineer recalls. “You’d try to do something, like run a query, and the system would just blow to shit. Every day there was an outage.” But Halligan knew how to sell. Among his first hires were a head of marketing and a head of sales. Those guys assembled an old-fashioned phone sales operation, with an army of low-paid telemarketers who would badger companies into signing up for a one-year subscription. The salespeople targeted small business owners, whose needs were relatively simple and who were, typically, not very tech savvy. Eventually some customers would become disenchanted with the software and refuse to renew for a second year. By then HubSpot’s telemarketers would have found new customers to replace the ones who were leaving. By 2011, HubSpot had about five thousand customers. That year, the company raised a new round of funding and used the money to acquire a company with good engineers. The new team threw out the old coders and began rewriting the software from scratch. By 2013, when I arrive, HubSpot is selling a much better product. The software is still not perfect, and one program in particular, the content management system, needs a lot of improvement. The code is not based on cutting-edge computer science or sophisticated artificial intelligence algorithms. These are just fairly simple programs that automate basic marketing chores, like sending email to a list of contacts. But friends of mine who use HubSpot tell me the software can more than hold its own against other marketing software products. One market research website, which rates software based on customer reviews, ranks HubSpot in first place among marketing automation programs. Better yet, all those years of selling a weak product have forced HubSpot to get really good at generating hype. The vast majority of HubSpot’s employees work not in engineering or software development, but in sales and marketing. They spend their days cold-calling customers, cranking out blog posts, posting automated email campaigns, flooding Twitter and Facebook with promotional messages, running webinars and podcasts, talking to user groups, and preparing for HubSpot’s big annual customer conference, an extravaganza with musical acts, comedians, and inspirational speakers. Over the course of seven years, Halligan and Shah have built a hype machine that goes beyond anything I’ve ever encountered. There seems to be nothing HubSpot will not do to get publicity. In 2011, the company took advantage of a service that Guinness World Records offers in which anyone can suggest a new category, set a record, and get an official Guinness World Records title. A spokesperson for Guinness says HubSpot came to Guinness with an idea to hold the “world’s largest webinar,” and then won the honor by holding a webinar that drew 10,899 participants. The spokesperson says HubSpot paid Guinness $8,700 for the service. HubSpot’s record still stands, though more than a dozen others have tried and failed to do better, according to Guinness. So far, HubSpot has devoted all of its energy to selling software. But in 2013 Halligan and Shah are getting ready to point their hype cannon at a new customer, with a new product. The product they will sell is HubSpot’s stock, and the customers will be investors on Wall Street. Wall Street, I’m pretty sure, is going to eat this up. I take the job. Four The Happy!! Awesome!! Start-Up Cult One month later I’m driving home from my first day on the new job and telling myself that everything will be okay. Sure, my boss is half my age. Sure, I have no idea what I’m supposed to do. But it’s only been one day. “It’s great,” I say, when I get home and find Sasha and the kids waiting for me, anxious to hear about Dad’s big new job. I tell the kids about the beanbag chairs and the Nerf gun fights and the kitchen with the giant wall of candy dispensers, with every kind of candy you can possibly imagine. The kids are seven years old now, and of course this sounds exciting to them. They can’t wait to come to the office with me. They’re going to bring their Nerf guns. “I’m sure we can do that,” I tell them. After dinner I pull Sasha out onto the porch and tell her what I’m really thinking. “This might be a mistake,” I say. “That’s what you said last time.” “Yeah, and last time I was right.” It’s galling to think that I may have leapt from one bad situation to another that’s even worse. What the hell is happening to me? After years of steadily climbing up some imaginary corporate ladder, I’m now turning into a serial screw-up. I glance through the window of the sliding doors. The kids are in the living room, fighting. They fight all the time, and with such passion that sometimes I think we should find an exorcist. They have been through a lot over the past couple of years. They’ve seen Sasha going in and out of the hospital, and then leaving her job. They’ve seen me lose my job at Newsweek, then take a new job in San Francisco and disappear for weeks at a time. They’ve seen me exhausted, burnt out, and depressed. They’ve heard us talking about moving to California. They’re frazzled. We all are. Whatever happens at HubSpot, the best course of action is to hunker down, pretend to be happy, and let our lives regain some stability. That doesn’t mean I can’t bitch to my wife about it. I tell Sasha about Cranium and Wingman not being there. I tell her about the guy who I thought was someone’s administrative assistant and who turned out to be my boss, and how I’m sitting in a room called the content factory, crammed in with two dozen people. Inside, something has happened. My daughter is screaming. She sounds like she has been set on fire. “Want a paper bag to breathe into?” Sasha says. “No, I want a plastic bag, and you can put it over my head and tie it around my neck.” “That’s the spirit,” Sasha says, and we open the door and head inside to face the mayhem. Every new HubSpot employee has to go through training to learn how to use the software. That’s a good idea, and it also keeps me from having to worry about what I’m supposed to be doing here, or why Cranium, who hired me, still has never come by to say hello or talk about what he wants me to work on. Training takes place in a tiny room, where for two weeks I sit shoulder to shoulder with twenty other new recruits, listening to pep talks that start to sound like the brainwashing you get when you join a cult. It’s amazing, and hilarious. It’s everything I ever imagined might take place inside a tech company, only even better. Our head trainer is Dave, a wiry, energetic guy in his forties with a shaved head and a gray goatee. On the first day we all go around and introduce ourselves, and tell everyone about something that makes us special. Dave’s thing is that he plays in a heavy metal cover band on weekends. Dave is part teacher and part preacher. Every two weeks he gets a batch of new recruits, and he goes through the same spiel, showing the same slides, telling the same jokes. He’s good at it. He loves HubSpot, he tells us, unabashedly. He’s had lots of jobs, and this is by far the best place he’s ever worked. This company has changed his life. He hopes it will change ours as well. “We’re not just selling a product here,” Dave tells us. “HubSpot is leading a revolution. A movement. HubSpot is changing the world. This software doesn’t just help companies sell products. This product changes people’s lives. We are changing people’s lives.” He tells a story about a guy named Brandon, a pool installer in Virginia. His business was struggling. He could barely get by. But then he started using HubSpot software, and his business took off. Soon, his company was installing pools all around the country. He was rich! Eventually he was doing so well that he hired someone else to run his pool company so that he could become a motivational speaker. He travels the world spreading the gospel of inbound marketing, transforming the lives of thousands of other people. “This guy has become a superstar,” Dave says. “He’s a rock star. And it all started with HubSpot. That’s what we’re doing here. That’s what you are part of.” The truth is that we’re selling software that lets companies, most of them small businesses, sell more stuff. The world of online marketing, where HubSpot operates, has a reputation for being kind of grubby. In addition to pool installers and flower shops, our customers include people who make a living bombarding people with email offers, or gaming Google’s search algorithm, or figuring out which kind of misleading subject line is most likely to trick someone into opening a message. Online marketing is not quite as sleazy as Internet porn, but it’s not much better, either. Nevertheless, Dave is laying it on thick, and the new recruits are nodding their heads and seem to be eating it up. Most of them are right out of college, clean-cut and well scrubbed. The guys wear khakis and button-down shirts. The women wear jeans and boots, and lots of makeup, and they have paid attention to their hair. The guy next to me has a buzz cut and just graduated from some college in New Hampshire. He tells me that he lives with his parents and commutes an hour to get here, but he’s thinking about moving closer to Boston and getting his own place. I feel ridiculous. I definitely don’t belong here. When it’s my turn to tell a little something about myself, I make a joke about how I’m friends with all of their parents, who have sent me here to keep an eye on them. The joke falls flat, which it should, because it’s a shit joke. I’m nervous. I have to come up with something. What makes me a special snowflake? How am I different from everyone else here, other than the fact that my hair is gray, my cholesterol is too high, and I’m probably the only person in this room who has had a colonoscopy? I say something about being the parent of twins. The other recruits just look at me. Dave ushers in a parade of executives who give us inspiring talks about what a great company we’ve joined. I’m not only older than all of the other trainees, I’m also older than all of the executives. Assistant trainers lead various courses during the day and give us homework assignments. A woman named Patty does most of the training on how to use HubSpot’s software. What we’re selling is not one single product but actually a handful of separate programs that can be purchased individually or as a bundle. The bad news is that some of the programs aren’t especially good. I’ve already been using the content management system, or CMS, which is software for writing and editing blog posts, and it’s awful—buggy, slow, prone to crashing, incredibly limited in its functionality. HubSpot’s CMS is a tinker toy compared to WordPress, the most popular blogging software, which also costs nothing to use. I can’t believe HubSpot charges people money to use its CMS, or that anyone is gullible enough to pay them. Then again, a lot of HubSpot’s customers are small-business owners, so maybe they don’t know any better. Or maybe they think using WordPress would be too much of a hassle. Maybe they would rather pay for HubSpot because then they can call a tech support line and get answers to their questions about how to use the software. They probably also figure that over time HubSpot will improve the software and add more features. There’s a program for sending out email. It automates the process, so you can blast thousands of people with a sequence of email messages that will be sent out on a schedule. Another program lets you store a database of customer contacts. There are tools that analyze the traffic to your website, to see which pages are attracting the most visitors and how much time people spend on a particular page. There is a search engine optimization feature that helps you load up blog posts with keywords so that people are more likely to find your page when they do a search on Google. One of our assignments involves inventing a fake company and fake product and then crafting an email campaign to sell the product. HubSpot’s software lets you set up a series of emails in a tree structure. You write one first-round email that goes out to everybody on the list. For the second-round email, you might create three versions—one for the people who deleted the first email without opening it, another for people who opened the email and looked at it before deleting it, and a third for people who went one step further, who clicked through on the link in the first email and looked at your website, but then left without buying anything. Then you create a third round of email messages based on the possible responses to the second email, and so on and so on. The goal is to keep pushing people toward your website until they buy something. Once they buy something, you set up a new campaign and try to get them to buy something else. You can set up a campaign with multiple steps, aim it at a list that contains thousands of names, then press SEND and let the software go to work. At HubSpot this happens on an incredible scale. Every month, HubSpot’s customers send out, in aggregate, more than a billion email messages. And we’re just one of dozens of companies selling tools to automate the work of sending junk around the Internet. Now I’m a part of this. I’m working for the people who fill your email inbox with junk mail, the online equivalent of those pesky telemarketers who call you at dinnertime to sell you new windows or a set of solar panels for your roof. I rationalize this by telling myself that while the work might be ignoble, it’s not necessarily evil. We’re not Hitler. We’re just annoying people. Sure, arguably we are making the world a little bit worse—but only a little bit. That’s what I tell myself. Online marketers have invented euphemisms to make the work they do sound less awful. For example, we’re told that our email campaigns do not involve badgering people, or pestering them—rather, we’re “nurturing” them. “Lead nurturing” is a big thing in the world of online marketing. If someone doesn’t open our first email, we’ll nurture them again, and we’ll keep on nurturing them until they finally cave in and buy something. HubSpot doesn’t just sell this software—it also teaches people how to use it and in general how to be more effective at selling stuff online. At the annual customer conference, Inbound, thousands of online marketers flock to Boston to learn new tricks. One involves using a misleading subject line in an email—something like, fwd: your holiday plans—to dupe people into opening the message. “Boosting your open rate,” they call it. At the conference HubSpot also shows off new features and products, like one that puts a tracking cookie on the computer of everyone who visits your website and keeps track of every page they visit. The software can even send you an alert when someone comes back to your website for a second visit—so you can call that person immediately and say, “Hey, I see you’re on our website! Is there something I can help you with?” That’s the business we’re in: Buy our software, sell more stuff, make more money. There’s nothing wrong with that, but that’s not exactly how HubSpot bills itself or describes what it does. The motto of the Inbound conference is this: “Come together. Get inspired. Be remarkable.” In training we’re taught that the billions of emails that we blast into the world do not constitute email spam. Instead, those emails are what we call “lovable marketing content.” That is really what our trainers call it. That is the exact term they use. The convoluted logic behind this is that “spam” means unsolicited email, and we only send email to people who have handed over their contact information by filling out a form and giving us their permission to be contacted. Our emails might be unwanted, but they’re not, strictly speaking, unsolicited, and therefore they are not spam. And even though we and our customers send out literally billions of email messages, we’re not trying to annoy people—in fact we are trying to help them. Sending one message after another, each time with a different subject line, is how we discover what someone wants. We’re learning about them. We’re listening to them. Thus, what we’re creating is not spam. In fact, the official line is that HubSpot hates spam, and wants to stamp out spam. We want to protect people from spam. Spam is what the bad guys send, but we are the good guys. HubSpot has even created a promotional campaign, with T-shirts that say MAKE LOVE NOT SPAM . This is breathtaking and brazen. This is pure Orwellian doublespeak. Night is day, black is white, bad is good. Our spam is not spam. In fact it is the opposite of spam. It’s anti- spam. It’s a shield against spam—a spam condom. To me this seems like complete bullshit. Of course we’re creating spam. What else can you call it when you blast out email messages to millions of people? For years after I leave HubSpot I will continue to receive “lovable marketing content” from HubSpot marketing people. The messages are addressed “Dear Marketing Fellow” and offer a free software download or invite me to check out an e-book. Some are addressed to Heinz Doofensmirtz, the CEO of Doofensmirtz Evil, Inc., because I once filled out a form using that name, too. “Hi Heinz,” says a note from my good friend and former manager, Wingman. “Do you know the ROI on Doofensmirtz Evil, Inc.’s marketing efforts?” In December 2015, as I write this, I am still receiving them. Just this morning I got one from a “senior growth marketing manager,” offering me a six-hour course about inbound marketing and a certification. Once I pass an exam, I will get a “personalized badge and certificate.” I can add this to my LinkedIn profile, or even “proudly hang it on your desk,” my friend from HubSpot writes. I get loads of these emails, all sent under the names of real people at HubSpot, often from people I know and worked with, including Wingman. The emails are set up to look like actual personal email messages. Instead of coming from a generic address like offers@hubspot.com, they come from an individual’s HubSpot email address and include a sign-off with that person’s name and title and Twitter handle at the bottom, under a closing like, “All the best,” or “For the love of marketing.” This is what we learn in our training sessions. This is what we’re taught how to do. I can’t tell if the people around me actually believe this rubbish we’re being fed. They seem to, but maybe they’re just playing along. As for me, I am completely transfixed. I’ve never seen or heard anything like this. Have you ever received a call from one of those annoying telemarketers and wondered what it must be like on his end of the phone? How many people are in the room where he is sitting? How does he talk people into buying whatever he’s selling? How did he learn how to do this? How does he rationalize what he does? The online version of that telemarketer ’s world is the one that I’ve now entered. I’m in the Land of Spam, learning how to send email to lists of names in the hope that some teeny tiny percentage of the recipients will open my message and buy something. It’s appalling, but also fascinating. I have to learn more. “You all must be pretty special to be here,” Dave, our trainer, tells us. “HubSpot gets thousands and thousands of applications. Just to be sitting here in this room means you’ve climbed past a lot of other really exceptional people. Did you know that it’s harder to get hired at HubSpot than it is to get accepted at Harvard?” That line about Harvard is one that gets tossed around a lot. I hear it over and over again. Halligan likes to tout it. I have no idea how they came up with the claim, but Harvard has a 6 percent acceptance rate, so I suppose they just figured out that in a certain year HubSpot had hired fewer than 6 percent of people whose resumes they had seen, so that make...
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