This Old Guy Joined a Tech Startup. You Won’t Believe What Happened Next

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From his first day at "inbound marketing" company HubSpot, Dan Lyons knew he'd made a mistake. Hachette Books

The orange penises are a bad omen.

It is April 15, 2013, Dan Lyons’s first day at HubSpot, a digital marketing company based in Cambridge, Massachusetts, with a lot of hype and a decent chance of going public. A journalist by trade, Lyons has recently been laid off by, ahem, Newsweek and, after a blog-editing stint, is joining HubSpot in hopes of cashing in on the startup gold rush he has spent so much time writing about. His job title, “marketing fellow,” is not impressive, but at least it’s academic-sounding, and Lyons was pleasantly surprised by his interviews with HubSpot’s chief marketing officer, pseudonym Cranium, and its founders, MIT graduates Brian Halligan and Dharmesh Shah.

But now it’s the big day, and Lyons finds himself waiting at HubSpot’s front desk while a baby-faced receptionist makes call after call in search of someone, anyone, to come retrieve this middle-aged man claiming to be a new employee. Lyons, 52, looks around, at the orange walls and orange desks, at the uniformly 20-something HubSpotters with their orange T-shirts and orange laptop stickers, at the ubiquitous HubSpot logo, a circle with three knobbed arms meant to resemble an orange sprocket. “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,” Lyons writes in Disrupted: My Misadventure in The Start-Up Bubble. “These orange cocks are all over the place.”

There are other red flags. Like the group of guys who meet every day at noon to do pushups, or the “seating hack” policy, by which employees swap seats every three months. There’s the dichotomy between how HubSpot peddles its “inbound marketing” software—as a turnkey solution that eliminates companies’ need to market via manpower—and how HubSpot runs its sales and marketing operation: with an enormous call center full of Red Bull–guzzling salespeople with lead quotas right out of Glengarry Glen Ross.  

But mostly there is HubSpot’s aggressive culture, with its myriad rules of etiquette and groupthink masquerading as innovation. Even though HubSpot is, at this point in 2013, poised for an initial public offering that could make many of its stakeholders rich (including Lyons), behind the scenes, a low-level chaos reigns. “Arriving here feels like landing on some remote island where a bunch of people have been living for years, in isolation, making up their own rules and rituals and religion and languages,” he writes. “Even, to some extent, inventing their own reality.”

Disrupted is Lyons’s first book, though not his first stab at comedy: For more than five years, he was the mind behind Fake Steve Jobs, a blog “by” the late Apple founder that portrayed Jobs as an out-of-touch megalomaniac. (“If you are traveling this week, I’m told that people who don’t have their own jets are being forced to subject to some humiliating patdowns.”) Real Steve Jobs was not a fan of Fake Steve Jobs (although Bill Gates was), and Lyons discontinued the blog after its muse’s death in 2011. But Fake Steve did earn Lyons the attention of people in television. Two years ago, he became a writer for HBO’s Silicon Valley, and it was in Los Angeles, amid the crass punch lines and fart jokes of the writers’ room, that he first realized his tenure at HubSpot might make for a book.

“I saw how fascinated the Hollywood guys were; they found this stuff really interesting and worthy of satire,” Lyons says. “Somewhere in that process, I started thinking, Oh, there’s something in this.” 

Even though Disrupted is laugh-out-loud funny from the first orange sprocket, Lyons is reticent to consider it a takedown. “To me, the book is about me trying to learn something new and struggling with that,” he says, repeating a few times the phrase “an old guy taking a job.” In the book too, he emphasizes that some people are happy at HubSpot—some of them almost fanatically so.

But Lyons’s experience at HubSpot only gets stranger after day one. He almost never sees Cranium, Halligan nor Shah. Instead, most of his time is spent with Zach, the 20-something manager of the “content team,” and an assortment of other bloggers who sit around and dream up misfires, such as the Blog Topic Generator—“Why We Love Cervical Cancer (and You Should Too!)”—and all-night “content hackathons.” (“We don’t have to call it a content hackathon,” Lyons tells Zach. “We could just say, ‘We’re pulling an all-nighter to write blog posts.’”) Eventually, he finds himself working under “Trotsky,” a potential ally who turns out to be borderline unhinged. It is Trotsky who tells Lyons that he doesn’t have enough HEART (a HubSpot acronym for humble, effective, adaptable, remarkable and transparent). It is Trotsky who suggests to Lyons that not only do his HubSpot colleagues not like him, but perhaps none of his colleagues have ever liked him. It is Trotsky to whom Lyons eventually delivers his resignation.

Lyons may not see Disrupted as a takedown, but HubSpot certainly isn’t happy about it. In the window between the book’s completion and publication, it emerged that efforts by HubSpot CMO Mike Volpe (i.e., Cranium) to obtain a copy of the manuscript were allegedly so aggressive—hacking and extortion—that the FBI launched an investigation. Volpe was fired and HubSpot Vice President of Content Joe Chernov resigned after the scandal; Halligan was sanctioned for knowing about it and failing to alert HubSpot’s board “in a timely fashion.” No matter: Last month, the company opened its second office in Dublin, which joins offices in Portsmouth, New Hampshire, Sydney, Australia, and Singapore. HubSpot plans to expand into Japan later this year.

There is some meat with the potatoes in Disrupted, as Lyons takes detours from his experience to point out how HubSpot lines up with broader trends: rapid growth, outsized valuations, risky IPOs. But Disrupted is at its best when offering a glimpse into this world where flair isn’t something you wear on your suspenders so much as something you embody as a person. “The joke that [Silicon Valley producer] Alec Berg always makes is that we don’t even have to make anything up,” Lyons says. “All we have to do is be like journalists and hear about real things.”

Correction: An earlier version of this story incorrectly stated that Joe Chernov was fired in the wake of the hacking and extortion allegations. He resigned.