Book Review: Disrupted: My Misadventure in the Start-up Bubble

Dan Lyons’ “Disrupted: My Misadventure in the Start-up Bubble” is laugh-out-loud funny in places, as one would expect from Dan, creator of the Fake Steve Jobs blog, comic novelist, and a writer for HBO’s Silicon Valley. But it is also an unexpectedly personal and serious book. Dan doesn’t just lob one-liners from the sidelines, but frankly chronicles his own missteps on a not-very-successful journey of personal reinvention from career journalist to marketing professional at age 52. Along the way he raises some uncomfortable questions about the technology industry.

After being “unceremoniously dumped” as Newsweek’s technology editor and a brief stint editing an economically unsustainable website, he joins HubSpot, a Boston-area marketing automation company. As Dan notes, “Online marketing is not quite as sleazy as Internet porn, but it’s not much better, either.” As if to compensate, his new employer has made “changing the world” its mantra. HubSpot turns out to be the Platonic form of the wanna-be tech company, amping every inane startup trope to 11 while neglecting the actual technology part (the company makes mediocre software with which to spam prospective customers). Most of the humor comes from simply holding a mirror up to its management (or lack thereof), “the Cult of the Orange People” culture and “adult kindergarten” workplace trappings, all of which the New York Times succinctly describes as “self-satirizing”. The excerpt in Fortune captures a lot of this.

My vote for the funniest part is the chapter about attending the Dreamforce conference and realizing that as over the top as HubSpot’s marketing antics may be, they are but a pale east coast imitation of Salesforce:

“There’s an art to this kind of horseshit, and Benioff is its Michelangelo.”

“Now, here in the Moscone Center, the P. T. Barnum of the tech industry is giving a master class in how the game is played.”

“Sure, Benioff is full of shit, but so are we, and Benioff is way better at being full of shit than we are.”

(Note to Dan: don’t rule out Salesforce as a future employer. Seriously).

Wrapped within that tortilla of humor, the book contains two meatier critiques of the technology industry, with HubSpot as poster child but hardly the only offender. One is labor practices that both exploit younger workers (who seemingly are easily distracted away from the size of their paycheck) and cast older workers in a remake of Logan’s Run, with no discernible happy medium between. As a guy who was twice the age of the average employee at HubSpot, Dan experiences the ageism firsthand (plus the CEO of HubSpot is dumb enough to advocate it in a New York Times interview). He also takes aim at tech companies that never make a profit yet whose founders and early funders do extremely well, even if no one else does. “Grow fast, lose money, go public, get rich. That’s the model.” While the book has precipitated some discussion about tech’s treatment of both the young and the olds, not so much for the second topic.

But the book has become a circus unto itself, beyond the one featured in its pages. Fulfilling every author’s wildest promotional fantasy, HubSpot executives evidently tried to obtain a copy of the manuscript before publication. This led to the CMO/co-founder being fired by the board, the CEO “reprimanded”, another executive quitting before he could be fired, all with a chaser of an investigation by the FBI. HubSpot utilized a tone-deaf PR strategy of stonewalling that will surprise no one who has read the book, only allowing that there was “some fishiness” and “really aggressive tactics”. The FBI characterized those tactics as possible extortion and hacking, although they ultimately didn’t press charges. Dan has yet to get an explanation of what they tried to do to him and wonders whether he missed some bigger malfeasance HubSpot was worried would be uncovered in the book.

Reactions to these events have added to the spectacle. HubSpot sympathizers and Boston tech fanboys rallied around the company and basically acted like the Patriots fans most of them are (i.e. the type who would loudly maintain Tom Brady’s innocence – and deity status — even if he were convicted of multiple felonies based on incontrovertible evidence and a full confession). Outside of Boston, VCs who never miss an episode of Silicon Valley were disdainfully harrumphing on Twitter that they had no plans to read the book. How dare he mock these noble entrepreneurs busy changing the world? Struck a little too close to home perhaps, but it underscores the need for an alternative playbook for those companies that aren’t, in fact, “changing the world”.

I’d retain at least a modicum of sympathy for HubSpot and the ridiculous company they have created except that even after all this they’re still out hyping their culture and belief in “radical and uncomfortable transparency”. No acknowledgement whatsoever — much less explanation – of how that vaunted culture led to executive dismissals and an FBI investigation. Or how to reconcile their stonewalling on the whole episode with that deeply held commitment to transparency.