Something to readChanging jobs
Disrupted
A memoir of a veteran journalist's misadventure inside a venture-funded software startup
Why it’s worth your time
Dan Lyons's Disrupted shows how a company's culture can feel very different from inside than it looks on a careers page. A longtime technology journalist who lost his Newsweek job in his fifties, he took a marketing role at HubSpot, a Boston software company flush with venture money, and wrote about what he found. Read before a startup offer, it can sharpen the questions you ask.
What to ask before joining a startup
The book · About 5 hours of reading · Buy or borrow
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- Read the memoir with your own workplace in mind.
Watch how the company's language, its talk of a mission and its word for being let go, shapes what people feel free to say. The epilogue covers what happened after he left, including, as Fortune reported, two executives he'd reported to leaving the company over alleged attempts to get a copy of his book.
- Write the questions you'd ask before joining.
Before your next interview or offer, write four questions: how the company makes money and when it expects to, who you'd report to and how much time they'd have for you, what happened to the last person in the role, and what the range of ages and backgrounds on the team looks like. Ask the ones you can, and notice which answers come back vague.
Good moments for this: before you say yes to a fast-growing companywhen a company's mission talk starts to gratewhen your new boss is much younger than you
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Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
Asking the same question of someone who isn't on the hiring panel, such as a person who left in the last year, tends to give you a truer read of what a hard month there looks like.
What might make this harder
Ask in the interview how people at different career stages are supported, and talk to someone who's been there a while. A hiring manager with a plan for you tends to matter more than the perks.
Questions people ask
What is Disrupted by Dan Lyons about?
A 2016 memoir by a technology journalist who, after losing his job at Newsweek, joined the Boston software company HubSpot as a marketing fellow. He describes a young culture he found cult-like, absent bosses, perks paid for by venture money and the push toward going public.
Did HubSpot respond to Disrupted?
Yes. Co-founders Brian Halligan and Dharmesh Shah published a response in April 2016 defending the company's growth strategy, culture and products. Fortune's Dan Primack noted that it didn't address the book's claims about ageism.
Is Disrupted worth reading if I don't work in tech?
Probably, if you're weighing a job at any fast-growing company. Its themes, culture talk and perks standing in for management, aren't unique to software.
What it says, and how it holds up
Lyons arrived at HubSpot with a vague title, a pile of stock options and twenty-five years of magazine writing behind him, and the book is what he made of the experience. His telling suggests a loud culture can also be a way of not managing people. HubSpot, as he describes it, ran on enthusiasm, jargon and Friday parties, while the managers who hired him had little idea what to do with him.
Lyons was known before this for the Fake Steve Jobs blog and later wrote for HBO's Silicon Valley, and he tells this story for laughs too. It's also one man's side of the story. HubSpot's co-founders answered that spring, defending the company's losses as a trade for growth and pointing to good employee reviews of its culture; Fortune's Dan Primack pointed out what they left unaddressed, including ageism. Josh Bernoff, a writer who discloses ties to both sides, found the chaos believable, thought the products worth more than the book implies, and read it as a list of lessons for Lyons and for the company alike.
For a large, established employer, the warnings about burning cash for growth matter less, and the ones about who manages you and how people are treated still apply. And if you lead a team that skews young, Bernoff's lessons for companies, about severance, jargon and making room for experienced hires, may be the part worth reading closely.
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Picked by Truest and described in our own words. The original belongs to its creator. Last updated October 9, 2026. We sell a career membership; where that’s relevant above, we say so.