Dan Lyons on Hubspot, Startup Culture, and That Whole FBI Thing

Illustration by Gluekit for ‘Valley Speak’

At age 55, Dan Lyons was an accomplished tech journalist and a writer at Newsweek when he was unexpectedly fired. Taking inspiration from his tech coverage, he switched careers and joined HubSpot, a Boston-based marketing software company. With most of the staff half his age, strangely elusive bosses, and a frat house-like workplace culture, HubSpot was an odd fit for Lyons. His new book Disrupted: My Misadventure in the Start-up Bubble chronicles his experience at the startup, which he left a few years ago. He now writes for HBO’s comedy about startup culture, Silicon Valley. We chatted about his time at HubSpot and that whole situation where someone might have tried to steal his manuscript.

You started working at HubSpot as a “marketing fellow.” What exactly does that mean?

I jokingly told someone once that I think it means, “You’re old, you’re not management, we don’t know what to call you, so we are just going to make up this title and give it to you.” I mean, it had a sort of quasi-academic sound to it.

How would you describe the workplace environment at HubSpot?

It’s really fun in a lot of ways. I’ve actually talked to people in the last six months who said to me, “Oh, I have a friend who’s interviewing at HubSpot,” or “I’m thinking about going to HubSpot. What do you think?” And they’re always kind of asking me in the context of “I get the sense it didn’t go well for you, so should I stay away?” Actually, no. It’s a really really fun place and if you fit in, it’s great. The culture is very upbeat, it’s very positive, very peppy and enthusiastic and that’s a big part of fitting in there. I have friends there. I have people I really like and they really like it and I totally understand why. But for me, I guess it wasn’t necessarily a great fit.

HubSpot has been recognized as a good work environment and made Glassdoor’s list of “Best Places to Work,” but you say in the book that it’s the cruelest place you’ve ever worked. How do you think workers in this industry are treated?

That’s a very good question. I think there’s a dichotomy. I have some examples in my book of people who I think were treated very badly and harshly in a way that even they were taken aback by and just couldn’t comprehend. Then there are other people for whom it really is the most fantastic experience of their life and it goes great for them. I think both of those things are real. I don’t even think they are mutually exclusive.

Since you wrote the book, there have been reports that people at HubSpot allegedly tried to get an early copy of your manuscript. Have you gotten more answers about what happened or what’s going on there?

I was interviewed by the FBI and they wouldn’t really tell me what they were investigating or what they had found. And then they did tell me that they weren’t going to pursue any criminal charges. I asked them, “Well, could you tell me what happened?” Or I asked HubSpot, “Can you guys tell me what happened?” I still have no idea why Mike Volpe was fired and why Joe Chernov quit before he was terminated and why Brian Halligan was sanctioned by the board. I still don’t know and I was worried because I have a family, I have two little kids. I didn’t know if someone was breaking into my house and hacked my computers—I didn’t know what happened.

So I filed a FOIA, a Freedom of Information Act request, trying to get the FBI to turn over documents and, after several months, I got some. They are heavily redacted, but they indicate that it wasn’t about trying to get hold of my manuscript—or it wasn’t just about that—but it was also about extortion and digging up information on other individuals who had some sort of power to stop the book from being published and were trying to extort them, or manipulate them and prevent the book from being published at all. Which is very scary and serious and not at all what I imagined.

Since you’ve written the book, have you talked to anyone from HubSpot about it? Has anyone reached out to you, or has it kind of just been silence between you guys?

Silence. I have a couple friends who I haven’t seen. I also worry because the thing that came out in the FBI documents is that it seems they were paying people or encouraging people to come see me and have lunch with me and find out what’s in the book, or get hold of the book, or something like that. So now I don’t really know when people from HubSpot write to me, like what they are up to. I haven’t really had any contact with them. I would love it, I would still love it, if someone there would just tell me what happened… If they would have asked me, like, we would love to see the book before it gets published, I would have shown it to them. It’s really a book about me and age and reinvention and failure. I don’t know why they went to such great lengths to be so sneaky and to extort people.

If you could do it all over and take the job at HubSpot, would you?

No, no. I think that’s my full answer.

Dan Lyons will be speaking at a free event at WorkBar Cambridge, 45 Prospect St., Cambridge, MA, on April 6th at 7:00 p.m.