My Millennial Meltdown
Dan Lyons, legendary Apple antagonist and startup scourge, talks about the perils of navigating Silicon Valley’s weird work culture
Hosted at Second Home, “Chew The Fat” is a series of conversations with high profile entrepreneurs, founders, VCs designed to stimulate, motivate and inspire. They recently brought writer Dan Lyons to our Spitalfields abode to talk about his misadventures in millennial world.
Currently a co-producer and writer for the hit HBO series Silicon Valley, Lyons was previously technology editor at Newsweek and the creator of the groundbreaking viral blog “The Secret Diary of Steve Jobs” (AKA “Fake Steve Jobs”). His memoir Disrupted: Ludicrous Misadventures in the Tech Start-up Bubble detailed a hideous year he spent trying to re-invent himself at a startup called HubSpot. This hilarious interview about his New York Times bestseller was conducted by Oliver Smith, a Senior Reporter at The Memo.
Chew The Fat: First of all, how did Fake Steve Jobs start?
Dan Lyons: Very much by accident. I was a reporter at Forbes magazine, just sort of a right-wing business magazine in the United States. No one who works there is right wing, but the owners are. It was the old fashioned right wing, the pre-Trump, the ones who now seem liberal — the ones who don’t pay taxes. But it was a very boring job, we only came out every other week. There wasn’t a lot to do.
It was great as a journalist, but I was bored and I wanted to learn about blogging, so I started a bunch — the three big blog platforms in that day were Blogger, WordPress and Typepad. I started blogs on all these different platforms just to learn HTML, because I was a print guy and I was old enough — I wasn’t 17 — to realise, ‘Oh shit, when this print thing falls apart, which it’s going to do, I’m going to be out of work’.
However, there was a book by Robert Scoble called Naked Conversations, and it was about blogging and this idea that everyone should have a blog — there’ll be no such thing as PR, there’ll be no such thing as media, there’ll be no need for any of it because everyone will just have a blog, you know? There were a couple of these CEOs who did have blogs where they were supposedly being transparent — but it was all bullshit — and I was a big fan of Private Eye here, and I loved the secret diary of every character, John Major or whatever, and I thought, ‘What if you did a piss-take on somebody and it was their blog, that they were horrible, secretly really a horrible, horrible person?’.
I tried different people, and somehow I seized on Jobs. I didn’t know much about him, but nobody did because he was very reclusive. So I thought, ‘That’s great, you can make him anything, so no one will know’. I just did it for a few weeks, and I thought, ‘Okay, then I’m going to shut it down’, but there were people reading it, and that felt, ‘Oh my god, this is the first thing I’ve ever done as a journalist that anyone ever paid any attention to, it’s like the stupidest thing ever, right? So I’ll keep doing it because it kind of had an audience’.
“Fake Steve Jobs was the first time I realised how powerful the internet was as a publishing medium — it was very immediate, the audience was right there, the readers were right there, the readers became part of the show, they were, like, writing the show.”
The audience was people like you who loved Apple so much they would read anything [laughs]. If you did the same thing about Sergey Brin, there’s not a big passionate Sergey Brin audience out there, right? I wasn’t aware of it, [but] there was this Steve Jobs cult out there, and they were so hungry for anything [that] they would take a fake. It was really fun because you could wind them up and you could make fun of them and they didn’t know that the joke was on them. People started sending in ideas and links and Photoshops, it started to write itself. It was the first time I realised how powerful the internet was as a publishing medium — it was very immediate, the audience was right there, the readers were right there, the readers became part of the show, they were, like, writing the show.
At one point I wrote a book based on it, and then I developed that as a TV show, a cable show, that never got made, but I realised — even in the process of developing this cable show — even if it did get made, it would suck compared to the blog. The blog was just the thing. That was the experience there. It looked really bad, it was really, really ugly and poorly designed. One time I did a redesign and people said, ‘No, we liked it ugly, it looked better when it was really crappy-looking’ [laughs]. But it was very seat-of-the-pants and probably the most fun I’ve ever had. It was very addictive.
I kept having these points where I thought it would get big enough that I [was] going to get caught, because I was doing it anonymous — nobody knew who was writing it.
How many people knew who you really were?
Dan Lyons: For a long time, nobody outside of my family really knew. At one point, the publisher of Forbes wrote a blog post, saying, ‘Who is Fake Steve Jobs?’ and set up a reward if anybody could figure out the identity of Fake Steve Jobs. It was literally a guy I know. I was at a conference with him and he was like, ‘We’ve got to find this Fake Steve Jobs’, and I was like, ‘Yeah we do’ [laughs].
At one point he wanted Fake Steve Jobs to come and write for Forbes. I had been asking those fuckers for a raise and they didn’t give me one, and then I was like, ‘Well, how much would you pay me for this Fake Steve Jobs?’ [laughs]. I kind of wound them up a bit, and then I saved the emails because I thought, ‘When I do get caught and they go to fire me, I’m going to say, “Wait a minute…”’. He was actually one of the first people I told, and then Forbes pretended they were happy about it. They actually ran it for a year on their website, then, with me publicly [with] my name on it. We tried to put ads on it, but nobody ever wanted to put ads on that content because it was incredibly rude.
That was the other thing, I’d boxed myself into a corner in two ways. When you’re doing an anonymous blog, it’s very hard to sell ads because nobody wants to just send money to someone anonymous. The other one is that it was so rude that nobody would advertise against it, nobody would put their brand next to it. Most of it was okay, but every once in a while there would just be one really nasty one…
What about Apple and Steve Jobs?
Dan Lyons: They never said anything, and I didn’t cover them at Forbes, I covered like IBM and EMT — boring big companies. I went to Newsweek later and then I did have to cover Apple, and it was one of the most awkward exchanges ever. I had to email them and say, ‘I think you know who I am’, because it was all the PR people at Apple I’d been making fun of for years, comparing them to prison guards and making up terrible stories of them hypnotising Walt Mossberg from the Wall Street Journal. I also made a lot of enemies among my fellow tech journalists.
I finally went to dinner with one of the PR guys at Apple who said, ‘Look, officially, we love you, we think it was great, ha ha ha. Next level down, officially, fuck you, we can’t believe Newsweek hired you’, and they tried to keep Newsweek from hiring me. ‘But less officially down below all that, we all read the blog and we all think it’s hilariously funny, but we can’t say that, right?’. He said, ‘My mother-in-law reads it and every time you make fun of me she sends me a link saying, “You’re in Fake Steve today, this is great!”’. I don’t think Steve Jobs liked it. He claimed he did at one point. I don’t know, it was a weird experience.
“I don’t think Steve Jobs liked it. He claimed he did at one point. I don’t know, it was a weird experience. I always wanted to meet him, but I never did. I was too chicken.”
So the Apple guys would never invite me to events at Newsweek, but I would call and be like, ‘Hey, I saw this thing about the iPad’, and they’d be like, ‘Oh god, did we not invite you?’, and then they would send me an invitation [laughs]. Then I’d go, and none of them would talk to me, they would stick me by myself up in the back.
At the iPad introduction there was this Apple engineer who was a fan of the blog and who I had met, and he was working the event. He came up to me and Jobs was, like, talking to Al Gore or something, and he was like, ‘Look, Jobs is in the front row, let’s go, right now, you go down right now, boom! I’ll take your picture and run away’ [laughs], I was like, ‘No, I can’t do it’, I totally chickened out. He was like, ‘Just do it, he has no choice but to laugh, right?’. But we didn’t do it. I was terrified — I always wanted to meet him, but I never did. I was too chicken. When he became sick, I couldn’t do it anymore and so I just shut down.
But you were a tech journalist, and you’ve been a tech journalist in some of the years since. Five years on from Fake Steve Jobs, you must have some feelings about the company and some of the decisions they’ve made in the last five years?
Dan Lyons: When Steve Jobs died, I came back for one day and wrote this long, very sappy poem because Steve used to write bad poetry. I would imagine Steve Jobs, you know, he signed his name in all lower-case letters — he was so pretentious — and I always thought, like, he probably sits at home and writes bad poetry at home that he doesn’t show anyone. Anyway, so I would write these really awful poems — you know the poems they have in Private Eye when someone dies, ‘So Farewell Then’? So I copied that, and anytime someone would die, he would write, ‘RIP, rest in peace so and so’, and he would write this really stupid tribute poem to someone that was actually making fun of them. It was a complete knock-off of Private Eye, it was not original at all.
So when he died, I wrote ‘Rest in peace, Steve Jobs’, and then I shut it down. Then I thought, ‘What if you had Dead Steve Jobs?’. He’s blogging from the afterlife — he’s in heaven… But you know he was very OCD, right? He had everything white… There was a legend that one time he had them repaint all the buildings at Apple because the white was just a tiny shade off the trucks or something like that. He was very, very anal. I thought if he died and went to a place where it was like heaven but there were tiny, tiny mistakes and he doesn’t know, ‘Am I in heaven and they fucked it up? Or am I in hell and this is hell for me?’, I thought that would be his… And he could be meeting famous people in heaven and telling them what jerks they are and who he likes and who he doesn’t. Then he’d be watching Apple and commenting on how Tim Cooke is screwing it all up and doing everything wrong. He’d be up there going, ‘No, no, no, Tim, not the watch, not the watch, not the watch!’ [laughs], ‘That is not a good-looking watch, Tim’.
There’s a guy in Poland who made the Fake Steve logo, which was Steve Jobs sitting in the lotus position with a laptop and a bong. And I had him remake it with a laptop and a harp, and he’s sitting on a cloud, he has a halo over his head like an angel [laughs]. Then I just never could come up with… I don’t know, I just never could do it.
“Steve Jobs would be up in heaven going, ‘No, no, no, Tim, not the watch, not the watch, not the watch!’ ‘That is not a good-looking watch, Tim’.”
I also think, with this tax thing in Ireland now, I think it’s kind of funny. It’s classic Apple. When this EU thing happened, I wasn’t following it, all I knew was they went to Ireland to cheat the United States out of taxes, right? So they were using Ireland to screw us, then it turns out they screwed the Irish out of the little bit of money they were supposed to give them. It’s like, ‘You guys are pure evil’, they’re so awful, I think Steve would’ve loved that. Steve would be going on about why they shouldn’t have to pay tax to anybody, why they’re bigger than any government, more important than any government…
Back in the day when I was writing, it was when the stuff came out about Foxconn, when the workers were throwing themselves off the building in China, so the company responded by just putting up nets to catch them [laughs]. It’s like… Not really getting at the fundamental problem, here, ‘Maybe we’ll look at why they’re jumping off the building… No, let’s just put up nets to catch them’, like, ‘Solved, they can’t die, you’ll just land on a net, don’t bother!’ — such an Apple way of solving the problem [laughs].
Then Apple tried out these statistics at the time, saying, ‘Okay, they’ve had 14 suicides at Foxconn over the last six months, however, if you look at the whole population of that compound, right, that’s actually a lower suicide rate than China overall. So actually, we’re preventing suicides’. They said that with a straight face, I was like, ‘Are you out of your minds? If everybody started jumping off the roofs of Walmarts and killing themselves, we wouldn’t average it out against the world’, you know?
Steve went to China and visited a factory, and then he got upset because he felt that it was unfair that he had to look at that kid suffering in the factory — he had to eat all that… So anyway, I think you can have a lot of fun. Some people said we’d do Fake Tim Cook, but can you imagine a more boring thing than Fake Tim Cook? Real Tim Cook is already so boring — gets up at four, rides his little exercise bike in his little house in San Francisco, finds a way to screw some supplier out of two cents per part… That’s Tim’s idea of an exciting day.
“Can you imagine a more boring thing than Fake Tim Cook? Real Tim Cook is already so boring — gets up at four, rides his little exercise bike in his little house in San Francisco, finds a way to screw some supplier out of two cents per part… That’s Tim’s idea of an exciting day.”
He’s a terrible public speaker. I never thought Jobs was a very good public speaker either, and everybody was like, ‘Oh my god, he’s such a great presenter’, I thought he was always so wooden, but Tim is so bad. He’s from Alabama so he’s got that Southern voice, and he’s always trying to say things like, [in a Southern accent] ‘We are so excited’, but he’s not excited at all, right? He’s like, ‘We are just so thrilled’, and it’s like, ‘No you’re not, you’re not thrilled at all’, and it’s like, the same Mac you’ve been selling for five years — the Mac hasn’t changed in five years. Really. It’s the same Mac, the same product. The phone hasn’t changed.
It’s like, ‘What have you done, Tim Cook?’, ‘Well, we’re making a lot of money’, you know? I think that would be Steve’s rant, that they should do something cool. I don’t think Tim is that kind of guy.
After Fake Steve Jobs shut down, you spent a few years as a tech journalist, and then you decided to make the jump into tech and that went really well?
Dan Lyons: I was always kind of jealous — you watch these start-ups, and even the bigger companies, and you see people getting rich, you see people making crazy amounts of money. It’s irrational amounts of money, but they also always seem to be having so much fun, like, so much more fun than we were having.
No, really, you get very jealous, especially the last 10 years as a journalist, for me, I was at Forbes, then we started dwindling, then I went to Newsweek and they were already dying, but I just really wanted to work at Newsweek because it was a cool, special place. But you’re constantly working in a place that’s slowly going out of business, you’re always waiting for the next round of lay-offs. You know what the macro trend is, if you’re a business journalist you can see where this ends, right? There’s no resources to do anything, so we could see what we should do online, but we never had the money to do it. So it’s just kind of sad, and I always wanted to be at one of these places [that was] just booming.
The famous line that Eric Schmidt said to Sheryl Sandberg when they offered her a job at Google was: ‘If someone offers you a seat on a rocket ship or a spaceship, don’t ask which seat, just get on board, just go for the ride.” That must be great. So I always had this jealously, I guess, or fantasy, to work inside a tech company. At various times I thought about crossing over, and then my hand got forced because I got laid off at Newsweek finally, which was not really a surprise. I looked around, there was nothing else in media, the whole business was going out of business, so I thought, ‘Now’s the time’.
“I always had this fantasy to work inside a tech company. My hand got forced and I got laid off at Newsweek, which was not a surprise. I looked around, there was nothing else in media, the whole business was going out of business, so I thought, ‘Now’s the time’.”
So I started talking to tech companies, and ended up making the mistake of going to this start-up in Cambridge — I live in Boston so it’s near me — that was pre-IPO, supposedly kind of a sleeper, an unknown company that nobody had heard of, and I thought, ‘Well, that might be cool’. It was about 500 people so it wasn’t like a big giant like Google or Apple — not that Apple was looking to hire me [laughs].
The more typical path for a 50-year-old journalist who gets laid off would be to become a speech writer at IBM, or this sort of corporate brand journalist. I had a bunch of friends who were doing that — one went to GE, one went to IBM — and you’re kind of like a house pet, you’re kind of kept in-house and you write for the blog, you know? They have cushy jobs. So that would’ve been maybe a better path, but instead I went to a start-up called HubSpot, which was growing really fast, and young, and I thought [it] would be maybe more of an adventure.
So this is what the book is about, and the title is Disrupted because it refers to both this idea of disruption — all these companies talk about, ‘We’re disrupting this industry’ — and the other half of it is my life being disrupted. I have young kids, I had kids later in life. So it was interesting.
I think the chief mistake was that the two founders hired me, but then they passed me off to the CMO and the CMO didn’t really have anything for me to do, didn’t want me around, and he passed me to another guy who passed me to another guy.
So I ended up stuck in this room and realised pretty quickly, ‘This was — okay, I’ve made a mistake’, but I thought, ‘Okay, I’ll stick it out for a year and just watch and learn, or maybe I’ll learn to navigate politically and I’ll….’, it’s always at these start-ups you can talk yourself into a new role, you can create a job for yourself… Every time I would try and do that, though, I would make things worse [laughs]. So it turns out I was terrible at all that corporate stuff — I didn’t know how to do any of it at all. So I sort of made a lot of mistakes.
“HubSpot was a place where the average age was 26. There was one guy my age, a little older than me actually, and as soon as I joined he found me and was like, ‘Seriously, we have to go to lunch’. We would sit there and talk about all the ways, big and small, that we were both being humiliated by the people we worked with.’”
So it was a place where the average age was 26 and there was nobody my age — there was one guy my age, a little older than me actually, and as soon as I joined he found me, he’d heard about me and he was like, ‘Seriously, we have to go to lunch’, I’m like, ‘Okay…’ [laughs].
So we started hanging out, and then we would go to these lunches together. There was a mall across the street and we’d eat in the food court at this mall, it was horrible, and we’d just kvetch about, like, ‘These kids…’. It’s one thing to be an old guy in a company but you’re sort of revered or you’re the owner or the founder, but if you realise you’re an old guy and they look at you like, ‘No, you’re a shithead, you lost your job and we stuck you in this box, but you suck’, right?
So this guy had owned his own company, made a lot of money and lost it all in the dotcom boom, and then had to get a job again. So it’s very humbling, is one way of putting it — another way of putting it is humiliating, right? So we would sit there and talk about all the ways, big and small, that we were both being humiliated by the people we worked with.
“It’s one thing to be an old guy in a company if you’re the owner or the founder, but if you’re an old guy and they look at you like, ‘No, you’re a shithead, you lost your job and we stuck you in this box, but you suck’, right?”
Then we were sitting in this food court, and of course all the other people from the company were eating in the same food court, and they would see us sitting or walking together at lunch and I realised that what we look like to them is when I go to Dunkin’ Donuts. I go to Dunkin’ Donuts and there’s always, like, five 90-year-old guys in, like, BMW windbreakers and World War II hats, like, ‘Ah, fuckin’ Obama, Jesus Christ’ — all pissed-off old guys. And I thought, ‘Oh shit, we’ve become those guys’.
So I told him, ‘We’ve got to stop having lunch, man, we’ve got to stop doing this, we’ve got to split up or we’ve got to take separate routes and meet up someplace where they can’t see us’. We would meet literally out in the suburbs on Fridays when we were working from home, because I didn’t want to get pigeon-holed as ‘the two old guys’. I wanted to pretend I wasn’t really old, ‘I’m hip, maybe I should colour my hair’, then I thought, ‘No, that’s crazy’. But yeah, it was a very weird thing.
This was a place where anything they heard about that happened in California at a start-up, [they were like], ‘We’ve got to have that’. So we had foosball tables, we had ping-pong tables, we had video games — they had a little section where they put a bunch of musical instruments for people that just wanted to ‘jam at some point, man’. Nobody ever jammed, they just left that shit there, like, who’s going to do that? ‘Let’s go jam’. They had all these chalkboards where people could write inspirational messages to each other… It was just, to me, very goofy — I am very cynical and sceptical — a lot of free beer, parties, sort of like a big frat house, mixed with a Montessori kindergarten, mixed with a Scientology compound [laughs]. The frat house part is obviously, they literally were like bros. My first day, they gave me a tour and they were like, ‘Oh yeah, at noon there’s a push-up club here in the lobby, guys get together’, and I was like, ‘Hell no’. They were like, ‘If you get to 100 you get a badge’.
“My first day, they gave me a tour and they were like, ‘Oh yeah, at noon there’s a push-up club here in the lobby, guys get together’, and I was like, ‘Hell no’. They were like, ‘If you get to 100 you get a badge’.”
It was all bright, basic colours — the infection is spreading globally now. I was in Poland in May and even they’re like, [in a Polish accent] ‘Ja, we’re hip, we have the beanbag chairs’, ‘We’re cool, man, we have, like, conference rooms with beanbag chairs’, and I’m like, ‘Dude, I’m, like, 50, I don’t want to sit in a beanbag chair and have a meeting’.
At first I was like, ‘Yeah, these are the places I’ve been visiting as a reporter, I totally want to work in one of these crazy places. This looks insane but really fun’. I remember going to Huffington Post, I wrote an article about Huff Post when I was still at Newsweek, and I thought, ‘They’re having so much more fun than we’re having’, you go back to Newsweek and everyone’s like [mimes choking] in their office — people just hanging themselves [laughs]. At least at Huffington Post they’re all alive and they have great, cool infrastructure and stuff — it felt more like a start-up.
So I went in thinking, ‘This will be cool, yeah I’m older, but it’ll be okay’, but in the end it just didn’t end well.
When did you realise that it wasn’t right for you?
Dan Lyons: There was one big point where — we went through training, and they had this whole language — a very culty language — it was just like the first two weeks were sort of a tip-off. They were talking about ‘delightion’ — we’re in the business of delighting people but we call it ‘delightion’, it’s a made-up word. One plus one equals three — our software’s so magical it makes one plus one equal three. And then they would talk about ideas, ‘I like that idea, Oli, but I don’t think it’s one plus one equals three enough’, and I’d be like, ‘What?’ [laughs].
So I started feeling that I [wasn’t] really fitting in with these people. And when you got fired they called it graduation, and you get this very cheery email saying, ‘Hey team’, everything was team, we were all a team. People would wear orange clothes for work — orange was the colour — so people would wear the company colours to work, they’d go out and buy their own orange clothes. They were so proud to work there, they loved it the way you would love a sports team. So we’d get these cheery emails, ‘Hey team, just want to let you know that Derek has graduated and we can’t wait to see what he’s going to do with his superpowers on his next big rock star adventure’. They’d tell us we had superpowers — ‘What’s your superpower? My superpower’s writing, what’s yours?’, ‘I don’t have any superpowers dude, I’m a 52-year-old man, I have high cholesterol’, ‘What makes you special?’, ‘I’ve had a colonoscopy, have you? No you haven’t, I’m the only one in this room, it’s awesome’ [laughs]. The kids would look at me like, ‘What the fuck?’. They were all really earnest, they’d just got out of college, they had their first job.
“The team at this start up would tell us we had superpowers — ‘What’s your superpower? ‘I don’t have any superpowers dude, I’m a 52-year-old man, I have high cholesterol’, ‘What makes you special?’, ‘I’ve had a colonoscopy, have you? No you haven’t, I’m the only one in this room, it’s awesome’. The kids would look at me like, ‘What the fuck?’.”
They would tell them, ‘Do you know, it’s harder to get a job here than to get accepted at Harvard?’, and trust me, nobody at this place went to Harvard. But it’s this weird statistic where the acceptance rate at Harvard is, like, 6%, and so if you took less than 6% of everybody who applied for your job… I don’t know, anyway… McDonalds and Walmart both make that same claim in some stores. Seriously, in some locations it is statistically harder to get a job at McDonalds than it is to get into Harvard.
I think the turning point for me was — well the graduation’s freaking me out because people were graduating all the time, like, seriously, the turnover’s really, really high, and they would just vanish. You’d get the email and then you’d look over and be like, ‘Oh, Oli was just there, he’s not there’ [laughs], you realise the whole desk is gone, he’s cleaned out. My first week I had lunch with this young woman in my department who came to me and said, ‘I know you’re a journalist, I had this blog before I came here’ — she had just graduated from college — ‘I really want to write a book about marketing to millennials, she had a blog about millennials, could we go to lunch and [you can] tell me a little bit about how to write a book?’. So we had this great lunch and I was really encouraging her to just sit down and, ‘Just don’t wait for somebody to give you permission to write a book, just start writing the book, just do it and I’ll help you if you want me to look at chapters. First, get a chapter outlined, bla bla bla’, I was just trying to encourage her. So we went back to work and that night I get an email from the boss of our department saying, ‘Hey, just wanted everybody to know that Lindsey graduated’, I’m like… I wrote to her, like, ‘Why didn’t you tell me this when we were having lunch?’, she was like, ‘I didn’t know, dude’. She just got home and got told, ‘Don’t come in tomorrow, you’re done, bye’ — that was it, no reason, no explanation, just, ‘We don’t like you, you’re not HubSpotty enough’. That was the other thing, you had to be HubSpotty, and there was a HubSpotty way of doing things and I could never figure out what it meant to be HubSpotty.
Anyway, so the big turning point for me was the teddy bear. So basically we were in the business of spamming people — spam email campaigns — and so they considered themselves like ultra-spammers, we were the best spammers in the world. But we didn’t call ourselves spammers, it was a very Orwellian thing where our spam wasn’t spam because we made it and we don’t do spam… So they called it loveable marketing content, but it was spam.
They would do things like — if one of the founders wrote an article someplace, we would all have to hit Twitter all at once, we had like 500 social feeds with the same link to the same article, and they wouldn’t even rewrite it. They would just send the same tweet. It was so stupid; it was the worst social media thinking I’ve ever seen in my life. I mean, you and I and all of us send the exact same worded tweet with the same image…
So we got a thing saying, ‘Dharmesh, the co-founder, wrote an article today — he’s a LinkedIn influencer, he’s a thought-leader — he actually didn’t work at the company, he had invested in the company and founded it, but he didn’t have any day-to-day role, he was never there. But he wanted to tell other people how to run companies even though he never ran a company. So he had this idea, and they told us, ‘Just send this lazy tweet out now’, and I’m like, ‘I’m going to look at it first, I want to see what it is’.
So I read it and it was basically this article that said — there’s a picture of this in the book, I think — ‘I really believe we should always be solving for the customer — SFTC — so I used to put an empty chair at our management meetings and that represented the customer. We’d all have to pay attention to the chair to remind us, but the empty chair wasn’t enough so I’ve started bringing in a teddy bear and I call her Molly. Molly represents the customer. To me, Molly is a reminder to us every day’.
“When I was at Newsweek my boss won the Pulitzer Prize for a biography of Andrew Jackson, a really powerful, intellectual guy. Now I’m working for this fucking idiot who brings a teddy bear to work and writes about it, and thinks he’s great and an intellectual’. I was really depressed.”
We had customer personas — probably a lot of your companies do — and one of our personas was called Olly, the owner, who owns a business, and the other was Mary marketer. So he combined Mary and Olly and made Molly the teddy bear. So I’m like, ‘This is insane. This is bona fide crazy. This is absolutely bullshit nuts’. I’m sitting there thinking, ‘How has my life come to this? I’m 53-years-old, I came here from Newsweek. When I was at Newsweek my boss won the Pulitzer Prize for a biography of Andrew Jackson, a really powerful, intellectual guy. Now I’m working for this fucking idiot who brings a teddy bear to work and writes about it, and thinks he’s great and thinks he’s an intellectual’. I was really depressed.
My manager was this very young, nice guy, and he used to work at Google. Our monitors were facing each other so I was like, ‘Hey, dude, did you read this article?’, ‘Yeah’, ‘The teddy bear thing?’, ‘Yeah’, ‘What do you think of that?’, ‘It sounds pretty good’, I’m like, ‘No, no, no, come on, what do you think about it?’, and he wouldn’t break. I’m like, ‘Come on, this is insanity, right?’, and he’s like, ‘No’.
So I said, ‘So you’re telling me when you were at Google, if Larry Page wrote a thing saying, “I’m bringing a teddy bear to meetings all the time now and I want everybody else to do this too”, you guys would’ve all just said, “Oh, Larry Page, great”, you wouldn’t think he was insane?’, he’s like, ‘Well, start-ups are different, start-ups are eccentric’. That was what scared me more than the guy bringing a teddy bear, was the fact that no one — not one person — would laugh about it. You couldn’t find one person even in a bathroom to [laughs raucously]. I realised [that] they really did believe that this was a good thing.
I called this friend of mine who was like me, he was a journalist at Forbes and he crossed over into marketing, and he’s kind of one of the people I had talked to when I was making this transition. But he’d gone to this big, very serious company and he rose up and became head of digital marketing there. I called him, I told him about the teddy bear and I was like, ‘You got to tell me, man, I know I’m supposed to bite my tongue, but is this what it’s like?’, and he was like, ‘Oh, no, dude, this is really crazy even for corporate. This is like Jonestown, get the fuck out of there, this is bad. If the guy has a teddy bear, you need to run. Run now!’. So I started making preparations to run, and I just never said anything to anybody about the teddy bear.
At Newsweek, if someone had brought a teddy bear, we would’ve all brought in teddy bears and had them in bondage gear, have Smurfs sodomising teddy bears, we’d steal his teddy bear, we’d hang his teddy bear, set his teddy bear on fire, we would’ve been awful, we would’ve tormented that person… And I’m not saying that’s a good thing either… It was just very, very strange.
“At Newsweek, if someone had brought a teddy bear, we would’ve all brought in teddy bears and had them in bondage gear, have Smurfs sodomising teddy bears, set his teddy bear on fire, we would’ve been awful, we would’ve tormented that person… And I’m not saying that’s a good thing either… It was just very, very strange.”
It was just a world that I didn’t belong in, so I did leave, and then after I left I thought it would be a funny book — not just about being the old guy trying to fit in there, but also some larger thoughts about start-ups. There were some ways in which I came to understand the tech industry from the inside out that I’d never realised from the inside.
What was their reaction to the book?
Dan Lyons: That was the great twist. As I was finishing the first draft — a year ago July — I started looking at it like, ‘This is kind of mean, I’m kind of making fun of these people. I’m making fun of the CMO for being too false’, and I was almost starting to think, ‘Maybe I should try to be more understanding’. As I was doing this there was this sudden announcement from the company, they said, ‘We’ve promoted this guy to CMO’.
Someone sent me a link, it was right after the market closed — they went public while I was there and pulled off a very successful IPO, and stock just continued going up and up and up. They fired the CMO for attempts to get hold of a manuscript and the whole matter was turned over to law enforcement. I was like, ‘Holy crap, is that me? Is that my book?’, and it turns out it was.
In the next couple of days they tried to dodge the press, they did everything wrong from a PR perspective — they died by a thousand cuts instead of just owning it. So they still won’t tell me what they did, but there was some kind of hacking thing where they decided they’d try and get hold of the manuscript to read it.
Later I got hold of FBI documents — because the FBI interviewed me and them, there was this whole FBI investigation, seriously, really bad — and it turns out that they were also planning to extort either me or the publisher or both. They were going to try and dig up dirt on us by hacking or hiring people, and then try to extort us into not publishing the book [laughs]. It was like, ‘The book’s really not that bad for you guys’, but suddenly it was, like, the worst crime ever, right? So then I was like, ‘Now I don’t feel so bad, now I can just go ahead and make fun of them’. They published an article after the book came out, essentially saying that everything in the book was true, but they still feel bad that I wrote it or something [laughs]. They weren’t happy about it, but it’s not hurt their stock or anything. At the end of the day, the book really isn’t about them.
That’s the other thing, they were so self-centred that they really thought, ‘Someone’s going to do an exposé on us’, I was like, ‘Dude, I hate to tell you, no one would read an exposé on you, no one’s heard of you guys. It’s not really about you, it’s about the weirdness of being someone from the last century stepping into an extreme example of start-up culture and finding it very weird’. It could’ve been another company, it just happened to be them.
“It’s about the weirdness of being someone from the last century stepping into an extreme example of start-up culture and finding it very weird’. It could’ve been another company, it just happened to be them.”
So you became involved in Silicon Valley [TV series] during this process?
Dan Lyons: Yeah, so while I was still working for HubSpot — I started in April, I realised by about the end of the calendar year, like, I’d tried a few ways to get a different job, it didn’t work out, so I thought, ‘Okay, I’ll wait until after the Christmas holidays, until about April, and I’ll just slide out’.
As I was doing that, literally out of the blue, I got this call from an agent — several years before this, back when I was doing Fake Steve, I had developed a TV show [but] it never got made and I thought that was the end of it. But the guys who made Silicon Valley were aware of that show, and they just asked me — if they got renewed for season two — would I come out and work with them on season two.
“When I got the call from Silicon Valley, I was literally at a digital marketing convention in Salt Lake City as a reporter for HubSpot — looking over this railing thinking, ‘If I jump off this will I die, or will I just be a vegetable? Because I don’t want to be a vegetable, but if I know I’ll die…’”
When I got this call I was literally at a digital marketing convention in Salt Lake City as a reporter for HubSpot — looking over this railing thinking, ‘If I jump off this will I die, or will I just be a vegetable? Because I don’t want to be a vegetable, but if I know I’ll die…’ — I’m watching these poor, sad marketing drones sliding through the thing getting their slop food, and the guy in LA is like, ‘Do you think you want to do it?’, and I was like, ‘Oh, dude, definitely yes. If you could see where I am right now you’d totally know. Yes, I will definitely be there’.
So then I thought, ‘Okay, that’s my out, I’ll just leave HubSpot and I’ll do this for 14 weeks, and I’ll find some other job after that. Then they said, ‘No, no, no, we want to make it a leave of absence. We want you to come back afterwards’, and I was like, ‘Really? Because you really don’t seem to like me very much…’. I still have never figured out why they did that, except maybe they wanted to get some publicity out of it, I don’t know.
I did go back, but the last two months were really bad. Then I had this other experience that I’d never had before. I’d heard of this, I had friends who work in corporate jobs, where you’re in a company and they want to fire you but for some reason they can’t fire you, so they decide that they’ll just make you really miserable so you’ll quit — they just drive you out. I was always fascinated by that phenomenon, like, ‘What must that be like? What do they do?’, right? So when I got back, it became clear to me, ‘Oh, my boss is doing that to me, but this is great, this is hilarious, I’m just going to see how long I can keep this going. What will he come up with every day? What new thing will he come up with, mind fucks, to get me?’, and he was really good at it. This guy had been in corporate life his whole life — he was a former PR guy, then marketing, he was really pure evil — and he and I had been very good friends. It was almost as if there was part of me that was floating above my body in these conversations with him, admiring him, like, ‘Oh my god you really are good at this, you really are good at being mean’.
So I watched him do this to me and it was hilarious on one level, but even trying to distance yourself from it, it was still very, very hard to… After a while it started to get to me, I started really — I couldn’t… I would be in fear going to work every day like, ‘Oh my god, what’s going to happen today?’. In retrospect, writing about it, it was really funny because he was really very creative about it.
“I would be in fear going to work every day like, ‘Oh my god, what’s going to happen today?’. In retrospect, writing about it, it was really funny.”
I have a friend who worked in biotech, and when this was first going on I asked him, ‘I think this is what’s happening, remember when you told me about how people do this?’, he said, ‘Oh yeah, that’s totally it’, and I said, ‘How do you know?’, he’s like, ‘Oh I’m doing it right now to a woman at work. My boss told me there’s this person in my department we’ve got to get rid of, we can’t fire her because she’s a woman, she’s protected class, so I’m just making her life a living hell until she goes’. I’m like, ‘That’s what you do for a living?’, he’s like, ‘Well, you know, I have to…’. So he got rid of her, then, six months later, he got a new boss who did it to him. I was like, ‘Oh my god, the whole corporate world is just people doing this to each other all the time’. That was one thing I’d never experienced before about corporate life, it was really hilarious. That’s what people live with all the time.
Did you “graduate”?
Dan Lyons: [Laughs] I did. That boss who got rid of me finally, knew that — I had confided in him when we were friends, when he first joined, I thought this whole graduation thing was stupid, and he did too. He actually originally came in thinking how crazy the place, but he eventually drank the Kool-Aid. But he knew that that was — so they didn’t use that word. I was the only person I ever knew who left. I had a friend who got pushed out and she said, ‘Fine, I’ll go, but just please don’t call it graduation’, but they insisted on calling it graduation, I don’t know why. But in my case I gave like six weeks’ notice saying, like, ‘I’m putting together this podcast for you guys, I’ll hand it off, do a nice transition and at the end of the year I’m going to start this new job’. I came in the next day and they say, ‘No, today’s your last day, bye. Pay ends, healthcare ends, everything’s over today, bye. Give us your laptop, get the fuck out of here’. Meanwhile, I didn’t know, I came in and saw an email that had been sent around to the whole thing saying, ‘Just want to let everybody know, today’s Dan’s last day’, I’m like, wait a minute, fuck, I didn’t know this [laughs]. But they didn’t call it graduation, but yes I did graduate. I think they were very glad to be rid of me.
“I came in the next day and they say, ‘No, today’s your last day, bye. Pay ends, healthcare ends, everything’s over today, bye. Give us your laptop, get the fuck out of here’.”
Towards the end I was also amusing myself by coming up with the worst possible marketing ideas I could think of in meetings, which is really fun. I’d just spent the summer writing for Silicon Valley and writing the most insane shit you could possibly — all day long you sit in a room with 14 or 10 people who are really funny and you just think up the stupidest shit you can think up all day, right? It’s amazingly fun, sort of [laughs].
So I came back and I just thought, ‘I’m just going to keep doing that every day but at a real job and see what they do’. It did not go well. I had an idea to shoot a woman out of a cannon [laughs] and they looked at me like, ‘Really?’, and I was like, ‘No, no, that would really be great, think of the attention we’d get, as long as she doesn’t get hurt… She flies through the window; she lands in the company wearing an orange tracksuit…’ [laughs].
Writing [Silicon Valley] while you’re working in that sort of company, that must’ve felt a bit bizarre?
Dan Lyons: It was so weird, but it was also really good. It was very intimidating because all of these people had worked on a lot of comedy shows and I’ve done a funny blog… So these are all TV writers who have done this for years and years and years, they’re very, very fast. So mostly I was kind of listening and learning.
So I had spent a year in a place where I had really felt there was something wrong with me because everybody else was really earnest, and I just thought I was a really bad person, there must be really something wrong with me. You start to think you’re the crazy one. Then finally I was in a room with other people who were even worse than I was, and I was like, ‘Oh okay, no, no, I was just in the wrong place, if I were in a place like this I would be okay’. So it was great just to be among people like that.
So I worked on Season Two and then I went back last summer and worked on season three, but that was it. It was very fun. I don’t live in LA so it’s hard to do that for a living anyway, but it can be in some ways a tough way to make a living.
[In the tech community] do you think we’re in a bubble at the moment?
Dan Lyons: I think we are, but I think it’s different than the first one. I covered the first one, and I think valuations in some ways are way above historical norms, in other ways not, but I think — when you look at the number of unicorns that existed when the term unicorn was coined in 2013 — I think there were 39 of them — by a year later there were 80, and a year later there were 230. I don’t think there were suddenly hundreds of companies worth billions and billions of dollars that didn’t exist, so I don’t know. I think that’s a function more of there being a lot of money chasing a few deals, which is sort of the definition of a bubble, right? Things get inflated because all the money flows into this one thing.
“In Silicon Valley, the bad stuff all dies, the good stuff stays, and then everything dies down and you regroup and you lick your wounds and people get laid off and they moved to different companies, and then they all start up again. So it’s sort of like this very quick cycle of death and rebirth that happens out there. It works for them, I guess.”
Uber having a very, very high valuation is very different than Pets.com having a very high valuation. In the dotcom bubble you had companies that were just crazy and pointless and going public because they had dotcom in their name. It was a public market mania where now, oddly enough, the public markets are not really completely participating in this. It’s more in the private sector, and you have these late-stage rounds that are very, very highly valued. So it’s a different phenomenon, but I think there’s certainly a sense of valuations being inflated.
I also meant it as sort of two meanings: the other is just the reality bubble, the filter bubble, that start-up people live in — ‘We’re making the world a better place’, and, ‘We’re so special’, and ‘We’re so different’ — and that this sort of denial of reality, ‘You can lose money forever and ever’. Things like that.
But yeah I think there’s a certain frothiness to it now, but I also think that that’s kind of how Silicon Valley works. It works by having these manias that create lots of cool new stuff, and also 10 times as much bad stuff. The bad stuff all dies, the good stuff stays, and then everything dies down and you regroup and you lick your wounds and people get laid off and they moved to different companies, and then they all start up again. So it’s sort of like this very quick cycle of death and rebirth that happens out there, and I think that’s kind of a model that works, I guess. It works for them anyway.
It’s rough on the local economy. Right now to rent an apartment in San Francisco — or anywhere in the bay, or to buy a house — is pretty much impossible because we’re at the peak of this thing. That will all crash — people go through these wild swings that I think are different than not even a century ago when I began my career. When I began to work it was still the world of you kind of went to one place, you work there your life, companies lasted a long time. Companies now are shorter lived than they used to be, so there’s just this rapid cycle.
And I think it’s not just in Silicon Valley anymore now, this model is sort of being embraced elsewhere, like London — you guys are having this big start-up boom. So that brings with it lots of suicidal implications about people changing jobs every two years and being out of work a lot, or in between jobs a lot, which is a new thing.
You’ve written a satirical blog about one of the greatest CEOs ever, you’ve written a book about your previous employer that’s fairly critical, what’s the next step in your career?
Dan Lyons: Depression [laughs]. I pretty much now have really boxed myself into a corner, no one will ever hire me, right? I did this interview with Terry Gross on NPR — she’s a really big deal in the States — she’s very earnest, and she was like, ‘Were you afraid when you wrote this book that no one would ever hire you again?’, and I was like, ‘Yes, I was very afraid’. But I do think that my ulterior motive is I really don’t want to work, so I’m trying to find ways to make it more and more impossible to ever — I thought Fake Steve would end my career, like, after doing that people would tell me, ‘You’ll never have a career if you keep doing this blog’, and then unfortunately people kept wanting to hire me.
“Part of this journey through the start-up thing was coming to realise what you’re not good at. I wasn’t very good at writing marketing blog stuff, and I did kind of suck at it. You think, ‘An idiot can do this, I should be able to do this’, and I couldn’t. But it also made me realise what I really love to do, which was being a journalist.”
Part of this journey through the start-up thing was coming to realise what you’re not good at. There’s all this very glib talk about — and all these books about — personal reinvention, and ‘the brand of you’, and you just have to be a lifelong learner, and I think that’s great, that’s cool, but it’s also kind of painful and takes you sometimes to places you’d maybe rather not go.
What I realised is I really wasn’t good at this. I really wasn’t very good at writing marketing blog stuff, and I did kind of suck at it and I did kind of fail at it. And you don’t like to admit that you’re not good at something — especially something that you don’t respect, you think, ‘I should be able to do this, an idiot can do this, I should be able to do this’, and I couldn’t. But it also made me realise what I really love to do, which was I really like being a journalist. So maybe instead of being like, ‘Okay. I’m just going to throw in the towel in’, maybe it’s just a matter of saying, ‘Go back to doing what you do, maybe you’ll make less money, but at least you’ll be happy’. I think that was what I learned is that I was trying to be something I wasn’t, and that wasn’t probably going to be a good recipe.
What’s your best behind-the-scenes story from your time in Silicon Valley?
Did anyone see season three with the horses? So the way that came about was last summer — we had always had that scene, the old guy, the new CEO is a rich guy — where would Richard have to go to have a meeting with him? Oh I know, he has a ranch and he’s gone to his ranch… We wanted a joke about ‘what does an old rich guy in Silicon Valley do with his time?’.
So we had this scene that Richard has to go up to the ranch to see him, and we’re working — we are in two different rooms, and we are in one room, and Mike Judge was in the other room with all of his guys. Mike Judge is like Beavis and Butthead, like, really nasty, King of the Hill kind of things — he loves sick, childish humour. And this guy came running in and he was like, ‘Oh my god, we just had an idea. When Richard goes up to the thing, what if he’s breeding his horse? His mare is breeding and it’s in the background but we never say anything about it, it’s just happening in the background and what they have to have a conversation like this and there’s two horses fucking right behind him?’. And we were like, ‘Oh my god that’s so sick’, and then the guy was like, ‘Have you ever seen video of horses fuck?’, like, ‘No’, he’s like, ‘Ugh’ [laughs].
We literally just — we had a big screen on the wall like this and you could pull up anything you want, and it was like, we’ve just been watching videos of horses fuck for the last two hours [laughs] We were just in a room, a bunch of grownups just watching horse sex, right? And then we were watching, like, ‘Oh my god, this is awful’. That was the best thing for me, you could waste so much time. We would go on these terrible digressions and just watch really stupid videos and the worst funny stuff you could find online.
On the theme of that, advice for aspiring screenwriters? How do they get in that room?
Dan Lyons: The funny thing for me is I fell into it and then immediately fell right out, too, so I’m probably not the best person. I think the traditional path [is] you go out there after college — it’s really about who you know and about connections and having a friend in the business. It sounds horrible, but from what I could tell — and you take a job as an assistant. You literally assist somebody for a couple of years, you hang around in the room, and then you work your way up and you go from that to being a staff writer, and you move up and up and up in those ranks.
The other aspect is writing screenplays, having samples, just don’t wait for someone to give you permission. Start writing screenplays. It helps to know the format, you can read screenplays and see how they’re structured, read a couple of books about how screenplays are structured. There’s a big difference between film writing and TV writing. They’re structured differently.
Then a lot of people write scripts for a show they enjoy, so they’ll write a sample script of Blackish or some show, never intended to be sold to that show, but just to get an agent. Then you get an agent who maybe tries to place you with on a job someplace.
What did you tell your kids when you were working at this place, and what do you think your kids’ work life will be like?
Dan Lyons: My kids are only 11 — I have twins, a boy and a girl — and they were seven when this all happened. It was very funny to me because I had written for years and years and years as a business journalist about layoffs and creative destruction, but you don’t realise until it hits that every time that happens that’s 10,000 people who all have families. I also never realised that you get laid off and the kids go along for the ride. It’s not really something that six- and seven-year-olds should have to deal with. My wife and I would always talk about [whether we] should shield them from [it]. We had to tell them, ‘I got laid off at Newsweek, I’m taking this new job’, so they had to watch me struggle with that. I think it was tough for them.
Then at HubSpot I would come home every day like, ‘Oh my god, the latest ridiculous story’… One thing we had was a thing called ‘Fearless Friday’ where we got this memo from this person, I don’t know who she was. Some woman in the department had read Sheryl Sandberg’s book Lean In, and there was a thing about ‘do what you would do if you weren’t afraid’, [but] I think Sheryl Sandberg meant in terms of your career.
[The colleague] was like, ‘We’re going to have a thing called Fearless Friday and on this Friday we’re all going to stop what we do and do something fearless — the only thing you can’t do is you can’t do your regular job, no matter how busy you are, you have to do something fearless. I was like, ‘What are we going to do that’s fearless, jump out of a plane?’. I totally forgot all about it — ‘Yeah, delete the email’ — because I’m that kind of employee [laughs], ‘That’s bullshit, no, I’m not doing that’ [laughs].
So the night before Fearless Friday, this woman next to me says, ‘So what are you doing for Fearless Friday?’, I was like, ‘When is that?’, she was like, ‘IT’S TOMORROW! You were supposed to sign up and join a team!’. I was like, ‘Oh christ…’, so I looked at the teams, one team was going to make little paintings on the floor, they’d get poster boards and paint from the art store; another was going to write a blog post for Buzzfeed — I don’t know why that’s fearless, that doesn’t scare me at all; the other was going to write thank you notes for customers. It was so stupid, so insanely stupid.
So I chose the blog post one. It was kind of like one of those team-building things — we had to meet in a room like this at the beginning of the day — the woman who was organising it was just so thrilled that she was in charge of the whole department for a day. She was like, ‘How are we going to know today is a success? Just by being here right now we’ve already won’, I was like, ‘Well fuck it, let’s go home, let’s go’ [laughs].
“The woman who was organising ‘Fearless Friday’ was just so thrilled that she was in charge of the whole department for a day. She was like, ‘How are we going to know today is a success? Just by being here right now we’ve already won’, I was like, ‘Well fuck it, let’s go home, let’s go’”
I did my thing, and then I wandered around seeing what everybody else is doing, and I found the team making pictures — I wanted to put these in the book, but the publishers said it would be too mean — they were horrific, they were horrible paintings that weren’t even — they were words like, ‘Marketing is not just arts and crafts’, or pictures of the HubSpot logo. It’s like, you have a day to paint and the only thing you can think to paint is about work? And they were really proud of them and so I was like, ‘These are amazing, can I take pictures?’ So I got them all to pose holding their pictures, and I took pictures of them all. God forgive me… [Laughs].
We had an end-of-day meeting where we had to all then regroup and talk about what we had learned, and the team leaders all got up and gave presentations with PowerPoint [about] what their teams had done. It was just insane. So I went home and I showed my kids the pictures, and they were like, ‘Dad, those suck! Grown-ups made those?’, I was like, ‘Yeah, these are grown-ups!’, and they’re like, ‘We could do that better in kindergarten! This is what you do at work every day?’ [laughs], I was like, ‘No, I don’t do this, I wrote a blog post…’. So literally the next day they were like, ‘Have fun at kindergarten, Dad, bye!’ — they started making fun of me [laughs].
Then they found out that people at work have Nerf gun fights, and my son was like, ‘That’s awesome’, so he wanted to come to work with his Nerf gun. So he did. The two of them came into my office with Nerf guns and had fights with these twentysomethings, hiding behind the desk like, ‘Dad, this place rocks!’, I was like, ‘Yeah, it’s great kids…’ [laughs]. So they thought it was insanely stupid, even they knew how dumb it was.
On the other hand, I often say to them — they’re 11 now, so I look around and I say, okay, so, genomics — we live near Cambridge and a lot of our friends work in biotech. Genomics is about to change the world, it’s already changed the world, but not in my lifetime, in their lifetime, 100 years from now, how different is the world going to look? AI is another one… Transportation… Anyway, I keep saying to them, ‘So many amazing things are going to happen in your lifetime, and if you start thinking about that now, at 11, and start thinking, “Okay, first I’ll get a good education”, you can be part of that. You can be the ones who actually make artificial general intelligence actually happen because nobody’s cracked that yet. Maybe you’re the ones that crack the genome and figure out how to cure diseases or how to reprogramme people’.
So I actually think we’re in probably the most exciting century, the shame is that I won’t get to see it, but I really think their work life could be really, really exciting if they put themselves in the right place. I feel like we’re in this weird inflection point between 20th century work culture and 20th century industry and we’re getting to this new thing, and I just happen to have been caught in the middle of it, and my age happens to be a shitty one.
If you were in your 60s in 2008 when the economy collapsed, you could kind of call it early retirement and slide out; if you’re 22 coming into it today, it’s okay, your expectations are built around this, you can change jobs a lot; but if you’re just that slice — me and the people 10 years either side of me — we kind of came into the workforce with a certain set of expectations about what work was like. When I started at Forbes, we had literally a pension plan — a defined-benefits pension plan — and a 401K.
My dad worked at one company [for] his whole career, retired with a pension, healthcare for life, so we came from that world. I think we entered the workforce with expectations that that was what work was like and the rug kind of got pulled out from under us. I don’t think it’s any mean villain that did that, I think it’s a period of change that needs to happen, it’s just we’re kind of caught in the whirlwind of it in a way.
I think my kids will have it better in some ways — they’ll be coming into the workforce 10 years from now roughly. I think it’ll be an exciting time for them. I hope. That should be my next book…
When I read Disrupted I saw it less as a Silicon Valley exposé and more of the writer, you, just coming to grips with your own — it’s going to sound hard, hopefully it won’t depress you — obsolescence in the modern job market. But in a good way [laughs].
Dan Lyons: [Laughs raucously] no, dude, you’re totally right.
To use a tech phrase, I think you add a lot of value whatever age you are. My question was if you were to look dispassionately at the book and you in it, is the way you view your time at HubSpot a case of maturity vs youth or the excesses and that vapid, saccharin ‘yay, go us’ culture, particular to tech?
Dan Lyons: I’ve thought a lot about this and I think I would’ve been just curmudgeonly in HubSpot when I was 25 as at [coughs to cover up his age]. I worked at Gawker briefly, right after I left HubSpot, and that was the most — even I was just like, ‘Okay, these guys are so dark, I can’t take this’, it’s really dark, like, really, really dark. But they rant about Buzzfeed, because Buzzfeed were like the HubSpot of media and they had, like, [mocking] pyjama day when everybody wore their pyjamas to work! The people at Gawker just despised all that, and I was like, ‘Yeah, I hate that too, ugh’.
The people at Gawker were not as obsolete or mature — they were in their 20s but they were just as cynical and prickly as I was. Actually, that was the irony, I found I fit in at Gawker — day one I was like, ‘Ahh, my people, yes’, I loved everybody there. I was way older than everybody there and they kind of looked at me like a mean, old grandpa, but at least [it was] behind my back. But I did fit in better there.
“ I found I fit in at Gawker — day one I was like, ‘Ahh, my people, yes’, I loved everybody there. I was way older than everybody there and they kind of looked at me like a mean, old grandpa, but at least [it was] behind my back. But I did fit in better there.”
But I think you’re right. I did a conversation a couple of weeks ago at another event with a guy onstage [whose] question was, ‘Being a print journalist in 2016 is like being a blacksmith’. I think a lot of my journalist friends are doing this now because we’re really not old enough or rich enough to retire. So [you find yourself] scrambling, saying, ‘I’ve got to take whatever skills I have and find a new way [to] use those’, and that’s not so easy to find.
The other thing is that I think age bias is a real thing, and I had never encountered it before. At Forbes there was a huge range of ages — people right out of college right to retirement age — at Forbes the joke was that people would die in their office and you wouldn’t notice for, like, a year and a half. There were people who had just been hanging around for years not doing anything… But even at Newsweek — I worked for a much younger guy, but there was a range. So I’d never been at a place where everybody was just all young and you stood out because of your age — that was a weird thing.
Since then I’ve become more aware of what an issue it is in the tech industry, but I’m not sure if it’s confined to tech. I guess it’s probably media start-ups…
If you could give a single piece of advice to a start-up on their culture, what would it be?
Dan Lyons: So one is there’s this line from HubSpot’s cultural manifesto that says, ‘We’re a team, not a family’, and it came from the Netflix culture code. Reid Hoffman at LinkedIn talks about how your job is a tour of duty — you’re not coming here for a career, you’re coming here for a year or two, we’ll get what we can from you, you’ll get what you can from us — it’s more of a transaction — and then you leave. I think in this race to change we’re throwing aside some aspects of managing people that were actually good, even though they may seem antiquated.
So I think companies and business are still about people. I think there’s an urge in start-ups to make everything measurable and everything’s a system, and people are just this widget that plugs into the system and our boss would never come around and talk to us — the CMO would never just take us out to lunch like, ‘Hey, how’s your kids?’. He would do these relentless surveys, we’d do these NPS surveys all the time, like, ‘On a scale of 1–10 with 10 being the happiest day of your life and one being — how happy are you?’, or, ‘On a scale of 1–10 how likely are you to recommend this place?’. They’d look at all this data, everything can be measured, and they were like, ‘Okay, we’ll look at the data. Ooh, this department isn’t happy, let’s try to crank the dial up here’, and it was like, ‘No, dude, just walk around and talk to people’.
“I think in this race to change we’re throwing aside some aspects of managing people that were actually good, even though they may seem antiquated. Companies are still about people. I think there’s an urge in start-ups to make everything measurable. Everything’s a system.”
I feel like people in the sales department were put on really, really brutal monthly quotas — they were put in these telemarketing rooms where they just had to call, call, call, call, call all day. So I think in some ways start-ups — I think if you’re going to really build a long and lasting culture you have to remember that companies — whether it’s 2016 or 50 years ago — it’s still about people, it’s still about treating people with respect and building a place where they can thrive and be their best. Some of that sounds old fashioned and stupid, but that would be my advice — spend more time thinking about the people you employ and the responsibility you have to provide them with meaningful work and something that’s sustainable.
The company HubSpot was incredibly successful despite all of this batshit stuff they did. What do you chalk their success down to?
Dan Lyons: HubSpot have been successful in some ways — their revenues are growing — [but] they still don’t make a profit, I’m not sure that they can make a profit because their business model is very costly. So they’re essentially buying dollar bills at face value and selling them for 75 cents. So they have been successful and they do a lot of things really, really well — they’re really great at hiring young people, they’re not very good at retaining those people, but they don’t need to. They have this idea of just burning people out and churning them out, and doing that over and over and over. I think maybe that model can work if you define success as floating an IPO and getting rich, which is a pretty good definition of success, I guess…
Their culture is great. I hated it there and a lot of other people did, and we all left pretty quickly, [but] there are a lot of people that love it. What happens in a really strong culture –which is another phenomena I had never been aware of — is that you get rid of the people that don’t fit, and you keep the people who do. So the Kool-Aid keeps getting more and more and more concentrated so the people who like it, really like it. I’m aware that there are very, very happy people at HubSpot. But there are also very, very happy Scientologists.
“What happens in a really strong culture –which is another phenomena I had never been aware of — is that you get rid of the people that don’t fit, and you keep the people who do. So the Kool-Aid keeps getting more concentrated so the people who like it, really like it. I’m aware that there are very, very happy people at HubSpot. But there are also very, very happy Scientologists.”
They’ve done something right — they’ve built a company that can grow. I’m not sure it’s for everybody though, but maybe it shouldn’t be. Maybe there’s no need to ever have a company that hires anybody over 40… They have big problems with diversity. I looked around on the age axis and realised there’s no other people my age, then we had a company-wide meeting — 500/700 people — and I realised there are no black people in this company, this is all white people. Then it was not even all white people, it was all one kind of white people — it was a very narrow slice of the Caucasian population. There were women, but the women didn’t really have any top roles. I think diversity is a big, big challenge that they have.
I think if you gave those Silicon Valley guys a truth injection — Mark Zuckerberg and stuff — they would tell you, ‘We pay lip service to diversity because we have to, but in reality we think the best way to do this is with a bunch of twentysomething white guys. Seriously, just give us twenty-something white guys, we’ll pay lip service to the rest, but if we did anything like that it would slow us down’. So again I don’t know if you’d call that a success, I don’t know if that’s a successful company, it’s successful in certain ways but they certainly haven’t successfully hired a diverse range of people.
I think at the end there has to be more to this than just trying to grow fast, lose money and cash out really quickly. Too many people in the world of start-ups now are just trying to — they don’t even care what the product is, it’s just, ‘Let’s get some traction and try to flip this thing, sell it and make money. It’s a hustle, it’s not really a company, it’s not really trying to do anything meaningful, it’s just a hustle. That’s something I think we should be wary of.
Second Home is a creative workspace and cultural venue, bringing together diverse industries, disciplines and social businesses. Find out more about joining us here: secondhome.io