354 - Mike Massimino: You Can't Control the Outcome, So Keep Doing What You Love

Transcript

This isn't your average business podcast, and he's not your average host. This is the James Altiger Show on the choose yourself network. Today on the James Altiger Show. We always hear these stories, and I've never personally experienced it, where you start doing something just for your own pleasure, of course. Yeah. And then it's like you turn away and you turn back, and suddenly it's this huge thing. Like, that's gotta be an exciting feeling. I originally thought I'll make some jokes on this blog. I sent a link to one friend of mine saying, check this out. And apparently, he passed it around to other people. That's how it started going. So I've got Dan Lyons. Dan, thank you for coming on the show. You have a fascinating career. Thank you for having me. And I mean, I've been a fan of yours now that I realize it. I mean, I've read first off, you had a best selling book last year, Disrupted, but I'm gonna tell what that book's about. You were a screenwriter and co producer. You have to describe that on the TV show Silicon Valley, which is one of my favorite shows. By the way, I worked at HBO 1. So it's really funny. I went to your LinkedIn, and it says you both worked at HBO, even though you were Oh. Yeah. I was an employee. You were, you know, a writer. Yeah. So, but I don't know who to say I worked for. I wanted to list that as a job on LinkedIn. I was like, well, who did I actually work for? I I don't know. There's some production company, I think, for a show. Right? But I mean, I don't know what they call it. So I just put HBO. Might have been HBO. Might have been HBO as the production. Ultimately, they're paying for us. Yeah. So so and, before so disrupted, you know, mentioned Silicon Valley, but it's also about your time at what was a so called hot tech company that IPO called HubSpot. Many people use it. They have they have, 28,000 customers now. When you were there, they had 10,000 customers. Is it 28,000? Yeah. Yeah. And, you taught the book's fascinating because, we're kind of moving backwards in your career, so people will see why it's fascinating. It's fascinating because you were double the age of the average employee there and all the culture shock and and a kind of a really interesting no holds barred, almost attack on the tech IPO ecosystem. But, before that you were at Newsweek, Forbes, all these old media companies, you were a journalist. And right when it seemed like things were going well in your media career, media, of course, has been turned upside down. You were laid off. You were scared. You didn't know what to do. You ended up at read write then HubSpot and then, of course, Silicon Valley. So now now that I went backwards, I wanna start at the beginning. You were at Newsweek and you get the call. You're you're what? You're 52? Yeah. You're 52 years old. Okay? I'm 49. If I got the call that 52 is, like, the worst time I don't I don't mean to panic you any further. 52 is, like, the worst time to lose your job. Yeah. Because you can't get another one. Yeah. Because it because also you're you've priced yourself out of the market. Right? So you're you're you're getting paid like what a a 52 year old at Newsweek should be getting paid after 30 years of career, and but they can they know they can hire 4 or 5 kids to do not what you do, but that's what they're being told to to do. Yeah. And so you have to call what happens. That was literally what my boss said. And she was your friend? She's my friend. I've known her for ages. I've known her since the eighties. She had been at Newsweek, then left Newsweek. I joined Newsweek. She came back after Tina Brown took over Newsweek. It was sort of the different Newsweek than the Newsweek I joined, you know, because they went through a couple of sales and whatever. Anyway, they always say to you, they want this. You know, it was, like, not her decision to handle it. And you called BS on her. You said, who is they? Yeah. And because she was the executive editor. Yeah. And she's like, I think they just wanna hire 5 kids right out take your salary and hire 5 kids right out of college. And, to be honest, I mean, I mean, I'm a business journalist. I write about coming I knew the financial reality of the world I was in, and it wasn't good. And I kind of thought, if I were running this place, that's probably what I'd do too. I I maybe you know, the people who left when Newsweek went over to the and be merged with the Daily Beast, most people almost everybody from Newsweek took a package and left. And for some reason, they wanted me to stay. I would have been better off to take a package because those people got nice packages when they left, you know? Could could you have then I know you tried to negotiate and they kinda just shut everything down. -Yeah. -But could you have Like, if I were you then, I probably would have threatened to sue. I Here's what And not that I'm a litigious person, I've never sued or been sued in my life. But I would have I would have had, look, here's a paper trail where you encouraged me to not take the package. I feel like you did that for your own economic reasons and not mine. You owe me the package you gave everyone else. Oh, that didn't occur to me. And I I was thinking quite the opposite that if I do that, it would have been an age bias case. Right? I don't think anybody ever wins those. And then then my my real fear was, like, you'll never work again because now you'll be marked as a complainer. So you might get some penny anti settlement out of them, but it won't be enough to live on forever, and you'll never work again. So I thought I'll just shut my mouth, go get another job. I also, I think, kinda naively didn't think of myself as old, and I kinda thought, I'll get another job. I'll find something. But, you know, I wouldn't think of you as old either. Like, you're 52. I'm 49. I don't think of myself as old. Right. But yeah. But but but, you know, I oh, I forgot to mention one other thing, which is that and I this is why I've been a fan of yours for over a decade. You're also, you were anonymously fake Steve Jobs. So you had this hugely popular blog that was hilarious. Yeah. You know, pretending to be Steve Jobs and all these crazy scenarios that you would put Steve Jobs in, like, where he's just this, like, arrogant narcissist, you know, employer that was just hilarious. And then you eventually stopped it, but you kinda had this degree of of fame as well. And and I would think that they wouldn't you you were kind of, you know, a a key resource for them. Yeah. I I mean, when I originally went to Newsweek, it was the old Newsweek. The Washington Post owned Newsweek, and they wanted the fake Steve blog. That was part of the deal. And so I signed to the Did they buy it? No. They didn't buy it, but we were gonna license. So I had it previously, it was at Forbes. And Forbes was paying me a set fee every month to run ads on the site with a kicker that if if traffic went ups beyond a certain thing, I get a little more. But basically, you know, and it was the same deal at Newsweek. And then in the summer between when I, like, I made this deal, I said, okay, I'm gonna take a month off and I'll start in September, say, Steve Jobs got really sick. Came out on stage at an event looking really sick. They didn't say he was they said, oh, he's fine. Blah blah blah. But I just had a terrible, terrible feeling. And, and I said to the newsfeed guys, like, I can't. I I wanna still wanna start the job in September, but I can't I can't really do that blog. I just feel it would be wrong. And and Steve Jobs, though, he kind of enjoyed the blog. Right? It's unclear. I may maybe he did. Maybe he hated it. I don't know. He might have hated it, you know. He might have just hated me making fun of him. I mean, I was always trying to do things like like have fun. Like when you mentioned, like like putting him in unlikely situations. Like, I bought a car. I bought a minivan. We had kids, and I I needed a minivan, so I went and bought a used minivan. And I always get screwed when I buy a car. I'm a terrible negotiator. And, but then I left, and I was doing the blood stuff. I was like, oh, I'm there. Imagine how would Steve Jobs have done that? Like, he would have gone in and just set that place on fire, you know? And so I wrote this whole fake thing about how once in a while, you know, even though I'm a billionaire, I'm super rich, sometimes I just like to you know, I wasn't always this way. I used to get screwed by car dealers. Sometimes I like to just go in and ruin a car salesman's day by, like and there's a long elaborate prank. It was really wish fulfilling. It's like what I would love to do, you know, if I had, it's like how Larry David says, like, he can be he gets to say all the things that we all wish we could say. It was like to me, that's what fake Steve was. It was all how I wish I could be. But, anyway, so so Newsweek said fine. Stop the blog. And then they thought, well, maybe maybe we'll do a different blog. Did you do fake Sergei Wren? Yeah. Or I thought, yeah. I tried a couple different things, and nothing ever worked. The jobs thing was unique. It was it was the only one that really worked. But, and then for a while then when he came back, he had he had a transplant, and and he came back. And it was like he's, you know, born again. So I revived, and I came back too. And I was writing about what it's like to be have, you know, David Pogue's liver and, you know, blah blah blah. But he was also this kinder, gentler Steve now, and his PR flak, Katie Cotton, would always be like, you know, whose liver did you get? Because you're being too nice now. And he's like, no. You know, I've seen the you know, it was just but even then he got sick again. I was like, now I'm really stopping. I'm just doing it. It was very addictive. It was hard for me to stop because I loved, like, I loved writing it. Like, I just loved it. And did you start it on a whim? Like, was like, you were just doing it on your own. Right? Yeah. No. No audience. Nothing. I just was doing what I wanted. You know what it was. Okay. It comes back to what we originally talked about. I'm working at Forbes on the print side. I realized print is pretty much dead. I'm in my forties. I'm an old guy. What what and and and even though I agree with you that print is dead, in fact, you see the the width of Forbes from the nineties to now, it's like 1 third the size. But but what was making you was it just that? I mean, that yeah. That was that was hyperbolic. I I didn't mean to say it was, like, dead dead, but I could see that the future was the Internet and Internet publishing. Or at least I thought that would be interesting. And I thought I gotta learn how to blog. I have to learn, you know, so remember there were 3 platforms on those. There was WordPress, Thinkpad and Blogger. And so I thought, I'll just start a blog on each of those platforms and try to learn, like, literally learn HTML, how to embed photos, like just just honestly how to do it. Right? And then I tried to learn a little bit of, you know, when you go to the HTML view and how to embed code and do stuff like that. So I wanted to become I wanted to develop some facility with with with that, with the tech the technology. And I didn't really care about the content. And so I thought, I had a ThinkPad blog that was like about my, you know, leftover stuff from journalists. I had a, WordPress blog that was something else. And and on Blogger, I tried a bunch of different things. And I just, you know, stumbled on, oh, what if a CEO had a blog, but he was a real prick? Like, he was a real can we use Yeah. You know, what what if he was because, you know, Robert Scobble is always going around saying remember Naked Conversations? Robert Scobble had a book, Naked Conversations, about he and Shel Israel wrote a book saying, every CEO should have a blog. We don't need the press anymore. They're disintermediated. Just have a CEO blog. And and I remember thinking, that's crazy because most of the CEOs I've met, like, if they really were honest, you know, they're Right. Sociopaths. So, then I thought that could be really funny. Like, it was also, there's a, you know, there's a British humor magazine, Private Eye. Yeah. And they do a regular feature. Every edition, there was a thing called the The Secret Diary of so and so. It'd be like John Major or whatever, Prince Charles. They make fun of somebody. And by writing their own diary, Elton John, you know. So I thought, oh, you could do sort of a secret diary like like Private Eye does, but you could pick a CEO. I tried to run. I had c I did try Sergei Brin. Didn't work. Like, Sergei just I don't know. It didn't work. But somehow and the Steve Johnson was kinda fun, but I didn't do much with it. I did it for a few weeks, 4 or 5 weeks, and then shut it down. And someone revived it, or or or people started writing, like, wait wait. And I didn't I wasn't even looking at I had a couple comments. I wasn't even looking at whether people read. So I I relaunched, and I looked at the traffic. I was like, oh, there's, like, a 1000 people reading this thing. And I I remember saying to my wife, like, we we had little babies, and we're walking the babies in a stroller. We had twins. And I was saying, you know, this is weird, but, like, I think this might be something. Like, there's they're, like, a 1000 people, and you could see where they're from. You know, you you can look at the stats and see, oh, this guy somebody from Russia is reading this. And, you know, they were all over the place. They're mostly US. But it was just this weird moment from where I thought, wow, this is, this could actually be something. Isn't that kind of exciting, like, where you always hear these stories, and I've never personally experienced it, where you start doing something just for your own pleasure, of course, and then it's like you turn away and you turn back, and suddenly it's this huge thing. Like, that's gotta be an exciting feeling. Well, that must be kind of like what your career is like. I mean, you sort of just struck out and on your own and, like, off you go. And now you've built this thing. Right? I mean, that Yeah. But I I, like, think about it all the time. I don't turn away from it. Oh, yeah. I mean, I sent a link. I I originally thought I'll make some jokes in this blog. I sent a link to one friend of mine saying, check this out. I'm doing this funny thing. And apparently, he passed it around to other people. And that's how that's how it started going. But, like, yeah, it was very weird. And I think really took off because Steve Jobs himself had such, was such a powerful figure, had such a cult following. I mean, this was right around the this was right around the time of, like, let's say, the peak of his mythology. It was before the iPhone. It was like yeah. Like a year or even more before the iPhone. Like 06, 5 Yeah. Something around like that? 5 maybe. 06, I mean. But I think the the original jokes were things like like when the Mac was such a joke that he'd be like, so but he was so deluded, you know? He's like, man, the Mac is crushing it. We we just got our new market share in from IDC. We're we're up to 1.7%. We are killing it, man. Like, watch out. We're gonna hit 2% soon. You know? Like, it was really making fun of, like, the diluted Apple fanboy mindset. And and then I remember I did one about the phone when there started being rumors there were gonna be a phone. And I had him he went off to the to the rainforest with Sting. He went to, like, Peru, and they did Ayahuasca, and they tripped for a couple days. And they were, like, huddling on the floor of this mud floor. He and Sting were, like, huddling together. And then and then he said he came back, and he had an epiphany. And he said, I had this huge epiphany about the phone. It's gonna have one button. And he goes and and and everybody was like, what? It was a joke. Right? Because they're like they're like, no. It has to have 123-456-789, then the 3 of us. So it has to have 12 buttons. No. All other phones have 12 buttons. Our phones are gonna have 1. Right? I I thought of this while I was tripping on Ayahuasca. One button. And it was, like, funny, like, Apple joke about how we're gonna and then, of course, the phone came out. It had a screen with, like, one button, and everyone was like, dude. I was like, no, no. I just tried to think of, like, the stupidest, the most pretentious thing you could think of. Right? But they didn't. So, yeah, I kept having these lucky breaks. But it was, it was it was it was just basically writing comedy all day long. And was this your first Because obviously, you then became a comedy writer for Yeah. So it's a good value. But was this your first attempt at, like, humor writing? Because I wrote I wrote a few novels that, nobody knows about, but I published 1, 2, 3 Yeah. 3 novels. And the Well, the first one's a collection of short stories. Very serious, very grim, and depressing. Then I wrote a very funny comic novel. I think it's right. A funny novel and then a second funny novel. And how did they do? No, not not too well. But, So they didn't they didn't give you a career? No. Were you depressed about that? Yeah. In fact no, no, no. It was only 2 books. I wrote a collection of short stories, then a novel. The the Steve Jobs thing turned into a 3rd book, which was a novel. But no. So I, in fact, when I started the fake Steve thing, I was working for us, and I was trying to write another novel. And it was a really I wanted to get a serious novel. I was gonna write a historical novel. It's gonna be really serious. I was gonna be a real writer, you know, like Hemingway. I was gonna be you know, I was gonna write the you know, a serious novel. And I've been working on it for a year. Yeah. I mean, it sucked. It was so bad. Right? It just sucked. It was historical, about a period that I don't know enough about. It had no void. It was terrible. And then I started doing the fake st thing as a way to, like, avoid working on the book. And I remember one point thinking, like, I gotta put this blog down because I gotta get back to doing the real I gotta work on my book. And then at some point, I just realized, oh, the blog is the thing. Forget about the book. Like, the book is dead. And this it saved me in a way the blog saved me from this horrible project that, you know, I maybe still would be trying to work on now. So you were why were you trying to keep yourself anonymous on the blog for the longest period of time? I kind of thought it would add to the allure. Like somehow it occurred to me, nobody knew it was me. Actually, a bunch of people knew. Right? My friends knew. But somehow I thought I remember thinking at the time, like, if everybody knows it's me, nobody's gonna find it that interesting because I'm kinda boring and, like, you know, ruin it. Right? Somehow the idea of the mystery blogger that nobody knows who it is, like, could be funny. You know, it could be, like, not funny, but, like, it would be a cool thing. Like, that would help the thing take off because it'd be, like, this added element of mystery about who's writing it. And I was right. Like, that that added to people like, oh, who's writing this blog? You know? And it and then and then once I was outed, a lot of people were like, yeah. Now it's not so interesting. So Did did you see traffic drop off the same time? I did. And then it came back, though. But then, over time, I stuck with it. I was gonna quit. Then I said, I'll stick with it. And then traffic crept back. And I think it never hit the biggest month was the month that I got busted by The New York Times. That was like through the roof. Yeah. And it came back down. But it still settled in at like a 1000000 uniques a month. Like, it was pretty good. That's a lot. Yeah. It was pretty good traffic for and and it started running itself. Did you sell ads on it or anything? Forbes used to put ads on it. And then I started making fun of the ads that Forbes put it was putting on it, and then they got mad at me for that. Like, I had to stop doing that because it was like people complaining about the ads saying in the comments, like, I hate these ads. And, like, yeah, I really I hate them too. And, like, but look, you know, somebody's you know, don't people complain about ads, but you gotta pay the bills. That's right. Yeah. So I was, like, you know, just don't look at them. Put it on an ad blocker. I don't care. You know? But but Did you know, Mike Smith at Forbes at that time? 2007, 2006? He was the I didn't know him. He was the COO of forbes.com at the time? No. Because there was a guy named Jim Spannfeller there. Oh, yeah. Jim was his boss. Oh. Then maybe I met Mike Smith, but I don't you know, I had a couple of meetings with the ad guys, but I didn't really know them too well. So so so, again, you did you you you you're kind of like this master of reinvention. Like, in you love writing. You you got an MFA in creative writing. Correct? Yeah. Yeah. And then you you kinda divided your your career initially between, attempting to be a novelist, being a journalist. Was the was the journalism just an outlet for the writing, like, you really wanted to be a novelist? Yeah. So That was the way to pay the bills. And so so was it I mean, was that I mean, you were a journalist for a really long time. Was that kind of soul sucking? No. Because in the ultimately, I ended up loving being a journalist. And and, by the time I got to Newsweek, I used to I used to I was one of those people that would really say this, but really mean it. Like, I really felt I had the best job in the world. Like, I loved what I did. I didn't I wasn't gonna get rich. You know what I mean? I wasn't you're not gonna get rich as a journalist. But I loved meeting people. I loved talking to them, interviewing them, trying to figure out what's a good story. Like, I really, really loved especially at Newsweek. At Newsweek, because they had a lot of impact. So if you wrote something if you had a cover in Newsweek, in those days, it still meant something. And, yeah, I got to meet I went to, like, Lawrence Livermore Labs and met these fascinating scientists, and you could write. It was no, it's, like, unbelievably fun. It was great. I really loved being a journalist. So then so then, you know, you're you're, the fake Steve Jobs guy, you got this great position at Newsweek, I think you had just started their their tech blog, or you were about to We were about to. Yeah. Yeah. Which is similar to how, you know, ultimately, you know, if you think about it, like, recode spun out of the Wall Street Journal, you know, something like that. And then you get the call. You're 52. We're laying people off. No. You can't even get 6 weeks severance, only 2 weeks severance. And I know you worked it out a little bit, but it was No. And I was like, can I stay on cut my salary in half and just keep my job? Like, I'll find a way to live on half the money, or at least I'll start that way, I'll I'll give me 6 months, and I'll look for another job. Like, no. Nothing. Bye. Get out of here. Like, it was Well, did you find out, like, why it was so harsh? No. Like, you never kind of got back in touch with, the the woman who was the editor and Yeah, Drew, no. What happened? No. And, and then she didn't end up blasting there either, so she ended up getting. I wish we could call her right now and find out what happened. Yeah. She she might not be happy about that. But, like so so you get off the phone, and, I mean, when I was reading this in your book, Disrupted, this is kind of in the beginning of the story, I was, like, really stressed out, like, because I'm putting myself in your shoes, like and I was even thinking as I said is I said to somebody, 52 has to be the worst time because you're still quite a ways from what people consider retirement age. You know, you had 6 year old twins, so you're thinking about college and expenses and other things for them. And like you said, it's gonna be your career was in this kind of old media, which didn't really exist anymore or was disappearing. I would be I think I would I think I would just it would just be damaging to myself. I I wouldn't know what to do. Yeah. It it was. It was, Yeah. It was Your wife had just quit her job. Right? Yeah. She was a high school teacher. And Very lucrative job that she gave up for for you. Yeah. Yeah. Hers Yeah. They're high paying. She's teaching at a private high school in Boston, and she had very bad, migraines to the point where she'd be in the hospital a lot. And and just managing life was just a bit much for her, and the kids were having a hard time. And so, we we had this conversation. Well, over time, we had it many times. We finally said, you know what? Because I had been ready to get laid off at Newsweek for a long time. And then when they started talking about doing a tech blog, for the first time, I thought, oh, oh, this is gonna be okay. So I said, look, I think things are solid here, you know, for now. So why don't you and even if they're not, like, you can't just keep doing a job that's destroying your health. You just can't that's what's, you know, the this other yeah. More to life. Right? So, by the way, we we we pass off that comment as an obvious thing, but, I think many people go into jobs where they have this gut instinct that they're not happy with it. And sometimes, okay, maybe I'm not happy today or maybe, you know, the boss is in a bad mood today, but in general, I love this job or I like what I'm doing or I'm learning my I feel growth in my life, and I'm happy with the certainty, and there's always new things that I'm exploring. Like when you're a journalist, there's new people you could talk to, you might be improving your skills or salary, there might be an idea that you're contributing to society. So so but if you get that real gut feeling that something is not working out, you kinda have to do something about it. And that's it sounds like that's what your wife did with her her job. Yeah. And she loved she loved her job. She loved teaching, but it was just, her health was very, very bad. And so yeah. So she we talked about it, and we we said, let's let's, you know, cut back a little bit. We'll make adjustments. And, and then and then, literally, it was June. I think she had just finished her last week of school, and they knew she wasn't coming back. She had told them she wouldn't renew in the fall. And then, yeah, I got this call. And and at the time, News Hook was talking about they had Andrew Sullivan's blog, remember, for a while? And they were gonna do a tech blog like Andrew Sullivan's blog, like so that they were gonna build out these blogs. And I would be the tech Andrew Sullivan, which I thought, oh, this is this is really good. I like this. This will be, you know, sort of like fake Steve, only in my voice. But I've been looking for a new thing to really latch on to. That'll be great. And I liked blogging. Right. So so you were a known talent, meaning they couldn't just replace you with, like, 4 college kids. Like, you already proved that you could build a successful blog from scratch and you had, you know, kind of the the humor skill, as well as the journalism skill. So I still don't understand why they laid you off other than some kind of like weird economic thing or maybe this woman had it in for you. I don't know. I know a lot of people were getting getting at the same time and and a lot of people who, who had been there for a while. And, yeah. No. It wasn't it was it was just a tough time. I mean, they were losing a lot of money. I think they didn't know quite what to do. I think they wanted it was a culturally, you know, you had these Bezos own it at that point or not? Or Don Graham still own it? No. Well, that was The Post, but The Post had so The Post sold Newsweek to Sydney Harman, the Harman Kardon guy. Okay. And then we were independent for a little bit. And then Harman turned around and wanted to get Tina Brown as the editor. But Tina would only go if they merged with the Daily Beast. So suddenly, we went from being independently owned by The Post to owned by Sydney Harman to now being owned by Barry Diller and merged with the Daily Beast. And that even seemed like, well, okay, but really what it was was a takeover. So all of Tina's people took over. Everybody from Newsweek is gone. It was just a bloodbath. And then you had these kids from the Daily Beast who had never worked in print, trying to put out a print magazine. And they, you know, for better or for worse, publishing a print magazine is a skill. You know, it takes It's a beast. Yeah. Well, I mean, it takes this institutional knowledge of how do you get that that book out on time every weekend. And so suddenly we're running late and we had these overruns and then Tina would hire in all these big name friends of hers from the New Yorker and they were taking over departments, but they didn't know what's going on. And the news people were all leaving. And then you had these, I had, like, you know, for a while, I had no editor. Then I had these editors who, like, didn't know anything about business, but, like, they were being put in the business. I had literally one person call me and say, I'm editing your story this week. Can you come down here and talk to me? Sit just at my desk rather than Yeah. Sure. I'll come down. Sit sit with Okay. So I just want to know, like, venture capital. What exactly is venture capital? Like, I I have a friend or my brother or something who works in venture, but I don't do we need to explain what venture capital is? Like, no, this is a business story. But, you know, it's a good question. Venture capitalists is and, you know, like, it was some story saying they've raised this is a company that's raised 50,000,000 in venture venture funding. Do we need to explain? I don't really quite know what venture funding is. Like, you're the business editor, you know. So it's like it was chaos. Right? So he kinda knew, like, oh, this is all going sideways. One of these days, I'm I'm gonna get out. I'm gonna get killed. I thought, well, I'll just hang in and wait to get laid off. And when I get laid off, then I'll find out. That was that was a dumb move. That was a mistake. I think there's a there's a couple of things. I mean, look, I wanna get your your main story of HubSpot, and then I'd love to talk about, Silicon Valley, and and, of course, your your book disrupted covers both of those. But it seems to me you made a mistake when you didn't take the package. K? It wasn't offered a package. Oh, you weren't offered a package. They said you don't no. You're not you you can't have a package. We want you to stay. It was like it was on their dime. You couldn't just sign up for a package. Okay. You couldn't have begged for it? I mean, I could have begged for it. I should have just done that. Because there's a there's a saying I always live by, which is take the cash. What it's offered. Yeah. But it doesn't matter how much upside opportunity you have. If there's cash right now, take it. Really? Yeah. Oh, that's good. That's good advice. I I because then you could you know what you could have done? Then you could have waited a month, and you could have gone back to Newsweek and say, hey, can I have a job? Yeah. Exactly. Or, the other problem is they were the packages were all based on years of tenure. So some people who have been there for a long, long time did pretty well. I had only been there 2 years at that point. Say 2 yeah. Because I was gonna say 4 total. So I wouldn't have got that much money. But I'm gonna tell you My package wouldn't have been much. I'm gonna tell you another mistake. Not a mistake, but this is just my suggestion. So don't take don't take this this one away. It's just No. I It's just how I think and I see when you described the Tina Brown, how she got involved, it wasn't just that she kind of had took editorial control over Newsweek, she made a business deal. Tina Brown is an editor, but also a businesswoman, very much a deal maker. And I feel like you should have done more of a deal with your blog, fake Steve Jobs. Whether you're gonna shut it down or not. Like, you could have said you could have pitched a dream. I'm gonna start a network of fake this and Right. You know, we're gonna bring on comedy writers. It's gonna be huge. We're gonna it's gonna be like crack.com, which also is owned by, you know, Barry Diller, and, it's gonna be it's gonna be great. I feel like you should have done more of a deal there. No. That's that's seriously really good advice. And Anytime somebody wants something from you, you should go into deal mode. Yeah. This I I wish I had met you, like, seriously a long time ago. Well, you have very good deal guys in your camp, like Ari Emmanuel and so on, but this is just how I think. Yeah. Not anymore. Well, but but, but Yeah. The one thing I always had with the fake Steve thing is I had this big audience, but I could never figure out how do I make that into a company. Like, I would sell ads, but they're pathetic. You know, you don't make much money on that. And I I never could figure out, like like now, looking back, I realized what I could have done is transition that from being because I had the audience. So what do you do with that audience? I think what I should have done is become just an Apple blog. And then, yeah, there's other Apple blogs, but fine. Step from behind the curtain, be me, and just be this big pro Apple like what what John Gruber is with Darren Firebaugh. Just do one of those. And, unfortunately, I was always somewhat sarcastic and cynical about Apple. I was, like, making fun of the Apple world. You can't do that. You have to be a 100% pro Apple, you know, bootlicker kind of Apple guy. But that would have been a way to make that into a business, maybe. You're even, you have that as another silo of kind of a set of Apple blogs. One is about the Apple stock, another is about the Apple products with affiliate fees to the Apple products. So there's there are ways to think about it where you could have done a deal instead of just handing over the ad inventory. So And or or there was a really smart editor at Forbes who said you should turn this into an investor newsletter. Like, you've got an audience now. Start I was like, I don't know anything about I'm I'm not qualified to be anybody's investment adviser. I think his point was like, nobody is. Yeah. Yeah. But and that might have been a way. But I I Yeah, I'm terrible at thinking about business, about how to monetize, like how to make a business out of something. I'm seriously bad at it. Okay. So then you you started applying for jobs. We you know, you got you you were temporarily at 1 blog read right, which wasn't a bad blog, by by the way. I thought that was a decent blog. I don't I don't even know if it's still around, but I used to read it. Kinda tiny, but I think it does still exist. Yeah. And then you ended up at what was perhaps in the Boston area, the the hottest tech company, HubSpot, which still exists now. It's a public company, and you figured and you and you were the old man there, like at the ripe old age of 54 or whatever it was, how old were you? 52. 52. Yeah. And and you you were double the age of the average employee, and it was really like a culture shock. Like, you get there, your boss wasn't there, your boss's boss wasn't there, nobody knew you were supposed to arrive, then some 27 year old kid, shows you around, and he turns out he's your boss. Yeah. Like, were you depressed? Oh, well, more more anxious and depressed. Like, kind of panicky. Like, oh, crap. What have I done? Like, maybe I've made a huge mistake. Right? That was I didn't get depressed until later when it started to really, like, weigh on me. But at first, I was just freaking out. Did you cry that first day? No. I think I would have cried. You would have cried? Yeah. Yeah? I remember when I first left my first kind of corporate job for an entrepreneurial thing, and then that day I lost the our biggest customer, I did cry. I'm like, did I just make a big mistake? And, like, tears came to my eyes. Yeah. So I cry a lot. I cry at movies very easily. I tend to be kind of emotional. But, no, I I I was still kind of thinking, like because I went into it thinking this. Okay. I thought about going into a corporate job for a long time. As a tech reporter covering these companies, I remember thinking very early on, I had a friend who went to Microsoft in, like, 1988. Yeah. And so ever since then, I thought, like, man, I should cross over. Anyway, I knew no matter where I go, there's gonna be an adjustment. It's gonna be different than media. Maybe not gonna be as freewheeling or as crazy or as kooky or little did I know. But I mean, I I had this idea was gonna be uptight and stiff and, you know, you're to bite your tongue. I did realize I'm gonna have to bite my tongue and not be as blunt as you can be as a journalist. So I had sort of resolved, like, this is gonna be a tough thing. So expect, like, just take a year. Like, listen, sit back, watch, chill out, try to find a place for yourself. Your first job might not be the first position, may not be the right one. But, like, hang out and try to negotiate you around and create your own role. Like, these places are kind of fluid and malleable. Just relax. Don't panic. But of course, I was panicking, you know? Did you have other like you were interviewing around, did you have other potential offers at the time? Yes. I had a really good solid offer in California, and I've often regretted not taking that. Although, who knows if it would have worked out? You you mentioned it, but you didn't mention the company. And I like to say because it's like My guess was it was Google, but I don't know. Yeah. I can't say. Okay. But imagine if it had been Google, and look at the stock price in 2,000 what year was that? 2012. And look at it now. Yeah. It's probably a double. But still, you had HubSpot options as unpleasant as it was. No. And and I thought, well, there are And by by the way, you don't even hold back. In the very beginning of the book, in the in the intro, you say you joined a company run by charlatans, and you basically implied this was, like, the scammiest you don't hold back I didn't really going in. I didn't know that they were. Later, I came Yeah. No. Of course, later. Like, but you don't hold back in the book. Yeah. No. No. I don't. But but but going in, I'm here's the thing. So say instead of going to a like, one of my friends from Forbes now works at GE and he runs a GE reports. Very nice, cool thing, and he's a journalist. He's a great journalist. Another guy does the same thing at IBM. Like, yeah, you can go into a big company and you do your little job and blah blah blah. But I thought I was a startup. Like, I I interviewed with the 2 founders. Right? And they really liked me, and I like them. Like, these guys are really smart. I like these guys. And I'm working with these guys. Like, here in this place, I'm gonna be a big shot. I'll be able to, like, hang out with the founders and talk to them. I don't know what my role will be, but I'll I'll figure I'll find a way to add value here. I'll do something that'll help these guys. You know? I'll you know? Whereas at a big company, I thought you'll just get swallowed up, and it'll just be drudgery and, you know, editing blogs or When you were interviewing with them, was there any sense that you should, outline the specific role? Or Another mistake. Well, it did it felt fairly specific at the time, going in, but I didn't scope it well enough. And I didn't scope who exactly am I gonna work for. Now mind you, all this I I would love to get your advice on this, and I have my own thoughts about, like because I've given other people advice based on this. I have also heard, though, of several other people who took the same job at HubSpot. Like, I wasn't the first person this happened to where they said, yeah. Yeah. We wanna do this high end content. We wanna real journalists, blah blah blah. And then they got in there and was like, oh, no. But we sit over there on the corner, and you you're working for her. So yeah. But I one lesson I learned from this is I think you really have to have a well scoped like, you know, when you have I've had a lot of interviews, they're like, well, we don't quite know what the job is gonna be whatever you make it. I'm like, oh, no. No. I don't want that job. Like, oh, that's stupid. Let's stop to take a quick break. We'll be right back. I always hear almost the least important thing to negotiate is salary. Yeah. Everything else, you you need to have a bigger list than them. So then you can give them the nickels and take the dimes when you're negotiating. And part of that is, title, responsibilities, org chart, where you fit, even vacation time, you know, all these all these things that need to be Right. Discussed. And also going in there with a solid plan of what they need and having them sign off on that. Because then you're then you know it's a hole that you're going to fill. Right. Yeah. Well, the the yeah. I agree. And I should have done a better job of that. And they were kinda funky in that they have no org chart, and they refused to make an org chart. And they won't ever say people were clamoring for an org chart. They're like, no, no. We're an experimental company. We don't have an org chart. So you can't know where you where you work, but, or who you work for. But the other issue I had was that the 2 founders had hired me. And and even after I'd been there for, I don't know, 5 or 6 months when was it? I started in April and about in August. So, yeah, 4 months. Right? I realized things aren't working out. And so I went I set a meeting with the 2 founders again. I said, look, basically, you know, you hired me not to do this. You know, and then you handed me up to the CMO. He handed me to this other guy who handed me this other guy. And now I'm in this box with a bunch of, you know, people writing, you know, lead gen content. Like, that's you you shouldn't be paying me what you're paying me to do lead gen. You can get, you know like, that's there's no point in that. And I'm not helping you doing this. And I'm not even very good at lead gen. So, but here's what I think you need. I think you need this high end publication separate from the blog, you know, and it should be this and should look like this. And I've already talked to the guy who runs the art department. He really wants to do this too. We'll do big high impact art. We'll do video, and we can call it this. And, you know, I had a big proposal. Now, unfortunately, I had already pitched that proposal to a guy who was, like, above me, and he'd already said no. So then I went, okay. I'm gonna just go to to the boss. And the 2 bosses said, we love this is yeah, this is exactly what we need. In fact, one founder got up and said, I have these other ideas, these components I want to add to it, blah blah blah. It's like on the whiteboard. I'm like, unbelievable. I went home and told my wife, like, it totally worked. Like, I went in, I pitched, and they loved it. But it turns out the CMO, I think, was pissed that I went over his head and set it through channels, and he didn't want anything to do with any of this. So the problem I had was that the CEO the the 2 cofounders who hired me did want me to do x, y, and z. It was just all these layers of people beneath them who didn't. And they were the 2 cofounders had kinda checked out. So it was, like, didn't really matter what they said. That's another thing I didn't know going in. I guess I should have done more due diligence of, like, what are the politics of this place? Who are these people? I think it's hard to know though because, like, you kind of implied I mean, in your book, this was happening all across Silicon Valley as well. Like, just all these companies were starting up, trying to blast through sales while while losing money every year, and then going public to take advantage of the fact that there was an open IPO window at the time. So everyone was getting rich. Like, people were making, you know you know, like, take a company like Instagram. Instagram existed for 500 days and then was sold for, you know, multiple 1,000,000,000 of dollars. Like 500 days before you sold? Yeah. So that's that's what that's what was happening is people were starting not because they had a dream, even though, you know, you you mentioned in the book so much there was so much kind of what you called hub speak. You know, you're at HubSpot, they call the you you called the hub speak. All this, like, inspirational mumbo jumbo jumbo to excite customers, excite investors, and so on. I think that was happening across the board. Everyone thought they were changing the world when they were just, you know, building an app to keep track of the times they went to the bathroom or something. Yeah. Yeah. Yeah. Well, that I I was just talking to someone earlier today, or tell you what's anyway, about this idea that no matter how well you scope out a job, you really don't know how it's gonna go until you just gotta get there. Yeah. You can try to figure and I was saying to someone, it reminded me of like marriage. Like, I had a friend who was dating this woman for a long, long time. She wanted to get married. He couldn't quite commit. He didn't know he loved her, but he didn't know, and blah blah blah. And What didn't he know, do you think? I don't I don't know. If he said he loved her, what what do you think he didn't know? I'm always curious about this. I know because it had been years. Like at this point, I think it was more his fears were about himself. Like, am I gonna be able to handle this? Right? But my my point is, you know, you get married, you love the person, and even no matter even if it's all good, you really don't know. You make this commitment for the oh, we're gonna be married for the rest of our lives. How do you make that commitment? You don't know what the rest of your life is, but you have to just do it and then find out. Right? Or or you'll just never do it. So the same with the job. I feel like you you're gonna take this job and see how it goes. And, you know, you know, I knew within you know, well, once that happened with that where I pitched on the other idea and then the other guy said, you know, stalled it, I knew then, like, okay. This isn't gonna work out. I should just leave. And I just started thinking, I'll I'll just I'll stop. I'll find a way to phase out and do it politely and nicely so I won't, it won't won't won't won't ruffle any feathers. I'll just sort of, like, slide away and find another job. You know? But yeah. Because that that's not the worst thing. Sometimes you take your job and you find out Yeah. That's not the right job. So you just, you know So what so what kept you there? Well, I was planning to stay till April, which would be my 1 year. And in March, I got called out of the blue and asked if I wanna go be a writer on Silicon Valley. And And and and, just to connect the dots there, like, it's funny how you you kind of mentioned, Larry David earlier. So you had made kind of an attempt at, I guess, a cable show version of the fake Steve Jobs blog, and Alec Berg, who sought or was involved with it in some way? I don't know. I sold a show to the Epix network in 2009 or so 10 called Icon based on the fake Steve Jobs blog. And my collaborator was a guy named Larry Charles. Oh, yeah. Larry Charles is Who works with Larry David. Yeah. He was a director on Seinfeld and Bruno, Borat And, of course, all the curves. Yeah. So and he's brilliant. And I really loved him. It was a great experience working with him. And then the show didn't get made, but still. And then a couple years later, Silicon Valley pops up at HBO, and they put Alec Berg, who also is from Curb and Seinfeld, in as the showrunner. And he knew Larry Charles. And I had had some meetings with Alec around my fake Steve show. So, that's how it was a fluke. So the funny thing was I was devastated. Talk about, like, I probably did cry when when the finally, when the epic show finally when they finally they stretched us forever and ever and had us writing other things. And then finally, they just said, we're not gonna make any shows. I remember Why do you think they didn't make it? Well Steve Jobs' health, I guess, was probably a factor. Yeah. Yeah. But they did then they decided not to make any scripted show. Epix has never made any scripted shows. They've made they they decided to do comedy specials Yeah. And to run other people's content. They were, for a time, thinking they were gonna become an original carry original content. And they'd so but, yes, Steve being sick was probably part of it. I I never really got a good reason. But, I think it was maybe internally they had hired this development woman from CBS to go buy them a slate of programming. And she did, and she was developing all these shows, and I was mine was one of them. And then maybe they just didn't like any of the shows, or maybe they decided scripted was gonna be too expensive. I never really because she more or less said so I only dealt with her, so I don't know what was happening above her. And then she ended up leaving. Mhmm. That'll kill it. Well, I mean, she left after my project. After they didn't make any shows, it was like, well, why why why is she there? She's there to develop shows, and they're not making shows. So she just left. But it makes sense then that, like, Larry Charles and Alec Berg would reach out to you, because you knew you had already been writing kind of a humorous version of Silicon Valley with the fake Steve Jobs, and that's what Silicon Valley, the show is. Right. And they read that much for Silicon Valley knowledge necessarily. Like, you had 30 years of knowledge. Yeah. So they they they yeah. That was right. And and the most of the writers there are just straight comedy guys. They they have a tech consultant. They bring in different people. But yeah. And I think yeah. So it was kind of, and to me, it was like, oh, I went from, like, the worst point of my life, like, oh my god. Because I was ready to move to when the icon thing was happening, I thought, like, I'm gonna go to LA. I'm gonna be rich and famous. I'm gonna have a big house in Malibu. I was ready to do the whole thing. Right? Like, I was I thought, oh, never occurred to me that, like, oh, no. A lot of pilots don't get made or whatever. You know? So, yeah, I was so I went from being, like, thinking I was about to become mister Hollywood to just being devastated. And then from that, though, 2 or 3 years later, just completely out of the blue, yeah, I got that call. And then I was like, oh, this is great. Then I went through the whole thing and, like, I'm back. It's just going to show you, though, that, like, networks, some you know, they always say it's not your 1st tier connections, but your 2nd tier connections that provide you the most opportunities. So you created these 2nd tier connections, you know, they weren't your close cohort, but they were people you had indirectly dealt with or, you know, directly for a short while, but they are the ones who come back to create opportunity for you. So a second tier means what? Like, 1st tier would be, like, I knew Larry Charles, because I worked with Larry Charles. So that's 1st tier? Yeah. The 1st tier might be just the actual people who are, like, let's say, you know, the ones you like, you could call your friend a g who once worked at, you know, Forbes or whatever. Like, that's, like, 1st tier. Like, you're gonna pick up on a phone call, and he takes the call. 2nd tier is just, like, one removed, like, either one of his friends or someone you knew distantly, but you're no longer in touch with. Yeah. You know, and, but those are the ones who, you know, if they're looking for someone, they expand out their their brain, like who who can I find and they They make a few pops? Yeah. Oh, yeah. Yeah. Well, that that that's right. That's I didn't know that the 2nd tier are typically Typically where people find jobs. Really? Yeah. Oh. There's, like, some research on this. I'll I'll track it down and send it to you. Yeah. Cool. Yeah. So, yeah. So that's what that's how that happened. And, but it was only, like, for 3 or 4 months. It was, like, a writing season. Tell me what that's like. So so you you get the call, did you have to pitch it's like so the season 1 had already happened, and it was a it was a very good season 1. So, obviously, you got renewed for season 2. You're working on season 2. A, where did the co producer title come from? Oh, well, that was my 2nd year. So my 1st year, I was I had title of staff writer. Co producer is not a good title. It's not a big title. No. It sounds like the s**t. Right? But, actually, the way it works in the TV business is there's about 10 or 12 titles. And you just it's a union shop, and you basically just keep working your way up in titles. Co producer is the almost at the bottom. It's like us 2 steps above staff writer. Like the staff writer, then maybe story editor, and then co producer. Like and then from co producer, there's producer, senior producer, blah, blah, then there's co the executive co executive producer. Like, there's a whole list of producers above that. So co producer so it's one of those things like I'd love to impress if that was a Oh, yeah. I was in the TV business. It looks cool. In the TV business, it's like where you'd be when you were, like, 27 years old in your 4th year out of college working there. Like, you find what it basically means too is anything below that as a staff writer, I forget what the cutoff is, but it's definitely for staff writer, maybe story editor, you get paid a weekly salary for every week you work. You just get paid and not very much. Co producer, you get a quote, and you get paid by the number of episodes. So if it's a 10 episode show, you get 10 x whatever your quote is. You know? And you get, like, when it when someone buys it on iTunes, you get another check? Well, you get if you have a I think that's if you have a story writing credit. You get residuals on ones where you have where you got a writing credit. So first the first season I worked on there, I got a writing credit. So I would get these little residual checks once in a while when it aired someplace else. My second season with them, which was season 3 of the show, I had a coproducer title, but I never got a show credit because there already there were more than 10 writers. So they gave out 10 things, and I was like an extra. So I had a better title, but I didn't get a show credit. So I don't think I ever get any residuals from that year. So so you, and you describe this in the book. You're at HubSpot, all these problems were happening. And, I mean, I encourage people to read disrupted because just every aspect of what you dealt with was dysfunctional, and and you kinda show how that wasn't just isolated to this company. But, I mean, I I wanna talk about Silicon Valley in a second, but, the the show, but Silicon Valley, the real place, also you described as so dysfunctional, like, it's sort of like people get their lucky hit, and then they're kind of blessed as gods in Silicon Valley in part because of the lucky hit and in part because of, you know, self worth becomes equated with net worth. So you have all these, like, huge venture capitalists that are famous that make never make a good decision again. Yeah. I I like to think that the the the difference between a venture capitalist and one of those people who wins the the lottery, wins the Megabox, whatever. It's just that the Megabox guy, then for the rest of his life doesn't go around thinking he's a genius at everything. You know what I mean? He knows. I just I just won the lottery. It's fine. But the guys in Silicon Valley now seem to think, like, no, I I could invest in biotech. I think so. I you know, like and then you have Theranos. Right? Like, oh, sure. We you know? Yeah. We know everything. You know? I think, yeah, there's a But like John Doerr went to CleanTech. He he did such a good job on, like, Amazon and all all those companies and Netscape and everything. But then he went into CleanTech that did nothing. Yeah. Well, and and, and yeah. I don't know. So I think there is a tendency to yeah, to people to believe that these guys know more than they do. Some all yeah. Look. Some of the some of those venture capitalists are very, very bright people. You know, I don't think they can predict the future. I think that's you know, maybe that's the nature of the beast too. You make a lot of dumb bets. Right? That's how that business works. You've been on And yet though, you look at, like, the best companies. Like, forget about HubSpot for a second. Like, there are legit good companies run by very smart people. Google being a great example. Yeah. I mean, those guys are geniuses, and Google is, like, a great, magnificent company. What's Facebook? Facebook, Amazon. Yeah. You know, Apple did and I'm gonna throw Disney in there just because it's run by extremely smart people. Yeah. So what wasn't as it seems like there's 2 types of companies that make it to the $1,000,000,000 level. There's the ones that are really smart in providing some sort of value to the world, and then the ones like HubSpot or I'll just use HubSpot as an example because that's in your book, where they emulate as much as possible, you know, they they kinda check the box on as many things as possible to make them seem like one of the good companies, and then they go public. Yeah. And because they're able to tell that story, we checked all these boxes. They're still growing, and their stock has gone way up since I left. I mean, you know There's a 2 and a half $1,000,000,000 market cap right now. 2 and a half $1,000,000,000 now? Yeah. See, I sold my stock. My I didn't have that much. But, like, the day it unlocked, I was, like, I'm getting out of this. I have I have no investment savvy at all. Like like No. No. But you maybe you did it correctly because you knew you were afraid given what you had seen inside the company. Since then. I should have just sat on it. I should have just kept it. Right? I had It's hard it's hard to know that. I know. You can't predict. But but again though, here's here's where it gets back to, like, you're at HubSpot, everything was dysfunctional, but you're still and you say like a fluke, but it was still out of, like, your ability to constantly reinvent. Like when you were a journalist, you said, okay, I'm in print, I'm gonna learn this new economy stuff, I'm gonna learn how to blog, and then you did you you combine that with your humor writing and your journalistic knowledge, you made fake Steve Jobs. So that kind of was this long route that wasn't a fluke that took you to Silicon Valley, the show. And so you had this ability to reinvent yourself that was you planted all the seeds years in advance, and so opportunities happened. And so so so so HubSpot gave you an opportunity to take 14 weeks off. That's actually a pretty good thing that they did, and you could work on the show. Yeah. So you get to the show And it was their idea. They because I said, I'm gonna leave, because I thought this is it. This is how I'll save face. This lets me leave the job that isn't very good and just be like, oh, I'm going off to work in Hollywood. And then, you know, after that, I don't know. But, like, you know and they my boss there came up with the idea of, like, look, I got a better idea. Why don't we give you a leave of absence? You can continue to vest, keep your health insurance, and come back after the season. I was, like, I mean, you're super generous. Right? And and I think that there's, my gut is there's, like, a selfish aspect to that in that then as they're getting closer to IPO, you're in their back pocket. Oh, we also have this guy who worked on the show, Silicon Valley. It's just kind of like a a sentence in the news article, but it it it provides it could potentially provide some weird legitimacy, you know, additional legitimacy to what all their other efforts. Or a little buzz. They they were very they like buzz, and they wanted to be able to say, like, well, that show Silicon Valley is kinda based on us. Did you know that we're the model for that show? Like, what no. You're not. But but then they because these conversations were all happening before the first season even aired, I think. Or maybe the one episode had aired. Right? Because no. It's April. Right? So yeah. Or Right. Because you were contacted before they were even renewed for the 2nd season. Yeah. Before they were even airing the show. They had they had aired one episode, I think. And then they sent me rough cuts of the rest of the season that hadn't even been finished editing yet. So they, but and I said, yes, I'll definitely go if they get renewed. And then they did get renewed. So there was a period where I was sitting there going, I don't know if they're gonna get renewed, so I'm not gonna say anything yet. And then they did get renewed, and they said, okay, we definitely want you to come. So then I went and talked to them. The other the other aspect of it, I think, there was buzz. Buzz is they they early on had a conversation with PR, brought me in with my boss and said, like, alright, so can we get a cameo for Brian Halligan, the CEO, on the show? Can we get them to place HubSpot logos or products? They didn't make product, you know, like, swag in the set. Can we get this? I was like, no. You can't have any of that. Like like, can we get a mention of HubSpot in a script? Like, they wanted and, like, stuff that I couldn't promise anyway, even if I wanted to. Right? But they were that was, I think, their interest. And then they found out no. And then I think I think they realized, like, oh, this isn't doing us any good from a PR thing. So when I came back, they didn't really want me to come back. I think my boss wrote to me right toward the end of the time I was in LA and put sort of said, yeah, do you really why do you really wanna come back? Maybe you don't wanna come back. Just as a friend, I'm saying maybe you don't wanna come back. Right. And you had said that was his technique he'd used to basically push out another employee. Yeah. And I think that was his his way of telling me, like, don't come back. And maybe again, in right then, I should have just said, oh, yeah. I'm, I'm not coming back. Thanks. It was great, and I really appreciate it. And, but I'm gonna go do something else. Could you have you do you think when he sent that mail, knowing his ulterior motive based on his prior or your prior experience with him, could you have then negotiated, hey, I'm fine. You know, give me a couple weeks severance. Speed up my vesting for the 1st year, and then I'm done. Yeah. Maybe after I should've done. I did call them. As soon as I got the email, I said, dude, what's going on? Like, is this are you telling me like, is this, like, your nice way of saying don't come back? Like, and if it is, cool, just let me know. He's like, no, no, no. I just don't know why you went. I was like, why are we doing this dance? Like, you know, blah blah blah. But, yeah, right then I might have said, I don't think they would accelerate your vesting, but I would have I invested a year and a half. I didn't really care. But, because I knew I wasn't gonna I knew I was gonna come back And then miserable. Well, just look for another job anyway. You know what I mean? Or hope that I would get hired back to Silicon Valley for the next season. Oh, and then yeah. And then when I when I came back, to Boston, I got a call from my agent in LA, and they said, oh, yeah. You did great. They love you. They definitely wanna hire you for next season. So you're all set. You're on the show. So I was like, oh, okay. I'll just I'll just quit now. You know what I mean? Well, hang in. I'll find some other job to do for the next 6 months. And then in April or May or whatever, I'll go back out to LA. And this time, I'll probably just move there and stay there. You know? So so so I wanna I wanna ask you about Silicon Valley a little bit. So you're in the writer's room, like, there were 10 writers in 10 episodes, so like you said, the the showrunner kind of gave a writing credit to to each writer. Yeah. But you're all involved, I'm assuming, in pitching ideas for each show. How does it work in a writer's room? Because, like, let's say, take a novel, one person writes it. It's not like a writer's room writes a novel. Why on sitcoms, there's like 10 people writing a 30 page script? Or more. Right? Some rooms get even bigger. But yeah. And I, I think partly because this model has grown up over decades. Right? Especially comes out of the network world where you had 22, 24 episodes to do, and they were every week. And you were really writing by the CD of pants as you break off and, like, you might do episode 1, you do 2, you do 3. And, I mean, there's a showrunner, but, like, basically, it was much more live. Right? Much more so you needed an army of people. And over time, you know, budgets went up, the money got bigger, so they just could hire bigger and bigger rooms. And they sort of carry that over to the cable world where not all cable shows have this model. Like like, Curb Your Enthusiasm doesn't have a big room. They have, like, 3 guys who work with Larry David. In fact But but Larry David but Curb Your Enthusiasm is, like, a very unique model Right. In that he writes an outline for of 3 or 4 pages, and then all all of the actors are essentially improv comedians, and they improv the scenes Right. Until they get him upset. Like, it it from what I read, they they keep on, like, playing the scene over and over until they figure out how to get him arguing, and then that's the scene. Yeah. And Silicon Valley doesn't seem to be run so differently in the sense that, you look at the main cast, like, Erlick Bachman's, the comedian TJ Miller, very successful comedian. They're all they're all successful comedians, even like, you know, Martin Starr, who plays, Guilfoyle, is not a stand up comedian, but he was in Judd Apatow's Freaks and Geeks where he got his start. Like, all these guys, like, grew up in comedy. And improv. Yeah. So Thomas and TJ are both improv background. I think Zach, who plays Jared, is also a big improv guy. Yeah. So, this is two different questions. But why the model exists, I don't know. I think it just has crept up, and that's why they have this big room. True Detective, for example, only had 1 or 2 people. Like, they're gonna do a season now of True Detective with Nick Pizzolatto and, Milch. What's his name? David Milch? Yeah. David Milch. They have a PD book. Yeah. Two guys, which is, I think, the efficient way to run a show. They have, like, a real voice, and it's just that. But the way it does work, anyway, which I didn't know to run out there, is you sit in a room. You have basically the world's longest business meeting. You sit in a room for 14 weeks before shooting even begins, at least on Silicon Valley, with whiteboards all over every wall and a big conference table. And Alec Berg sits there, and Mike Judd sits there. And the rest of us kinda sit around the the table. And this on that show, there's 4 main guys, Mike and Alec. And then each of them has sort of a lieutenant. And it's really their show. It's really those 4 guys. The rest of us are there. They're like, we hit and you basically have a conversation. You just chip in talking, talking, talking, talking. You don't write anything. There's people at the side of the room who are writing down everything that gets said, who keep a log of every day's transcript of literally every day's con of of every day's conversation. And then occasionally, Alec gets up and goes to the whiteboard and starts going, okay. So episode 3, let's see. See, steam 1 will be this, and he starts writing on a whiteboard. I'm like, everything. And then at the end of the day, they take pictures of the whiteboards. And finally, after all of that, Alec will go and write an outline. So does he have already an idea of the arc of like, when you get there for season 2, does he already have an idea of the arc of season 2? Well well, we didn't when I got there. So we got there literally in day 1. It was like, okay, season 1 ends with them winning TechCrunch Disrupt. What would the next morning look like? Like, literally, what happens the next morning? So so and and if I remember correctly, it's that's when all the VCs are calling, and that's the arc of the whole season. Yeah. So yeah. So my thing is, like, you know, VCs are gonna be, like, you know, crawling all over them. And then then Did they not know that? Like, were your was your role in the writer's room to basically explain what would happen? Yeah. I mean, they they had it. I mean, I don't mean to take credit. But I mean, like, yeah, that was partly why they asked me in. It's like, what would tomorrow look like for them? And I was like, okay. Good. And then and then the idea of they get sued by by Huly. Right? Because they their idea was, oh, so this is great. So now they've killed they kicked Huly's a*s. They go in. I was like, no. No. No. No. Huly will sue them. Like, why would Huly Hulu Hulu stole it from them? I was like, I know. That's why Hulu will sue them, because that's what big companies do. They'll sue them and then tie them up. They can't they don't have money to compete, so they'll end up the lawsuit is just foreplay for, you know, for them to say, oh, now we're gonna buy you on the cheap. Right? And so then we say, no, this really happened. Here's an example. Here's an example. And they go, oh, so they're like, oh, that would be cool. So wholey sues them? Like, wow. We also had to deal with the idea that Peter Gregory, the actor who played Peter Gregory died in real life Oh, I didn't know that. During season 1. Yeah. Wow. Yeah. So then we're like, okay, he can't be in season 2. Obviously, they had written around him for the end of season 1. But what are we gonna do in season 2? And we said, let's have a big funeral for Peter Gregory. And then we can work into that dramatically. And at the funeral, Gavin Belton will now tell them he's suing them. So then it's like, okay. So now what happens? Now they've been sued. How do they get money? No one will rate all the venture capitalists go away. That'll be funny. So we went and we talked to Marc Andreessen and said, what would happen, you know, in a lawsuit? He's like, yeah. No no one will touch you now. If if Julie is suing you, everybody thinks you're a roadkill, so you'll never be able to raise money. So who would you go to if you were in that situation? Andreesen was like, well, you might go here, you might go like, who would be bad money? Who who would who who are the 2nd and third tier financiers? So we wanted, like, a really bad money guy, you know, just to complicate their lives. And they ended up with that Russ Hanneman character, the guy with the doors that go up like this. So so so did Marc Andreessen say a specific name, or did he say you'd go to some, you know, billionaire who got lucky? Yeah. He he had various ideas, like you might go here, you might go there, and you might go overseas, you might go international to people who either aren't very savvy or aren't very nice. So, yeah, he had we had this, like, session with Andres and we're, like, we all went in the whole writing room. We flew up there. Like, every year, they do a field trip. They spend, like, a week going around Silicon Valley. It's a blast. And Andreessen was just, like, holding court, and he had so many ideas. And I think he really wanted to be a cameo in the show. He had, like, seriously, he's pitching ideas to Alec Berg. He's like, okay. You want another one? Here's another one. Like, he just had, like, loads of ideas. And one one night, they had dinner, but only the 4 main guys. Not there were all the rest. The rest of us scrubs. Like, we had we literally get like a per diem and you go out and buy yourself a hamburger, right, or burrito. But the big guys had a dinner with it was Reid Hoffman, Mark Pincus, and maybe it was Stoppelman from Yelp. I mean, anyway, I know the first 2 and a third and a third. Or maybe it was Drew Houston from Dropbox. I can't remember. And the next day, I so we all meet in hotel lobby. We're gonna go out for the day to visit our companies together. And one guy said to me he goes, yeah. We met with these guys last night. He's like, you ever heard of these guys? And it's something Hoffman. I said, Reid Hoffman? He's like, yeah. Yeah. LinkedIn guy? Like, yeah. Yeah. He's like and some of the guy, Mark I said, Mark Pincus. He's like, yeah. He's like, yeah. He goes, are those guys people know them? I'm like, yeah, dude. Like, people yeah. He's like, are they rich? I'm like, yeah. And he's like, well, how much are they like how how much are those when I switch? So I said we added up the the net worth of the 3 guys anyway. And it was like, well, you know, Reid Hoffman's got like, what, 4,000,000,000. The other guy is 2, whatever. And he he was like Like they didn't even know. They had dinner last night with these, like, multi billionaires, and they were just like, oh, really? You know, like they anyway, they were, And then, you know, people, as the show caught on, people in Silicon Valley, in the real Silicon Valley, wanted to meet the writer guys. Like, so it's been this weird symbiotic relationship where they kind of feed on each other, you know? And, yes, it is interesting. Did the actors go up as well? Not with us, but they may maybe they do on other times. But we just we for us, it was just the writers and a couple of the producers, you know? And, we did a meeting once that year too with all these tech journalists around the table. Oh, I think I remember that. Is that where TJ Miller says, you guys have to realize we're making fun of you? No. Because TJ wasn't there. It was just writers again. But it was, like, Quentin Hardy and Oum Malek and, Brian Lamb. It was all these all these friends of mine, and, like, it's really fun. Right? And then the TV writer guys afterwards were, like, they're just like us, man. Like, they just they dress like us, and they could think about stories the way we think of, like because the the tech journalists are like, oh, yeah. You should tell them the story about this or that. Like Brian Lamb told the story about getting the iPhone, that moment when Apple lost the iPhone in a bar, and Brian got it, and Gizmodo got it, and then he tried to, like, ransom it back to Jobs. That's how that story got in season 2. Because Brian Lamb told that whole story, and they were like, oh, we gotta have Richard do that with Gavin Belson, like, get the phone. Right? That was, but yeah, they were all they were the TV writer guys were all kind of interested in the journalists, and the journalists were interested in the TV writer. They're very similar kind of people, you know, except one group is paid a lot better than the Who's paid for? Oh, the TV guys. So some of them. Some of them get paid pretty well. So you go back you get back to the the writer's room. Now you have all these ideas for Marc Andreessen, plus Alec has some ideas. Yeah. Again, what are they so are you, like, pitching funny dialogues or filling in facts? Yeah. Yeah. Making jokes. And then we we sketched out the whole season, so we had it. We worked it from outside in. So we had 1, 2, 3, and we had 10, 9, 8, 4, 7. Like, we had 1 in the middle. I think it was 6. It was, like, impossible. Like, we we got to here, we got to here, and then we couldn't figure out how to make the 2 connect. And literally, it got so bad. Like, we spent, like, like, weeks sitting there, like, all day, and nothing would couldn't we'd get it all sketched out. Like, yeah, that's it. And they'll be like, no. They said Al would erase it all. And then one week, he sent us all home. He said, just had the main 4 guys came into work, and we all got the week off. He's like, because, you know, we're making things worse. We have too many people in the room. Like, it's really they really agonize. That's the one thing I never knew about comedy, or TV in general, but comedy, I think, especially. Like, it's really agonized. These are not happy people. They're stressed out, like like this isn't funny enough. Because then you think it's hilarious. Then they do the table read. They bring in all the actors and do a table read, and it would just die. And they all look at each other, like, oh, s**t. Does it does the table like, I always imagine, like, in on those you know, so so like you said, all the actors sit around the table and they read the script. Are they reading it? Like, is it really supposed to be funny then? I mean, it's funny when they're acting it, because then they're performing. Is it really funny when they do it to you? They're getting laughs, you know? And, And the real laughs, like, I mean, people are like People in the room are laughing, you know? And then but, like, one time we left 1, and it was like even I could tell, like, oh, that didn't go so well. And I looked over, and Mike Judge was sitting at the table, like, because we all leave, and it's just like Mike and Alec and a couple of the top guys stay. I think the actors even leave, but the HBO execs stay. Right? And that's when they get, like, the word from the HBO. And I can see Mike Judge, I guess, like, waiting, like, waiting to hear what the FBI guy said, because, you know and they were gone for, like, an hour. Then they came back and, like, alright. We're gonna have to start over on this one. Like, like, I guess they just didn't like it. But I went to a Simpsons table read when I was out there one summer, and I thought it was hilarious. I thought it was great. People were because they they let a real audience come. Not around, but they let a few people come in, guests, to get real response. Like, I brought my kids and stuff. And so we're all laughing because they're doing the voices and everything. It was it was funny as hell. And at the end, I said to the guy who invited me, this producer, writer guy, I was like, that was good. He's like, oh, no. Didn't you see so and so's face? I'm like, no. He's like, oh, no. That was terrible. Like, we're gonna be up all night, like, rewriting this. This is that was like a bomb. Like, they they really want, like, joke density. You know, they want joke joke, like, you don't have a big law. Do you think that's the big the difference between I mean, there's so many sitcoms on TV right now. You think that's the difference between, like, the Simpsons, which has been around for a 1000 seasons, and Silicon Valley, which is clearly, like, you know, already achieved, you know, comedic cult status, and and kind of these weaker sitcoms, you know, that just just don't go anywhere. They're not really funny. There's a laugh track or whatever. Yeah. Like, maybe that intensity is is what what drives the Yeah. It's not funny. It's hard. I think it's hard to be funny. I I was I wasn't that funny. They they were And you were a humor writer. I mean, you did the fake Steve Jobs. Yeah. But I was, like, I just shut up. I didn't pitch jokes. Like, those guys are like once in a while, but, like, most of mine sucked. I mean, they were they were funny. Like, I I couldn't What's the difference? Like, what I don't even know. And, like, also, why why wouldn't you take a guy like TJ Miller, who's a stand up comedian, writes comedy for for his live his other living, would he ever be in the writer's room and say, no. May have the actors say this because it's funny. They didn't have the room, but they what they did is they would shoot the script. They would shoot the scene with the actors, and then they would do more takes of letting the actors just, improvise. And a lot of what sent them on the show is that. So you start to think, like, as one of the writers who spent, like, 14 weeks here, like, why did you even have us? Like, a lot of the episodes because I would leave, you know? Then I'd watch the show months months later. I'd be like, those episodes don't look like anything like what we wrote. So why even have us? I mean, we were just and I think even that's the process. It's like, spend 14 weeks with a bunch of writers, quote unquote, like, churning out stuff and getting basic narrative arc and blah blah blah. Then you go in and shoot that, but then you ask the actors to it. And then the the real you know who the real writers are? Like, the director, whoever directs the episode, and the editor. Like, basically, Mike and Alex sit there and cut the episode together. And they move stuff around. Like, yeah, maybe that was on page 2 in the original, but we're gonna put that scene over here now. And it really happens in the editing. Like, that's how they make a TV show. Well, it seems like the arc also because that's where all all the tension is. It's where the problems of all the characters are. Like, whoever kinda outlines the the overall thing, like, I bet you that didn't change so much. No. Right. So you gotta get to the you gotta start at the beginning, get to the end of season of episode 10. And like this, you know Yeah. Like like, you know, he Richard has more and more problems, you know, running his company, raising money, and the problems get more and more difficult until this sort of, you know, climactic ending. Yeah. Yeah. And they get yeah. So and there's so there's all these little decisions that have to get made. And I think What about the structure of, an episode itself? Like, is it, you know, people say there's 3 parts or 10 beats or, like, how do you write, like Oh, yeah. Yeah. A TV script or an episode? A lot of shows, they do 3 acts. I think they do act 1, act 2, act 3. Alec Berg, for whatever reason, does not believe in that. So there is no official act structure on those scripts. It's just all one thing. He just write but even so, you roughly when you're looking at it on a board, you can kinda tell this. That's sort of roughly what you would think of as act 1. There's act 2, act 3. But he does not use he doesn't like to think of that structure. So he just has 27 I don't know how many minutes it is, but x number of minutes of stuff. In fact, then the question is, like, do you have it all up on a whiteboard? You're like, how many pages is that gonna fill? And then you're like, how many pages? How many minutes is that gonna fill? So you it's very rough. But he he's I think those guys have just done it for so long. Like, he can tell, you know, where it is. So let me ask you a question. I've pitched this. If I take an exaggerated version of that, like, let's say some billionaire gives away all his belongings to charity, all his money to charity, just enough to live in Airbnbs and, you know, get food delivered and things like that. People are kinda interested in this idea and this concept, and even the story of me has been in the New York Times and and so on. Yeah. I'm not a billionaire, but I'm taking saying an exaggerated version. But you're close to a billionaire. Right? No. No. Nowhere. Nowhere. A fraction of a fraction. But, what how throw an idea on the wall. What would you what what what would be a problem that person would have that could be, like, a TV show? Originally, I thought that could be a a scripted character within another TV show. How can that be a TV show? Like, that's like a Seinfeld character, like George's cousin who Yeah. Yeah. He's like well, is he homeless? I don't know if I call him homeless. Right? Life's like, is that homeless? I don't know. I guess it is. Like, my well, he lives in Airbnb, and he's a millionaire or he's a billionaire, but he's homeless. Right? Like, he's no. My kids thought I was homeless initially because they're because I wrote about it, and their their friends' parents read my writing, and their friends were coming up to them and saying, you know, Josie, is your dad homeless? Okay. And, yeah, they didn't know, so they came and visited me, and obviously, I wasn't homeless. How old are your kids? 18 15. And where do they live? About 60 miles north. Oh, in New York state? Yeah. Yeah. Yeah. With your ex wife? Yeah. Wow. So they did they flip out? Well, they called me and asked, and then they visited. And I was actually staying in a very nice Airbnb. I actually wasn't staying in an Airbnb then. Oh. The story was I had helped someone 10 years ago make some money, and we'd become friends. And he wasn't staying in his place, and he had a beautiful, beautiful magnificent place. So I was staying there. It's like a 2 story bookcase, penthouse. And, so my kids were like, you know, daddy, you're not homeless. Like, you know, and so that's even the idea of it being minimalist is sort of ludicrous when when there actually are homeless people out there. But, like, what's what's kind of For one's a reality show. Right? That's the most obvious one. It's like Yeah. So let's say not reality show. Yeah. Because but yeah. Because you need so what sets it in motion? Right? There's the guy. There's the character. But what sets it in motion? Someone has something has to, Well There has to be I have to have a problem, or this the character has to have a problem. Or it's the other one. The the other the other one, you start with before. Like, so the stasis is whatever your life was before, building to the decision to, like, throw everything away. Right? Like, that's where it begins. Like Okay. And I don't know what brought you to that moment. What brought you to the moment of of throwing everything away? It's a long story. We'd have to that'd have to be a separate podcast. Yeah. Oh, okay. We'll we'll do another one. But but, so but that's that's the moment. Right? The guy snaps and just says, I'm selling everything, giving everything away, whatever I'm gonna do. I'm gonna have 15 did you pick a number 15? Was it a real number? Like No. No. It was just you put a constraint on the number of things. Yeah. No. It was just, the New York Times story about it, said I'm gonna go read that. 15 items. Yeah. But it's roughly that. Like, I have, you know, a couple outfits, and everything has to fit in, like, one carry on bag. Wow. So there are some rules. Like, there are constraints. Like, I won't buy something unless I throw something else out. Yeah. Yeah. And so and I have no books because I have a Kindle. Right. So but So yeah. So but But then what happens to that guy? Right? Yeah. It seems like What gets you through the season? Yeah. Season 1, right? What's the arc of that season? We should do this. We should, we should brainstorm on this. Because it's gotta be something. Maybe he I don't know. Alright. Think about it. Yeah. Yeah. Right. Homework assignment. Yeah. I know that. Because I'm I'm I've realized something about myself over the years. It's like, I'm not very good, like, on the spot, but I'm the type that, like, an hour later, I'm driving on the road, like, and I think, oh, I should have said that to that guy. You know, like, when someone insults you, and I always think of the good comeback, like, a day later. You know what I mean? I Usually usually, I'm pretty good, but when it comes to, like, this one thing, I'm having a I'm having a hard time. Can't I can't get through it because maybe there is no, you know, maybe it's just interesting, like an anecdote, but it's not an interesting story line. There's no story. I was thinking he could be, you know, working in a as a shelving books in a bookstore, and no one knows, and he's always, like, solving people's problems, you know, in some weird way. But then still, like, it doesn't write itself. Like, some TV formats, like even Silicon Valley, not that it writes itself, but I feel like, like you said, what happens the next day after that he wins the TechCrunch thing? Okay. We know all the venture capitalists will be calling. They're gonna go into a feeding frenzy where they'll do ridiculous things to, you know, convince them to get money. Then something bad will happen where they're no longer able to get money and, you know, kind of works its way through. But that's still right. But then they still get the thing I noticed about TV, because I always thought, like, oh, they then the rest of it just happens. Like, no. Like like, they sit there and sweat bullets for weeks with a team of people. You imagine. So the situation you just mentioned. Okay. This is the deal. Blah blah. Now take 10 people who have done a lot of writing, who are pretty smart, funny people, sit them in a room, and just let them brainstorm for a week, like 8 hours, 10 hours a day with whiteboards and, like, see what you get. But that's that's the process. And with the same kind of naked fear, except even worse is like in your case, if you can't think of anything, well, it's no big deal. In their case Right. They're paid. They have they have to air. Yeah. They they somebody has to go on the air. Right? Like so I asked Alec about that because I was like, with Oxy, we're so far in advance. It's only 10 episodes, and we're working in the summer. And then you shoot we're gonna be fine. With Seinfeld, they would be at the like literally the brink, like the night before, and they would rip the whole thing up or it would all fall apart. Like, they really were going almost live. Like, in that terror of not knowing, like, s**t, man. We gotta have something, and it's like Thursday. You know? Yeah. Like, they really lived with that deadline pressure, which and he said and he also said to me once, and he just said, like, you know, that's why they're not all that good. Like, they're not all good. They're not all equally good. Some some of the shows we did weren't that good. Like, we knew it. Like, we're just sorry. It's Although Larry Larry David, you know, who who, at least for the first, whatever, 6, 7 seasons, I don't know how many seasons, he had interesting I mean, he was the one rewriting at the end on that Thursday night or whatever. Him with Jerry, I guess, but Larry David was, like, doing a lot of the writing. And he had, I guess, the philosophy that he was gonna do a storyline for each of the 4 characters, like a main storyline, and then have them intertwine. And this was kind of new, and that kind of drove that was like that was like this unique force that kind of drove each episode. Yeah. You know, part part partly, that was like a leadership skill. He didn't wanna disappoint any of the actors and keep them he wanted to keep them all motivated. But and and then the other thing he did, and maybe I'm explaining this out of turn. You probably know all this. No. I don't. I actually don't. He he would fire the writing staff or most of the writing staff each year because he'd get new writers to tell their New York stories to have new story lines for the characters. So that's where Alec gets Alec does the same thing. Like, that room turns over, it turns over. So there's not which is And Alec was one of the few people who stayed. Right. He survived because Larry liked him. Yeah. Yeah. I didn't know that was his wife. But, yeah, I knew he had done several years, but I didn't know that Seinfeld room turned over constantly. The the so does the Silicon Valley. I'm like, I had heard a lot of shows, you get hired in, then you just stay for the 7 year run of the show unless you really, you know, do something horrible. Like, basically, and they might add more people, but you could stay. But in that room, it just turns over and turns over. Even so and I think for the same reason. Alec And do more Silicon Valley stories? Yeah. Like, he got all of mine. Like, he doesn't need me anymore. You know what I mean? Right? What does he need me for? Right? Well, I mean, there's always new ones and new interpretations of the stories that are happening. Like, what's going on in Silicon Valley right now? What's hot? What's not? So they always need someone who can interpret the news. But they'll get every year a new batch. They had Dick Costello one season when I was Oh, yeah? Yeah. He worked 2 days a week. Came down and spent 2 days a week in a row. He he was in an episode in season 3, I think. That's right. Yeah. He got a cameo on that little, dinner scene or something. Yeah. Yeah. He he wrote the foreword of, one of my books. Did he? Yeah. A book I wrote in 2013 called Choose Yourself, he wrote he wrote the foreword. He's a good guy. Right? Yeah. He's a good guy. Yeah. I like him. Yeah. I I got to know a little bit. And, He's a funny guy too, you know. He went to, I'll tell you a little story that I think he either told me or no, he told it in a speech. He was in Second City, you know, the improv group. Oh, yeah. And there was once a reunion of all the Second City guys. So he runs into Steve Carell, who's from, you know, The Office and and so on. And, you know, they're all saying what they're doing. Of course, Steve Carell is doing The Office. He's done many things. He's done many movies. And Dick Castell is, like, well, I'm the CEO of Twitter. And Steve puts his hand on Dick's shoulder and says, sorry it didn't work out for you. You know, because you're not succeeding as an improv comedian. Yeah. Yeah. Yeah. Yeah. Yeah. Oh, well. Yeah. And that's it's a it's a good, consolation prize. Yeah. Yeah. So so okay. So so you're in the room, and are you helping to to figure out the critical plot points? Like, what's your proudest moment from from that first season you were doing with, you know, the second season of Silicon Valley, but your first season there? I think those plot points about the lawsuit and about how they would have you know, what would happen to VCs and and, yeah. And a few other contributions. There was a a big there was a sequence in the middle of that season where, I forget the name of the company, but some company offers to buy them and then they want to merge them. And there was there was a big problem in the middle plot wise that we couldn't figure out. And I I managed to sort of crack the code a little bit and put together, like, the glue to get from here to here, you know. And and so there were certain ideas of mine that showed up that were kind of fun. I had a joke about tech they're not tech they're not real reporters or tech they're not real journalists or tech journalists. Like, we don't think these guys are gonna go to jail for you or that kind of so a few things here and there. But, I like, Russ's there's some lingo that was used in the show that kind of became, you know, lingo in Silicon Valley. Like Russ saying he was no longer a 3 comma guy when he he went less than a1000000000. Yeah. Like that has become a thing that people talk about. Yeah. I don't know who came up with that line. But it sounds like there's a writer on the show named Dan O'Keefe. And it sounds like something he would say. But I don't know. That might have even come out in shooting, you know. And they had that tequila, Tres Comas? Tres Comas? Oh, I don't I don't remember that. Russ Hamlett, yeah, had his own brand of tequila called Tres Comas. But it was like, get it, like, 3 commas or something. I think was Yeah. Then they were gonna actually make a branded tequila, the show. Or Mike and Alec, or whatever. They were gonna make they were actually gonna make a tequila like the one in the show and sell it. I don't I don't think they would do. So so so then you're you're you have this great exciting time. It's like your dream job. It's what you have been aiming for since getting your MFA and creative writing. Yeah. Yeah. Yeah. And then you got after the 14 weeks are over, did you consider trying to stay in Hollywood and maybe pitching some other shows to Larry Charles or whatever? Or Yeah. Yeah. No, I did. And I did do that. And I pitched some things and, have had some meetings. And I've and then and the original idea for Disrupted I had was like, oh, this could be a movie or a TV show about the old guy working in a cookie company. And I thought, if I do it as a spec script, it won't it would be hard to sell. What was the movie that where there was, like, an old guy, De Niro. Right? Oh, yeah. Yeah. The intern. Yeah. So yeah. So as I'm so I sold the book. So I thought I'll do a book. Then the book, just like with fake Steve, if I had gone in with a TV show cold, like, I got this idea. It's like a guy like Steve Jobs, they were like, no. But, like, because they had the book and Larry Charles read the book, and he liked the book, then he's like, now I have a vision because I can see you have to start with some IP. Right? So, I thought I'll do a book. And then then I can go into studios and networks with this book. Yeah. And then as I was writing the book, someone said to me, what's the book of mine? So that's about this funny book about an old guy. They're like, oh, like that De Niro movie. I'm like, what De Niro movie? Like, oh, it's coming out next month. It's it's De Niro. I saw a trailer for it. I was like, oh, s**t. So I don't know if that killed off the potential for I mean, my book's different than that. But, yeah, but that was my original idea. And then so I've had a couple of meetings. I pitched it as a family comedy at ABC, but didn't didn't go. I've had some meetings where I pitch it to different people who have read the book and want to talk about adapting it. Or it's just, you know, hard to get it, like, set up at the right place. And then I've had other ideas. You know, I've had other show ideas that I've tried pitching, but so far nothing has gone. So you go after the 14 weeks are over, you go back to HubSpot. And was that such, like, you know and then and this is after they kind of were encouraging you to leave. So it just seemed like things just went straight to hell when you got back. Yeah. It went pretty bad. Like, that was, like it was very clear, like, we really you didn't get the hint, so we have to make it more we have to be give you more of a hint. Like, yeah, we really would like you to leave. And I think there's a lesson here in that, you know so you're I'm always asking your age, you're like 54 then at this point? Yeah. You're there at a year and a half. You're working to save it. Yeah. So you're 54. You had obviously achieved some some highs and some lows in your life, some some dream things. You'd published novels, you'd worked on a TV show, you worked for a hot tech company, you worked for the best journalism places, but bad things happen no matter what. Like, you know, every life is almost like a TV season. You have, like, the overall arc, but then ups and downs in every show. Yeah. And how did you deal with kind of going from, like, this amazing high of working on, you know, one of the best shows out there right now to back to hub HubSpot? Or, like, didn't weren't you pounding the table? Aren't you guys gonna treat me better? I was just I'm on the hottest TV show in the the world. Yeah. I know. I I wasn't. And, I mean, I kind of felt like I I must I must have some some talent because it was just on the show. You know, whatever. So I I but no. Like, it's just I went back and it was, like, really, really no. You're, like, failing. You suck. You can't even do this. Like, I was like the I was supposed to put together a podcast, and and it's like complete the boss I had was just telling me, like, you suck. You're not even doing this. You're failing. You're not gonna make it here. You know, this is only for the past. Did you bite back? Like, and say, look, I just put together the best TV show in the world, and now you're telling me I can't even be, like, a gopher on a podcast? I didn't know. Like, you know, it's like, you know, it's funny. Like, that kind of abuse, you sort of internalize it and start to believe it. Like, it starts to get, like, maybe Like a Stockholm Syndrome type of thing? Yeah. Maybe I really do suck. Maybe this guy's right. Like, I'm totally failing. I keep trying, and I'm trying to make a go of it. And, yeah. No. I I yeah, it's very, very destructive. It really is very, very I mean, there was part of me that thought, like, you know, this is unfair. But but it was more just like whether it's logical or not, this guy wants me to leave. Like, he wants me to go. And finally finally, I did pull him aside and said, look. I don't know why you're riding like this. I'm looking as far as I can to get another job. I will get out of here as fast as I can. Okay? I promise you. Right? And, you know, just lay off me. You don't have to ride me. Like, you you the message got through. I get it. You want me out of here. I will leave. Just give me a few weeks to find a job and just get off my back, you know? And then that didn't last long. He sort of said he would. But like, it was it was just toxic. And he and I had been friends, you know? So it was weird. It was a weird psychological yeah. Well, I think I think, you know, at this time, to to kind of set the scene, HubSpot was getting closer and closer to an IPO. They had filed their financials, and And so probably everyone was kind of jockeying for position. Nobody wanted to be let go right then before the IPO. Yeah. And everybody was stressed out. It was a very stressful time. I mean, he had stress from his boss. And, yeah, I think they were really wanted to get through the IPO. And I kind of wanted to just hang out and at least be there for the IPO, which I think was October November of what year were there? 2014, I guess. Who uses their product? Because I've never met anyone who uses their product. It's kind of like a Salesforce sort of product. Right? Yeah. It's it's marketing automation. So it's a little it's mostly small businesses. Small companies. And they keep track of customers who shop in their store? Yeah. Yeah. Send them emails. Yep. And you can launch you can write a blog, and you can track who visits the blog, and you can create, a call to an offer. Like, you can create an ebook. And then you might have a blog post about about the blog post might be, 7 tips for making a great podcast. Right? And you read it. And then it says, wanna learn more? Download our free ebook. Everything you need to know about making a podcast. And you click on it. And to get the ebook, you have to give them your email address. I mean, that's the call to action. So you you and then I you've given your email address, and then they send you the the ebook. Now you can read. So and a lot of it is content aimed at small businesses. So little mom and pop firms or flower shop or plumber. So, like, you know, it actually is very valuable to small companies that don't really know anything to say about how to be on the Internet or how to make these things. How do you Snap? Can I use Snap as a marketing tool? And then they'll create an ebook and gate it behind a form. And you, you know and then they just stop badgering those leads. They throw the leads over the wall into, like, this pit of telemarketers who just hand you to you. And it's a subscription model. So it's SaaS. It's delivered over the cloud. You sign up for a year subscription. Okay. And so so you're getting closer to the IPO. They're they're they're pushing you out. You kind of survive to the IPO. Right? Yeah. And and then, the second you confide in this your your boss is the character you call the character Trotsky throughout the whole book. That's not his real name. You you mentioned your own name in the epilogue. But, you kinda tell him at one point, okay, you're gonna quit. But then immediately, he puts you through the system and and escorts you out. Yeah. Yeah. That was weird. Like, I I it was right before Thanksgiving, and I found a job that would start in January. So I'm like I funny, when I tell the story now, you know, I think back, and I think I'm like such a creature of, like, I don't know, working class or middle class values. Like, I I it was very important to me to, like, not to always have a job, you know? Like and so it's very important to me, like, okay, I'm gonna start January 1st in a new job. So I gave them notice, and I said, look, you know, so it's, gonna be Thanksgiving next week. So everybody be out most of the week anyway. Then we'll come back. It'll be December, except the last 2 weeks of December are the holidays. So but, basically, I'll take the next few weeks and make sure the podcast is handed off to someone else. We get a nice glide path there. And, and then I'll leave for the Christmas holidays, and I'll be done. Like, in most places I worked, I think that would have been, like, normal. They'd be like, okay. You know, we'll pay you through the end of the year and, you know, you do your thing, do the hand off. And, like, that would seem to me normal. In fact, I thought, nice. I could have waited and just waited till December 15th and said, sir, you're all married. Or I would never tell him at all. But anyway and that was a Thursday, I think. Wednesday, whatever day it was. And he said He called me later. He's like, Yeah. Can you come in tomorrow and just, we'll start up, you know, all the paperwork and you're gonna set up an exit interview. The HR people want to talk to you about yeah. Yeah. Sorry. I'll come in tomorrow. So, I went in, and there's an email. I checked my email. I log in, check out my email. And there's an email from the CMO telling everybody, oh, just from, like, the day before. Saying just want you to know, you know, Dan is leaving, and we wish him all the best, and his last day will be today's his last day. So, you know, and I was like, today's my last day. What? Like, no. I and then I was like I said to my boss, like, dude, what's this? And he's like, well, come on. Let's go. Let's go talk right now. And, like, we went into this little room, and he's like, here's your exit paperwork. Here's your termination letter. Give me your laptop. Thanks. Don't touch anything. Bye. And, Did you get paid through the end of the year? I wasn't going to, but then I had a little bit and did get paid through the end of the year. But, at first, they were like, no. Everything stops tomorrow. Your health insurance stops tomorrow. Everything done. Bye. See you later. Bye. I said, wow, dude. That's cold. Like, that's like, I don't I don't know if I ever did anything to make those guys really hate me that much. And I don't think I did because I've heard from other people, like, the same there was a woman who got fired after 12 weeks. First job out of college, I said, you're just not excited enough. 1 Wednesday, see you by. Don't even take your stuff. We'll mail it to you. Just get your coat and go. We'll mail all the stuff, all your little knickknacks on your desk. We'll put them in a box and mail it to you. Like, people would get canned all the time. Did she did she cry? She cried. She was a young woman from not from Boston, suddenly walks out into the cold in February, like literally, it's the middle of winter. She's 22 years old. Her parents are in South Carolina, Southern North Carolina, and she's all by herself in this city with no job and no savings. And and, yeah, it just breaks down crying and then, like, has to knowing she has to call home to her parents and who are, I think, kind of strict and a little old fashioned and weren't, you know and disappoint them and tell them, like, you know, I I know you put me through college and everything, and I just screwed up. Like, it was horrible, like, this poor kid. She said her parents actually were very nice to her. Her parents were Yeah. Sure. Understanding. But So so so you you leave, and then you what's you you do this epilogue to your book, like you you leave, you write this book disrupted about this experience, and you and definitely, I encourage people to read it. It's a page turner. You can read it in like a couple of days, and so much stuff happened to you. But the epilogue was fascinating. Apparently, they tried to, like, hack into your emails to find the book, and people got fired at their highest sea levels and, like, did you ever find out specifically what happened? No. I mean, it won't tell me. I mean, I've asked. But so they they, I was writing the book. At one point, I got an email from the CEO asking me what's the book about? I told him, said blah blah blah, I went back and forth. Then he went dark. But a month later, I'm at my desk one day at the end of the day, and someone sends me a link. Dude, is this you? And I open up a link and it says, we fired our CMO for cause. We sanctioned our CEO. And this other guy, who'd been my boss, VP guy, resigned before we could decide whether to turn in. I was like, wow, that's harsh. Like, they actually included him in the press release even though they didn't have he'd already left. And the investigation must have been at a high I mean, the FBI was mentioned. Like So they said and says we've turned this all over to law enforcement. We've conducted our own internal investigation with a law firm, determined this is what we need to do. So these guys are gone. It was and it was efforts to obtain the manuscript for the book. They didn't say who I think. It's gotta be me. And this thing, you know, I get a call from the FBI saying, Yeah, we're investigating this and we need your command as a witness. I'm like, great. Now they'll finally tell me what's going on. But the FBI won't tell me, and the assistant US attorney won't tell me. They asked me a million questions, and I answered them all. And then they I did a FOIA request, and I got some documents and heavily redacted, though. But basically, there was more than that. There was some sort of conspiracy to extort me or extort the publisher. They were gonna try to get dirt on someone and then say, if you don't kill this book, we'll release these compromising stuff. Right? But I never had any blackmail threat. The publisher swears he never had any blackmail threat. So it might have just been there So how did this even start? Like, how did this how did anyone know there was something bad going on? Like, who I that's the other thing. I don't know. Apparently, I think someone internally found out about it and ratted them out to the general counsel. So it was a whistleblower? I think so. And the whistleblower oh, and then also some according to the FBI docs, there was some kind of a John Doe lawsuit filed in California that they thought it says which HubSpot people thought might be related to the extortion attempts. Like, they were trying to extort someone in California. I I don't know. Like, you can't really even reading these things, and I should go back and look at them with fresh eyes. But I I poured through these things. I could never piece together what had happened. Now the thing that drives me crazy is HubSpot commissioned this full report by a law firm, and they have it. The board members all have it. They could just give me a copy. So I'd at least know. Like, did they hack my computers? Did they break into my house? You know, I don't know what they did. Now it may be, one lawyer suggested me, maybe that really the reason the whole thing was dropped is they talked about doing all these things and sort of started doing some stuff and then got caught. And so nothing really happened, so there's nothing to worry about, which maybe is the case. But I don't know if they would then fire everyone. Right. Yeah. What's the what's even are they guilty of, like, conspiracy to maybe do something? Like, I don't know. Yeah. Right? So I so just so I don't know. So I have never been able to figure what they did, but it was very scary in the sense that, like, I was writing this book about them being a bunch of goofballs with a kooky culture and, you know, talking about changing the world. I never thought they were like really, really dangerous bad guys. Then I think maybe they are, you know? I don't know. Well, there's that kind of money involved. I mean, you know, the founders went from having whatever money they had to, you know, 100,000,000 more. So it's a it's a lot. They don't wanna be, you know and they had tens of thousands of customers. They they, you know things get dangerous. Well, I think also there were I Why don't you go back to Silicon Valley, and now you have a whole story with that? Right. Exactly. Right? The guy getting hacked. That's not a value. But there was also, I think they were more concerned about gossipy stuff about maybe people behaving badly at work. And, that they thought was gonna be in the book, which I didn't know anything about any stuff like that. And even if I had, I wouldn't have put it in there. I wouldn't try to, like, you know, ruin someone's marriage or whatever. Like, you know, I I the book is supposed to be a funny book about me and kookiness, you know? It wasn't a big dark investigative expose of this company. Blah blah blah. You know, nobody cares about it. That was the other point. When I was selling the book, like, every publisher that I talked to said, you know, they like the book, they like the pitch, and a bunch of people bid on it. But they're like like but we don't care about the company. This can't be a book about this company, because nobody gives a s**t about this company. Right. I think I really see the book as, the company is in is in the background, and it's a book about someone in their fifties going through this major life crisis and how he solves this problem. Yeah. Yeah. Something that everybody in their fifties is gonna go through to to some extent, you know, there's a spectrum. Yeah. No. No. I know. So but in their mind, like, they're so in their bubble that they kind of thought this is a book about hustle. Like, that's how it got played in the Boston media and how they've distorted it. It's like, this is a guy who hates husband. He's writing a book about hustle. It's like, not a book about hustle. It really isn't. And, frankly, after the book came out, then, of course, other people got in touch with me, and I have heard some things. And I thought, oh, I wonder if they thought I knew that. Because if they thought I knew that, and if they thought that might be in a book, that probably would have scared them. But it was things that I didn't know at the time. Then now, of course, I hear, but I'm like, oh, that was Can you say any of them? No. Yeah. Okay. I'm sorry. Not on tape. Some of it's horrific. And then so the next summer, did you go back to Silicon Valley? Or While I was working on the book, I took a break, went out to to LA for 4 months or 3 or 4 months and worked again on the on season 3. Was it fun? Yeah. I mean, it's kind of fun. I mean, it's I just tell people, it's a lot more fun to watch the show than to write the show, to be on the because you just sit there doing nothing a lot. You just hang out in rooms, you know, talk and listen to other people talk. Because imagine a business meeting with 10, 12, 14 people in it. Yeah. You know? And you're not the main person. You're down at the other end of the table. I would sit there with Dick Costa like this, like, sometimes for a whole day. Like, a whole day just looking at each other while other people talk. Every once in a while, I'd be like, Dick, is that was that accurate? I'd be like, yeah. No. I think that's well, you know, and they'd be like, okay. Thanks, Dick. Bye. Boom. Boom. Boom. Boom. Like, like, just you spend a lot of time doing nothing. And then, when they were filming, were you ever there? Yeah. Yeah. So a little bit. And that was really cool. I always wanted to see how a show gets made, you know, and, like, the cameras in the rooms and stuff. Again, it's, you know Yeah. To me, it was very cool, and I I liked it. And so what are you doing now? I am writing another book. I have a contract to write a book. And What's it about? Workplace issues and sort of building on some of the stuff that was in Disrupted that is be not about HubSpot, but about aspects of of work that I think are interesting. And I may I'm still trying to develop Disrupted as either a movie or a TV show and keep having meetings about that. So yeah. Alright. Well well, Dan Lyons, author of Disrupted, I highly recommend everyone read the book. I've I've actually read it twice now because I read it when it first came out, and I read it in preparation of this podcast. Really? Enjoyed it both times. 2nd time had the epilogue. I I don't think I remember reading the epilogue the first time, so unless it came out later. Right? Did or what did you have the epilogue at the was on the first book, but there was a little more in the paperback epilogue. Did you get the paperback? No. No. I had the I had the when it first came out. But you know what? On Kindle, I think they've updated it now. Oh, okay. Maybe you got the updated epilogue. Yeah. Maybe. So so well, I highly recommend the book, and I also recommend, people watch Silicon Valley. It's one of my favorite shows. So thanks very much. Thanks very much. Next time on The James Altiger Show. By the time this podcast is out, this book will be out. What if this book just doesn't do well? And you get, like, the worst reviews and, you know, you've worked so hard on it. You know, the more you work on something, the more it is. It's funny. I've come to peace with it because I've thought about this. Listen, I would love to hit number 1 New York time bestseller, but I'm also like, if I didn't get on the list at all, how would I feel? My ego would be hurt, and I'd be sad, and I'd be frustrated. But I believe, like, I've become so at peace with it already either way, whatever happens, it's more important to me to get the message out than to get the result. I haven't put my whole life into one book, where if like, as an athlete, my whole life was around being a college player, making pros, and if I didn't make it, then my life was over. This isn't my whole life one project. And I think if it doesn't hit the list or it doesn't do this, like, what's the lesson? I think what's the lesson is a very important mantra. Hey, everyone. Thanks so much for listening to this episode. I really hope you enjoyed the show. I wanted to just say thank you to everyone who has rated and reviewed this podcast on Itunes. I really enjoy reading these. It means a lot to me and I'm grateful for your support.