My First Million - The insane true story behind MTV

Episode Date: May 29, 2026

Sam & Shaan's hard-won CEO lessons in one guide: https://clickhubspot.com/eokb Episode 829: Sam Parr ( https://x.com/theSamParr ) sits down with Tom Freston to talk about the insane story of starting MTV and shaping America in the 80s and 90s.  — Show Notes:  (0:00) Intro (4:04) Millionaire by 26, broke by 33 (8:49) The first days of MTV (no frontal nudity) (14:14) Music Videos (19:03) How to spot culture-changing talent (27:12) Making your employees party together (31:56) Nickelodeon, SpongeBob, and Building Legacy IP (35:21) Programming for a Specific Audience (37:33) The Facebook Acquisition That Almost Happened (41:25) Founders Who Refuse to Sell (43:29) Rupert Murdoch vs. Sumner Redstone (45:23) MySpace, Big Bets, and Getting Fired (47:55) Inside the writers room (51:33) Oprah Calling  (54:00) The End of Monoculture and the Creator Economy — Links: Unplugged - https://a.co/d/0ef6YVu2  — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

My MTV Hit List. MTV. MTV. MTV. MTV. We grew the company from zero to billions in revenue. Yeah. We were a high margin money machine.

It was sort of the height of the cable TV revolution, which began to deteriorate in the early 2000s with the digital revolution. You helped create South Park, Chappelle Show, Stephen Colbert. We had Jimmy Kim along. You got to start there. Bill Maher got his TV starred on Comedy Central. You're recruited by Steve Jobs. Same with Geffen, who is one of the most successful media business guys there ever is.

You, I think, made an offer to buy Facebook. Is that right? Yeah, we were the first people. We went back and forth and we put a bit on the table and they turned us down. What was it? It was like $1.7 million. Billion, excuse me. When you were, like, trying to spot winning people or creatives, was there like a common theme?

Yeah, well. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. I was trying to think of the way that I could introduce you. Tom helped found MTV, which was one of the most important networks when I was raised. Like going home and watching TRL at like 3.30 was like the greatest thing ever. But then you also owned VH1, Comedy Central, which meant you helped create South Park,

Chappelleau show, John Stewart's Daily Show, The Daily Show, Stephen Colbert. We had Jimmy Kim along. I mean, he got to start there. Bill Maher got his TV starred on Comedy Central. Yeah, it goes on and on and on. And then also, this is a business podcast, you grew the company from zero to billions in revenue. Yeah. Billions.

We got up to like $8 or $9 billion. That includes consumer products, which became a big thing for us because we would own the IP of all the Nicktoon Spongebob. Yeah, you own Nickelodeon. So Ren. That actually was the biggest business. Nickelodeon was? Yeah. By far.

I want to talk about that business, but I just wanted to like show like the traction, not only from a cultural, like, you had your impact on culture, but also, the business side, which those two aren't always correlated. Yeah, it was a wonderful business. I mean, we were a high margin money machine. It was sort of the height of the cable TV revolution, which, you know, began to deteriorate in the early 2000s with the digital revolution. So, yeah, we had amazing business model. I mean, because we had three revenue streams. We had subscribers, which is like one-third to 40 percent, you know, from cable operators or satellite operators, advertising and then consumer products, movies, and other things that we would do. How old were you when you started it?

I was the oldest guy when we started MTV. The development team was seven or eight people, and I was 33, and I had front of business in India and Afghanistan. We used to design and make clothes and sell them to better stores here and in Canada and a couple of other countries, and I knew nothing about that business, but I wanted to live in India. Were you like a hippie and you just like went over there? I wasn't a hippie.

I had been working in an ad agency in New York, and they assigned me to Charmin toilet paper, and that was like the last straw for me, a line I couldn't cross, and a girlfriend, ex-girlfriend called me from Paris, said, oh, man, you can't sell toilet paper. I'm going across the Sahara Desert. You should just come with me, quit your job, don't do this. I was on a plane like, you know, 10 days later.

Which is weird because I think I read that you graduated number one in your class from getting your MBA at NYU. you. I did that. Yes. I went to business school primarily, originally to stay out of the draft because Vietnam War was raging. And then in business school, I encountered people like Peter Drucker and professors I was really entranced and turned on by business. And then when I got out of there, I basically decided I'd do menial jobs and bartend my way around for a year and sort of take what people would call now a gap year. So I worked like an Aspen in the Caribbean. And, you know, there was a well-rounded experience. I'd recommend for anybody to do.

I was sort of the King of the Road kind of phase for me. Then I came back and got a job in an ad agency, which was interesting on another level working at a big organization, a creative organization at its heart. And then I quit and went traveling, across the Sahara Desert. We split up.

I kept going. I ended up in India and Afghanistan because I had met another woman in Greece. She said, oh, you should go to India. That's like the Holy Grail. It's the greatest show on earth. In the 70s, it was, you know, 60% of people were under the poverty line. It was really way before, you know, the 90 economic reforms in India that really transformed a place.

So I decided I wanted to live there. Then I said, well, what am I going to do? How can I support myself? Because he couldn't get a job there in those days. And she had told me this woman in Greece, she had lived in Kathmandu, and she would make and design her own clothes. She was a former clothing designer who was sort of dropped out from New York City. And she would live in Kathmandu, like a queen. She would make and design these clothes and then take them overland and sell them on beach resorts in the Mediterranean in the summertime.

She had her own sort of vertically integrated conglomerate. And I said, well, what if I scaled that up and I could do better stuff than the commodity imports and find partners and build businesses and factories? And our peak revenue at the time was probably $8 million. But that was then. What year was that? This was 1972. So that could be like 40 million today, right? It was good.

I mean, I was, I had my first million in my 20s. How old were you? 25, 27. I was probably no, 26, 27. Did you make a million? Were you going to take home anything? Well, yeah, I made it, but it was, but you've probably known it was on paper. Oh, yeah.

It was on paper because it was all tied up in inventory. It was tied up in receivables. You know, you found I had to pay for goods in advance. It was fun. When you wound it down, I think you're what, like 30? A 33. I wound it down. I mean, I really got yanked out of the business because in Afghanistan there had been a communist coup that kind of drove me out of there. And then I doubled down on my business in India. And then, of all people, having endured strikes and blackouts and dust storms

and all these delays and having to pay, hustle Jimmy Carter put us out of business because he put an embargo, not a tariff, but an embargo on clothing imports from India. So did you walk away with anything? No, I ended up smuggling three tons of clothes over the St. Lawrence River to meet a delivery date at Bloomingdale's. We were doing a big, they called the India, that was it called a fantasy India. And I shipped clothes to Canada and then brought them in, you know, try and put a dent in my debts. But I ended up broke, bankrupt, and deep in debt, you know, just like had my whole business yanked out from under me. It was the hardest work I'd ever done or would ever do.

Hey, everyone, really quick. If you're enjoying this episode on CEO stuff, so delegating, having hard conversations with your team, hiring, then I've got something for you. So the team at HubSpot, they actually went and put together a bunch of best practices that Sean and I use in our own companies. And they put it together in something that's really easy to read and understand.

And so if you want to just save yourself 10 years of headache and heartache, then you should check it out. I wish we had this a long time ago. It would help me a lot, but there should be a QR code on your screen that you can scan or a link in the description. So check it out. It's totally free and totally awesome. You're 33 and broke. Yeah, broke. And I'm going, coming back to New York and all my friends who they've grown up, they've got married, they have mortgages or whatever. So I said, I've got to change careers. I need a new line of business.

Well, I said, I heard that you read a book. Yes, I bought a book. The only self-help book I ever bought. and it was the first edition, What Color is Your Parachute? You're the second successful person I've talked to in the last month that said that book changed their life. That book so changed my life.

And it is a simple premise. You have a series of skills that come out of your personality and you've built them and they're transferable from one industry and other. You can change careers. You can do different things.

But at the heart of it, there's a few things used to think about. You basically want to do something that you love and you're attracted to. I mean, that's an o'brose. It would be great to get a business, you'd go to work in a business that's also not only that you love, but it's ascendant. So it looks like there's some forces that are making this business rise. And then they gave you all these exercises to determine what skills you have and how you match them up.

So I sat around my kitchen and did them all and I said, voila, I want to go in the music business. Now my brother was in the music business. I used to watch him. I say, well, I could do that. but I had an encyclopedia acknowledge of rock and roll music. Okay. I got hired at the company that would become MTV and MTV Networks in March of 1980. When they started the company, when you guys all started the company, it was eight of you trying to figure it out.

I think I read that you got like 35 grand a year. That was their first year's salary. That was, I got more than anybody. Everyone else was getting 30. What did you get? I got 35. What was the seed money to start it? we had a when I finally got a proof we were the child of American Express and Warner Communications it was a joint venture why would American Express want to be in the TV business good question they got into Warner Cable in the 70s that developed this interactive thing called Cube it was going to be interactive television if you can imagine such a thing QUBE and it was a test they had in Columbus Ohio and American Express thought this would be a great way for you can imagine such a thing QUBE and it was a test they had in Columbus Ohio and American Express thought this would be a great way for

them to get into the interactive television business, which is the first, you know, iteration of it. So they formed a company and they said, we're going to, we're going to bid on and get franchises in big metropolitan areas because no one had cable. It only really existed in rural areas. So then they said, well, we're going to have to feed the system. We need to feed it with some channels of programming. So they started a second smaller company, Warner Amics Satellite Entertainment Company, or it's a mouthful, Wasak. And they started the movie, the movie channel, which was sort of like HBO. It was 24 hours of movies, just movies.

Was it, is that the precursor of HBO? No, HBO had been around since 74. It was doing uncut movies, and that was a big innovation. And it was using a satellite, which was our other innovation. We would not use broadcast towers, but we would bounce off a geosynchronous satellite, 23,000 miles up there. This does to sound like outer space stuff. And this little satellite company, we had Nickelodeon, and then we were going to launch a whole, you know, portfolio of channels.

MTV was one of them. It was called, we're going to do a music channel of some kind. And it would be, instead of being a broadcast network, these things would be what we call then narrowcast. We're only going to program one genre, and we're going to do it to one segment of an audience. Because before it was like ABC, there's only like four channels, and it was like, we've got to do everything for everyone.

Yeah, every, and so basically, no one... It's like we're going to be a niche network. We're going to be a niche network, do one thing all the time, do it really well, build up a relationship with our viewers. And, you know, so we were sort of existing on the side of the highway. And that was a, you know, a wonderful place to be because the major networks would live or die on their shows. People knew the shows. They weren't really that conscious of whether it was NBC or ABC or whatever. We were going to be places, not shows.

So you're going to watch MTV, you're going to watch Nickelodeon. Was that a new idea? Yeah. The people who ran this company came out of the radio business. The media business have been so boring and unchanged for so long. The big innovation in the 70s was FM radio that would kind of take over the AM dial. And they would have, instead of these general interest stations, they would be like they would have genres like soft rock or, you know, free form rock and roll music.

So they kind of gradually sliced away the big A.M. radio stations. And that was the model they saw happening in television, too, niche programming. What was your seed funding? $25 million. That's a shitload. Yeah, it was a shitload of money. But then again, you know, we almost ran down to zero before we really had a business. What did you spend if I, okay, so it was eight, eight of y'all making $35, so nothing.

But you have $25 million. Well, it was eight people who developed it. And by the time we launched it, we had hired other people because we had to, you know, run a network. We were running a 24-hour network, seven days a week. Which was insane because one of my heroes, Ted Turner, he had the idea of CNN, and that must have been a little bit before. Well, a few months before. So CNN, ESPN, Us, USA Network, we were all starting at the same time. It was really the beginning of the modern, but can cable network business.

We were kind of pals. Yeah, yeah. We were all trying to break down the broadcast monopoly that had like a 90%, 95% market share. Who all thought we were idiots? Which is funny, because, like, it's, you've been around long enough that I'm going to ask you about it later. Like, you've seen cycles of, like, the innovator then gets disrupted and et cetera. It becomes like, you know, the main guy and gets disrupted. I think I read that by year five or year seven, you were doing like 70 million in revenue. Is that right? Yes. So that's like a pretty fast rampout. I mean, $25 million is a lot for... Well, $25 million was the cost. I mean, we started with no...

I mean, the $25 million was how much we had to, you know, invest in this company before we went broke. You know, so show me your business. We're going to give you a pot of $75 million. Let's see if you can get your business plan, which I think originally was four years to break even. Let's see what you can do. And we were stalled. And we had to, you know, figure out a hail merit. pass to kind of save us because the cable operators who really had to carry us, and they were

monopolist at the time, they didn't want to pay 10 cents a month for MTV. What was the business model? The business model was multiple revenue streams. We're going to have this narrowcast kind of programming strategy, and we're going to get into all these cable systems. But what really had to happen was the cable guy had to come and wire America. And so we were also waiting for what we thought was the inevitability of cable TV coming to every household in America. And you'd get 10 cents per cent. We would get for MTV, we would ask 10 cents a month, so $1.20 a year. And then that was only to be like one third of the revenue. The rest was to come from advertisers. And how many subscribers did you have? In year three or four, when we were running out of money,

we had only like two and a half million subs. We were really behind schedule. So only $2.50, that would be $3 or $4 million. year and subscriber revenue. Did you have any other revenue? We barely, barely. We had some advertiser revenue, but we didn't really have big enough numbers to attract advertisers of any significance.

So we were running low, and the roadblock we had was that the cable operators were going, no way, we don't, by the way, we don't even like this music. This is like something from the devil, you know, this is rock and roll, and these guys were more like Elvis Presley fans

or Bible thumpers, the guys who controlled the cable industry way back then. Which is funny because they experienced the same thing, with Elvis. Yeah, exactly. But then, so we needed an ad campaign. We said we have to really go for broke. I knew because I was the marketing guy. I would go to these towns like Tulsa, which actually had MTV from day one, 100,000 homes. So you had a little microcosm where you could see what would happen if MTV was in a community, and people went crazy for it. What did they like about it? They just liked it, that it was 24 hours of music videos. People had never seen music videos before.

So this is a network that looked like, where the hell did this come from? We just, it just, one day it showed up on their TV set, and there was all these groups they'd never heard of with all this fast cutting, this whole new visual style. And it was funny and irreverent and looked like some underground thing. And here it was on my cable TV. I didn't have to order it or anything. So if you were a music fan, you're going, wow, this is fantastic. Which is interesting because MTV doesn't do music videos anymore, but I watched music videos all day on YouTube. So I have to, like the music videos are still relevant, I think.

They make more music videos now than ever. That's what I thought. Like, what about that behavior? The idea of a music video, I guess if you pitched it to me in the late 70s, I would sort of react in the same way that I would react if when TikTok, like, so you're telling me I'm just going to watch people dance on the internet or I'm going to watch like people play video games on the internet. That sounds silly, but then I actually find myself doing it all the time.

Was there like a conversation where it was like, someone just going to like pretend that they're singing and play music and that's what we're going to be into? Well, the birth of the music video was basically in Europe. Television had not been deregulated, so there was, or radio. So the radio stations didn't even play music. If you can remember or you'd read history, there were these pirate radio stations that existed on boats off the UK that could play like radio like American-style radio where they would be playing records all day. So they said since we can't get on the radio, because there's no radios playing music, we need to get on one of these television shows.

Like in the UK, there was a show called Top of the Pops. Yeah. And people would make music videos to use on that show or, hey, why not put them in record stores? That's where I saw them. I was living in Berlin, and I used to go to this record store, and they had a little tiny TV, and I'd see music videos for the first time. And it was kind of like playful and low-key and lo-fi. And it was another way to reach the consumer to promote the sales of LPs.

The CDs hadn't even arrived yet. So this new business came out of a need just to how do we find some exposure for our product, which was the album. So then, you know, but America didn't really have any exposure to the music videos because we had radio stations that played music all day long. They didn't have such a need here. So when we started MTV, we only had 160 videos. and they were largely from the UK or Europe, largely from the UK from independent acts. And then when people saw these could really help sell records, we could sell a lot of records. And, you know, gradually the Bruce Springsteins and the ZZ tops started making them.

A new artist like Madonna would come on the scene who found video to be a really great imager for themselves. And they could use it very effectively and smartly. And gradually this business developed making these things, which, you know, still exists today. even though MTV, you know, for a whole bunch of reasons, just sort of gave up on them, which, you know, I think was a mistake, obviously a mistake. You were able to, like, find and employ all these amazing creative people.

So, like, Steve, I forget Steve's last name, the guy who started SpongeBob Square Pants. Steve Hillburn. No. And then Mike Judge, who did King of the Hill, Darya, Beavis and Butt Head, and then most recently Silicon Valley of the TV show. And then Matt and Trey,

from South Park, like all these amazing people. When you're talking to a young, unaccomplished person, because I think Steve, the SpongeBob SquarePants guy, I think he was a marine biologist. When you were like trying to spot winning people, not even ideas, was there like a common theme? Yeah, well, first of all, I really consciously wanted to make the company,

like it was an eccentric. We were not a traditional media company. We were like this eccentric place that we would thrive on sort of offbeat, leading-edge talent, whether that be musical or comedians or whatnot, and we would try gradually bring them into the mainstream. So we kept our, you know, pop culture kind of moves up from the street. So I wanted to have a really young employee base that was pretty loose and, you know, casual. I think I said that your, I think I read that your dress code was no frontal nudity.

That was it. Yes. We had the worst dress group of people going in and out of any Manhattan office building, which would be a tie for today because no one seems to have a dress code. But in those days, everyone had to wear suits and ties, and it was really kind of straight-laced. But I wanted it to be a fun place. And I wanted all the employees to know that our main aptitude was creativity and taking risks. So I would put creative people in charge of these networks.

And I wanted to send a signal to the employees that creativity and finding people and nurturing them and having these relationships was absolutely core to our business. because I and people wouldn't stay in there a long time people would come and work a few years and leave but I wanted there always to be like a long line of creative people who wanted to get a job at our company we were like a talent magnet in a way and very good at spotting things we would look for people who were sort of immersed and lived on the popular culture of the day it wouldn't be unlike say record companies have a and our people who go out and try and spot young bands and they would you know hire those bands and, you know, hopefully have some hits with them. But we would have people who, you know, when we started, for example, yo MTV Raps, we really put hip hop on the stage for America. We were the first people that really, it came from two interns. Well, there was an intern and a production assistant who lived downtown New York,

who were part of the original hip hop scene in a way as fans. And they would be champions for that within the company. and they would bring this cast to characters that they knew to us. But did you get it? Like when you saw someone rap for the first time, you were like, oh, I get how this could be big, or was it like I'm good at hiring people or just letting them do whatever?

I was good at, I guess, hiring people who were good at attracting people and had good instincts and good taste. You know, you need someone who was well versed in the popular culture, who had good instincts, who had diplomatic skills, was able to spot talent. and build relationships with these people. It wasn't like everybody we hired or got behind was a success.

But we were, you know, we would find people like Mike Judge at animation festivals. He would go to places then where a lot of this young talent who had ideas in their head and they were animators, but they didn't want to go to Hollywood and get immersed in the factory animation scene. I didn't meet him. The first thing I saw was a short called Frog Baseball, Beavis and Bud. It wasn't even called Beavis and Butthead. And it was like maybe a five-minute thing

that this guy who worked with us named Abby Tricoulli, who was an animation freak. I mean, he would go to all the festivals. He saw this in Austin, Texas. And it was Beavis and Butthead, and they would have a frog. And Beavis would throw a frog, and Budhead would hit it with a bat,

which sounds kind of grim and gruesome. But just their attitude and sensibility and the way they laughed and the way they were dressed. said, well, this is, so the whole green lighting process, if you will, was like, you know, a minute. Well, that's been, that's hilarious, these guys. How do we get this guy, Mike Judge, inside the tent? And how can we make it easy for him to kind of develop a series with this? That we, well, how do we do that?

So we made a deal with Mike Judge and we started cranking out, you know, how, well, they can sit on a couch and rate music videos and talk about music videos, which is like, like, how, how we're, we imagine some people in our audience would be doing and make it funny. Matt and Trey, when they came to us with South Park, the head of programming at MTV at the time, Brian Graydon, he had commissioned a Christmas card to send to like 3,000 people. And it was a six-minute thing with these foul-mouth kids who became the South Park guys. And I think even at the time, wasn't there like still a talking turd? Like, was it?

And that was, again, that was a case of what green light that. We needed a hit desperately on Comedy Central. that took like a minute. Okay, let's do that. Were you like, these guys are going to be special? Or were you like, they're just one of many? No, these guys are going to be special. By the way, this is the most original thing we have seen for a while.

It's softbeat. There's nothing else like it. It's pushes the edge. It's funny. It's irreverent and it's going to get attention. We made six episodes with them. First one was Cartman getting an alien up his ass. He's like an anal probe, I think.

They like the anal probes, yeah. I know, it's funny because this last season, where they really go to town on the Trump people has been their most successful in terms of ratings and buzz and everything. I mean, they're really, they're great guys. I'm friends with Matt, you know, to this day. And, you know, their success has been just great to watch.

I mean, then they did the Book of Mormon on top of that. They're talented guys. Yeah, they're generative. All right, let's take a quick break, and I got a question for you. When a buyer asks AI for a solution like yours, does your business come up? Most companies have no idea.

And by the time they found out, they've already lost the deal to another company, that did. HubSpot has AEO, which helps you show up in the moments when the right buyers are looking for a company like yours. Before the first click, before they fill in the form, that is the moment HubSpot AEO is built for. Check out HubSpot.com, the agentic customer platform for growing businesses. So I hire creatives, and I'm trying to get, basically like I hired content people. And the best ones are oftentimes the biggest pains in the asses. And also, I love it. So it's kind of like a love-hate thing. But I'm always looking at.

for ways to increase my batting average of like finding young talented people and giving them a shot and increase the likelihood of a hit rate from, I don't know what your hit rate was, but like, let's say it's like 30%, try to get to 60%. Yeah. Well, that's exactly the same challenge we would have because they are a pain in the ass. I mean, that's the beauty about them. They're difficult. They really had a point of view and it was hard to move them from it or they had no point

of view they didn't want to do something and they didn't want to be told that they wanted, you know, they kind of follow their own North Stars. and we would generally hire people who, if they were going to be on the air, they basically had a project under their belt when they came to us. They were selling something. People would come, you know, we were, they want to sell because they'd want to get on one of our networks.

But finding the employees who would basically be the talent pickers or people who have to work with talent, that was a whole other skill. You know, these were people who didn't necessarily, you know, make things, but they would power creators. I would hire someone who would be basically the talent picker, if you get what I mean. Because I realize at some point I don't have necessarily the instincts to do it myself because I was a little bit older and away from the action,

which always seemed to focus on what's going on with 20-year-olds. What did 20-year-olds want? So the best thing is how can you best connect with those people? I mean, I wasn't like an idiot, but I would find like a woman like Judy McGrath. And she would always say, what we have to do is hire aberrant people, because it's going to be aberrant people who are a pain in the ass, but they're going to bring us the most success. What's that word mean? I've never heard that.

They are trouble. And they're like, they're not mainstream people. They were people may be sitting in the back of the class when they were going to school. And they don't have a lot of respect for the system. They're on an individual agenda, you know. There's small things that companies do in their culture that have big, big shifts and shape the culture. For example, one of my favorite companies to read about is this company called Rackatin.

It's like eBay or Amazon of Japan. And they don't have cleaners in their offices, even though it's like a, you know, a 10,000-person company or whatever. Because every day at 4 p.m., the employees are expected to spend 30 minutes cleaning their area and tidying their area. And then, like, they have like assigned jobs. Like, this person takes out the trash, whatever. And like, the idea being is like, we want to sweat the day. details. There was there anything that you did that you found other companies should implement in order to get their people to do more things that could get them fired at another company,

but at your company could give you like a 10x outcome. We would have parties that were kind of, you know, I wanted the place to have a bit of a wild vibe to it. Yeah, I heard at one of your parties, I think it was John Stewart. He was like, maybe he was thinking about signing with you guys to host the Daily Show or he had just signed. And he goes to the holiday party. and he sees you on the ground in the street because you were on someone's shoulders chicken fighting and you like fell over or something like that. And he was like, and he was like,

these guys are drunken idiots. I'm in the perfect place. We had a lot of that. We used to have these girls. He couldn't do a lot of this stuff these days, but we used to have these girls in like, you know, short pants with bandoliers filled with shot glasses and holsters that had tequila bottles in them.

And so we would have what basically were like wild parties, and get-togethers and social things. At my company, we don't do, like, that many, because I've got kids, and so, like, I go home. But, like, I do think that, like, intentionally hosting parties, it sounds so obvious and silly, but I actually do think that, like,

shifts culture a little bit. Yeah, and if you have a party, it's not a plus one party. I mean, people aren't bringing their husbands or wives or boyfriends or girlfriends. It's the people who work together, so try and build the bond up with them. So I want the salespeople to get to know

some of the people in the animation department. You're a salesperson, you're also, you know, we got to sell, we have to sell this creatively because we are just small guys still and we're up against these big networks. So how do we take this creative ethos we think really powers our business and apply it to accounting and sales and other things like that? And let's have these people socialize together and become friends. People love working there. You say when we had the pandemic and the office culture disappeared for a few years and isn't

fully back yet. We used to have people who slept in their offices. They would be there 24-7. They couldn't wait to come in. It was like the center of their social life. What was the average age, do you think? Uh, 20s. Were a lot of people sleeping around with each other? Yes. Was that good or bad? Well, you know, a lot of are married and they're still married. I mean, it was, but I would tell my co-workers, I'm like, this only ends well if it ends in marriage. Yeah, there was that problem. But, you know, you have a lot of young people. They're working really hard. They're, you know, 16, 18 hours a day.

They're consumed with their work or 12 hours a day. I mean, the only place they're meeting people is at work. So, you know, people start having relationships. We would also, you know, show people what we're making and what we're doing. And when I would speak to the employees, we would have like these town halls where they could ask me anything they want. I would always lead with all the creative successes that we have in. talk about the risk that we've taken and which risks have paid off and maybe which risks haven't and then show programming and talk about who is behind it and have some of the creators come out

and how we revered say John Stewart or Stephen Colbert or John Oliver and the stable of talent we were able to grow there to have be there some interaction with that and the staff rather than focusing on our financial results. When I was speak to the company as a whole, I almost never spoke about our financial results. I never spoke about our relationship. to Viacom, which was our parent company, which in many cases was a sin because the parent company always wanted synergy between the various divisions. The other divisions might have been, you know, Simon & Schuster or whatever. But we're, no one came to work there to work for, you know, Viacom. Viacom was this abstract public company. We don't even know what it does.

They came to work at MTV or Nickelodeon. And then I had to knit together, how do people at Nickelodeon who were largely better dressed and maybe came from a school teacher's sensibility, good for kids, more socially, socially conscious than the MTV or VH1 people. How do they all kind of fit together and think they're on the same team? Can you talk to me about the Nickelonian business? You said that was the biggest business. I lived on the street from Sesame Street. You call it you lived on the street?

Sesame Street is 63rd. Yeah, my in-laws live on Sesame Street because that's where... It's run now by... It was been run for a long time. with Nickelodeon alumni. I've always been interested in that business because I think they're independent still, right? The Jim Henson Company?

Yes. There's the Jim Henson Company and then the Sesame Street Workshop and I'm not sure of the exactly, Jim Henson Company is kind of separate from Sesame Street Workshop. But it's still a multi-billion dollar independent company. Yeah, and it runs on public broadcasting. They license the public broadcasting. What does it take to create a show or a piece of content that becomes legacy? and do you think can last for two or three decades?

Well, you never know in advance. You're always hoping you're going to do that. That's the home run. So not that it only lasts for decades, but you're able to also spin it off into, you know, consumer products. That's where the real money is or motion pictures. That's what we would do, you know. And historically, these characters would be chosen by,

in sort of the factory world, the commodity children's space, but they would try and pick something and say, does it have, the word they had was toyability. Toyability, that means like just the character become a toy. What can't become a toy? You know, that we had a show called Angry Beavers. I mean, you know.

I watched that when I was a kid, yeah. There wasn't anything there, but our criteria for green lighting as show and going in and producing it had nothing to do with toy ability. It was, were we in love with these characters? And did we think it could be a good show and get good numbers and resonate with the audience, in spite of the fact that maybe it isn't going to be a consumer products, Bonanza. So we were really thinking because it goes back to the creator,

the creator who had these characters in his head, probably wasn't thinking about toyability either. He had a more crystallized, simple idea as to what could happen here rather than what would be the eventual spin-offs. And maybe he didn't want to interfere with that. He wasn't that interested in toys. So we would do things that we were in love with. And a lot of them turned out to have, you know,

with SpongeBob and Rugrats and so many, there was a lot of consumer products that we could crank out and feature films. Because when we got linked up with Paramount, we set up film labels there on the lot, you know, for MTV and VH1 and Comedy Central and Nickelodeon to develop films that would use the IP that we had generated and made famous on the television network.

I have this feeling that a podcast must have one of the following three things in order to be good. You need to have a unique perspective. So, for example, that could be LeBron James talking about basketball. It doesn't matter if he talks on the worst microphone ever. People are going to love that because LeBron James is one of one. The second thing is really high-end or unique production. For example, if you get the best voice actors and it has the best sound effects, you're like, okay, I like this because it's like a total immersive experience. or the third one is world-class delivery,

meaning a comedian. A lot of comedians that I listen to on podcasts, they can talk about anything, but they're so funny and good at delivering it that I'm into it. And so when I think of podcasting, I'm like, okay, those are like three attributes. Can I lean in on one of them?

Did you think of attributes for some of your shows where like if it hits one or more of these attributes, this is a winner? Yeah, we used to have this thing we called filters, which is sort of like that. Does it pass through these filters that we would have. The Nickelodean people were very conscious about having some kind of pro-social appeal.

Up the top of my head, I mean, we used to think, I mean, we had basic values like nonviolence, pro-kid, things kids liked. It was fun. It was funny. It was irreverent. And also does it have sort of a modern presentation? We were trying to position ourselves as the sort of, I hate to use this word, but sort of the, the hip or children's network, the cooler children's network versus Disney, which

was the powerhouse children's operation. We wanted to be sort of the modern version of the Disney thing. So those would be some of the filters we draw through. I can't have to go back and remember what they might have been for MTV or VH1. It usually had a lot to do with its appeal to the very specific core audience we were going after. Did you have a name for that person? The ultimate person was a 24-year-old. That's who we would program to, 22 to 24-year-olds.

and that teenagers we would never talk about anyone younger than that or have them appear on the air because the minute people 24 are older saw a teenager, they were going to say goodbye. They didn't want to be part of some teeny bopper network, even though teenagers were maybe one-third of our audience. They were never showcased on the air. But we would also get people who were older watching. But the core audience was on MTV was 18 to 24-year-olds.

then we would really move it to like 22 to 24-year-olds. I was reading about you. And I think when I think that you said in the book, you were fired because you didn't buy MySpace and Rupert Murdoch bought it. And you were fired by... Sumner Redstone? Yes, Sumner Redstone, who was a mogul.

It seemed like a real jackass, though. And then you were recruited immediately, I think by Rupert Murdoch and a few other people to join, you know, whatever they had going on. But I don't think you took it. I think you're recruited by Bono. I also think you're recruited by Steve Jobs, and you had some affiliation with him. Same with Geffen, who is one of the most successful media business guys there ever is.

You knew Bowie, Jagger, all these guys. You said you bought Andy Warhol's old house. You, I think, made an offer to buy Facebook. Is that right? Yeah, we were the first people. We offered like $800 million cash with like a $900 million earn out, if you can imagine. Tell me the Mark Zuckerberg story. Well, this guy called me up one day, Kevin Wall, who I knew from the music business,

said, hey, I got this guy. You know, we were aware of social media was coming on, and we were aware this is a big paradigm shift. What year? This would have been 19. This is 2005. So how old is Facebook? Facebook was still only programming to college kids. Oh, was it like three years old?

I guess so, two, three years old. And their revenue was like $7 or $8 million a year. and Mark Zuckerberg had just moved to California. And the business thing they were wrestling with, he came in to see us in Times Square. And I always remember he was like wearing a hoodie and flip-flops. It was February. And I had to meet us at the MTV offices

because I figured it'd be younger and it'd be interesting. He wanted to see what that was like. And he's only 21? Yeah, and their big challenge was, do we want to expand this to high school kids? Because it's just college kids that could really be on Facebook, the Facebook. Is it going to be a mistake to expand our target audience to high school kids?

The revenue was $8 million a year. I remember this. But we saw that, you know, social media was going to be a big force in the business and was going to grow because people now could, you know, they could connect directly to each other. The gatekeeper era was going to begin to fade. But we didn't have the capabilities or skill set to. really create our own social networks. So maybe we buy somebody else's and bring it in house. So he came to see us, but he must have felt something good because discussions ensued

with his team. There was a fellow named Ova Van Adda, who I believe was the first CFO. And we went back and forth and we put a bit on the table and they turned us down. How big? What was it? It was like $1.7 million, billion, excuse me. One point seven, how much cash? 800 or 900 million. It was 800 and 900 million in cash. The rest was an earnout. Okay, so Zuckerberg. He did not want his MTV.

Eventually we got turned down because the negotiations happened at a lower level than me. But I do remember at one point, he was going back to Dobbs Ferry, New York for Thanksgiving. And this guy, Michael Wolfe, who was kind of heading the negotiations from MTV Networks. He said, you know, I could offer Mark Zucker. a ride on the plane, and he'd basically be like a captive audience for five hours or so. And, you know, maybe we can make some headway in the negotiation. Obviously, it didn't work out. You got on the plane, though?

He got on the plane. His parents picked him up at the airport. Yeah. So this is really way back in the folklore. Why didn't you invest in it? That's a good question. We weren't thinking of that. We were thinking of like buying and owning something.

We had been a company that sort of grew organically, and we had never bought any. thing. And we weren't really like a venture. We weren't really set up as a venture firm. And our company was always, the parent company was always sort of operating on a shoestring in terms of how much money we can really invest in our own businesses or buy other ones. I don't think we were thinking of doing an investment. That might have been a clever way to go. But they turned us down and everybody else showed up at the door. You know, it was Microsoft, Yahoo. Everybody wanted to buy Facebook at higher and higher amounts. I think about that all the time to be 21 or 22 and being offered to be a billionaire and just the gall that he had.

And I find that to be fascinating. And it's refreshing. You know, people would start a company and their purpose wasn't, well, one day I'm going to sell this company to Google or Facebook or somebody else. They wanted to start a company and have it work, you know, and grow to the tree to the sky. It was the same thing with Steve Jobs and Bill Gates and Paul Allen and Phil Knight. They all started companies because they thought that was interesting fun. They saw something in the culture where they thought they could slide in with an innovation and make a business. But those people always end up richer.

Yes. Not always. They're owners. They didn't check out. That's not to say you can't sell your business and do something else or sell your business and maybe stay with it. But these guys were true believers. Did you know Steve Jobs? Well, we went up once to see him at, this is before the, we went up to see him and we wanted to talk about maybe doing a joint venture with MTV and Apple.

this is before iTunes. There's this guy who worked with me who had a digital name Jason Hirshorn, and he made the cases to Steve Jobs that iTunes wasn't the way to go. The way to go was to put together basically a music streaming service, which would have been like Spotify.

And Steve Jobs was adamant about no. That's not the way we're going to do it. We're going to do, we had the iTunes model. And, you know, he gave us a nice tour, the Pixar Studios, and, you know, We had a fine relationship, but he was someone we, of course, really idolized as an icon for us, a guy who could lead creatively. He was also, by the way, a pilgrim from India. Oh, yeah, yeah, yeah.

Not to compare myself to him, but, I mean, he had a, he didn't have a straight-ahead business mindset. Yeah, he made for his team, Bill Gates. He was like, Bill, you need to do some acid. Great. Which other icons did you? I read a ton of biographies and I'm always like trying to find like who I can learn something from. Which icons did you meet that you were like, this person needs to be studied? Well, there's Rupert.

What do you think about him? Well, you know, he's a bold buccaneer kind of old school classic media mogul. I can't say I agree with the results of some of his political programming. but you've got to give him credit for a guy who take big risks. What was he like? Well, he, I got to know him a fair amount because his wife, Wendy Dang, was good friends with my wife, Kathy. So we would go on trips together and so forth. But, you know, he's quite, you know, he could be fun.

Was he a alcoholic? I think so, yeah. I mean, but he'd travel, the difference between him and my boss, who was Sumner Redstone, they were about the same in terms of age. Rupert was a little younger, but they were both big moguls who took. took bets. Sumner was always focused almost entirely on people who might be screwing him so he could sue from an antitrust perspective. He was a former antitrust lawyer or the stock price, whereas Rupert Murdoch would fly around the world endlessly in his 727, and he would

really understand the machinations of how the operations all worked. There's not very many good biographies on Rupert, so I've been able to piece together a few, but there's a cool document. documentary about him a little bit on HBO right now. And there's stories about him being, the company being huge, billions in revenue, and he was still calling editors for certain headlines. I mean, like, you should change it to this, this, and this, and people will buy more magazines or newspapers because of that. He knew the business. Whereas, I mean, he really knew how the business worked. It's something like that he can make a contribution to. And they'd say, oh, you know, it's the boss he wants to do this. It's like, it's not just the boss who wants to do

this, but he may well have a point. He had credibility with his underlings. I heard he made huge bets just over one little conversation. Like, I think it was, they bought Myspace, right? He bought it on a weekend. Yeah, I heard it bought. With no due diligence. How much did he pay for it?

$560 million. And it obviously was shit. It was the wrong bet. At the time, that was, you know, you got to remember in 2000, we had the Time Warner AOL merger that was a disaster. That was the real first linking of a new media and an old media, legendary legacy media company and that kind of blew up.

So everyone was paranoid about making big bet on digital media after that. So now it's like five years later. He just lays out on a weekend with no due diligence buying this social media site that we have been looking at and we're aware of in Santa Monica just bought it over the weekend.

And he became, because of that purchase, he became like, oh, he's the new media savant. He's like this old dude. but he also gets this because he's buying this hot up-and-coming media company which of course, or new media company, which of course didn't work out, but this really aggravated my boss Sumner-Redinor Redstone

who really had never heard of MySpace until he heard that Rupert bought it. And he fired you just because... Well, I think there might have been other reasons, but a primary reason, like he told Charlie Rose, was that, you know, I had the prize and I let it go and I let it go to Murdoch. And MySpace was the prize?

Yeah, which ended up dissolving and being sold to Justin Timberlake for $35 million years later. So it wasn't much of a prize. Were you able to make money on this as you went? Personally? Yeah. Yes, we had, you know, when we started, like I told you, everyone was making $30, $35,000 a year.

There was no stock options. People wouldn't even know when a stock option was in 1980. It wasn't like part of the normal nomenclature. You know, we just can't believe we have a job here. We're on a crusade. This is the greatest thing. It's going to be the greatest thing. We're going to sweep the nation with.

this thing. So they were like crusaders, but then we decided we, in 1995, Warner Amics needed money and they made one third of the company public. And everybody got like a little bit of stock options. So we started seeing that the one, we were this hot company where MTV networks. MTV was the first name. It was a really hot commodity. So you get a, you know, everybody had a little taste. And then we got bought when we were sold. So all those stock options vested and paid out, but, you know, in today's, no one was becoming a billionaire or even a millionaire. I want to ask about riding rooms. This is for the folks out there who have a business that does at least $3 million a year in revenue. Because around this point, that's when you're able to

look up after being heads down for years building your company, and you realize two things. One, you've done something great, but you're still a long way from your final destination. And two, You look around and you realize, I am all alone. I've outrun my peers, which means you're now making $10 million decisions alone by yourself. And that is when mediocrity can creep in. My company, Hampton, we solved this problem by giving a room of vetted peers of other entrepreneurs who are going to hold you accountable, call you out on your nonsense, and help show you the way. Because the fact is, is that there's only a tiny number of people in your town who know what you're going through and who have been there.

and they're hard to find. And if you can find them, it's hard to have this explicit time, this explicit place where you sit down where the rules are clear that we are here to help each other and to be one another's board of directors. The biggest risk is not failing.

You have a company and it's working. You're going to be fine. But the biggest risk is waking up 10 years from now and saying, shit, I barely grew in business and in life. And for people like you who are ambitious, wasted potential, and regret is what we want to help you to avoid. We have made so many of these grue. groups and we have a thousand plus members. And I know this stuff actually works, whether you work

with Hampton or you get your own group on your own. But having a group like this, a group of people who you meet with in real life once a month, it can change your life. It changed mine and I know it will change yours. So check it out, joinhampton.com. I was listening to you and John Stewart talk about that. And the idea of a writing room is foreign to me because, A, when I'm creative, I'm by myself. I prefer just to like, you know, my old company. I used to have to have to write a bunch of articles a week. And I was like, I just need to go into a room by myself and not talk to anyone. What did a writer's room look like? And what do you think made a writer's room successful in order to get the best outcome from a group of people? Well, I get it that is in my

book in a bit. We didn't really have writers for a lot of what we did. At MTV, there was stuff was really written individually. We didn't have a writer's room per se. At one point, Rupert Murdoch and Barry Diller launched the Fox Network, which was going to be not just a broadcast network like the others, but it was going to focus on younger people. And they were putting on soap operas

like Melrose Place and Beverly Hills 90210. So I said, well, our creative people are always trying to do something a little more ambitious. Why don't we do a soap opera? So we developed one.

And it was developed with this company and Boona Murray, really successful folks, great people. They were young at the time. And it came to me and it had a budget and in that budget was a big line item for writers.

And I said, you know, we don't really have that kind of money to hire writers. We're probably going to make stuff for $100,000 an episode or something like that, but we wanted to do it regularly. And we had a lot of other financial needs for the money. So they went back and came back to me with, okay, we're eliminating the writers. What we're going to do is find seven or eight people and stick them in a loft down on Broadway and Prince street. We found this loft. And we're going to put hidden cameras in and we're going to tape them. And then we're going to use what our real skill set was at the time was in post-production and

editing. We will edit all this action from these kids and all this interchange into these episodes. And that became the real world, which really launched the modern version of reality television. That was 1992. But, you know, that was the birth of the real world. And then And, you know, for the first season, the people who were in it, they had no idea they'd become reality stars because such a thing hadn't existed yet. Now when they cast people to be in these various reality shows, which are everywhere, everybody knows they have to have sort of an outsized personality and, you know, be controversial and whatnot. But the success of the real world was just exploded because we found out young people wanted to see other young people on television. They wanted to see, they get a lot of social clues and whatnot. the real world, we were doing a thing with Ozzy Osbourne and Sharon Osbourne.

And Sharon Osbourne was driving around in the back of a car with our head of programming, Brian Graydon. And she says, oh, you know, this day is crazy. If there was a crew following me around, you know, it would be an amazing reality show. So Brian, done, that was it. That became the Osbournes, which was the first celebrity reality show. Now there's like 50 categories of reality shows. There's a whole industry around them.

What was the conversation like where you said? but we're not doing this writer stuff. Was there a unanimous agreement in the room? Yes, yes. Everybody said, everyone wanted to do, let's do something. You know, we've got to get the show on the air and let's, this is a good idea. We could actually make this better than ever, make it real. Whose idea was it?

Well, Boona Murray had the idea. There was a fellow who was a champion for it internally named Doug Herzog, who eventually would go on and become the head of Comedy Central. And I'm sure there's some other people's names involved that I'm forgetting right now. Did you, were you on the board of own? Oprah's, is it on? I wasn't on the board, but I was hired by Oprah to be a consultant. When I got fired from Viacom, I went to Burma, which I had known from my travels in Asia,

which was like the crazy uncle of Southeast Asia run by a military dictatorship. There's no media there. I just wanted to disappear with my wife and just kind of rethink and see if I could get some epiphany about what I was going to do next. And I got back to this place. up in the jungle, and I got back to the hotel on a boat. You had to go everywhere by boat, and there's a message, and there's a message for you in the office. They didn't have cell phones there, nothing. Oprah Winfrey called. Were you Starstruck? Yeah. I go, what? Oprah Winfrey? I don't even

know Oprah Winfrey. Why is she calling me? So I got back in New York, and I called her, and she said, yeah, I called you. I saw that you left, and I saw you got a big cheer, which I write about in the book, When I left the company, there was like all these people in the lobby to send me off. And says, I'd love to meet with you and talk with you. And why don't you come up to Montecito and I'll make your breakfast, which I did. And we become good friends. She helped me promote my book recently. I did an interview with her.

And I loved Oprah. I mean, there's no easier person in the world to speak to. She's curious. She knows a little bit about everything. And she knows how to talk to people like, you know, nobody's business. So, I mean, that's what she does for a living, right? She's always done that. So she's been able to carve out and set up this whole, like, modern media business.

She was one of the first people, like in the creator economy, which people would use that word today. I mean, here you have a creator who's, she's at the center of a media enterprise, you know, her ethos and her thing, you know. Does she still, is that still its own company? Own is owned by Discovery. It was originally called the Discovery Health Network. And so she did a joint venture with Discovery, David Zazlov, much in the news. He called Oprah and he said, look, we'd like to change this Discovery Health Network, which is just sort of laying there.

And what have you came in and made it the Oprah Winfrey Network? And we could have something really original and noteworthy. And so she hired me as a consultant. And I did that for a couple of years. Man, it's just so crazy. I wonder if this stuff still exists. Like the way that I've been, you know, I've studied Ted Turner. That's my hero.

The way that it seems is like because cable was like the pipes, if you get in the pipes, the likelihood that you're going to be a somebody was a lot higher than a little bit than what it is now. That was the era of the monoculture in a way. You know, there was where things were controlled by editors and there was a barrier to get in. Now anybody can. Which is pros and cons. Yes.

Con being if you were one of the, if you were Oprah, like it was awesome. Yeah, because you had a built-in audience. You had a head start over everybody. You know, here you are. You're scrambling. You've built a business basically on your own wits, your personality, but you're competing with, like, an infinite amount. Yeah.

Everybody's their own broadcaster. Well, do you have any advice to that? Like, you've been on top of the game for, like, three generations now. Where do you think things are going to go? I know that I've heard you talk, like, where you seem a little frustrated with the rise of digital because that kind of made MTV less relevant because it kind of messed with the business model and mess with the market. which made it all possible.

Do you have any predictions on where it's going to go or tips on how to succeed right now? Well, you know, you see things emerging to me. I mean, I really don't look at everything, but I look at stuff like in the so-called creator economy. And you can see there's stuff. There's things now like Patron or Substack or everything where I always... Patreon. Yeah, Patreon, rather. What I would do if I was 25 years old, you know, because I'm thinking, well, the same things,

how could I align the things I like and care about and say, you know, if I could work for some type of enterprise and learn the business and enterprise that's really about powering creative people and getting them more famous and more relevant. And how do you do it? I mean, you have to sort of be a master of social media these days. And you have to have an intrinsic quality that will allow you to stand above everybody else, which is truly everybody else. Well, you know, what's funny is my company, The Hustle, it was a daily newsletter.

which at the time was people kind of laughed at it, but I was like, I think this can get to a couple hundred million in revenue if we do it right, and we sold before we got there. But my competitors and, like, where the company that I sold now is, like, hundreds of millions in revenue was possible. That was right. But I was inspired by Ted Turner. I read biography.

He's my hero. And I knew all, so I studied cable. So I read about cable cowboys and Liberty Media media. Like, I studied like crazy. I've studied you like crazy. and at the time in 2014, right around when I was starting the company, BuzzFeed was popular and Vice was popular. But what was going on was their business models were going down because Facebook was pulling back reach so they would get less clicks. And I was like, well, where's like the last bit of real estate that I could fully own and not rent?

And it was newsletter, newsletters. And you know who I got that idea from? Bob Pittman. Oh, really? Bob Pittman had this thing called the pilot group. I know. I had dinner with Bob Pittman last night, strange as it may seem. I mean, it's just a synchronicity. You're one of your co-founders. He's a co-founder.

And he had this thing called the pilot group where he would fund newsletter companies, one of them being Daily Candy, which sold for $100 million. I heard about that story, and I was like, I'm just going to copy that and do it with business news. And so that's how I started my first company, which we ended up selling four years in. They're also involved Ben Laird. I'm trying to remember the name of the letter he had. Yeah, Ben, for Thrillist. Yeah, I was just like, I'm just going to do what those guys did. It was good.

I mean, the newsletters had an era. Digital media had an era. Well, they still do because substack and Patreon, which you're talking about, they created their company because they saw what I was doing and they're like, yeah, that's cool. But we just created the technology for it, which obviously is far more lucrative. Do you regret selling that company? No, because I was broke. I didn't pay myself much money.

The business, the year I sold it, we sold it in February, the trailing year we had done $12 million in revenue. that moving forward year, that forward year we were going to do like 18. So it was growing like a weed. It was doing great. But I paid myself like the first two years, like two grand a month. And so I was broke. The last couple of years, I started paying myself a little bit more money. But a few things happened. I sold in February of 21. So the Black Lives Matter protests were happening. COVID was happening. And I felt the world was like going to end. And so the second that I had an opportunity to kind of cash out and have financial security for forever, I was like, I will do that in a heartbeat.

So I don't regret it, but I regret being in the position to sell it, meaning I wish I could have owned it forever and still, like, had both outcomes. Obviously, that's not possible. There's a different form of the innovator's dilemma. What is that? The brokenness of scrambling with no money when you have a life to support. Well, my biggest takeaway from that air is I should have paid myself more money. But, dude, thank you for doing this. I've enjoyed the conversation very much.

Yeah, I could talk to you all day. It was you were the man behind the scenes of the content. that shaped my childhood. Well, it's been great. And it's been, you know, I've summarized it all in this book, which was a lot of fun to put together unplugged. It was good. I read it this past weekend.

It was awesome. We didn't even get to it because I've seen you talk to it in some other podcasts, but like you got busted for having hundreds of pounds of pot on you. And what they used to say advice, they said, what are you doing? We're doing a lot of stuff that's really smart and a lot of stuff that's really stupid, which is sort of another version of the high and low.

That's awesome. And they don't do that. Yeah. Well, thank you. All right. We're off. I feel like I can rule the world. I know I could be what I want to.

I put my all in it like no days off. On a road, let's travel, never look. Hey, let's take a quick break. I want to tell you about a podcast that you could check out. It is called The Science of Scaling by Mark Roberge. He was the founding Ciro of HubSpot. And he's a guest lecturer at Harvard Business School. The guy's smart.

And he sits down every week with different sales leaders from cool companies like Clavio and Vanta and Open AI. And he's asking about their strategies, their tactics, and how they're growing their companies as, you know, head of sales or chief revenue officer. If you're looking to scale a company up, if you're a CRO or a head of sales, just looking to level up in your career,

I think a podcast like this could be great for you. Listen to the science of scaling wherever you get your podcast.