Tech Brew Ride Home - (Bonus) Jason Calacanis Interview

Episode Date: April 22, 2023

Again, this is a republishing of my Jason Calacanis interview from the Internet History Podcast. Sponsors: Bloomberg.com/careers Learn more about your ad choices. Visit megaphone.fm/adchoices

On April 4th, 2023, around 2 in the morning, a man was found stabbed multiple times on a sidewalk in downtown San Francisco. Hey, who did this to you? What happened next turned the story into a political firestorm. Reports have identified the victim as Bob Lee, the founder of Cash App. From Bloomberg podcasts, this is Foundering, the Killing of Bob Lee, beginning April 16. Welcome to the Internet history. History Podcast. I'm your host, Brian McCullough. Some of you know I took a quick trip out to San Francisco last week to grab a couple great interviews, and this is the first of those. Most of you

know Jason Calacanus from his many high-profile endeavors, such as his podcast, especially this week in startups, where actually he hosted us in his studio for this conversation, his launch conference, and inside.com, and many other things. But older listeners will remember, Jason as one of the most colorful personalities of the dot-com era in New York as the publisher of Silicon Alley Reporter. And Jason also played a key role in forming the modern media landscape as the founder of Weblogs, Inc. We talk about all of that and much, much more, including how he's such a nice guy these days, in this fantastic conversation with Jason Calacanus.

Jason Calacanus, thanks for coming on the Internet History Podcast. It is a pleasure to finally be on. You've done 150 episodes. 120. 120. Or you're 120. I guess I'm 120. So were you either didn't know who I was, or did so many people mention me that I'm on,

or did you want to warm up your interview skills for the first 100 with people who are not important? I am a one-man band. Ah. So I take them as they come. Got it. All right. I kid, of course. Right, right, right.

But you know what? I just want to tell you. It's really good. I listened to three or four episodes. Oh, cool. Absolutely fantastic. My favorite was Joel from Gizmodo talking about how I gave him PTSD. Right, I remember.

That was absolutely fantastic. I mean, I don't, I'm such a nice guy now, but I used to be so hardcore, and I used to give people PTSD, and now I don't. He seems to be a very sensitive man, so. I had no idea. He worked for Denton. Denton and I were, like, brawling all the time, but I'm getting ahead of myself. Well, all right. So let's start with your Brooklyn native.

So is that where the attitude that you're talking about comes from? Well, I was born in Bay Ridge, Brooklyn, which is pretty far out. It's working class. It's where Saturday Night Fever. Saddenight Fever, was there correct? It's where the Verrazano Bridge connects from Staten Island. So if you're from Staten Island, that's pretty horrible. If you're from Bay Ridge, that's not that horrible.

But in the 70s and 80s, being from Brooklyn, and into the 90s, actually, being from, Yeah, including the 90s, 70s, 80s and 90s. Being from Brooklyn was not cool. You were not a cool person if you lived in Brooklyn. In fact, if you went to Manhattan and you tried to get into a club, and we used to go to Peter Gation's clubs like Limelight or the Tunnel, the Roxy, Mars, Palladium,

and you showed them a driver's license with Brooklyn, they would hand it back to you and say, no B&T. Do you know what that stands for? Bridge and Tunnel, which means you came through a tunnel or a bridge to get to Manhattan. But now I go back and I'm going to be in New York in two weeks and everybody's like, hey, come see us in Brooklyn. I'm going to Brooklyn. I'm like, so I leave and it gets cool.

Okay, that's noted. So your dad was a restaurateur or a bar owner? He was a bartender who then had his own bars. So he had two bars in the 70s and the 80s, yeah. Did you work for him? I did every job. My dad was a taskmaster and when I was probably five years old, I had my first job, which was after school, after first grade. We would go, my two brothers and I have one old and one young.

We'd polish the silverware. He'd give us like three bucks, a dollar each. We'd save our money up and buy toy soldiers with that. But then I was a porter, which meant I came to the bar at 6.37 a.m. Every Friday, every Saturday and Sunday after Friday night and Saturday night, my dad would still be there. He might have had a couple of drinks, and they'd be playing poker or backgammon in the corner. And the sun would come up.

I would get there, and we'd mop up the bar. So I literally clean up every beer bottle, wash everything. This is at the age of 10. I was in probably fifth or sixth grade, and I'd go out of my grandfather, who had the job as well, and we would clean the place up. So that's where I got my work ethic from, and that's where I saw a lot of stuff that a child should not see, which I think informs a little bit of who I am. Right.

But this is about the Internet. We're getting there. Because one more thing about you, you know, foundationally, you got to be a little bit of the Internet. You got into martial arts really early on, and that was a big deal for developing who you became, right? Yeah. When I was 15, I was getting kicked out of school. I went to Severian High School, and they decided I, in my sophomore year, wasn't going to continue on. And so it was a very cruel kind of thing, because your parents would pay your tuition for the year, and then you would be dead man walking when they decided to kick you out for the last X number of months. and so I was told I was not going to continue. And then I named Charlie Fasano, who was a teacher,

his first year teacher, but had graduated from Severian high school, told the principal brother Warren, who was a Severian brother, which are kind of like Jesuits. They're kind of hardcore. Those aren't the boxing. That's not the boxing order, right? I don't think they box, but they're tough. I mean, they certainly will smack you around,

and they did in that time era. You know, like literally, I was probably the tail end in the 80s was the last chance that the brothers had to smack a kid without getting in trouble. And he said, I think that kid could be something. He's just misguided. And the brother Warren, who had great respect for Charlie Fasano, because he had graduated a year early from both high school in NYU, said, well, if he joins Takedo, I'll let him finish out the year.

And we'll see if he's any good. So Dr. Fasano now, call my mom and said, hey, listen, Jason's going to get thrown out and da-da-da. But if he joins Take One Doe, he can stay. And so I came home. my mom said, guess what you're doing? And I said, what? She goes, you're trying to take one.

And then I became a black belt for the time I was a senior. I'm a sixth degree black belt. Now I taught for many years in Manhattan. People don't know that about me. I keep that very quiet because what I found over time is, you know, when people find out you're a black belt, they immediately would like to find out. They want to test that in this mixed martial arts age. Like, oh, you're a black belt.

Great. Let's get into a fight. I'm not, I'm 46. I'll be 46 in November. I'm not interested in any fighting. The discipline. That was important in terms of. I, you know, here's the thing. I watched my dad's business get taken by the feds because he didn't pay his taxes. So I watched my entrepreneurial model get crushed, right? And I then decided, hmm, you know, my dad is a bit of an alcoholic. He lost his business to not paying his taxes. I'm 16, 17 years old. And it put a drive in me. You ever see that movie, there will be blood?

Yeah. That's probably the closest analogy to... So you're saying you're Daniel Plainview? There was a competition in me for a very long time, and I think it's pretty apparent to anybody who knew me that I felt it was me against the world, and I was a very competitive person, and I wanted to win, and I was an outsider.

And I think that defined a large portion of my early career for better and for worse. And a lot of people were on the other side of that, so it was worse. But, you know, you evolve, over time. We're all very dynamic people. People are not static. That's one thing I've learned. So, you know, I try not to judge people as much as I used to. I try to not be as much of a samurai, insane warrior as I used to be. I try to be a little bit more of a Jedi these days.

So what I want to do before we get into your early career. Yeah. Because it turns out that about 70% of the audience of this show are kids entering tech today. They love dot com stories. Sure. If you could, let's set the scene of New York.com. Sure. By starting with before the web takes off. Sure. There's a lot of technical artistic people in New York because of the CD-ROM bubble. Is that?

Yeah. So what happened was in the 80s, there were modems, and you could dial up to a bulletin board. So my first computer in 1988 was a PC junior, and I would dial up on a 300 bond modem, eventually a 1,200. It was a vental, then a is. And there were these BBSs set up. A lot of them were rich kids in Manhattan. Their parents would get them an extra phone line. Some parents would get them three extra phone lines.

And they'd run a bulletin board system. It was a fancy computer, a big PCX, T, AT, eventually bigger computers. And you would put one phone line in, and you would dial up. You'd post some messages. You'd download some stolen software. Then I would dial up. I would have my war dialer on waiting for you to hang up so I could be the next person on if you get busy signals. We talked about that on Joel's episode, right?

Correct. And so then what happened was I became like a cisadmin or a junior sister. op on somebody else's who I'd never met. Eventually I went up meeting them. It was just a weird kid from Greenwich Village. But that was bubbling around in New York. The 2,600 guys were hanging out in the city group lobby, doing what's called phone freaking.

I got a little involved with phone freaking. I was involved with a lot of what I'll call questionable activities around technology in my earlier days. So my first business, when most people think it was Silicon Hi Reporter, was actually Jason's hot tapes. My dad had won a copy of the Empire Strikes Back off of a mafioso guy, a guy who owed him like three grand playing Backgam, and the guy said, I got a copy of the Empire Strikes Back for VHS.

This is before there were VHS rental stores, but my dad had a VHS machine. And the guy who owed him money said, listen, I'll take this Empire Strikes Back tape. I took it, and then I started charging kids to come up with my house and watch the Empire Strikes Back. It was out of theaters. There was no way to watch it. And then I started making copies of it.

It starts on copies for 20 bucks. I was like one of my first businesses, but the other business was I had a friend, Richard Amalfitano, whose brother was into some other things, and then he had a friend. It was all this craziness, but anyway, we used to copy, and we'd hack copies of, like, Chessmaster, and we'd make copies of Chessmaster or other games, and there was instructions on these BBSs of how to hack it.

You just go in, you change some hacks, you have to crimp the floppy desk to open it because they would be sealed, copy protected with a little, you know, you couldn't write over them. So we'd do that and we'd sell them for $10. So we basically were, and we'd still floppy disks from stores. I mean, we were doing bad stuff. We were bad kids. But at that time, also CD ROMs had come out, and computers started to have a CD player in them.

And when that happened, you could put data on it. And, you know, things like a company called Voyager was doing a hard day's night. And there were dial-up services like Prodigy and AOL that were. getting more and more sophisticated, and you didn't have to worry about busy signals, and computers started to come with modems in them. They didn't have internet cards yet. And in the early 90s, people like Jamie Levy were running around, and NYU had this ITP program, the Interactive Telecommunications Program,

and she had been making IPKs. And this is before the internet web pages, IPKs were interactive press kits. They were floppy disks that you put in your computer and you would see, like, a little bit of video, a little bit of, attacks, a little bit of words. So this idea that you could mix and have multimedia was going to be the future, and then you had dial-up services. So everybody was kind of swarming around these things. And in fact, the first magazine I did was called Cyber Surfer. It lasted for five episodes or issues. I'm probably going to fight with the publisher Starlog over the trademark. So I trademarked the name

Cyber Surfer. That was my online handle in the 90s. And what I'm sourcing from is the title alludes me right now, but there's this great oral history of the Silicon Alley Times that you're in, you're a part of. Yeah. And so the sense that I got from it was is that, so everyone's around for this early, nascent online stuff and the CD-ROM stuff. And then when the web comes, everyone feels like, oh, we can do it. We can go off on our own and do this. Yeah, there was a dial-up business that was Prodigy, and Josh Harris was doing chat rooms on Prodigy while he would rent an hour on W-EVD, 50 or something in New York. It was like a local channel right by Esther Place.

He would rent midnight to 2 a.m. It was very innovative. Josh Harris later from Sudo. He would get paid by the prodigy people to keep people in chat room because they were paying $3 per hour to be online. There was no flat rate yet. And then he would have people calling into his regular radio station. So he said if you're on prodigy, turn on your radio in New York.

If you're not on prodigy, call this number, get a disc, use this code. He would get paid a bounty for that. Right. So it's very clever to mix audio and chat rooms. But that was happening. So yes, you had people who were in the online camp, dial-up services, AOL, and then over here you had CD-ROMs, Voyager, Jamie Levy. People started to, Mist was a big hit.

And there was packaged software. So really technology at that time was about going to stores and experiencing it and buying packaged software. So you go to a store, you'd buy something. But when the Internet came out and we started to have web browsers, I was at Sony and I was working there and they didn't know what to make of the internet. So they made a Sony website

with the Sony logo and they brought me to some meetings and they said, hey, this person put up all the Billy Joel album covers and they put the track listings and we got to figure out what to do about this. And they went around the table

and one person was like, well, we could sue them or this person was like, well, we can do this and then I said, why don't we hire them? And everybody around the table I totally sign all the lawyers, whatever. And then all of a sudden they just were like, ah, forget this kid, you know,

and then of course years later, you know, they started to embrace it. So, yeah, the, you know, Razorfish started doing little experiments online, the blue dot was line, and it bounced the blue dot around. That was notable because nobody had figured out how to make animation yet. And you got to remember, the web browsers at the time,

they didn't have background colors. It was one font. You could make text flash or do other stupid stuff. But, you know, it was very nascent. And then people started to build, companies around that. Right, so let's set that also. Because it's New York, because Madison Avenue is there, a lot of the early, at least in Silicon

Alley companies, are essentially advertising, become advertising or creative companies like that. Well, you had media companies, magazines, you had news organizations, newspapers, and you had Madison Avenue, you had Wall Street, so those were the sort of primordial thing that this was also, but you also had art, right? And the downtown art scene was very, very, you know, was amazing at the time, and people forget this, but my first real job as a writer was writing for paper magazine. Paper magazine was very avant-garde, and they actually understood that the internet was going to be something.

I ran into David Herschkowitz at a party downtown at Barnies when there was a Barneys home, like 18th, and I think it was 6th. I don't, the downtown Barneys isn't there anymore, I don't think, but they were having some sort of party. I ran into them. I talked to him, I told them, I love the magazine. He's like, yeah, I'm putting the internet on my computer, so I went and I helped them, you know, I kind of taught them a little bit about the internet, and then they gave me

my own little column called Cyber Surfer Silicon Alley. silly S-I-L-Y. And it was just me goofing, like, almost like a Michael Musto kind of thing, just talking about the people who were doing it. Because there's a scene that's developing here, because there's meetups. Who is quite a scene. Yeah. Okay.

So, like, it's all these people that are all excited about what the web can be and are already doing all this multimedia stuff. And so you start attending these parties and these. I started throwing them, too. Right. So one of the first parties, Nicholas Butterworth and I, he had SonicNet, and we hosted a party together, just thousands of people started to show up at these things, just to see

what the internet was. Josh Harris would have parties at 600 Broadway on the corner there, where his pseudo studio was. And I was a kid from Brooklyn, and I was still living in Brooklyn at the time, and I would come with my khaki pants and my blue-collared shirt, I'd walk into a party with a bunch of models

and artists, and, you know, this is that period right after Andy Warhol and Keith Herring and a lot of the really interesting 80s art stuff. So this kind of became like, it sort of segued into that, like where you, this was like, oh, this is the natural extension of this, is multimedia stuff and video art. And it was kind of crazy. And I was like, I need to get a new wardrobe. I need to like be part of this. So I just went and bought some jeans and

black jeans, black jeans, black t-shirt, black shoes, and a black leather jacket. And I wore that for the next 10 years. And then eventually started Silicon Alley Reporter. So that Silicon Alley Reporter comes out of your experience with paper where essentially you're doing like a gossip column covering the scene? I was covering the people in it and just mentioning some of the technology, and then I said to David Hershey with, I want to start my own thing. We'll call it digits. And you'll be paper and I'll be digits. And I asked him to be partners. And he was like, we're really too busy. We've got a bunch of other things going on, but you should totally do it. And then I was like, well, Silicon Alley is what some people were calling this. Like, I'd heard the term

once or twice. It had, I think before I started using it, one or two people had used it, but it wasn't had stuck as a moniker and I said I'll do the Silicon alley reporter because when I was young and it's against the backdrop of our earlier conversation of just being a powerless kid who you know watch his dad fell and was now kind of trying to make his way in the world with a lot of fire in his belly I was obsessed with how people became powerful or famous but mostly powerful famous I wasn't super interested in but I was very interested in power and so I looked at I was I remember I was on same

Mark's place and I was just looking, I was having coffee and I was in some sort of cafe or something. There was an internet cafe called the At Cafe. It might have been there. But I just was looking at the magazines and I was wondering like, yeah, wow, David Hershey that's Picks who's on the cover. I put Chloe Savigni on the cover, put, you know, this person on the cover and that's power. And then I was like, because I was like, well, who are those people on the covers? That's really powerful. I look at Spy Magazine and stuff. But then I was like, wait a second, being on the cover is one thing, but picking who's on the cover. That's the guy I want to be. I just had this like crazy. idea about power. Like, if I could pick the person on the cover,

that I'm the baller guy, right? It makes total sense. At least it did to me at the time. So I was like, I got to start my own magazine. And then I'll be the most powerful point. You can be the arbiter of this scene. Correct. Yes. And that's exactly what I became. Right. And then to tweak everybody even more, I had seen like the new establishment lists or just different lists. And I was like, I will do the Silicon Valley 100. And so I had a meeting. Now you remember, I started my own magazine off my credit cards. I had, okay, all right, all right. Let's stop. Let's do this. Let's do this. So you type up a first issue, photocopy, go to Kinkos, become friends with the Kinko's guy.

You're just a one-man band at the very beginning. Literally my first investors were American Express and Visa. I went to the village printer on 43rd Street, and Josh Harris was having some sort of party at Roseland where Orb was planning. I can't remember, electronic music had just started. So I was hanging out at like parties with Bjork and chemical brothers because of my paper magazine access. And at this point, the meatpacking district, there was Mars, there was Florent, and there was nothing else in the meatpacking district except meatpacking and a printer. There was a printing company there. But anyway, the first issue, I had this revelation that if I got tabloid paper and I flipped it over, it would be eight and a half by 11.

but instead of doing it and putting a newsletter like Release 1.0, Esther Dyson, which was sort of part of my inspiration, Paper Magazine, Release 1.0. Hollywood Reporter, maybe, because you're a trade. You want to be a trade. A little bit. I mean, certainly the reporter came from that. Or I was thinking of that.

And I said, I think if I put a full image on the cover, it will change it from a newsletter into the magazine. And so I started to switch the cover to have a full image on it. And I started going around telling people this is a magazine.

People would look at me. I look at it now and I realized at the time I was so delusional clueless. I thought people were fascinated, but now I think they were appalled and or perplexed at this... Or felt sorry for you? Felt sorry for me, like this 24-year-old kids running around with a little photocopy saying it's a magazine.

Because we should say the way that you distribute this first issue is you go around by yourself, go into lobbies, and say, can I put this in the lobby? Yeah, so I went and I dropped it off at Flatiron Partners at Razorfish, at Sonic Net, at Sudo. And I was known for walking around Manhattan with a luggage cart with two or three hundred copies of it, literally handing it to people.

The other trick I had for distributions, a pretty good growth act at the time, was I had gone to Eureka Joe's, which was a cafe on 5th and 22nd. And you can't remember, it's like this is a little bit pre-Starbucks kind of taken over the city. There were a lot of, like, small newsroom cafe, Urika. you know, Yaffa. There was all these, like, cafe culture in New York. So I would put 10 copies in there. I put 20 copies in Eureka Joe's.

I leave, and I look around, and I look back to see if anybody reads it, and I see the guy come out from account. Take the 20 issues and throw it in the garbage, which tweaked me, obviously. So I go back and I take the 20 out of the garbage. The guy looks at me, and I'm just like, it's just my magazine. I'm trying to.

He's like, I can't let you do it. I'll ever do it. I said. I went back the next day. He wasn't there, the manager. I took the 20 issues. It's a stack of Village Voices in there and other magazines. I take it.

I put it inside every Village Voice, every other magazine. It gets an insert. And the first issue, we didn't have newspaper distribution. So I had my designer just scan, like, Home and Garden or Vanity Fair's barcode and put it on ours. Because I didn't know how barcodes in magazine work, but I knew I needed to have a barcode so people could pay for it. So we copied somebody else's barcode, and then we would go into the magazine stores

when nobody was looking and put them on the magazine shelves next to George magazine or spy, whatever. We didn't want to get money. We just wanted people to read it. Because you got, you remember, there was a zine movement at this time. We're 2,600 and a bunch of zines from across the country. We're all on a little shelf at Tower Records. Tower Records was the store where they sold CDs and used some albums.

Got to date myself. But there was a little section where you could get $2,600 or other than things. So there was a zine culture where if you want to hit your words out before the web, you just would print up a photocopy and give it to people. So two things. still on this first issue, and then we'll move forward. Number one, in the oral history, people describe, well, we all read it because it was about us.

Yeah. But number two, I believe that you had a scoop in there about Microsoft. Yeah, in the first episode, Microsoft was going to shut down. Microsoft had a program that Laura Stein was running where they were investing a bunch of money, and we found out that it was going to be canceled or was going to grow or something. They had some numbers that we got. And people would just give me all kinds of information.

So I was sort of like learning how to be a journal. I was a psychology major, and computer science started as a computer science major went to psychology. So I didn't have any experience in doing any of this, so I just printed whatever people told me. And I didn't really have much of a guide map to that. So we printed a couple of rumors, and that sort of made us notable. The New York Times picked us up for one of my events, for the newsletter. I was on Charlie Rose. People started to pick up on the fact that we had this magazine that was covering it.

And it's really one of the great things that if you get there first, and it's an underservice demographic, you become the standard, right? And we were standard. They think of you as the expert of this niche. We were the experts. There were a couple of other little publications at the time at New York. It was the most notable.

It was a weekly email, and I tortured those poor guys, Tom Watson and Jason Trevocus. Nice guys. Real journalists. And I was just more like going at it from a Vanity Fair or spy magazine Rolling Stone.

It was more like a Jan Wenner kind of approach to it, which was, you know, I'm going to be it, I'm going to be in it. I'm going to throw the parties. I'm going to be the, you know. Impressario. Precisely.

And so that was the approach I took, and it worked. Well, so I told you on Twitter, I went to the library, and I looked at their collection. And so it's fascinating because you can see not only your ambition for the magazine evolve, although they don't have the first issues. I think they start at like issue 18 or whatever. Oh, really? I'll get you the first couple. But it does start out where it feels more tabloidy, more.

I'm covering a scene. And then it evolves with the scene to now, listen, we're doing real news. We're covering a real event. Yeah, there's 75 people work there. More than half the journalists. We had $12 million in revenue in the top of year. So it grew pretty quickly. Did you raise any money to do it?

Not really, no. My friend Gordon Gould had, people didn't know this, put a little bit of money in a couple hundred grand. But that was like in year three or something. And he came to work there and he had a little bit of money and he put a little bit of money into it. It really didn't change the trip. at all. We had, Joanne Wilson was doing the sales, who was Fred Wilson's wife. Right. So that was another kind of funny thing. My first gig was reading business plans for Jerry, Colonna, and Fred Wilson before they had Flatiron, they had some local Acme Ventures. So I read

a couple business plans for them. They pay me a thousand bucks to read business plans. One of them was for Beverly Hills Internet, which became... GeoCities. And another one was the spot. And so, you know, they were probably in their 30s. I was 20s, and I just read business plans for them. But then I started the magazine. And they're like, this is a little too cold. And so you should probably pick one. And obviously, I made the wrong decision and went with the magazine instead of being a venture capital. This is a total tangent, so let's try not to go too far off.

But what was the VC scene like in New York? It's Jerry and Fred. That's it. That was pretty much it. There really weren't a lot of VCs. Alan Patrickoff, there were no angels, really. Esther Dyson was the only angel to speak of. So it was super nascent.

And most people didn't believe New York would play much of a role in the Internet industry. That was wrong. it obviously did. It was a really great confluence of art technology. You know, but it's gone. It's not the same thing. And it was a very magical moment, you know, in that time period, because the world got fascinated with the internet, because a lot of money was being made, and things were getting super big. It's very similar to now, except now people kind of expect it. And it's like, yeah, well, of course the internet's going to be huge. Everybody's got a smartphone. But back then, people didn't understand it. So literally... A great quote I found from you where you said that before

the internet came, the way people thought they would get rich was by winning the lottery. Like this idea of the entrepreneurial culture that we had now did not exist. It didn't exist. No. I mean, there were like shades of it out here where like Bill Gates got rich or Larry Ellison and there's a venture capital culture. But it didn't really exist in New York. And the idea that young people in New York City were the most important people for a decade, Literally, we were the most important people. Like, there's no reason for New Yorker to write a 6,000-word piece about me. There's no reason for me to be on Charlie Rose at that time.

It just that the Internet was so new. We were on 60 Minutes. It was just crazy, like the amount of attention we got for this very new thing. And it was a very avant-garde, you know, art scene where things were very new. And people were experimenting, right? And nobody was in it for the money. Far from it. People were in it because we just thought the Internet,

and there's a real difference between like Zuckerberg and people like that, and I think the people who started this kind of thing, you know, 10 years before Zuck, which was we looked at the Internet as freedom. We looked at it as a way to reach people, to communicate as art, as a way to stick it to the man, as a way to get around the gatekeepers. We thought it was going to change the world in a very positive way to make the world more just. Truth would be easier to get to. and the man and the gatekeepers would be blown away.

Now, a lot of that's true, and a lot of it's not true, right? And that's a really interesting thing. And I always, you know, when people say, what is it like? I think it's very analogous to, like, the 60s. You know, if you grew up in the 60s and you were part of that counterculture and you were part of that first wave, like, you thought you were going to change the world, and you did, right? Maybe they had some major influence in stopping the Vietnam War or whatever.

But then it kind of went away, and you have to be able to move on with your life that, like, yeah, the 60s are over. Like, you can take some lessons from it, but that's why I never stopped and look backwards. That's why you don't see me throwing like 10th anniversary or 20th anniversary parties for Silicon Island Reporter. I don't bring up Silicon Island Reporter. I don't bring up Weblogs thing.

I never bring up any past victories. I'm always looking forward. You know, to extend your analogy after the 60s, you know, in the 70s, you have, you know, Led Zeppelin and, you know, crazy parties and things like that. So at the height of Silicon Alley of the bubble, when you do have the crazy pseudo parties and things like this and I'm thinking of that 60 Minutes interview with the Razorfish guys.

Yeah. They're basically railroaded and like, right, right, when it's like, what do you do? Right, so the hubris. Was there a bit of hubris that came up the height of stuff? Well, there was. And when that 60 Minutes piece happened, I talked to Craig on the phone and I said, Craig, I think the 60 Minutes piece is going to be a hit piece. We're talking about Craig Canterick, by the way.

Yeah. Which I'm an investor in Mouth.com, his company in Brooklyn, full circle. Right across the street from my office, yeah. There you go. And so I said to Craig, listen, it's going to be a hit piece. The only time 60 minutes does stuff is a hit piece. So just be careful. Like, don't do anything.

He's silent. And he said, did you already tape with them? I said, yeah. I said, what did they tape you doing? It's like driving my 69 convertible Mustang and dyeing my hair blue in the sink. And he's like, do you think that's bad? And I was like, oh, my God. So then when I met with them, they were trying to really manipulate me on camera to say crazy stuff.

They got Josh Harris to say crazy stuff, because that's just like pulling a string. But I took a different approach. I said, I'm going to be the serious guy. And the guy was interviewing me. I forgot his name. He just passed, but it was a really cool guy. Were they safer maybe then? It was Bob safer.

And he says, so you guys are going to crush the, you know, everybody in the world. No, it's going to change the world. He said, well, people look at this, and they see young people getting this rich, this quick. You know, what should they think of it? And I just looked at him, and I said, get you safe. to it. And he said, but you know, should these companies get this big and people have this much power and get this much money and that people are becoming worth hundreds of millions of dollars? And I just looked at and I said, get used to it. And it turned out to be one of the more pressing

things I've said and more accurate things because if you think about it now, we're very used to now people starting companies and then becoming worth billions of dollars in five, six, seven, eight years, tens of billions of dollars even. Because what I saw very clearly at that time, which I think maybe Bob Safer, you know, all these other people probably would eventually see just maybe six to 18 months after I saw it was once you give people a broadband connection, they'll never take it away. And I had seen the early statistics about broadband, and I had played with broadband connections. And really, there was this big jump between not having a high-speed connection and having it. And watching people struggle on a low-speed connection,

then seeing high-speed, it was very clear to me that we would have high-speed mobile phones in our pockets, high-speed connections everywhere. It was obvious because I had seen the early Wi-Fi tests. I'd seen POM and it was like, there's no doubt that you'll be watching video on your phone. It's obvious to me. This is in 96, 97, 98. So I learned this little technique, which was just eventually assume everything goes 100x. Everything becomes 100 times cheaper. Everything becomes 100 times more powerful. And I just approached every problem I saw like that, that the problems would be sorted out. And that made it very clear. And then I had heard from one of the guys who was working on cable, maybe at a

excited home or whatever. He said yeah, somebody told us we could take their cable away when they rip it from my dead dying hands. And I always stuck with me like, God, this thing becomes broadband and it becomes global because we started to have people from other countries talking to us. I just said to myself, well, let's just assume

everybody has internet access and everybody hasn't. Then the marketplace is going to go from tens of millions of people for any one company to billions. Well, that's like a thousand X or 10,000 X. So as big as everybody thinks this is, it's going a thousand X. I mean, there were only

5 million people online when we started these companies, and there were only one or two million of them were probably broadband. So when you started to see 10 million people on broadband, we're like, if this thing hits 20 or 30 million broadband users, it's game over. I was like,

10, 10 million, went out, 10 million, went out one billion. Right, right. So obvious. So before we go to in the direction of weblogs. Do one more thing for me because I like people to give me color about the dot-com bubble bursting

because I feel like for the tech industry it's like the Great Depression was for our grandparents. So do you remember feeling oh, the jig might be up? Do you remember a moment? Well, I knew it was. I mean, because when I saw companies like the globe, that was when I really knew it

because the globe was run by two dopey kids. And I met them who has been on the show. Stephen Patternott. Not that one, the other one. The other one. Yes. So these were really dopey kids. I mean, I don't mean to be, well, you know, Jason 1.0, but they were not impressive. And they were taking this company public for hundreds of millions of dollars,

and it was valued this thing. And I went to a party with them, and I hung out with them, and I was just so underwhelmed. And I realized, oh, my God, these guys are totally over the head. This is a complete, utter scam. You felt like they were almost like a front for... I think they were dumb kids who were being manipulated by older bankers, money people behind them. I think they probably feel that way, too. And so I just basically wrote a blog post like, this whole thing's a scam.

Because at the time, I just thought I always had to be the effort guy, like the candid, blunt person from Brooklyn, and that's how I would accumulate my power. It's just by being the most honest guy in the room and the most connected, right? And it turned out to be a pretty good strategy because people listened to me, and I met a lot of people because I was always viewed as candid. But that's when I knew it was like a real scam. and that there was all these bankers doing crazy stuff. And then I remember, cosmo.com had met with some VCs, and the VCs liked their business so much that they decided to shut their VC firm

and start urban fetch and be a competitor. And I was like, okay, this whole thing has changed. We should say those are early delivery companies, what we would think of as, yeah. So Cosmo was a great company. They would basically deliver you whatever you wanted. It was basically movies, right? Before Netflix, before broadband.

They would just bring you DVDs within an hour on a bike messenger, and you can get Hagenas or whatever, and there was free delivery, then eventually became $5, but they would bring in like H&H bagels and the New York Times and whatever you want.

It was really great. But then Urban Fetch came and they did everything half price off and free delivery with no minimums and they would just burn through tons of money. But it was obvious that this was not going to work out. And when, you know, everything came apart, I had to like let go of,

I had to go down from like 80 employees down to like 10 or 5. And then 9-11 happened. And we really got a really good perspective on what's important in life. It was very interesting was I had, remember there was a book called Digital Hustlers that came out. But before that book came out, it was going to be like visionaries. So this publisher had, you know, this kid was coming to interview people, Josh Harris, myself,

bunch of people. It was like the pioneers. That's the oral history book that I've been referring to, yes. Digital Hustlers, yeah. So digital hustlers was supposed to be called, like, visionary pioneers. But then because the dot-com bubble happened, the publisher called it hustlers. And I got really offended by it because then they just changed the whole spin of the book to be like where. And I was like, you know what, fuck you guys.

Like, I was never a hustle. I didn't get rich on this. And I was never any for this reason. So I just, a lot of my friends went and they kind of, Josh went up to an apple orchard and upstate New York, Josh Harris from Sudo. Other people went on vacation. A bunch of people went to Vegas and did drugs. Other people have told me that it was almost like, especially in New York, that the old media people

and there was like a sigh of relief like this fat is over. For sure. For sure. It was like, fuck these kids. Thank God. They have no power. was like, you know what, fuck you guys, I'm going to be twice as strong. I'm going to figure this out. And that was that fighter in me having watched my dad's business go, and then I'm like,

now I'm faced with the same thing. Holy shit, I'm going to go out of business. Well, because I've said on the show before, if you look at the numbers, it's not like internet usage declined ever, right? No, no. And it's a straight line. And it's a straight line. And it's a straight line, and the broadband and people's ability to spend money, all the stuff was just going through the roof. So I knew it wasn't a fraud, but I knew there was fraudulent behavior that had occurred. So to me, that meant double down.

It's almost like if you're playing poker and you're playing perfect poker and then some joker is getting their money in bad and they suck out on you twice, and you're like, this is incredibly frustrating, this idiot, put all those money in with all this, but I have to keep playing with this person. I got to stay at this table because eventually I'm going to win.

So I stayed at the table, and I never took a break. I just went back to work. And I turned Silicon Island Reporter into venture reporter, started charging people $1,000 a month for access, a thousand dollars a year for access to it. We wound up selling all that to Dow Jones. My brother, Jamie, still works at Dow Jones. He had worked for me.

So I saved the business. I got two years of salary. He started Weblogs Inc. Because when I had Rafat, Ali, working for me, and Shenny Jardin from Boingbung had been working for me and Will Leach had been working for me. And I watched two of those

after they left me start blogging. And then Rafat told him, and Rafat had started the blog Paycontent.org when he was working for me. And he showed it to me. And I sat him down. Raphat, blogs are stupid. You're stupid for wasting your time on this.

But I'll let you do. on the weekends. See, he said you were very kind. This is the version of kind. Yes, yes. I was kind because I didn't fire him when I found out, I think is what he probably meant. Because most bosses at that time would have fired him. It's a different era, right?

It's Gen X. It's not millennials and this weird, you know, balance of power that shifted between employers. At the time, employers were got kings, and you were lucky to have a job in New York. And I was probably playing Ruffalo. I think the starting salary at Stoke and Airport was 25K, and then you got 30K if he made it six months, and you got 35K. I basically gave people 5K more every six months. At the time, Condon Nest was paying people $19,000 a year.

You were going to pay $5 an hour, quite literally $5 an hour. And so, I said to my, listen, dummy, this is never going to be anything. If you remove an editor from the process, you are going to write about every piece of nonsense. You're never going to have a sounding board. and the idea that you will publish without having somebody read your work is preposterous. You have no idea how to make a headline.

Your prose is filled with errors. This is an utter embarrassment. He sold it for $30 million. $20 million. And he says to you, yeah, but that's not the point. No, no, he didn't explain it to me. I got it because I watched Shennie, and then I realized, okay,

I had read that Raphat was making like, I don't know, six, seven, eight K a month. And I was like, I did the math. I was making double what he made for me. And I made some mention that he made some quip about doing it in his underwear. And to his credit, he studied me pretty

deeply in how I built the business and took notes. And he was very good at being, he was very quiet at first, and now if you look at him, he's got a little that Jason 1.0, which is he just says incredibly candid, blunt stuff about his peers, even.

and he does not care, and now people don't know what Skift is. I'm also an investor in Skiff, by the. Anybody who worked for me previously, I invest in their company, unless I fired them. But maybe, even if they fired them, I would probably invest. And Shenney was doing Boing Boing, and I was like, okay, wait a second. People are doing better work without editors or me than they did with me. Something has changed.

I was always a big fan of Bob Dylan, and I kind of based a lot of my approach. to my career on Dylan, which was at the time, in my mind said, this is electric. Folks over, it's electric now. People are not getting why this is powerful, but there's some power here, and there's something beautiful about this. And what it is, it's an unfiltered voice. Correct. And the unfiltered voice for nine out of ten riders is a bad idea. But for one in ten, it's the best idea. So it's just a matter of finding the one voice. Now, I wouldn't recommend most writers just go write a blog without an editor. They need an editor. but for Rafad or Shenney or Will Leach, obviously they don't need one.

And, you know, I don't give myself any credit for any of those people's careers. They probably would have been as successful, more successful how they would not work for me. But I was good at identifying talent. I could tell they were going to be talent. And I was like, okay, they're all doing this little tiny stuff

and this kid Nick Denton, who's a bit of a wet noodle in my estimation, he's got two blogs. He's got Gawker. I only knew about Gawker. He's got this Gawker thing. It's kind of like Spy Magazine Light. Elizabeth is writing it.

What if I did business-to-business blogs? So I talked to my, Patrick Ewing's retirement ceremony. I got tickets to Patrick Ewan's retirement when they put his number up in the rafters at the garden so that we'll date it. I took my former CTO at Silicon Empire, Brian Alvey, who I was in high school with,

I said, I have an idea. I have two years of salary. I can't pay you, but I can pay something to pay for the writers. I want to make 100 blogs, blank.weblogs, Inc. And it'll be the ink means business. We're going to be blogs for business. So wait, let me get on that. You want to do 100 because you're looking at Rafat and he's making, let's say, $70,000 a year.

Yeah, I always thought about scaling. So it's total scale. So if you can replicate that 100 times, you as a company will achieve. $700,000 a month of revenue. 10 million. So I said, we can build to, I said, these 100,000 each, is exactly the math I did with Brian at the game. It'll be a $10 million business. We can sell it for five times. We'll make 50 million bucks. We'll be rich. And I still, because I had gotten an offer for maybe $18 million from Alan Meckler to buy Silicon Airporter. I didn't take it. Alan Meckler ran internet.com. He was

kind of this like crumudgeonly sharp elbowed publisher from Greenwich Connected who was super connected with like the bankers. And he was actually really nice to me actually. So I don't mean to say that in a derogatory way, but I didn't take the money. That was a big mistake in my career. So I said, the next time somebody offers me tens of millions of dollars, because remember, at that time, I had this thing about,

I need to make a lot of money and be rich, and I need to be powerful. That was my only marching order. I wanted to be powerful and rich. And I wanted to also beat anybody I was in competition with. So I destroyed the at New York guys. I destroyed Allie Cat. I just, just anybody in my way, I just destroyed. And I specifically went after them.

Like, I knew the at New York guys were doing this weekly thing, so I launched Silicon Allie daily. Just to fuck with them. Well, let's stop too, because we skipped over the Silicon Alley. Talk about power. You are making the list. Yeah. So I'm sitting there in a meeting, and we had done three or four episodes.

I said, we need to make a list of the 100 most powerful people in Slovene Alley. So we sat around. I had like two or three freelance editors. And we got to 50 or 60 people we knew. So we only had 50 or 60. That was the total number of people working in Silicon Alley. Right. There were only 60.

But then the next. And we were putting lawyers on the list, headhunters on the list, PR people on the list. You would never include them, but it was just, there's a PR, you know, this lawyer is involved in Internet companies. So we emailed the 60 people and said, do you know anybody who's doing anything in Silicon Alley? And everybody emailed us two people. We got a list together. And we're sitting there and we're trying to figure out, like, how do we group this? I said, we're going to rank it from top to bottom.

And they said, how are we going to rank it? I said, I'm going to make a list. And everybody's like, don't do that. It's too divisive. And Joanne Wilson's like, don't do that. It's too divisive. And I just didn't take anybody's advice at that time for better or worse. Sometimes it was for better, like this situation, for worse,

when I didn't take the money, or go national. Joe Ann Wilson also, Fred Wilson's wife, was also like, we should be national. It was a big mistake. I wouldn't cover things outside of New York. I just wanted to be focused on New York. A big mistake. I could have built 100 million.

business like an interest standard. Long story short, I make the list, and I think Esther Dyson was number one, because I thought, well, she kind of inspired me to do this with at least 1.0, that'd be a nice hat tip. Nobody can argue with that. Putting a woman at the top, angel investor, smart person, it's a very savvy move for me.

Then I think I put DoubleClick number two. Double Click had like 50 people now. They'd raise the most money. When I met Kevin, Ryan, and Kevin O'Connor, they were at Poppy Tyson, which is where DoubleClick was born. It was like a little, you know, they became like, They were figuring out how to make banner ads run. They were actually a rep firm, too.

They would represent the ads being sold on other people's websites because people had websites, but no ad sales team. So I started doing that list. And then I said, I had gotten a phone call one day from Rolling Stone. And I was getting the press were calling me. I was, you know, this crazy kid. And my assistant, Linda Miller, had said, did you call back Yon from Rolling Stone?

I said, no. you really should call him back next day she'd you call back Yon from Rolling Stone I said no I'm kind of busy I don't have time for like a journalist from Rolling Stone I don't want to do any press right now I got my own magazine she goes don't know Jason John Wetter I said who's John Wetter Jan Wanner? Yon is the creator of Rolling Star

publiced her what? She said yeah I was like oh I love Rolling Stone so I immediately call him he said can you come up to my house I was like sure what time he's like two o'clock so I run up to his office at two o'clock, same day, he's got this incredible office. He's got my magazine on his desk. And he asked me questions, hey, do you want to be the president of Rolling Stone? Or what are you doing here? And I just started asking him for advice.

And he started marking up the magazine, and he taught me how to do a cover. And I said, hey, how do I do a cover on a budget or whatever? And he's like, well, what's your budget? I'm like, I think we're spending like $3,000 in the issue. He goes, okay, spend $2,000 of it on the cover. All that matters is having a great cover. And he called some people on the phone and gave me references to photographers to help me. And one of them was a guy named Frank McIllata who wound up doing my covers.

and we did these amazing covers that were very themed. So we did agency.com guys as men in black. We did razorfish. We had Jeff Dachshus holding up a fish and a knife. Very iconic things. Because again, back to my obsession with power, I was like, well, if I can get these themed things, I could be like Graydon Carter or Kurt Anderson.

You know, I was just looking at Grayden Carter, Kurt Anderson, and Jan Wenther are saying, like, I've got to be like those. Or Martha Stewart. Just have to be powerful. Just have to be powerful. We've got to get that cover going. So we did that.

And the list then became incredibly divisive. Right, because, okay. And then everybody returned my phone call. I was going to say, because then if you only have 60, then the strategy should be, the other 40 should be people you want to know. You throw them on the list to like... Maybe.

Anyway, we figured it all out. Then I was like, everybody come to my house, to my loft at the start at Lehigh building. I was living illegally in my loft. And I said, we're having a photo shoot at noon. Everybody come there. And I give people like 10 days notice. They all showed up.

Yeah. And they said, if you don't show up with a photo, you may or may not be in the 100. This is in the year two or whatever. So everybody came together. We took the photo. It was like, wow, this is powerful. And it was great because then for the rest of the year,

PR people would be lobbying me for their client's position. In fact, I had one girl I had gone on a couple of dates with, and then she started bringing up the Silicon Island 100. And I realized, oh, my God, this girl's not into me. She's working me to get her clients on this list. Well, and towards the end, I think the last one, like Peter Jenning. No, Sam Donaldson. Who put Sam Donaldson on because he was doing a lot of stuff.

and internet and we started getting all these kind of celebrities I mean my life became very surreal I was hanging out with like I was really into public enemy when I was a kid and then I got to meet Chuck D the guys from Led Zeppelin came to one of the Silicon Air reporters Sergey Brins people like lobbied to have Google at one of the Silicon Valley events so I was like fine we'll have Sergey I did a far side chat with them accounting crows just like all these famous people everybody wanted to be involved in the internet so they would come by our shows and hang out I became

with a guy named Jeffrey Epstein, who's very notable for horrible reasons now, but he would hang out at our events with Gillen, Maxwell, and just it was like the center of the world, right? I never met Donald, but it was truly the center of the world. All right, let's bring it back to weblog. So as we said, you want to scale, you want to go to 100. And how are you picking what the blogs are going to? I just picked whatever topics were relevant.

So I did social science. weblog sync, Wi-Fi.weblogsync, all these things were very interesting topics at the moment. So I just looked at whatever topics were under-service. This was always my playbook. Under-service topics. Each of those topics, one person is going to do... One person's going to do it.

Sean Bonner did apple. weblogs, Inc. Then, so I had lunch before I announced it with Nick Denton. I reached out and I said, hey, I'm thinking about doing something blogging. We went to have lunch. We had lunch down in... It's a pretty famous story. We had lunch down in Tribeca.

No, in Soho. West Broadway, and we couldn't be more opposite. He's a gay Brit. I'm a brawler from Brooklyn. Couldn't possibly be. But we were always very attracted to each other in a very like espri-de-corps kind of way because we're both outsiders and we're both, I think, we're fighting. We're both anti-establishment guys.

I think at our hearts. Anyway, so after I have this meeting with him, I tell him my plans to do business to business, he writes his blog post about how I'm the exact boisterism that blogging doesn't need and I'm everything wrong with blogging. Because just remember at that time, the idea that blogging would be a commercialized, flew in the face of blogs. They had no ads on them. And the idea of introducing advertising was...

This is before AdSense. Way before AdSense. In fact, Weblogs, Inc. was in the first Q1 report with Google for AdSense. We were their blog partner in Gadget, and then they had New York Times. So those were the two case studies when they went public. And so he wrote this, like, flame. He basically flamed me on his blog, and I was like, that motherfucker,

but he's doing to you what you did to your... Of course. Yeah, right. Yeah, so well played. Right. I finally met somebody who could be a foil. Right. And I think that's why people were so entertained by the two of us fighting because they were like, they deserve each other, right?

And you look how it's wound up. It actually makes sense in a way. So I said, I'm going to... How can I cause maximum damage? Because, you know, if you get jumped, or somebody sucker punches you. You really got to think through a retaliation strategy

that definitively ends it. Right? So you get sucker punched, somebody's got to wind up in the hospital, right? Somebody winds up in the hospital, somebody else got to wind up in the morgue. Like it's an escalation kind of issue when somebody bullies you. And so I was like, okay, I have to make this very clear to him that under no circumstances

can he ever take a swing at me again. Good on you. took our confidential lunch and you blew my launch. Like he just put this information out there. Everything I told him, like my plans. It was like a confidential lunch. So I called up Shanny. I called up a couple people.

I was like, I need to like get Elizabeth to leave Gawker. Come work with me and create a Gawker killing. So I try to convince Elizabeth and she's like, no, I'm going to work at New York Magazine. Elizabeth, this is a terrible idea. Magazines are over. You're the number one blogger in the world. Come with me.

I'll give you equity in the world. in the blog we create, and I'll buy you a new MacBook, and, again, back to my clue list, like, kind of, gosh kind of, like, approach to things at the time. And he's paying you $1,500 a month. I'll pay you $2,000. So I'll give you $2,000, a new laptop. You can keep it if you stay at work for me for two years, and you'll have equity, and that equity will become worth billions of dollars.

She said, no, I'm going to go to New York Magazine. I said, worst idea you could ever do. you're number one at something in the world. Trust me, I've been through this. I was number one in the magazines, you know, with the business with the Silicon Harbor. I became number one. When you're number one, you want to cement that position.

Don't bail on blogging. And she bailed on blogging. Went to do features. And then Sheenny said, you know, Jason, Elizabeth is great. You really want Peter Rojas. And I said, who's that? Gizmodo.

I was like, oh, the blog about like, gadgets, the fetish thing, because fetish was the section in Wired magazine. I was like, is there really enough information out? Is there really enough stories about Palm Pilots and all this other nonsense, BlackBarrays to make a blog? I mean, I like it, but it's not enough news. She's like, just go talk to him. So I talked to him.

And it turned out Nick had promised Peter Equity, but reneged on it. And, you know, Denton, as has come out, you know, is, you know, very Machiavellian in his approach in terms of pushing the editors to do things that maybe is outside their comfort zone. So he constantly wanted Peter to do things like, you know, sex toys or just other stupid stuff that, you know, Peter was a very serious journalist, you know, and he had a very particular vision for Gizmodo that was being corrupted by Nick, and then Nick had double-crossed him. So I said, if you come work for me, and I took him to Jewel Baku, which was a sushi place in the East Village. I was, and my friend knew the guy who was running it, my friend Barry Wine.

I said, can you get me a reservation there? I got an important deal. I got to close. So Peter brings Jill Ferenbacher, who did inhabit Tatt later, but she was his fiancé at the time. Turns out they're vegan. They're taking for sushi. So I take the guy from Joe Baku in the bag. I said, I know this is crazy, but they're vegan.

I'm trying to close this big deal. Don't worry about Jason. I got it. He goes out, buys vegetables. Comes back and makes all those vegetable sushi for them. I said, Peter, here's a deal. He's like, I'm in. That's like, great. Boom.

Then Peter's like, I've got to pick the start date. I was like, I can't do it this week because Denton's out of town. I was like, do tell me more. He says, yeah, he's going down to like hang out with all these celebrities down in San Paulo or somewhere in Brazil or whatever. I said, oh, really? Tell me more. He's like yeah, he's leaving on Sunday or whatever.

He said, oh. He's like yeah, it's got like a noon flight or something. I was going to try to have breakfast with him before but he's got a leave for the airport at 11. It's like, okay, cancel that. Tell him you talk to him, we get back. It's no big deal. He goes, okay, I said, then email him at 1 o'clock that you resign. So when he gets off the plane, that's the first thing he sees him.

We can just stick it to him and have a big advantage while he's away for two weeks on his first vacation. We did it. Peter did it. Just broke Denton's soul, crushed his soul. And everybody was like, Calicana stole Peter Rojas. And Peter wound up becoming a millionaire. I mean, to his credit, he understood that the equity was worth something. And when we sold the company, you know, 18 months after we started there from 30.

million bucks. Peter made millions of dollars. Wasn't that blog also always your most successful? For sure. Right, because you said, oh, who cares about gadget stuff? But this is right before the dawn of the golden age of gadgets, right? Yeah, so Peter taught me a couple of things that were very important. Number one, he felt that each

blog needed to have its own brand. He was correct. So remember how I just took nobody's counsel in the first company Silicon Air Reporter, and it got me so far. I was determined to evolve, right, when I went into my electric phase. for my folk phase. And he told me a couple things.

One, secret to blog me is showing up every day. Two, they need to have their own names, and I want my own logo. So I was like, okay, fine. And we paid Jill, his fiance at the time, like $600 to do the Engadget logo, which is an incredibly iconic one. And he just wanted editorial controls.

I said, fine. We don't need to be involved in everything. But then we spun out joystick, auto blog, cinematical TV screen. squad and a bunch of other blogs. Autoblog was the big one. And it turned out Autoblog actually made more money, but Engadj always had the most trapped.

Oh, because of the advertising. Yeah, we got Volvo and some early people to start. So, you know, without Peter, it would not have been the success it was. He wasn't exactly a co-founder because I started the company, brought Brian in, brought Peter in. But what you learn as you go is, I think he's definitely a co-founder. founder because he was there in the first year and without him there would have been no weblogs ink and it would not have had the exit it had so I get I'd say he's probably after you know me starting it

it was probably the most important person and then I was an investor on the board of gadget and you know with Peter anything any company Peter starts I'm the first investor and as you said you're the lesson you learned was the next time someone offers you money you're going to take it right And so AOL offers you money. AOL reaches out a guy named Jim Bankoff, who was a really nerdy SVP, you know, like bad suit, Dulles, but really smart.

And he had been Ted Leones' chief of staff. Now I knew Ted Leonson's, he spoke at our event, we're fellow Greeks, we had a friendship. Jim Bankov was just passionate about blogs, and he had a vision for AOL, to his credit, that they needed to have something after dial-up went away and content is what he thought it was and they wanted to invest and I had lined up Jeff Bezos and Jeff Bezos and then Mark Cuban was going to re-up because

Mark Cuban had put 300k into Weblogs Inc. for 15% of the company or something that you're 15% I think and then I had met with Jeff Bezos he was fascinated about Weblogs Inc and how we picked domain names had a big meeting with him he was going to put 500K Mark Andreessen offered to put 500K and then Cuban was going to put another $500K and we have $1.5 million and keep going. But then AOL came and they were like, hey, we want to put money

in, we'll do it, or we want to buy 49%. We want to buy 51%, then Ted Leon's call me. So this we want to buy your company. And I was on a phone call with Brian, we had maybe $150K in revenue. And we have five employees and then maybe 3,400 freelancer, some crazy amount of bloggers.

And we're on the call, Brian and our skipping back and he's like, what should we ask for? And I said, what do you think? He said, 10 million. I said, I think maybe 20. Because we had raised money at a $3 million valuation from Cuban, so I said, maybe 20.

He goes, no, no, don't ask for 20, we'll lose the deal. And so we're having this like dance, bank off, and we're talking about, hey, what's the price gonna be? What's the price gonna be? And I said, well, you know, what do you guys think? And they said, well, you know, we don't want to insult you, whatever.

you know, what would make you comfortable. And I just remember, like, somebody had said to me always double it. So I said, well, we think $40 million would be the right number. Paul, it's on the phone. And my partner was like, are you fucking crazy? He's like over a Yahoo Messenger like, are you crazy? And they said, well, we were thinking more like $25. And I was like, well, why don't we start with $30 and figure that out?

And then so we wound up selling for like $25 for the main asset and then five million for blogsmith later. So it was around to be a $30 million sale. And I remember sitting there with my wife, and I was like, and there was an earn out that we wound up getting. So that was good, too. And I was like, if we have millions of dollars, I wouldn't have to work again, and we could buy a house.

It was like a very surreal moment for a kid from Brooklyn. And I sat there and I hit refresh on my Bank of America account. Hit refresh, hit refresh, it refresh. Boom, the wire came through. And I just cried. My wife came in and she said, why are you crying? I said, no, my mom doesn't have to work anymore, my dad, my brothers. And it's just that, I think that chapter of my life, that hustle, that there will be blood,

I am going to destroy everybody. It was over at that point. Something inside you was validated. I think my fear was evaporated, really. I realized I had lived with the fear of running out of money my whole life. I had lived with the fear of my parents. you know, every fight they ever had was about money. And watching my dad fell and watching my dad go six fingers into debt with the government,

like I was like, well, maybe my dad won't have to go to jail now because I could bail him out, you know, or whatever. So it was this very cathartic thing for me that I didn't have to be at war for the rest of my life, right? And at 30, it was good because I didn't actually, you know, 32, whatever it was. Because, you know, being at war is exhausting. And that kind of competitive motivation is very powerful, but it's not the most powerful. The most powerful motivation comes from within, right? And so to want to see something exist in the world,

it's a slower burn, right? Or knowing you're doing the thing that you're great at, right? Like knowing you're great at something and you're deploying that skill in the world, that really is the ultimate. That's the ultimate flow experience. When you can dictate what you're going to do in the world and you can see the chessboard clearly

and you know you're going to win. You might not beat everybody, but you just know, like, I'm fucking good at this game, and I will win. I will figure out a way to win. I have no fear anymore. So I think my fear evaporated from that point on,

and that's when I was able to just sort of transition to another level as an entrepreneur. It just doesn't human being, too, because I just didn't have this fear chasing me that I was going to go broke. Well, to jail. Right, you were going to be okay no matter what, basically.

Precisely. That's why I'm a big advocate of people, when they do get that early sale, taking it, or, you know, being able to sell some secondary shares and sort of... And if you look, like, we sold after 18 months, Denton went for 15 years.

Right. I might have made more money than Denton at this point. I don't know how much he skimmed off of every year and probably some amount, but just in terms of cost of capital, He was at it for 15 years. I don't know. How much money is he going to wind up netting after all this?

He's got to pay back $50 million to the investors, $50 million to Holkogen. It was $140 million. I think I'll probably make $10 or $20 or $30 maybe. I don't know. And then he'll get Gawker back, and then he'll be back in the game. Well, to start to bring this to a landing, I'm going to, with your permission, alight over some stories, your time of AOL, netcape.com, that sort of thing.

Because, again, I'm into the history. Sure. And we're in the era that I was active in. So Web 2.0, to me, started to feel like things were coming back with blogging, the rise of things like Friendster and things like that. But also the conferences. Yes. So talk to me a little bit about that, about how important that was in terms of getting the band back together in terms of the tech industry. So I had a partnership for a couple of years with the guy named Mike Arrington.

And we were pretty close friends for a while there. And he really looked at, he was obsessed with how Weblogs Inc. had sold to AOL, you know, which is exactly where he wound up selling. And he didn't know how to make money from the business tech crunch. And so we were smoking cigars and we were at his place in Atherton. And I was going to do Mahalo, my new search engine company. with Sequoia, and I said, this is very simple. Just do conferences. Like, just break even on the journalist, but do conferences, you'll make a ton of money.

He said, do it with me. And I said, I'm too busy, but, you know, I said, do it for me. What conference should I do? I said, well, you know, if you were smart, the conference you should do is in New York, I did something called Ready Set Pitch, which is a New York Times article about Ready Set Pitch from 1996, where I had people come up and pitch fictional companies to Ted Leoneses and other people. And then people actually put money into them. And it was way before Shark Tank.

I came up with the idea. Because Aola was doing their greenhouse stuff at that time. Exactly. And I had been part of the greenhouse, and Ted me honest, ran the greenhouse, and so you start to figure out the whole circle of how networks work. And then, so I said, what we should do is I just acquired the domain named 20.com, which was going to be the name of Mahalo, but I liked Mahalo better. And Mahalo tested better with women.

So I said, we should just do, like, the top 20 companies, and we'll just do a one-day conference for 20 companies, new companies. thing, we'll call it the 20 conference. And it will just, back to that rabble-rous of fighter, I was like, some injustice, and this again, back to like, Mike is a hard-to-like person, especially with all the personal problems he had, which people can look up online.

Really horrible stuff, I'm very glad to have him out of my life. It was a very hard person to defend having a friendship with. It's like kind of being friends with Trump, like hard. And he, he, I said the demo conference is charging $20,000 to present. It's complete utter bullshit. Let's kill it. And so he just wrote a blog post.

Jason and I are doing conference. We're going to kill the demo conference because it's bullshit. All of a sudden it became two days. We made a bunch of money. We did it for maybe three or four years together and made millions of dollars. It became TechCrudge 50? TechCrunch 50 eventually. And then one day he stopped returning my calls.

And he said, and I had my daughter, who was now seven, so this was seven years ago. or six years ago. And he said, I said, you're not returning my calls, what's going on? He said, meet me at Sundance, place on El Camino Real in Atherton, Palo Alto, and we'll have a stake. We sat there and he just looked at me like a robot

and said, you know, I'm not gonna do the Congress with you anymore because I don't wanna split the money with you. You can sue me, but I'm an attorney, I'll probably win, and I'll drag you through the mud, and I'll win the battle because I have the blog. And I looked at him, I said, Mike, wanna ask me what it's like to be a dad? and my first child because he didn't call me when I had my kid and he said oh yeah I was being a dad

I said go fuck yourself and I will sue you he said if you don't like it sue me I said okay I'll sue you walked out and I sued him and then he went so scorched earth he called Marissa and yelled at Marissa on the phone he called a bunch of venture capital firm said if you work with Jason never worked with us and Marissa called me and I was like Jason listen I know you a mic are at war and I said I'm going to do my own conference launch and Marissa and Google backed my conference And they said, keep our 25K, take our name off of it. I cannot be at war with my guarantee. He's just insane.

You know, like Mike was a scorch earth kind of guy. So I kind of met my match in him, you know, like in terms of somebody who's willing to go to the math. And I just, you know, I reflected on it. And somebody who's very wise that, you know, jump in the mud with a pig, the pig enjoys it, and nobody can tell the difference. And I said, you know what? It's a pretty good advice. So I dropped the lawsuit with him, and I just focused on launch.

and I said, I'm just going to focus 100% of my energy on continuing this concept I had of giving free, letting people be for free, then I'm going to give away free tickets and free tables, and I'll just run it at a break-even. And sure, now we're six or seven years into the launch festival, and it's the largest event here in the United States. 15,000 people came last year.

I do it at a break-even. And I just build goodwill. And I got, you know, there's like a funny line in one of the Scorsese films where, I think it's Mean Street, it's where the guy's like, this guy owes me 20 bucks, you know? And I probably rightfully deserved some percentage

of the tech crunch sale, you know, not all of it, but probably 20% of it or something, because the majority of the revenue came from the events. And so the guy says, and one of the scores says he from, saying, that guy owes you 20 bucks, yeah, he's like, I'm trying to get that 200 bucks from that guy. He's like, that's the best $200 you ever spent. You never have to see that guy again.

And I realized, like, you know, not having Arrington in my life was this incredible gift. So even if he stole a couple million bucks me from that loss. This would be great because then he had all these rape allegations and all this other stuff in his life and who knows what the truth there is but there were so many of them that I tend to believe the women in these situations and he ran and hit in Seattle or whatever and I just thought God it's so great to get Arrington out of my life because he's just such a dark person and I knew he was a dark person right before all

that stuff had hit because he had called a friend of mine and Kara Swisher is the C word. And I was like, Mike, you can't call a woman the C word. Did you call our mutual friend? I won't say her name, the C word. And he said, Jason, she is a C word. I said, Mike, are you using it in the like, did you just get back from London or something

and people are using that word in a different way than we use it here? He's like, no, she's a C word. I said, Mike, I know you're Yankee, Mike, you're a provocateur. Please, do not behave this way. Don't call people these things because it's, It's bad for business, it's bad for you, it's bad for reputation. And Kara Swisher was like, he called her this, and I was like, he didn't.

And then she takes out of BlackBerry and she shows me an email from Mike, clawingless woman the C-word. I'm just like, oh, my God. And Kara Swish was like, how are you in business with this guy? Like, it's so bad for your reputation. That's when I was like, you know what? I got multiple people telling me not be in business with this guy. So I got out of business with him.

But to your point, Web 2.0, which Arrington, you know, and Tuck Wrench played a huge role in, you know, and Mike on his best day, leaving aside his horrible personal issues, if they're true or not. You know, Mike, on his best day, was a great writer. He was candid, he was blunt, he's a great thinker. And I like guys and gals who are, you know, debaters and sharp elbow. I love Nick Denton.

If you tell me right now I can have lunch with Nick Denton, I'd be like, great, it's probably a few people I'd rather have lunch with. I like the guy. I like these kind of people. I like people who got a little edge to them, right? but with Mike, you know, when the edge turns dark, you know, that's when you've got to kind of like get those people out of your life. It just got too dark. I want to end with a question about your angel investing generally, but I know you've spoken at length about this on this show.

My listeners, though, haven't heard the story, just briefly the Tesla story and the license plate, the number one Tesla license plate. Well, I became friends with Elon, and I'd say we're close friends. I mean, we have a really nice relationship for a long time, and I won't get into that. But I'll tell you things that are public. You know, like he struggled as he's counted in the most early days of Tesla. In fact, you know, Tesla was created. He backed Tesla, but there were some other guys running it. We've had him on the show.

Martin, or? The other one. Oh, okay, yeah. So they ran it into the ground and it was going to go out of business and he had to take over. I don't think he really wanted to. He was busy with SpaceX. But anyway, I wound up having the 16th Roadster. We became very good friends and we went to dinner one night.

He's actually told this story so I'm not speaking out of school. I never like to talk about personal stuff. It's much different than my earlier days again of trying to evolve as a human being. And it was just like. the rocket had blown up, second rocket had blown up for SpaceX. And there was a story in Valley Wag, back to Nick Denton,

where they're just like, Tesla's got four weeks of money left, and somebody was leaking the information. So I said, wow, tough week, huh? And it was during the financial crisis, and we're having dinner in L.A. Just two of us having dinner. And I said, what happens if you blow up a third rocket? That's the end of SpaceX,

because I'm out of money. He was negative at that point. So I said, I can give you a couple million bucks. I mean, I don't have tens of millions of dollars, but a couple million bucks, I can give a couple million bucks. Don't worry about it, it's okay. You know, I'm doing okay.

And he's trying to figure it out. And I said, well, it's gotta be some good news, you know, what's going on? And he had personal problems going on, all kinds of stuff. And he said, well, I didn't get one good news. Don't tell anybody about this, but he started showing me the clay. And it was on his Blackberry to just date the conversation. And he's showing me the model S, clays, that he had a secret, he had a secret room down at SpaceX,

and he had shown me the SpaceX facility before he bought it, like, or when he was buying it, it was just a big empty thing. He had like 20 people in the corner. And in another corner he had this, like, set up, like, pipe and drape, and there was a clay model in there, and he showed me the pictures of it. That's gorgeous. It looks like it's cooler than the Maserati Quadraport or whatever that's called. It's like that Porsche Panamara is kind of ugly.

This is like gorgeous. How much is it going to be? And he said, I think I can make it for like around 50 or something, you know, after the tax breaks. And if you make that car for 50K, you will change the world. So I went home, I talked to my wife. And, you know, I was like, poor Elon, like, it, probably. And I said, how much is it true about Tesla? He said, no, it's not true that we have four weeks.

I said, oh, great. He goes, we have two. I said, oh, shit. It's brutal. So I wrote two checks for 50K, and I put them in an envelope, I wrote a handwritten note. Elon looks like a great car, I'll take two. Folded it up to send it to him. He didn't cash it.

Five, six months later, the checks get cashed. And then two or three years later, I get, congratulations, your signature model number, zero, zero, zero, zero, zero, zero, zero, seven to him. And I said, oh, wow, you gave me those two. So I immediately forward to him, I said, dude, you don't have to give me number one. I should be in the Smithsonian. He goes, no, no, I want you to have it. So it's very, very nice kind of thing.

He's very loyal. There's a lot of people who are, like, getting obsessed with him right now. And, yeah, that happens in our industry. And, you know, you kind of ride it up and down. But he's one of the most down-to-earth, loyal, just normal people. And I think people project a lot into him and want him to be certain things. But he's like a funny, great dad, good person. and like amongst the most loyal friends I've ever seen.

Like just so loyal, like unbelievable to his friends. And just a really good person at heart. You know, very considered. I've heard people say like, oh, he's a robot. And it's like the last word I would ever use to describe anyone as a robot. He's hilarious and fun and a good person, right? So, you know, I think, you know, you build up karma over a lifetime. I think if you look at, you know,

at one point, Travis, somebody said something to Travis along the lines of like, Jason doesn't deserve a stake in Uber or something. And Travis said, oh, no, you couldn't be more wrong. Nobody who deserves to have been in the angel around Uber more than Jason.

The person was like, why? You know, fuck Calcutanus or whatever. And I was there when they were saying. And it was like, do you know, Jason held events for founders for the last 25 years? And I went to them, and he interviewed me at them. when I had red swoosh, when I had scour.

And by the way, it's one of your events that the Uber raises its... Seedram was open angel for him, was one of my little angel events. So, you know, I believe in karma. I believe people wind up where they're supposed to be. Because there's no way this kid from Brooklyn deserves where he's at, the station in life where I find myself. I know I am super aware that I am the luckiest guy on the planet and that I'm like way above my pay grade.

Like somehow I wound up in the NBA on an all-star team. like as the fifth man, you know, like point guard, maybe the sixth man off the bench, loved by everybody, but the team would have won anyway without him. I got lucky to be here, and I realized it more than anybody. And now I'm, I kind of feel like I'm so ahead of where I was supposed to be in life that I can really do interesting things. You know, I can really focus on what matters.

I talked before about, like, what is your motivation in this life, right? How do you find your motivation? I think when you're young, competition, being somebody, that fire in your belly is just awesome. But then at a certain point, you have to start to think about, well, when you do get that Bank of America Wire transfer and you hit refresh, and you don't have to worry about being poor or being broke again,

which I always found it's very obnoxious when people say it's not about the money. And if you ever been poor and have debt and then hundreds of thousands in debt, it is exactly about the money at that point. It's a very obnoxious, rich person thing to say, like, oh, I don't do this for the money. It's like, okay, then why is it not a nonprofit

or B Corporation, why don't you have venture capitalists who all they care about is return on investment? Make no bones a mistake about it. Like our industry is about the money. It's specifically about the money. That's why there's venture capital and IPOs. But you're really finding out what you're good at. You know, that, man, that's the real deal.

You can figure out what you're good at in life, and you can deploy it. That's where I am right now. I know I'm a good writer. I know I'm good at a conversation. So you use the Dylan analogy, so you had your acoustic period, you had your electric period, where are you, John Wesley Harding now, basement tapes? Where are you? I think I'm kind of like probably Empire Burlesque, which might be the last good album,

as far as most people are concerned. I see a lot of good stuff in Dylan. But, you know, maybe I am a road dog like Dylan. Maybe I'm, maybe I'll be insignificant for the last 30 years of my career. maybe there won't be another hit. But I'll be out there playing and I'll love it. Right, because he found his thing, which is he just wants to do the work,

the craft of going out and performing every night. That's it. So maybe I lose my voice like, you know, and whatever. But I love what I do. And mentoring and investing in companies, writing, doing podcasts. Like, I know what I'm good at. I'm good at communicating,

doing this podcast thing. I'm good at writing and I'm good at investing. I got a good eye for it. That is like for all the people who are up-and-comers in your audience who are thinking about it, figuring out what you're good at and refining your skill that's all that matters in this life like if you have skills

and they're giving all these young kids the false bill of goods they're telling them like there's some patriarchy stopping you or matriarchy starting you with this or just every the world's against you and there's victimization like if you have skills and you have passion for something you will never be a victim you can only be a victim

if they make you into one and you let them make you into one. You can hustle your way through this. It's done all the time. And that doesn't mean it's not easy. And people want to call me, like Nick Denton had a great time. He got his revenge, having Gawker call me a racist, because I believe anybody can lift themselves up. I don't really is racist to think that anybody can lift themselves up.

I think that's American. I think that's like American ideal is that you can focus your skill, refine it, and just pour your heart and soul into something, and become a successful individual. And if I look back on my career, I think like when I see Raffet and Shenney and Will Leach and all these other folks, I think they saw me going for it and were like, Jason's, I'm smarter than Jason. I have more talents than Jason. I could be more successful than Jason.

I think I gave them this, the ultimate gift I gave them was a dumb kid being successful. Because I didn't care. I was like, I have nothing. I have to go for it. I have to accumulate some amount of worth in this world. And I just see the young kids, they come into it and they just, they don't want to acquire skills, they don't want to refine their skills. It is all about your skill.

Writing, coding, design, and adding skills, whatever it is. If you have those skills, it is undeniable. You cannot be stopped. And that's how it was then. We were lucky to be there early, but we knew stuff. It's the same way it is now. Zuckerberg, you know, you can deride him for, you know, never really making anything original, other, you know, just copying friends

through pixel by pixel, you know, which is what he did. He just copied it pixel by pixel and put it on a better software platform. You know, you can ride those people for that, but what you can say about him is he's a relentless executor. You know, the skill set that Zuckerberg had and his ability to just relentlessly execute,

you have to admire, you have to admire that level of focus and skill. Just had that focus and skill. So for the kids listening, you know, I think right now we're talking about this like an internet history. I kind of feel like the first 20 years of the internet is the first inning. I really think it's like a hundred, 200 year story. So everybody's looking like, oh my God, you're the internet history podcast.

Like you're really in the maybe two innings in. We literally have four. We got another seven innings to play. That's why I'm so engaged. It's like Uber was not possible until smartphones and GPS. Well, Bezos has that day one building on the Amazon campus. What's that? Because he says the internet, we're still in day one.

For sure. So one of their buildings is called day one. It's literally that early. It's that early because you really have three or four times a number of people will be online in a very short period of time, 20 years or something, virtual reality. Some of the stuff that's coming is just mind-blowing in terms of how it can change things.

Well, Jason, I think that's a great natural place to end. Thank you for coming on the Internet History podcast and just remembering all that great stuff. It's a pleasure to be interviewed for once. I do all the interviewing in this town. It's nice to be interviewed once in a while. Nobody invites me on their podcast. You're a decent subject.

They shouldn't. I'll take decent. All right, we'll see what happens. When the ratings come out for this episode, I predict this will be top five. I'll take it. If this is the first time you're listening to this podcast, please subscribe to us on your podcast app of choice.

There's plenty more. great internet history where that came from. And if you're a long-time listener, then you know what to do to help us out. Rate and review us on iTunes. Because iTunes gives credit to reviews and ratings, and the more great reviews we get, the more people will discover us. As always, there's more info on our website, www.com. The show's Twitter handle is atnethistorypod.

and my personal Twitter is at Brian MCC. Thanks for listening.