Tech Brew Ride Home - (BNS) You're Not Killing It. Nobody Is Killing It. VC Legend Jerry Colonna

Episode Date: September 27, 2025

One of the very first VCs of the Internet Era, and especially the NYC tech ecosystem, Jerry Colonna reflects on his journey from growing up in New York to becoming a successful journalist and venture capitalist. Jerry discusses his transition to venture capital, the founding of Flatiron with Fred Wilson, and the challenges faced during the dot-com bubble and 9/11. He emphasizes the importance of curiosity and the human experience in his coaching practice, aiming to alleviate suffering and transform lives. Learn more about your ad choices. Visit megaphone.fm/adchoices

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GoogleFi Wireless is not subject to data traffic deprioritization during times of high network usage. You're not crushing it. No one's crushing it. There's no such thing as crushing it. There are good days and there are bad days. And let's stop with the myth-making and let's talk about the reality and the reality is building a company

is a magic act. You create something out of nothing and you get people to believe. That is fucking genius and fucking hard. Both are true. And just because you're struggling doesn't mean you're bad at the job. It just means it's hard.

Jerry, thanks for coming in to talk to us today. Thanks for having me. It's really kind of cool to transport back in time and be in this neighborhood again. Well, that's a perfect seg. It's almost like you saw my notes. You were Brooklyn born and bred? Yeah, yeah. Flatbush and then Benson Hurst.

And then middle of high school, I moved to Queens. I betrayed my hometown. Still was a Yankee fan, not a Mets fan. And then eventually moved to Long Island. But high school, you went to the Edward R. Murrow? That's right. Adam, yeah. Was it brand new then?

It was, I think we were the fourth or fifth graduating class. I keep banging into this. I'm going to push it back a little bit. Yeah, I think we were the fourth or fifth graduating class. I mean, I think the first graduating class was 77 and we were 81. It's prestigious now. Was it as prestigious then? Yeah, I mean, it was selective.

Saul Bruckner, who was the principal and really the genius behind it. And a guy named Aaron Silverman, who's not very well known, he was the assistant principal. I found out years later that they would actually carefully curate the student body. So it was a kind of funny school, it still is, I imagine. Your grades mattered. Your test scores were irrelevant. They were looking for creative talent, which is probably why Baskett went there. we were a kind of hodgepodge of misfit toys, if you will.

And, you know, aside from having my own personal journey with depression, it was an extraordinary experience. Were you contemporary with Basquiat or Tomei? No, I was contemporary with Marissa. Marissa, if you're listening, I miss you, dear. No, we were in a play together. She was a year behind me, as was Adam Yow from the BC Boys. Their class was much cooler than our class. But we were in a play in senior year, my senior year called Mid-Summer Night's Dream, the Shakespeare play.

And I played over on King of the Fairies, and I think she was to Tanya. No, no, she was one of the four lovers, which is like a central theme. the play. You mentioned being in this neighborhood. Listen, anytime even friends that were here that grew up in the 70s and 80s, New York, it's different. Well, this is what I'm looking for. So compared to New York today, what was growing up in New York like that? Well, you have to remember that.

So I graduated from high school in 81. And so I lived through, you know, the summer of 77, which was the blackout, which was the summer of son of Sam. And the thing about the blackout was we went for days that summer without electricity. And I think it was that summer, that fall when the Yankees were in the World Series. Did I mention I'm a Yankee fan? Yes. Yet again, the Yankees... That's right, that's right.

But the important thing was Howard CoSell calling the game and saying, ladies and gentlemen, the Bronx is burning. Because, you know, they had that aerial camera that panned out and you could see these fires going on in the South Bronx. So it was a pretty intense period. You know, the subway system was, you know,

I would take the subway first. I was taking a bus from one part of Brooklyn to go to high school. Then in the middle of my first year, my ninth grade, the family moved to Queens. And then I was taking a subway and I was taking, it took an hour and a half to two hours each way to go to school. So I became intimately familiar with graffiti and the challenges. So, you know, when I ride the subway right now and I get that very pleasant voice and the lights to tell you which side of the train the doors are opening, it's like, what the hell is this? This is not New York for me.

It feels foreign, or does it still feel like home in a sense? Both. You know, I live in Colorado now just outside of Boulder on a farm, which is crazy. Totally another story. But I'm staying in Brooklyn on Skirmarhorn at the Ace Hotel because my three adult children all live within Wauke. distance of there. And it's just like I went to dinner at my daughter's apartment on Smith Street and I was like yeah I dated a girl who lived there I did it a girl who lived there. I couldn't walk on this side of the street because

that was too dangerous and it was mostly a Puerto Rican neighborhood and I was coming from Carroll Gardens and you know identify as Italian American it's like and it's like a completely different experience and you Yet the architecture is the same. The diversity is the same. You know, trigger warning, I can curse. I'm about to curse. Please.

The world is fucked up. The country is fucked up. I land in New York and I feel at home among the diversity, even though I'm whiter than white. And I feel like that, diversity gives me hope. Fuck them. This is our country.

This is our country. And as I'm sharing this reaction, I'm recalling the feeling I had after 9-11. We'll end up talking about 9-11, because it's a really powerful experience for me. But I remember after the attacks, and there was such devastation, and I remember a couple of quick things.

The first was having grown up in Brooklyn, having been very, very close to, especially the Brooklyn Heights, Cobble Hill, Boreham Hill, Carroll Gardens community, I was very, very aware of and connected to the Arab-American community on Atlantic Avenue. And I remember September 13th, I was working at Chapie Morgan, and the city was just in this bizarre state. And I just put out this call to everybody on staff, and I said, let's go to Atlantic Avenue and have dinner. And we walked into a Libyan restaurant, and the whole strip was like empty because people were like, oh, Arabs.

You know, fuck you. And we just like bought out the restaurant and we hugged the owners. And, you know, after that, I took on responsibility as the co-executive director of NYC 2012, which was the Olympic bid effort. And I remember, which basically meant I went out and I did a ton of fundraising for that effort because it's really a tough effort. And I remember giving speeches. And one of the most profound things I talked about was why I think New York was targeted. And yeah, it's just like weird center of financial capitalism and it's like New York and it's all this stuff.

But, you know, I'd go to a place like Queens, talk to a, you know, local IBEW, Brotherhood of Electrical Workers Union, 30, 40, mostly guys sitting in the room, arms crossed. And I talk about the fact that in New York City, with our one million plus students, that there were 118 languages spoken in our schools, like, fuck you, that's New York. there's a power in that. And right now, I'm so angry because that feels once again under attack right now. We will come back to 9-11 because I think it's very important to your career trajectory. Before, I'm going to take it back to Queens College, but before I do one more thing on the Yankees, do you own A. Thurman Munson, Jersey? Oh, God bless you.

Because I... I... Fuck you. No. But I do remember the day Thurman Munson died. I was playing wiffleball on West 7th Street in Graves Inn, Bensonhurst. And one of my good buddies, Paul Botto, came running around the street. And Paul was like a huge Mets fan and would give me shit all the time about the Yankees.

And I was taking swings. And he said, Munson died. I said, I'll get the hell out of here. You just, no, no, Munson died. And, yeah, it broke my heart. All right, Queens College. Yeah, so. You get into journalism is where I want to go.

Uh-huh. So tell me that story, how that happens. So it's a, I ended up at Queens College, by the way, because in my senior year in high school, even though I was having a blast in this play, midsummer night's dream, I stopped going to class. I would spend my days like riding the subway past school, going all the way to the aquarium, Coney Island Aquarium, and just bailing on class.

And then I would come back to school after class to go to the rehearsals. So something was brewing. And what was brewing was a deep, deep depression. Anyway, I didn't get my shit together to go to school to apply to colleges or anything like that. And so I applied for and got into Queens College the day before classes, the last day of registration for classes. So that's how I ended up in Queens. And while I was there, I suffered massive depression in that first semester. ended up attempting suicide at the end of that semester between fall and spring semester,

ended up in the hospital for what would have been my second semester of school, kind of got patched together, went back together, went back to school, and started to do well. And because I'm a smart kid. and ended up winning a scholarship because of the way in which I had sort of returned. And there's a story I tell in my first book, reboot, in which a professor named Robert Green, I was struggling to pay tuition.

Tuition was, I think, something like $750 a semester, and I couldn't afford it. And after letter after letter after letter from the bursar saying, you owe us money. I very tearfully went in to see my advisor, Dr. Green, and I said, I have to drop out. And he said, not on my watch. And he said, I'm the sole judge. I'm going to give you the scholarship. It's a brand new scholarship. And it comes with a summer job. And he gave that scholarship to me. it paid my tuition for the next four semesters. And the summer job was working on the copy desk at a magazine on Long Island that was writing

about technology, of which I knew nothing. What year is this? 82, 83, something like that. At the end of that summer, I went into a guy named Drake Lindell, who was the editor-in-chief, And I said, hey, you know, it's been a great summer. I got to go back to school. You know, the summer job is over. And he said, where are you going?

And I said, well, I got to go back to school. And he said, well, can't you work part-time? And I said, doing what? And he said, I don't know. And he offered me a job on the spot, $5 an hour. And I started working part-time as a reporter. mostly because I was a bit of an annoying kid whereas I would copy edit a piece

or proof read a piece and I would like kind of improve it this headline sucks and I'd rewrite the headline and that kind of thing but I found my way as a reporter and what was kind of cool was that I would spend time in between classes Hello kids.

This is before the cell phone. And I would be on pay phones. And I would do two things. I would do interviews with a stack of quarters and call sources. And I had this little TRSAD, what we would call a laptop, but was just had an eight-line LCD screen that I would file stories from. Roughly an electric typewriter. Roughly an electric typewriter.

And it had an acoustic coupler. And so you have to imagine, I'm in the kosher cafeteria at Queens College, taking these couplers out of my backpack, attaching them to the payphone handset and hitting send while dropping quarters. Now, wait, I want to point out, because people might not understand. You're doing that because you're recording the conversation. No, I'm doing that to file the story. It was a modem. So it was a set.

a modem. And I had composed the story. Yeah. On this little LCD screen. To send it back in. Right. Yeah. So the the dial up that people old enough to even remember AOL, you're essentially sending the signal. Yeah. This is, this is pre-AOL. Yeah. No, absolutely. But what I'm saying was, is the way you're sending it is the sound that's going through the receiver. That's right. That's right. At 400 bought. Right. I started at 144 on my first modem. So that's because you're a young Okay, let me, the magazine, was it Information Week? Yeah. Good memory. Okay, so early 80s, what is, it's essentially an industry magazine? Yes, it was, its target audience was the chief information officer. So the guy, the folks, mostly guys, who would buy technology for big corporations. What is the technology that you're covering? I mean, the PC era is here.

Just barely. Yeah. Just barely. So what are you covering? Big Iron. Mainframes. IBM. You know, my first beat was what was called the bunch, Burroughs, Unisys, NCR, control data, Honeywell.

It was all these large mainframe manufacturers who competed with IBM. IBM was a premium beat. I was a young punk. but we would cover like a new disc drive coming out. But there were some pretty powerful stories like when HP introduced what was called the PRISM chip and it was a dramatic architectural shift. Or later I started covering what was then called supercomputers and I started covering the developments around what's known as Gallium arsenide chips, which,

was a different medium for making faster and faster chips or cray research, which had water cooled stuff. And by the way, all the stuff that I just said to you, I was an English major in college. So the dissonance of like covering all that stuff was just weird for me. But they just throw you at it. You don't have to have a background in it. So you're learning on literally on the... Yeah. I mean, I had... Looking backwards, right, I'll be. be 62 in December, looking backwards right now, and I did the same thing when I was a venture capitalist. Everything is auto-didact. Everything is self-taught. Is there a lesson there in the sense that people think that there has to be like some sort of certification for certain things?

Or is learning in the real world better? The dichotomy is false. You need both. There is a value in training. The value is don't fuck it up, don't do this wrong. But if you stop at the certification, and the same is true now as a coach, right? I've been an executive coach for 25 years. If you stop at that point, you're not really flourishing. The number one drive, the thing that made me a journalist, the thing that made me a really good investor, the thing that makes me a really good coach is curiosity. Curiosity. I mean, my kids will tell you, I drive you crazy because when I walked on the street, I stop and read the damn plaques, right? I'm endlessly curious. It drives me to constantly read one or two books a week. And who the hell knows what I'm reading? I mean, it could be

a book about, you know, Napoleon finding a way to feed you. his army just because it was interesting or the development of Siberia as a gulag. Like this is shit that I've actually read. The most important skill I had as a journalist was endless curiosity, curiosity about the world, but curiosity most importantly about people. But does being a journalist train you to do that? Because otherwise you don't have the content. If you don't uncover the story, you don't have anything to deliver.

So is that something that has served you in your later careers that's sort of like, well, if I don't do it, that self-starting of finding the thing? Yeah, I would reframe it slightly. I was a journalist because I'm endlessly curious. I became a really good investor because I'm endlessly curious. I became a really good coach because I'm endlessly curious. The thing I'm most curious about are human beings. Because as cool as it is to think about gallium arsenide chips that are water cooled or liquid nitrogen cooled. And it's kind of cool.

It's much more cool to think about how the human heart works. And so, but there was a training, right? And one of the earliest trainings that I had to do was learn how to ask a question. You're a journalist. I'll give you an incident. I remember talking very early on in my career at the magazine, I moved from being a reporter to being an editor, partially because of my skill as a writer and partially because of my ability to work with people. And I remember a reporter coming in, and I ripped apart his story because I was like,

You're not hearing the second question. So what do I mean? When did you start this company after I got out of jail? Why did you start the company? Like, whoa, you just missed something. Can we go back to you being in jail? Right. And I see this with podcast interviewers all the time.

I see this with coaches. They come in with a predetermined, I saw it as an investor. They come in with a predetermined list of things that they have to get to. Look, right? But you're holding it lightly. You're allowing the conversation to flow. And if you do your job right, I'm going to say something that you could not anticipate.

And that's where the gold is. And absolutely, I learned that as a journalist, and I use that as an investor. and I use it every single day today as a coach. In aid of getting to the coaching. You're a reporter on the beat through the early 90s? Yeah. So I became editor of the magazine. I was the youngest editor in the company's history.

We were number five in a five book market. Like PCMag? Our competitors were computer world, info world, PC week, not PCMag, which was more for the enthusiasts. That was a monthly. Same thing with PC World monthly. And MIS Week as well. That was a fair trial publication. I'm going to interrupt you for a second because I want to put context.

We live in a media ecosystem where tech is sort of all around. Tech is media, media is tech. But these were, this was a. it. Like, if you are, this is why Steve Jobs would give interviews to, whatever, if you're not in- Or Bill Gates would come to my office and sit there and take his shoes and socks off and then rock back and forth like the Asperger's person. No, just kidding. Because this is the only venue that they have to reach the tech audience as it existed. Correct. Correct. Right. There wasn't, I mean, during my time, the guys had CNET launched. Wired.

Yeah, although Wired was more about culture than it was about hard tech. But yes, this was back in the day when Dead Tree Media really dominated. And there's a transition that I ended up being a part of, which was moving away from paper. And you can sort of blame me for the demise of paper. Just kidding. But, yeah, that was the ecosystem. Study and play. Come together on a Windows 11 PC.

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In fact, my company launched a magazine called Home Computing because it was like, you're going to have a computer in the house, but yeah, go ahead. And then the Internet. Yeah, yeah, then the Internet. 1994 was when I first installed TCPIP on my PC. which for the kids, there was a time when your personal computer did not have the requisite software built into the bios to be able to actually use that damn modem to be able to do things. So you had to install TCPIP, I don't remember what it stands for, in order to connect. Wasn't that one of the reasons why Windows 95 was so, because they baked that in?

Or you could get it in 3.1 of Windows, I think. Well, I think that was part of the point one, because 3.0 was just such a trash that they had to fix a bunch of things. But I have a little story about Microsoft in that time. Okay, so we're going to fast forward a couple of years. I have left Information Week magazine. I am a director of what's called interactive media for the publishing company, CMP media. And at the time, what interactive media meant, we replaced paper with a petroleum byproduct,

also known as a CD, plastic. Okay, this was interactive. And really what was happening is we were taking the equivalent of a PDF and putting it on plastic so that you'd be able to read it that way. Or worse, we had a fax service where you could get stories sent to you. by facts. Okay. We emulated NY Times facts, which was crazy.

This was our interactive media thing. And right around the fall, it was like spring of 94, summer of 94, into the fall of 94, well, the spring, I began like, you know, Mark injuries and company at NCF. SA, Illinois, developed the first web browser. Mosaic. And, like, it was just mind-blowing. It was absolutely mind-blowing. Because heretofore, you used services like what's called FTP or ways to actually...

Gofer. Yeah, go-for. And it was all text-based, and there was no such thing as clicking on a link. You just... There weren't images. There were no images. And there was no sound. There was nothing.

and you were just typing, right? And in the summer of 94, Microsoft was launching something called MSN. And it was a competitor to AOL and CompuServe, which were kind of walled gardens that you would link into, and that was it. You would be on these bulletin boards. And AOL's revolution was the inclusion of a graphical user interface so that you could actually use a mouse and click on things to make things happen within.

And Microsoft was trying to build a competitor. And I was being recruited to be the head of editorial for MSN. And while simultaneously trying to build what became TechWeb, what was our first iteration, How do we replace paper and do this, you know, in the fall? And that experience was just like really heady time because those of us who were working on it knew that we were heralding the end of print that ecosystem that you were defining before. We knew that we were creating something new like what does an ad look like? See, this is not sticking to the notes.

There's stuff like Pathfinders happening around this time. Right, and hot-wired. You're all reaching for metaphors for what this is. So the thing, like the concept of a page view comes from, or you're selling ads by CPM, which was the old newspaper magazine model. But we had no standard about what an ad was. Right. We had to invent that shit.

And you're pulling from metaphors from the previous media and eras, but you don't have any idea where, like, this is different. It is interactive. Right. So that time period, the sense that you don't know where it's going. Yeah. Incredibly thrilling. I remember internally, we debuted.

So I'd spent that to me. I ended up turning down MSN. I'll tell you that story later. But I stayed at the company and continued to work on launching this thing TechWeb. And the plan was to launch it at a trade show called Comdex, which was in Vegas. And Zip Davis, which was our big rival, was launching their online service, their proprietary online service called ZDNet. And we were launching completely on the web. Now, you mentioned Pathfinder or hotwired.

Those were the only two general offerings out there. Everybody else was either partnering with a proprietary online service, like AOL or CompuServe, or not doing anything. And we were launching, not only were we trying to invent what does the CPM look like. And for those who don't know, CPM stands for cost per million. Okay. Our initial CPM for an ad on TechWeb, $15,000. By the way, for context, if you get a $30 CPM in podcast, $15 CPM and you're on Easy Street.

So because we didn't know. We were just making it up. We had no idea what, I mean, people are going to click on this thing? What's going to happen when you do it? So literally, we're inventing all this stuff going on. And we were only the third organization to really sell advertising at that point. Earlier in the spring, we had for a communications trade show called ComNet, I think it was. We published a daily, which was we basically had a simple HTML page that we published an article, maybe one paragraph, every day.

That was our trade show daily. But what we were doing was experimenting. Can you actually change the system from a weekly publishing schedule to a daily or an hourly publishing schedule? And as today, it is minute by minute. Minute by minute. There's no off. Well, I remember having an ethics conversation with this Harvard University professor. and I think about the things that we were having to invent.

You publish a story, and 20 minutes later you find out facts in the story are wrong. What do you do? Right? Because I come from a journalistic tradition where you have a correction down at the bottom and the next day or the next week or the next issue that comes out. In this case, do you correct the information while you still can? Do you correct the information? you're now changing history.

What is your moral responsibility? What was your ethical responsibility as you're inventing this all along the way? I mean, it was exciting, it was fascinating. I remember debuting this technology internally at the company in September. We were launching in November. And I remember a bunch of salespeople in the room,

and one woman stood up and said, you are taking food at the mouth of my children. You are destroying our business. And I said, if I don't do it, some other company is going to do it. This is like the essence of creative destruction. We had to invent moment to moment because if we didn't, we were going to just be run over. And it was partially the same thing about the web. I remember launching, and it was a big deal that we launched without.

our own proprietary network of modems that people would dial into and have a gateway on. I mean, that was radical at the time. We were dependent upon somebody finding a way to download a TCPIP stack, a browser, and to be able to connect to the internet, to be able to get to that information. But I saw the future. I mean, we saw the future. Slate insisted on launching with actual issues, even though the issues didn't matter.

Jerry, I think you and I are going to talk again because I want to go deeper on this, but for the interest of this particular conversation. I want to get into how you move to the side of the table of investing. Now, I want to point out that the journalist to investor route is not rare. It's been well-trodden. Right. Mike Moritz is probably the best example. Or an M.G. Siegler of a later era.

Right. So how do you... How did that happen? Yeah. Does someone approach you or is it your idea? I feel like it wasn't your idea? It wasn't my idea. What happened, and this is all relevant because it's all in the same time.

So summer of 94, I think that's where we were, I'm really in a dilemma because I'm trying to figure out whether or not I should take this job at Microsoft. I'm about to hit my 10-year mark at the publishing company. Internally, I never saw myself spending 10 years doing anything. Anything. And it's like, oh, my God, I'm going to be one of those old people in the company. And it was a really exciting job. But it would mean moving from Long Island where my wife and I had just started having kids

and we had a house and all those stuff to Seattle. and like, like, just hope. And so I was really in the midst of a dilemma, and there was this guy named Dave Weatherill, and Dave had launched, he had a marketing company, and he had stumbled upon a small software company, and they developed a competitive browser, competitor to Mosaic called Booklink.

And his metaphor was, was books, right? Turn the page, click on a link, new page, that kind of thing. Anyway, he was in the midst of discussing with Microsoft, well, no, he wanted to get all of our publications on their homepage. This was like the thing that we would do, right? And so he and I spent a lot of time. And he was, he was, he was an entrepreneur, so he was kind of fast talking and he would call me up and, and, I remember one day he calls me up and he's telling me all this exciting stuff. And I'm kind of listening, but not really. And he says, are you okay?

You sound distracted. And I told him about this offer from Microsoft that I was trying to sort through. And he gave me really liberating advice. He said, fuck Microsoft. You don't need them. And I was like, what? Because my thought at that point was I was going to be trapped forever. If I didn't take this job, but I wasn't sure I wanted to take the job.

And I also saw the future and I was like not sure and all this stuff. So I turned them down. And then a couple of weeks later was Comdex. And I'm at Comdex demoing what we call TechWeb. And in the intervening weeks, Dave had cut a deal with Microsoft to embed their browser in MSN. And Microsoft was launching MSN at the show and Bill. Bill Gates, was up on stage demoing something radically new, something you couldn't do before, which was log into your proprietary online service and go out and browse the web, except he didn't

have a signed deal to use that browser. And so while that was all going on, Steve K's at AOL turned around and bought Booklink. Kind of screwed them. And they announced it just before this all came out. So it was like, it was like crazy town. Anyway, I'm at my booth one day, and Dave is walking the show floor with Steve Case. And they come over and Dave introduces Steve to me. And Dave is singing my praises. He's a very, very kind man. And he's like, this guy's genius and all this stuff.

And Steve says, why'd you come work for us at AOL? And I said, well, do him what? He goes, I don't know. We'll figure it out. Like, that was my first exposure to, I don't know, we'll figure it out. And I was like, oh, I can't do that. But it planted a seat. And by the end of that fall, I was working for Dave launching one of the first internet-specific venture capital firms.

I always can't ever nail down the name. It's like, at ventures. Yeah, at ventures. Well, the official name was CMG at Ventures. Right. But we got the domain, Ventures.com. And so it became at Ventures. And how big is the fund?

Dan, it was $35 million. It was nothing. Okay. I have so many questions about this. Now, number one, what we're talking about is venture capital. You don't have experience with this. Zero. Okay.

I actually had to have a friend who had recently graduated from HBS, explain to me the way a venture capital firm works. I could go into that, but what I'm more curious about is what do you think your remit is? What are you going out to do with this $35 million? Realize the potential that I saw brewing all that year, which was reinventing media, figuring it out. Like, there is a whole new world out here. And, you know, to be honest with you, I had no idea that I actually might make money.

I had no idea. I was just fascinated by what was happening with the way in which we interacted with information. No, even the ethical questions I was asking before. You know, all the stuff that we see now, like social media is a source of division. Back then, we saw our social media as a source of unity. I mean, talk about naive, right? We saw instantaneous information as a good thing. We underestimated the importance of curation

or pausing and taking a breath before hitting publish. Right? I mean, we were just so phenomenally excited at the world that we were creating every single day. So you're largely investing in essentially, to come back to the term interactive media startup? Yeah, yeah. How big are the checks? Yeah, half a million dollars.

What is the valuation? Yeah. I mean, to put it into perspective, one of the first investments we did, I think it was my then-partner, Dan Nova, who's at Highland now, still. shout out to you, Dan, found a technology transfer. Universities will often develop technologies and then cut a deal to transfer the technology and create a company out of it. It's a long-tending practice. Well, Carnegie Mellon had done this, and there was a guy named Mike Maudlin,

who developed the world's first spider, which was the ability of the ability to be a bit of, which was the ability to crawl the web, follow links, and create a database based on that. That was the first search engine. It was called Lycos, L-Y-C-O-S. Why Lycos, Lycos is, I think, a Greek or Latin name for the Wolf Spider. And that's where his emphasis was. The cool thing about spitering the web and capturing information. You know, the minute I saw this demonstrate it, it was like, oh, shit, we're going to sell ads against those results.

I'm going to search on Best Toaster, and I'm going to get an ad for Toasters. And I thought that was cool. Now, like, I can't stand it. But, you know, at the time, it was like inventing stuff like that and realizing that, you know, we just changed information retrieval forever. I prompted you by asking for a valuation. So like, like us. Okay. So we bought 10% of that company or that transaction for a couple hundred thousand dollars.

And I think within a year, we took a public for $200 million. Yeah. Which we thought was phenomenal. But you are doing a two or $3 million valuation that becomes a $200 million. Correct. versus you get in at 20 million now and you're hoping for a unicorn sort of. Right. Or if you're talking about funding an AI company, you're getting in at a $10 billion valuation.

Well, let me ask you that. So let's get to Flatiron. So I think you're with the adventures for what a year? Just about two. Okay. Yeah, yeah. It was about a year in that I began to feel, well, two things. one, I had my own imposter syndrome going on where I was like, what the hell is going on?

I don't know what I'm doing here. And the second was I was just not happy in the partnership. And, you know, a complex set of reasons behind that. Some of which had to do with my now growing depression. But, you know, I was in an office in New York. everybody was based in Boston I would fly up there every week I was kind of miserable doing that

but I was seeing some cool shit and to our earlier point about this time I had an office on 17th and Park Avenue South what ended up being in the building were first round capitals first office was I believe and I remember having this crappy little office and you know

sitting at my desk with torn jeans and a ripped Yankee shirt and probably Yankees cap on and we'll name him later, this kid, Jason Calcanus walks in and that whole thing. But anyway, that was that error. And it was before Flatiron, but I was looking at transactions, looking at deals. Geographically, I want to point out, that is Silicon Alley. Yeah, it's the heart. The classical.

It's like right on Union Square. and it's, and it still is to. Yeah, today, all of the big VCs still have offices in that neighborhood. Right, right, right. So what is Fred doing? Well, Fred's at, Fred Wilson's at Euclid, Eucl partners. He graduated from Wharton. His undergraduate was at MIT in naval engineering.

He decided he didn't want to design boats. went to Wharton. And he was working, I think, from the moment he graduated at Euclid, and, you know, as a young punk investor, smart guy. But he and I met on a transaction called Freeloader, which was started by a guy named Mark Pinkus, well, Mark Pinkus and Sunil Paul. Mark, of course, went on to launch Zinga, which was probably his biggest success. What was Freeloader, though, because I recognize the name. Oh, Freeloader is crazy, crazy business model. Okay, to have a seat, everybody.

This was back in the day when people had the bright idea to run ads on your screensaver. So there was Pointcast, which was the Pointcast network, which would put drop news stories in between ads on your screensaver. So here's the idea. You're not using your computer, but you're still staring at the screen. And that's where Freeloader was. It was using the real estate, if you will, of the screen save. Well, and that evolved into putting ads in people's browsers as well. Remember, along the top?

I think we were doing ads in browsers before that. It was like we were looking for real estate, basically. What that evolved into is something called People PC, which is basically you get a free PC, but you have to look at ads all over the place. Yep. You know. Okay. You and Fred hook up on this deal.

Right. We're looking at the transaction together. Mark gets into a fight with Dave, Weatherall, because Dave, we've already invested in Likos. Mark wants to do a deal with Yahoo. Dave gets upset. This is before we've invested. Dave gets upset and says, no, you're only going to be able to do a deal with Likos because it's a competitor. Mark says, what the fuck?

That doesn't make any sense. There's a fight there. But Mark and I liked each other a lot, and so much so that Mark would regularly call me up for advice. Yeah, you owe me, buddy. And one day I'm passing to an airport, and he calls me up. And I had met Fred. Fred and I were going to do the deal, co-invest in the deal, and then we had to pull out. And Mark calls me up, and he says, Fred Wilson's leaving Euclid.

And SoftBank is going to back him, and he's going to raise a new fund, and you should be his partner. And I was like, that's a really interesting idea. Because SoftBank is already doing things. Like they were backing Yahoo already and stuff like that. I think at that point they had already put money into Yahoo. Yahoo, I think, had gone public. Right. And Moss has already gotten the religion and it's starting to.

Yeah. Yeah. I mean, Masa almost invented the religion. You know, the religion of hyperbolic investing. And what he was doing in the U.S. was there was sort of SoftBank U.S. And Fred knew some of the people there. There was a guy named Ron. I'm blanking on his last name, who was sort of heading up SoftBank's venture-style investing

arm in the U.S. But then they ended up creating multiple funds. But that was the, they were backing young investors like Fred or like Brad Feld. And,

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Right. It was like those were the twin polls venture. So if you hadn't gotten that backing, doing a startup in New York City, sorry, a venture fund in New York City, would that have been a difficult? raise? Oh, sure. I mean, it was a difficult raise at the time. And I remember when we launched, there was like headline news, you know, venture fund launches in New York City, right? Front page of the New York Times business section. However, shout out to Alan Patrickoff, who's in his 90s. And Alan has been in New York-based venture capital for 50 years, 40 to 60 years, 70 years. I don't even know how long. And shortly after Fred and I launched, I'll never forget this.

Fred knew who Alan was. I didn't know who Alan was. We get this phone call. We've been summoned by Alan. And so we go meet the Godfather. Yeah. And he was gracious and lovely and smart. And to be clear, there were people like Venrock were here and that.

But what was different about Flatiron was that we were. Yankee baseball cap, a grip t-shirt, ripped jeans, move fast, see things that other people aren't seeing, and just move and get in there. Endlessly curious,

willing to have the shitty office, not caring about status. By the way, different than even Sand Hill Road out in the valley because we didn't care about Porsches. We just wanted to build dope shit. People had to go to San Hill Road. You're saying you're out in the field.

That's right. We're just walking the streets here. I mean, it ended up developing like that a lot in San Francisco. What I'm saying is, is when you had to go to San Hill Road, you had to go to the mountaintop to ask for money. That's right. And you're saying, you're looking for the people and you're saying, hey, I'm going to give someone.

I remember, like our days consisted of going from, you know, you said before that was sort of the heart of Silicon Alley. we were going from office to office to office to office. And our offices were shittier than the company's offices. Because none of that shit mattered. Like what mattered was building good shit. I'm going to name investments from this time, but we're only going to be able to do a couple of them.

Yo-Yo Dyn Gaines-Ville, Vertical 1, Your Times Digital. Let's do Yo-Yo-Dine with Seth. Goetan. Seth. What did you see there? Well, let's back it up. I first met Seth when I was at CMG Adventures. And I brought Seth all the way up to Andover, which is where our offices were, or even north of Boston, for the Monday morning partner's meeting.

And I was like, this guy's brilliant. And he presented and my partners turned him down. And they just didn't like theft. And it drove me fucking crazy. It was like the straw that broke the camel's back. I was like, I don't get this. I really don't get this. And it wasn't universal.

There were partners who liked it, but they just didn't want to do it. and that was one of the first transactions that, you know, when Fred and I were talking about getting together and forming what became flat-iron, the original name, by the way, it was Acme Ventures. Bugs Bunny reference. Right. Or, no. Wiley-Cadens.

Yes, yes. You're right. And so I had this picture of like the frosted glass door with Acme on the front and like people would walk in. And it would be like this old, you know, film noir, you know, private investigator. Anyway. And Fred said to me, like, there's this deal. Yo-Yo-Dine.

And there's this guy. And I'm like, oh, man, we had the same taste. And I think Y'Iudine was the very first transaction that we did. It is Seth Godin. Let's underline that for a second. But what was Yoye Yodine? Real quick. Permission marketing.

So permission-based email marketing. So back in the day, Seth had a brilliant notion, which was rather than just spamming you, he'd tap you on the shoulder and say, hey, would you like this message? Opt-in. Opt-in. It was like revolutionary. And there were a variety of services that he was offering in that way. And, you know, what you're really getting was this.

endless fountain of creativity that Seth continues to be in this day. This is now 1996, so 29 years ago. And that was a really good investment for us. A big win. I believe your biggest, but you can correct me, would be GeoCities. Yes, that's right. That's right. I thought you were saying. Tell me the GeoCity story, and then I'll give the context of maybe the first glimmers of social media but tell me how you learn about GeoCities. Well, I first learned about GeoCities, actually, when I was at CMG Adventures. And it was then called Beverly Hills Internet,

and it was a dial-up service. I interviewed him, I can't remember the founders name. David Bonnet. Yes, I interviewed him years ago. Yeah, and David had, so just to set the stage, David had hit upon this brilliant idea. So the original business, he and John Reznor were the co-founders, you know they had a bank of modems and people could dial in and then through that get a

TCPIP connection and go out to the internet and all this stuff and he had this brilliant idea that maybe we could host homepages and there was a really really powerful thing that started to happen which was people started this is like pre-blogging people started writing real stuff and there's a one famous story of a guy who had been diagnosed with AIDS who began talking about his journey. Now, P.S. background. David and his former husband, Rand, David's husband, was the first openly gay judge in the state of California.

And he died from complications from AIDS. So this thing was fucking personal. This was really, really powerful. to give a form, to give voice to people who, for a variety of reasons, and boy, do we need this again now, who for a variety of reasons whose stories were not being heard and whose struggles were not being heard, was phenomenal. His brilliance was organizing those pages by neighborhoods, right? And so one of the most popular neighborhoods was West Hollywood, which was an LGBTQ community. and he gave voice.

It exploded in terms of traffic. So this is like spring of 96. Ahmed Adventures officially, but I'm making my way into starting this new thing with Fred. And one of our first investments was, you know, this. And Fred was fascinated with it. I had developed a good relationship with David. There was a complexity in that day of Weatherall did not want me back in the deal.

He was so angry with me for leaving. He saw SoftBank as a competitor and he thought, oh, you know, Jerry's like gone over to the dark side. I'll be damned if I let SoftBank in as an investor. We got in. And I don't remember the numbers, but it was. a several billion dollar return on our investment. Because it gets acquired by Yahoo, or did it go public first? It went public first.

It exploded. We used that. It refined it. It changed its name from Beverly Hills Internet. He had the domain name Beverly Hills 90210. That was like the cool thing. And we launched as GeoCities reformulated. Here again, we had to invent, well, what does it mean to put an ad on somebody's blog?

Because that's what it was. We didn't call it a blog, but what does it mean to put an ad on somebody's homepage of favorite cat names, which was a lot of the content that we saw? So think of it as Tumblr in some ways, you know. But again, you're getting at it like a definitely sub-20 million dollar valuation, and then you get a return of three or four billion. Well, it was sold to Yahoo. and that was a crazy story because Yahoo was also an investor, as was SoftBank,

or SoftBank was an investor. I don't remember who specifically held it, but the Yahoo representatives accidentally found out that Lycos through David was going to make a bit to acquire the company. I think we went public in the summer, and then right around Thanksgiving, there was all this stuff going on. The dream was that AOL, I think, was trying to buy Netscape. David wanted to combine Likos and GEO cities and buy Netscape. Likos and GeoCities were both public at the time. Yahoo got wind of this. they kind of made an offer.

It was a crazy time period from November. I think we closed maybe in January, February. And the final price was like $3 or $4 billion. So, you know, yeah, we went from a $20 million valuation or so to a $3 or $4 billion valuation. In the space, it may be two and a half three years, which is nothing these days, but back then it was a big deal. If this is not a big deal, tell me to skip it.

We'll skip it. But Calicanus helping you source the deal? No, no. He didn't source the deal because I brought the deal in. What Jason was really helpful for us on was, see, at the time, it was becoming really, really clear that there was almost a generational difference happening. And so what Jason did, we asked Jason to do.

We had, by this point, in addition to SoftBank, J.P. Morgan Chase, or its predecessor, Chase Capital Partners, was our prime backer. So SoftBank and Chase at this point, eventually SoftBank dropped out and it was just Chase. And they had a very good diligence process that was really built around an investment memo and investment thesis. And what Jason helped us do was sort of assess the market and write a memo. but Jason didn't find the deal. It was diligenceing. Yeah, he was diligent, he was kind of acting like a young associate would, which was go out and tell me who the competitors would. A scout, that's right. Okay, I have to get you to a board meeting in 10 minutes. So I'm going to alight over stuff and we're going to talk again soon.

The bubble bursts and 9-1-9-11 happens not at the exact same time, at around an 18-month period. Yeah. And... Well, it started that spring. March of 2000-ish. Yeah, with the collapse of the NASDAQ. Yeah.

You do not continue on in VC. Right. Well, I did for a year. Okay. I went from Flatiron to J.P. Morgan, which was our prime backer at that point. Again, this might, maybe we'll have to say this for the next conversation, but the bubble bursting, the 9-11, and you transitioning into a different career path, which is coaching. I'm assuming that's all related. Yeah.

I mean, August of 2001, do you remember the industry standard magazine? Oh, yeah. Biggest number of ad pages of any magazine in history. I mean, so big that we had to publish two editions a month. It was a monthly magazine. Okay, I was an investor, an industry standard. And that magazine went from 15 million in revenue to 50 million in revenue to 150 million in revenue to 50 million in revenue. And then bankrupt.

And then bankrupt. And the bankruptcy was a month before 9-11. I was headed into the Grand Canyon for two weeks of like off-the-grid. discovery of myself, I was heading into my 38th birthday. I was fucking miserable. In 96, when we launched flat iron, it felt like everything we touched turned to gold. By 2001, it felt like everything we touched turned to shit. And so that was a factor in my depression.

It wasn't the dominant factor, but the depression was real. and I had to say to Fred, I can't continue in this business. The way he tells the story was he fed me to the wolves at J.P. Morgan. The way I tell the story is I failed my partner. He went on to found Union Square Ventures with Brad Burnham. I'm an idiot. But I kind of took a middle way and said, all right, I'll go work at J.P. Morgan. I made four more investments, all of which were good.

but by February of 2002, I had had it. Like stick a fork in me, I'm done. I can't do this anymore. And so, yeah, it's all related, and it all comes back to an inner, what I often say is I was crosswise with myself. My inner and outer experiences were at odds with each other. The more success I had externally, the shudder I felt.

I want to end with this because I want to tie it together to the coaching. So you've been coaching now for it's 20 years. Still called Reboot? Reboot. We launched Reboot 11 years ago. I was a solo entrepreneur coach and then I'm more of that. By the way, there's podcasts that you could listen to as well. He's had two books about coaching and things like that.

Here's my final question relating to that. starting a company being a founder is rejection is failure over your shoulder sort of Damocles style from the minute the idea comes to even success you've been talking about depression

to what degree is that what you understand that makes you a good coach for executives and startups well I'll go back to the endless curiosity about human beings and how the human heart is. And I'm particularly fascinated by how the human heart breaks. I have said many times that all I'm really doing is going back in time to 38-year-old Jerry saving his life again and again and again. Because by February 2002,

the suicidal ideation had come back. And if I didn't change what I was doing, I was going to kill myself. And so despite all the success and all of that stuff, and I went into coaching, and I still, all these years later, am in coaching for one purpose only to alleviate suffering. Right. Now, I happen to have a point of view

about how businesses get built, and what are the challenges of leadership. So there's an intellectual site, of this, but that's all in service of people not feeling like shit. And if you have somebody who has power who feels like shit, what they end up doing is hurting other people. So by alleviating suffering, I'm not just talking about the suffering of the individual at the top of a pyramid. I'm talking about changing that person, helping that person transform so they don't hurt people who have less power. If there is, this is absolutely final.

If there's someone listening right now that is a founder at a company, executive at a company, and is feeling terrible. I know this is asking you for a bumper sticker like thing, but best advice you could give them just in terms of you're feeling bad now. A couple of quick things. Depression lies. One of the lies it tells you is that because you feel like shit, you are shit. That is not true. And you're not alone. One of the most important things, one of the things that has driven whatever notoriety I have

is my willingness to talk about things. And the reason I'm willing to talk about things is because we don't talk about things enough. Because that feeds the sense that I'm the only one who's struggling. When I first started my boot camps, which are my multi-day leadership immerses, on the first night I was very famous for saying the bullshit and the spinning stops here

you're not crushing it no one's crushing it there's no such thing as crushing it there are good days and there are bad days and let's stop with the myth making and let's talk about the reality and the reality is building a company

is a magic act you create something out of nothing and you get people to believe. That is fucking genius and fucking hard. Both are true. And just because you're struggling doesn't mean you're bad at the job. It just means it's hard. I can't top that.

Jerry, we're going to talk again, but thank you for talking to us today. Thank you for having me. It's been a delight to go down, man, tripping lovingly down memory lane. Some follow the noise. Bloomberg follows the money, whether it's the funds fueling AI or crypto's trillion-dollar swings. There's a money side to every story. Get the money side of the story. Subscribe now at Bloomberg.com.