
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.
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Interviewer
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Jerry Colonna
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.
Interviewer
Jerry, thanks for coming in to talk to us today.
Jerry Colonna
Thanks for having me. It's. It's really kind of cool to transport back in time and be in this neighborhood again.
Interviewer
Well, that's a perfect seg. It's almost like you saw my notes. You were Brooklyn, born and bred?
Jerry Colonna
Yeah, yeah. Flatbush and then Bensonhurst 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.
Interviewer
You went to the Edward R. Murrow.
Jerry Colonna
That's right, Adam. Yeah.
Interviewer
Was that. Was it brand new then?
Jerry Colonna
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 6 77, and we were 81.
Interviewer
It's prestigious now. Was it as prestigious then or.
Jerry Colonna
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 Basquiat 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.
Interviewer
Were you contemporary with Basquiat or Tomei.
Jerry Colonna
Or any 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 Yount from BC Boys. Their class was much cooler than our class. But we were in play in senior year, my senior year, called Midsummer Night's Dream, the Shakespeare play. And I played over on King of the Fairies, and I think she was Titania. No, no, she was one of the four lovers, which is like a central theme in the play.
Interviewer
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 then?
Jerry Colonna
Well, you have to remember that, you know, 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 black blackout was it 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?
Interviewer
Yes. Yet again, the Reggie Jackson.
Jerry Colonna
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. 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. I was taking a bus from one part of Brooklyn to. To go to high school. Then in the middle of my first year, my ninth grade with the family moved to Queens. And then I was taking a subway, and I was taking it. 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 that 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.
Interviewer
It feels foreign. Or does it still feel like home in a sense?
Jerry Colonna
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 Schermerhorn at the Ace Hotel, because my three adult children all live within walking distance of there. And it's just a. 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 dated 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, and yet the architecture is the same, the diversity is the same, you know, trigger warning. I can curse. I'm about to curse.
Interviewer
Please.
Jerry Colonna
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 em. 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 911 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 JPMorgan 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, fuck you. And we just 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 it, 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 this 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 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 1 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.
Interviewer
We will come back to 911 because I think it's very important to your career trajectory. I'm going to take you back to Queens College. But before I do, one more thing on the Yankees. Do you own a Thurman Munson jersey?
Jerry Colonna
Oh, God bless you, because I fuck you. No. But I do remember the day Thurman Munson died. I was playing in Wiffle ball 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 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 keep. No, no, Munson died. And, yeah, it broke my heart.
Interviewer
All right. Queens College.
Jerry Colonna
Yeah.
Interviewer
So you get into journalism is where I want to go. So tell me that story, how that happens.
Jerry Colonna
So 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 at Queens. And while I was there, I suffered, you know, 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 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 Greene, 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 this 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 but.
Interviewer
What year is this?
Jerry Colonna
82, 83, something like that. And at the end of that semester, 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 gotta go back to school. And he said, well, can't you work part time? And I said, doing what? I 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, like I would, I would copy edit a piece or proofread a piece 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 TRS 80, what we would call a laptop, but was just had an eight line LCD screen that I would file stories from.
Interviewer
Roughly an electric typewriter.
Jerry Colonna
Really roughly an electric typewriter. And it had an acoustic coupler. And so you have to imagine I'm in the Kochi cafeteria at Queens College taking these couplers out of my backpack, attaching them to the payphone hanger handset and hitting send while dropping quarters.
Interviewer
Now wait, I want to point out, because people might not understand, you're doing that because you're recording the conversation.
Jerry Colonna
No, I'm doing that to file the story. It was a modem.
Interviewer
So it was a modem.
Jerry Colonna
And I composed the story on this little LCD screen back in.
Interviewer
So the dial up that people old enough to even remember aol, you're essentially sending the signal.
Jerry Colonna
Yeah, this is pre aol.
Interviewer
Yeah, no, absolutely. What I'm saying was, is the way you're sending it is the sound that's going through the receiver.
Jerry Colonna
That's right, that's right. At 400 baud.
Interviewer
Right. I started at 144 on my first modem.
Jerry Colonna
So this is because you're a youngster.
Interviewer
Okay, let me. The magazine, was it Information Week? Yeah.
Jerry Colonna
Good memory.
Interviewer
Okay, so early 80s, what is. It's essentially an industry magazine.
Jerry Colonna
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.
Interviewer
What is the technology that you're covering? I mean, the PC era is here.
Jerry Colonna
Just barely. Yeah, just barely.
Interviewer
So what are you covering?
Jerry Colonna
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 disk 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. Yeah. Stuff. And by the way, all the stuff that I just said to you, I. I was an English major in college. Like so the dissonance of like covering all that stuff was just weird for me.
Interviewer
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 job.
Jerry Colonna
Yeah, I mean I had Looking backwards. Right. I'll be 62 in December. Looking backwards right now. And I did the same thing when I was a venture capitalist. Everything is autodidact, everything is self taught.
Interviewer
Is there a lesson there in the sense that people think that there has to be some sort of certification for certain things or is learning in the real world better than.
Jerry Colonna
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 walk down 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 his army just because it was interesting, or the development of Siberia as a gulag like this is 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.
Interviewer
But does a. 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 sort of like, well, if I don't do it, that self starting of finding the thing.
Jerry Colonna
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. 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 like, 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.
Interviewer
In aid of getting to the coaching. You're a reporter on the beat through the early 90s.
Jerry Colonna
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.
Interviewer
Book market like PC Mag.
Jerry Colonna
Our competitors were Computer World, InfoWorld, PCWeek, 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 Fairchild publication.
Interviewer
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.
Jerry Colonna
Tech is media, media is tech.
Interviewer
But these were. This was it. Like if you are. This is why Steve Jobs would give interviews to.
Jerry Colonna
Why 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.
Interviewer
Because this is the only venue that they have to reach the tech audience as it existed.
Jerry Colonna
Correct. At that time. Right. There wasn't. I mean, during my time, the guys at 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.
Interviewer
Race the rudders.
Jerry Colonna
Race the sails. Race the sails.
Interviewer
Captain, an unidentified ship is approaching.
Jerry Colonna
Over.
Interviewer
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Jerry Colonna
Reach sales professionals, not professional sailors.
Interviewer
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Jerry Colonna
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Interviewer
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Jerry Colonna
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Interviewer
But this, the PC era does happen. Tech is infiltrating first the offices and then every home starting in the 90s.
Jerry Colonna
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.
Interviewer
And then the Internet.
Jerry Colonna
Yeah, yeah, then the Internet. 1994 was when I first, first installed TCP IP 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 remember what it stands for in order to connect.
Interviewer
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, but.
Jerry Colonna
Well, I think that was part of the point 1, because 3.0 was just such 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 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 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 fax. Okay. We emulated my times fax, 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 Endreessen and company at NCSA Illinois developed the first web browser, Mosaic. Mosaic. And like, it was just mind blowing. It was absolutely mind blowing because heretofore you used services like what's called FTP or Waze to actually.
Interviewer
Gopher.
Jerry Colonna
Yeah, gopher. And it was all text based. And there were no. There was no such thing as clicking on a link. You just.
Interviewer
There weren't images.
Jerry Colonna
There were no images. There was no sound. There was nothing. And you were just typing. 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 the. 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 Tech Web, what. What was our first iteration? How do we replace paper and do this, you know, in the fall? And that experience was, this is 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?
Interviewer
See, this is not sticking to the notes. There's stuff like Pathfinders happening around this time, right?
Jerry Colonna
And Hotwired.
Interviewer
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. So.
Jerry Colonna
But we had no standard about what is what an ad was, right? We had to invent that shit.
Interviewer
And you're pulling from metaphors from the previous media and eras, but you don't have any idea where this is different. It is interactive. So that time period, the sense that you don't know where it's going.
Jerry Colonna
Incredibly thrilling. I remember internally we debuted. So I'd spent that some. 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, Tech Web. And the plan was to launch it at a trade show called Comdex, which was in Vegas. And Ziff 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, 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 right. And we were launching. Not only did we were we trying to invent what does a CPM look like? And for those who don't know, CPM stands for cost per million. Okay. Our initial CPM for an ad on Techaweb, $15,000.
Interviewer
By the way, for context, if you get a $30 cpm in podcast, $15 cpm and you're on easy street.
Jerry Colonna
So because we didn't know we were just making it up, we had no idea what. I mean, people 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, 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?
Interviewer
And as today it is minute by minute, minute by minute, there's no off.
Jerry Colonna
Well, I remember having an ethics conversation with this Harvard University professor and I, 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 of 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 is your ethical responsibility as you're inventing this all along the way? 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 out of the mouth of my children. You are destroying our business. And I said, if I don't do it, some other company's 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 TCP IP 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.
Interviewer
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.
Jerry Colonna
Right. Mike Moritz is probably the best example.
Interviewer
Or an M.G. siegler a later era. So how do you.
Jerry Colonna
So how did that happen?
Interviewer
Yeah, like does someone approach you or is it your idea? I feel like it wasn't your idea.
Jerry Colonna
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 this stuff, to Seattle and like, like to home. And so I was really in the midst of a dilemma. And there was this guy named Dave Wetherell. And Dave had launched, he had a marketing company and he had stumbled upon a small software company. And they, they developed a competitive browser competitor to Mosaic called booklink. And his metaphor was books, right? Turn the page, click on a link, new 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 an entrepreneur, so he was kind of fast talking and he would call me up and I remember one day he calls me up and he's like. 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. 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 not sure and all this stuff. So I turned them down. And then a couple weeks later was comdex. And I'm at comdex demoing what we call Tech Web. 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. While that was all going on, Steve Case 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 don't you come work for us at aol? And I said, well, doing 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, ah, I can't do that. But it planted a seed. And by the end of that fall, I was working for Dave, launching one of the first Internet specific venture capital firms.
Interviewer
I always can't ever nail down the name. It's like at ventures or cf.
Jerry Colonna
Well, the official name was cmg@ventures.
Interviewer
Right.
Jerry Colonna
But we got the domain ventures.com. and so then, so it became at ventures.
Interviewer
And how big is the fund, dan?
Jerry Colonna
It was $35 million. It was nothing.
Interviewer
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?
Jerry Colonna
Zero.
Interviewer
Okay.
Jerry Colonna
I actually had to have a friend who had recently graduated from HBS explain to me the way a venture capital firm works.
Interviewer
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 dollars?
Jerry Colonna
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. You know, even the ethical questions I was asking before, you know, all the stuff that we see now, like social media as a source of division. Back then, we saw 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.
Interviewer
So you're largely investing in, essentially to come back to the term interactive media startup.
Jerry Colonna
Yeah, yeah.
Interviewer
How big are the checks?
Jerry Colonna
Half a million dollars.
Interviewer
What is the valuation?
Jerry Colonna
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 universe, the technology, and, and create a company out of it. It's a long standing 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 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 spidering the web and capturing information. The minute I saw this demonstrated, I 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 I can't stand it. But at the time it was like inventing stuff like that and realizing that we just changed information retrieval forever.
Interviewer
I prompted you by asking for evaluation.
Jerry Colonna
So, like, 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 it public for 200 million, which we thought was phenomenal.
Interviewer
But you are doing a 2 or $3 million valuation that becomes a $200 million.
Jerry Colonna
Correct.
Interviewer
Versus you get in at 20 million now and you're hoping for a unicorn sort of.
Jerry Colonna
Right. Or if you're talking about funding an AI company, you're getting in at a $10 billion valuation.
Interviewer
Well, let me ask you then. So let's get to Flatiron. So you're, I think you, you're with the adventures for what, a year?
Jerry Colonna
Just about two. Okay, yeah, it was about. 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, in the partnership. And I, you know, 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. Capitol's 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 a Yankees cap on. And we'll name him later. This kid, Jason Calacanis walks in and that whole thing. But anyway, that was that era, and it was before Flatiron, but I was looking at transactions, looking at deals geographically.
Interviewer
I want to point out that is Silicon Alley. It's the heart, the classical heart.
Jerry Colonna
It's like right on Union Square. And it still is, too.
Interviewer
Yeah. Today, all of the big VCs still have offices in that neighborhood.
Jerry Colonna
Right.
Interviewer
So what is Fred doing? How do you get there?
Jerry Colonna
Well, Fred Wilson's at Euclid, Euclid 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 Pincus. Well, Mark Pincus and Sunil Paul. Mark, of course, went on to launch Zynga, which was probably his biggest success.
Interviewer
What was Freeloader, though? Because I recognized the name.
Jerry Colonna
Oh, Freeloader is crazy, crazy business model. Okay, have a seat, everybody. This was back in the day when. When people had the bright idea to run ads on your screensaver. So there was PointCast.
Interviewer
Right, right.
Jerry Colonna
Which was the PointCast network, which would put drop news stories in. 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, you know, using the real estate, if you will, of the screen.
Interviewer
Well, and that evolved into putting ads in people's browsers as well. Remember along the top, I think we.
Jerry Colonna
Were doing ads in browsers before that. It was like we were looking for real estate. Basically what that evolved into was something called People PC, which is basically, you get a free PC, but you have to look at Ads all over the place.
Interviewer
Okay, you and Fred hook up on this deal, right?
Jerry Colonna
We're looking at the transaction together. Mark gets into a fight with Dave Weatherall because Dave, we've already invested in Lycos. 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 Lycos 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. So much so that Mark would regularly call me up for advice. Yeah, you owe me, buddy. And one day I'm passing through 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.
Interviewer
Interesting idea because Softbank is already doing things like they were backing Yahoo already and stuff like that.
Jerry Colonna
I think at that point they'd already put money into Yahoo. Yahoo, I think had gone public.
Interviewer
Musk has already gotten the religion and it's starting to.
Jerry Colonna
Yeah, yeah. I mean Masa almost invented the religion, the religion of hyperbolic investing. And what he was doing in the US was there was SoftBank US and Fred knew some of the people there. There's 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 US but then they, they ended up creating multiple funds. But that was the. They were backing young investors like Fred or like Brad Feld. And then I'm Scott Hanson, host of NFL Red Zone. Lowe's knows Sundays hit different when you earn them, we've got you covered with outdoor power equipment from Cobalt and everything you need. Need to weatherproof your deck with Trex decking, plus with lawn care from Scotts and of course Pit Boss grills and accessories, you can get a home field advantage all season long. So get to Lowe's, get it done and earn your Sunday.
Interviewer
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Jerry Colonna
Yet, here are 15 reasons why you should. One, it's $15 a month.
Interviewer
Two, seriously, it's $15 a month three no big contracts.
Jerry Colonna
Four I use it.
Interviewer
Five. My mom used to say, are you. Are you playing me off? That's what's happening, right?
Jerry Colonna
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Interviewer
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Jerry Colonna
Well, it was always Silicon Valley and Boston, what's called Route 28. Right, right. It was like those were the twin poles of venture.
Interviewer
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?
Jerry Colonna
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 Patrick, 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, 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.
Interviewer
Yeah.
Jerry Colonna
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, ripped 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.
Interviewer
People had to go to Sand Hill Road. You're saying you're out in the field.
Jerry Colonna
That's right. We're just walking the streets here. I mean, it ended up developing like that a lot in San Francisco.
Interviewer
Right? What I'm saying is when you had to go to Sand Hill Road, you had to go to the mountaintop to ask for money.
Jerry Colonna
That's right.
Interviewer
And you're saying you're looking for the people, and you're saying, hey, I'm gonna give you something.
Jerry Colonna
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.
Interviewer
I'm going to name investments from this time, but we're only going to be able to do a couple of them. Yo Yodine gamesville Vertical one year times Digital. Let's do Yo Yo Dine Seth Godin. Seth, what did you see there?
Jerry Colonna
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, so even north of Boston for the Monday morning partners meeting. And I was like, this guy's brilliant. And he presented, and my partners turned him down. And they just didn't like Seth. 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 when Fred and I were talking about getting together and forming what became Flatiron. The original name, by the way, was ACME Ventures.
Interviewer
Bugs Bunny reference. No.
Jerry Colonna
Wiley Coyote.
Interviewer
Yes, yes.
Jerry Colonna
Right. And so I had this picture of the frosted glass door with Acme on the front, and 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 Yo Yodine was the very first transaction that we did.
Interviewer
It is Seth Godin. Let's underline that for a second. But what was Yo Yoyo dying real quick?
Jerry Colonna
Because 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 in 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 what you were 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.
Interviewer
A big win. I believe your biggest, but you can correct me, no, no. Would be geocities.
Jerry Colonna
Yes, that's right. That's right.
Interviewer
I thought you were saying, tell me the GeoCities story and then I'll give the context of maybe the first glimmers of social media. But yeah, tell me how you learn about geocities.
Jerry Colonna
Well, I first learned about geocities, actually when I was at CMG Adventurous and it was then called Beverly Hills Internet and it was a dial up service.
Interviewer
I interviewed him. I can't remember the David Bonett. Yes, I interviewed him years ago.
Jerry Colonna
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 one famous story of a guy who had been diagnosed with AIDS who began talking about his journey Now, PS Background. David and his former husband Rand. David's husband was the first openly gay judge in this 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 forum, 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, Jerry's 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.
Interviewer
Because it gets acquired by Yahoo. Or did it go public first?
Jerry Colonna
It went public first, yeah, 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? Cause 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.
Interviewer
But again, you're getting at it like a definitely sub 20 million dollar valuation and then you get a return of 3 or 4 billion.
Jerry Colonna
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 bid to acquire the company. And this is like, I think we went public in the summer and then right around Thanksgiving there was this, all this stuff going on. The dream was that aol, I think, was trying to buy Netscape. David wanted to combine Lycos and geocities and buy Netscape. Lycos 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 three or $4 billion. So, you know, yeah, we went from a $20 million valuation or so to a three or $4 billion valuation in the space of maybe two and a half, three years, which is nothing these days. But back then it was a big deal.
Interviewer
If there's, if this is not a big deal, tell me to skip it. We'll skip it. But Calacanis helping you source the deal or.
Jerry Colonna
No, no, he didn't source the deal because I brought the deal in. What, what j 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, what we asked Jason to do, we had by this point, in addition to SoftBank, JPMorgan Chase or its predecessor, Chase Capital Partners was our prime backer. 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, an 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.
Interviewer
It was diligencing.
Jerry Colonna
Yeah, he was diligencing. He was kind of acting like a young associate would, which was go out and tell me who the competitors were. A scout. That's right.
Interviewer
Okay, I have to get you to a board meeting in 10 minutes. So I'm gonna alight over stuff and we're gonna talk again soon. The bubble bursts. 2001, 911 happens not at the exact same time, but at around an 18 month period.
Jerry Colonna
Yeah.
Interviewer
And well, it started that spring March of 2000. Ish.
Jerry Colonna
Yeah. With the collapse of the NASDAQ.
Interviewer
Yeah. You do not continue on in VC, right?
Jerry Colonna
Well, I did for a year.
Interviewer
Okay.
Jerry Colonna
I went from Flatiron to JP Morgan, which was our prime backer at that point.
Interviewer
Again, this might. Maybe we'll have to save this for the next conversation. But the bubble bursting, the 911 and you transitioning into a different career path, which is coaching. I'm assuming that's all related.
Jerry Colonna
Yeah, I mean, August of 2001, do you remember the Industry Standard magazine?
Interviewer
Oh yeah. Biggest number of ad pages of any magazine in history.
Jerry Colonna
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.
Interviewer
And then bankrupt.
Jerry Colonna
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 in myself. I was heading into my 38th birthday. I was fucking miserable. Every in 96 when we launched Flatiron, 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 JP Morgan. I still. 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 because. And it all comes back to an inner. What I often say is I was crosswise at my. With myself. My inner and outer experiences were at odds with each other. The more success I had externally, the shittier I felt.
Interviewer
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.
Jerry Colonna
Reboot. We launched reboot 11 years ago. I was a solo entrepreneur coach and then morphed that.
Interviewer
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, here's my final question relating to that. Starting a company, being a founder.
Jerry Colonna
Yeah.
Interviewer
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.
Jerry Colonna
Yeah.
Interviewer
To what degree is that? What you understand that makes you a good coach for executives and startups?
Jerry Colonna
Well, I 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 side 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.
Interviewer
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.
Jerry Colonna
A couple quick things.
Interviewer
Yeah.
Jerry Colonna
Depression. Lies. And 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 were my multi day leadership immersives, 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.
Interviewer
I. I can't top that. Jerry, we're going to talk again, but thank you for talking to us today.
Jerry Colonna
Thank you for having me. It's been a delight to go down tripping, lovingly down memory lane. Yo, this is important, man. My favorite Lululemon shorts, the ones you got me back in the day. I think they're called pace breakers. The ones with all the pockets. I just got back from vacation and I left them in my hotel room and do. Dude, I need to replace these shorts. I wear them like three times a week. Could you send me the link to where you got them? Oh, also my birthday is coming up soon, so. Anyways, thanks, bro. Talk soon.
Interviewer
Looking for your newest go to's Lululemon. What's new gear drops on Tuesdays.
Jerry Colonna
Every Tuesday. Head to lululemon.com to shop. What's new gear.
Tech Brew Ride Home
Episode Title: (BNS) You're Not Killing It. Nobody Is Killing It. VC Legend Jerry Colonna
Date: September 27, 2025
Host: Adam (Morning Brew)
Guest: Jerry Colonna
This episode is a candid conversation with legendary venture capitalist and executive coach Jerry Colonna. The core theme is the myth of “crushing it” in Silicon Valley—why building companies is hugely difficult, how impostor syndrome and depression are common, and why open discussion about struggle is both necessary and humanizing. Colonna walks through his journey: from a working-class Brooklyn childhood, to tech journalism, to founding Flatiron Partners (one of NYC’s first big VC funds), to personal crisis and ultimately coaching startup founders. The episode’s tone is raw, reflective, and inspiring, offering both an insider’s history of the early internet and a meditation on leadership, vulnerability, and resilience.
The conversation is frank, witty, sometimes profane, and deeply humane. Colonna de-romanticizes entrepreneurship and investment — success comes with invisibly high emotional costs, and every “legend” is fighting a private battle. The show isn’t just a tech time capsule; it's a manifesto for honesty in leadership, a call to coaches and founders alike to drop the pretense and care for the human heart.
If you're a founder (or simply alive), Colonna’s central wisdom is this:
Struggle is universal and invisible. Curiosity, connection, and candor matter more than resumes. Resilience isn’t about never falling down, it's about getting back up — and being willing to ask for help.
Recommended Follow-up:
Explore Jerry Colonna’s Reboot podcast, and his books for more on founder mental health and authentic leadership practices.