Leap Academy with Ilana Golan - The Untold Story of Napster's Success, Collapse & Hard-Won Lessons | Jordan Ritter | E138

Episode Date: December 16, 2025

Jordan Ritter didn’t grow up surrounded by tech; he grew up on a farm, tinkering with computers in total isolation. But that early curiosity led him to co-found Napster, the file-sharing service that transformed music distribution. As millions of users flooded the platform, Jordan was instrumental in keeping it alive through sleepless nights and nonstop chaos. The success was massive, the failure was brutal, but the lessons shaped everything he did next. In this episode, Jordan reveals to Ilana the real story behind Napster, the personal sacrifices of innovation, and the mindset required to build something that leaves a legacy. Jordan Ritter is a serial entrepreneur, software architect, and angel investor, recognized for his work at Napster, the file-sharing service that reshaped music distribution and digital technology. Since then, he has launched and advised multiple startups in the tech industry. In this episode, Ilana and Jordan will discuss: (00:00) Introduction  (02:08) Growing Up on a Farm and Discovering Tech (06:40) His Journey into Hacking and Computer Security (12:37) Joining Napster and Disrupting the Music Industry (17:55) Experiencing Napster’s Highs and Crushing Lows (32:20) Why Jordan Decided to Leave Napster (40:16) Reinventing and Building Companies with Value (46:03) The Importance of Culture in Startups (52:19) Navigating Interviews and Culture Alignment (55:18) The Challenges of Starting a Business (1:03:30) Lessons Learned and Giving Back Jordan Ritter is a serial entrepreneur, software architect, angel investor, and co-founder of Napster, where he helped scale the platform to 60 million users. A four-time founder, he has built 20+ large-scale commercial and open-source products across 12 languages, developing systems used by millions. At Cloudmark, Servio, and Augment AI, Jordan built intuitive, scalable, and reliable platforms, and he now advises CoPilotKit on product strategy. Connect with Jordan: Jordan’s  LinkedIn: linkedin.com/in/jordanritter  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

If you want to be an entrepreneur, you want to build something on your own, or you want to be part of something early, there is so much misery. I actually talk everybody I possibly can out of it. Jordan Ritter was one of the original minds and co-founder of Napster, which revolutionized the way we think about music. Building something from nothing is challenging. There is an easy button. It's just not building companies. I don't like the word innovation. I think it's a nothing word. The word I use is ingenuity. Ingenuity doesn't blossom without challenge. In a startup, you're going to suffer anyway. With the wrong people, you will suffer mightily,

but with the right people, you will suffer happily. What it actually takes to build something from scratch, because it is a lot harder than it sounds. One of the reasons I start companies is because there's the easiest hard thing to do. What would be one thing that you wish somebody told you earlier in your career? Don't do it out of curiosity. Do it because... Jordan Ritter was one of the original minds

and co-founder of Napster, which revolutionized the way we think about music, from the way we consume music, the way we share it. And he completely disrupted the music industry and we're pivotal to what came next, which is Apple music, YouTube music, Spotify, et cetera, that you are probably all using today. So I love to drill down into this incredible journey

because what I love about Jordan is that he is an OBS person, just like I love, and he's very authentic. And I want to hear exactly how you think of starting something from scratch and how you build it. And Jordan since then has started countless adventures. I think we said six. And multiple exit has endless insights. And I can't wait to just dive in.

Jordan, thank you for being on the show. Great to be here. I want to take you back in time just a little bit to touch it because you've been tinkering with code, but also actually a music major. So take us back in time. It's funny how you had the seeds all away from where you are teen. The first vignette that comes to mind is age 13, living on a farm in a single trailer.

So I had my own trailer, which was really great back then. But you live on a farm, you know, it's not like a suburb or anything like that. Very humble beginnings. On a 286-12, so while everybody had 386s and 486s, I had this dinky Epson 28612 with 640K RAM, no more than that, and a 20 megabyte disk that I double space to 40. The interesting thing about this experience in having originally a 2400-Bodd mode, then to 144 is that the scarcity of resources of compute power of capability is actually what drove me to optimize to really drive an engineering mindset. I wrote my own mouse driver. I wrote my own

phyto opus seed dog serial interface layer dryer, which is how BBS is used to talk to comports back in the old days. But wait, you're on a farm. How do we even know about these things? I was an international baccalaureate student and I've been in gifted programs my whole life. So I got exposed to a lot of stuff at its very earliest stages. But yeah, I had dirt under my fingernails. That was a thing for me going into high schools. I was the kid who had dirt under his fingernails. Interesting contrast. At the same time, I was a musician. I loved music. I played five different instruments. My first one I ever learned. I learned in this podunk backwoods town of Texas called Malikoff. I learned flute, which is probably the worst instrument to learn, except I was sitting in

band surrounded by all these cute girls. So I thought I was very, very smart, and probably was actually very smart. Well, the dumb idiots made fun of me. I was sitting around these beautiful girls. So anyway, flute, clarinet, oboe, and then piano. And between the woodwinds, a lot of the fingerings are the same. And saxophone was my favorite. So all throughout middle school and high school, I was in all the bands, all the groups,

all the whatever's. And I legit thought that I was going to go to college and become a musician. So I started looking. But I was also in IB. and I took AP and I B comp sci, and it was just mind-nummingly simple and fun and easy. I was kind of the teacher's pet in that class, so it came natural to me, but it never occurred to me that that would be a career. And I'll just take a beat here for a second and say that I lived on a farm because my father

had built this six-acre, six-and-a-half-acre property of a wholesale nursery foliage. So he and I and my stepmom together built multiple greenhouses, huge shade houses, I was chief ditch digger, chief pot filler, chief irrigation. I had all the sea level titles back when I was 13. But what was interesting about all this is my mom herself had a costume jewelry business, originally called Dallas Gold Diggers, became Flamingo Gold when she moved to Florida. And back in those days, in the middle 90s, no one was called an entrepreneur. I didn't have that label and I didn't have that pride.

My parents were small business people. They were the middle class that Republicans always talked about. but they were never put up on pedestals. They were never lionized as being the great industry giants and the creators of everything in the world that's local that grows big. So I didn't know until later in my life that I was actually the son of two entrepreneurs. And so it kind of makes sense that I became an entrepreneur, but I didn't know it while it was happening.

It just had those examples, osmosifying into me. So that's the stage. I'm in high school. I'm playing all these different musical instruments. I really think I'm going to be a musician. but comp size stuff is really easy. I'm not rich, so I have this terrible computer, but I made it work, and it was awesome.

And because it was so minimalistic, it really got me into thinking about how to optimize, whether it's writing code or how to make something work or how to make it go faster, how to be really efficient with space, RAM, or disk, et cetera. So I started at age 13. I'm on BBSs at night. Only older Gen Xers are going to remember

the days of when you could call a phone number and it would rack up charges. right? And so if I was on the phone for too long, they were charging us by the minute. And so I would connect to all these BBSs at night. And then my dad would find out he'd get really mad at me for spending all this money just being on the phone. We'd take it for granted, right? We have these phones and we pay these cell phone plans and it all just works. But they used to charge us by the minute. How do you then eventually meet the Sean's, Sean Fennings and Sean Parker? Ah. So fast forward to college. I went to Lehigh University in Bethlehem, Pennsylvania, and basically entered as a sophomore due to a bunch of credit that I had from the International Baccalaureate program. And it took 24 credits my first semester, 21 credits my second semester, 18 credits my third, and 15 credits my fourth. You can see there's a little trend there. Coming out of IB, they never taught me moderation. So I went into school, and I had all this horsepower and all this capability, and I just went after it and just really enjoy.

it, but I burned myself out. And two years later, I left. I am actually a college dropout. But I think I learned all that I needed to learn, which was discipline and all that stuff. So I ended up moving to Boston. And there, I worked for an Israeli company called Netecht, like D-Tech, but with an end, and I became a paid hacker.

We weren't allowed to call ourselves hackers back then, because back then the Fed was literally hunting us. So you didn't want to call yourself that. So I was a security researcher. but I published a lot of great security research, and Boston was sort of the seat of power for computer security. Well, I lived on 199 Mass Ave, downtown Boston overlooking the Christian Science mothership, this gorgeous view.

Next door to me was the Boston Symphony Orchestra, and next door to that was Northeastern, and that's where Fanning was, but I didn't know. So the computer security stuff is relevant because I'm in basically the seat of all computer security in the United States. Boston was where it was at back in those days. and I'm getting pulled into the computer security underground. I'm making tons of friends. We would have these dinners called 2621,

which is a playoff of 2,600, the old Hacker magazine, but 2621 was 2600 for 21 and overs. So we'd go to a place where all the kids couldn't follow us, and then we had this thing where we would all whip out our latest exploits that we had written, and then the group would vote, and whoever one would get dinner for free. And this had the loft, and it had New Hack City, and it had CDC, and it had all these people who are still my friends,

We would all just show up. And this was just my new experience. As part of that whole exposure, I became exposed to another group called Woo Woo, which was a silly name describing the largest computer security underground group in the world at the time. It had over 60 people in it.

And it went on, Wu actually went on to become this group that birthed a bunch of billionaire businesses. It's been titled The Billionaire Hackers Club. So, you know, our founder, Matt Conover, he went on to do cloud volumes and a couple other things. Doug Song did Arbor Networks and now did Duo Security.

I don't know what he's doing lately. Jan Coom did WhatsApp. All these people were woo-woo people. That is where I met Fanning. Now, I am 19 at the time. I think he's 17, something like that, 16 or 17. He had no formal education in CompSai whatsoever, but he too was effing brilliant.

And so he was exposed to certain things. We didn't have good search back then. We certainly didn't have AI back then. So he did the best that he could. could with what he had. But his software was written by a 16-year-old. What year is that, roughly, Jordan? This was 98. 98 was when he and I first met. The web was taking it off. We were all starting to get broadband Ethernet. People still don't remember that, probably, from dial-ups to broadband

Ethernet. We had it in universities in the mid-90s, but we didn't have it until later residentially. And anyway, I'm in all these different computer security communities. I'm in the is, like I do it as a profession. My company gets bought by a larger public company. They put these handcuffs on me, these golden handcuffs. Like, here, we'll pay you, just go sit in a corner. I published one really big exploit that compromised 80% of the internet. And then they told me to stop publishing. That was fun. Just because once you're a large commercial public company, you don't want to rock the boat on anything like that. So that was the end of that one. It wasn't quite the end. But like, it was interesting because

That gave me a lot of spare time to go build another hacker group called K5 with some really amazing people, Windows Snyder, and Dave, Dave G, Dave Goldsmith, and a couple others. But again, this exposure to people who are all dabbling in the latest and greatest. So if I try to create analogies that are going to map to now, I think what was brilliant, even though hacking was either a black or a gray art back then, and for a lot of us it was gray, because you had to know what was possible, but we didn't do bad things with it. We had a rule, no mill, no gov, no money. Everything else was fair game.

But being in that kind of group, I think Fanning would probably say the same thing. Being immersed in a group of people like that, you're exposed to everybody else's ideas and everybody's working on something cool. One of my co-founders from my last company, I presume, we moved to New York. I presume is exactly having this experience where he is a bird of feather congregating together with all these other startup entrepreneurs. and they're all mixing ideas around the latest and greatest AI stuff. This makes a lot of sense, right?

Like who you surround yourself with will dictate a lot of where you're going. This is incredible. So I love that you're sharing that. So we were talking about chance, right? And being lucky. I think though chance favors prepared and there are things that you can do to improve your chances. The lowest common denominator thing that I've seen would be entrepreneurs do in the last 10 years is go to these startup meetups. Meetups used to be a big thing, especially before COVID, where, you know, chances are 90% of the people there are just pedestrians, just kind of gazing and looking at things, but there's like 10% really cool people.

And just by putting yourself in proximity to them and mixing ideas and mixing thoughts and hearing and being influenced, I think that's the other thing is you've got to listen a lot and be curious a lot, especially about the things that you don't know, just increases your understanding and increases your ability to engage others. So I would say that as sort of the earliest beginning for where Napster came from and Napster came out of the computer security underground. It's in the book. It's in the documentary that Wu Wu birthed Napster. It wasn't just me. There were a bunch of other hackers. One guy was running the back end. One guy was running the website. We were all piling in to help fanning. And my involvement came one summer. I think it was the summer of 99. I had gotten my golden handcuffs. I was building this other thing with some friends of mine. and Fanning, I think it was like May, maybe of 99, and he's like, hey, I'm right in the back end. It keeps crashing. You keep giving me feedback.

I was reverse engineering his stuff because we're hackers, and he wouldn't let us see the source codes. I'm like, all right, if I send it this, it crashes. And if I do it, it's likely a stack overflow. This is probably where you should look. And enough of those, and he got kind of maybe a little irritated with me, I guess, and said, hey, would you want to just take it over and let me focus on the client and you do the server? And I'm like, sure.

So that kicked it off. I spent the summer rewriting the whole thing, and then September came along. We raised our first 50K from a gentleman named Yossi Amram, who was the CEO of Valisert at the time, tempestuous character. And back in the early days of E.C., pretty much all of them were tempestuous characters in one form or another. Are you still working at the time, or did you already leave? So, interesting. September, I think maybe it was late August. Fanning came over.

I've been working with him, talking with him, engaging with him, talking with him on the phone. for months. And then he decides to come over. And I guess his mission was to convince me to join. But in order to join, in order to take Yossi's money, we had to move from Boston to Silicon Valley, to San Mateo in particular. And he wasn't sure I was going to say yes. And so he came one night. He came at super late. I guess it was 11, 1130 or whatever. What I didn't know was that he brought another really good front of ours, Larry, who's online handle was Lymefest. We call him Larry Lymefest. And Larry was the guy that did the website, needed a bunch of other stuff,

some community stuff, and eventually worked for me in another company and did some great stuff there. But he was so effing drunk that he had to leave him outside and he never mentioned that he was even there. He was like, Larry, you're going to fuck this up. Excuse me for cursing.

You're going to eff this up. You've got to come in and stay down there while I go up and talk to Jordan. Something like that went down. So I had no idea he was down there the entire time and he must have spent like 45 minutes or an hour with me. So he made his pitch.

He's like, this is going to turn into a thing. And I didn't know. I really didn't. no. My first startup exposure was an attack, and I had an exit. We'd been sold to a public company, and there was only one comma in my check, but it was still a sizable check for a young man of 20 years old or so. So I was like, I don't know. So I spoke to my very good friend, Dave Goldsmith, and, you know, he said something to me effective. Jordan, for people like us, good opportunities will come and go, but they will always come. So you can do this one, or you can wait for the next one,

but I think you're going to be okay. And that made me feel safe enough to go, yeah, you know, I'm single. I drive a jickster 750 motorcycle. I have mirror shades. I was the unintentional hacker cliche. And I'm like, yeah, screw it. I'm going to go out to the West Coast because I was born in L.A. I just ended up not in L.A. So I was kind of coming back to California that I never even knew. So anyway, yeah, I moved out with Fanning and Parker. Parker often gets way too much credit for his role in what went down. But it was the three of us in the Marriott Residence Inn in San Mateo. and the CEO at the time, Eileen Richardson, loaned me her BMW 325 or something like that to drive because I was there, my stuff was being shipped across the country, nobody had anything,

and so I was ferreting us to and from places and stuff like that. So it was really nitty-gritty. To me, they made movies about this kind of thing, right? I mean, you kind of couch-surf your way into the Silicon Valley. And it was real, and it wasn't like I live in a 10th story loft. with all these little toys and gadgets and stuff, but I choose to go couch surf. No, we were broke.

We were broken. Back in those days, you made 60K a year. That was the starting salary. And still, and a lot of people don't really put this part into perspective, it wasn't until Google came along in 2002 that engineers were put up on pedestals.

So Napster was still born in an era where engineers were items on a Gant shark. There were cogs in the machine. and you bought them by the dozen. They weren't thought of as the creators. They were thought of as the executors as someone else's great, amazing vision. So we showed up before we were supposed to be rock stars.

And it wasn't until later when engineers and entrepreneurs were made to actual rock stars. So it was really interesting dynamic between the executive team and the engineers at that company. There were five of us that wrote all of the code. There was the server team, and then there was Parker and Fanning and John Badaanza

was to make it. me like the quintessential client team, and then there was me, Ali Idar, and Jordan Mendelsohn as the server team. And pretty much through the first year, we had other people in the company, but no one really told us what to build. Fanning would have an idea, I would have an idea, Ollie would have an idea. And all the cool stuff that we did came just out of our own brains sitting there having a moment, you know, a serendipitous moment of clarity and going, why don't we try that? We need to pause for a super brief break. And while we do, take a moment and share this episode with.

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crazy growth things, and we're like, what is going on? So talk to me about it. Why did it take off like this? What happened? There was a confluence, I think, of a couple things. We had a lot against us. We never had the best executives. We never had the best lawyers. We never had the best investors. A lot of this is due to some familial issues on Fanning's side with his uncle. I want to go there in a second for sure. Yeah, it's fine. It is what it is. It's long. go at this point. But the things that we had going for us was the growth of broadband at the time. So universities were turning on their dorms with broadband. This was a huge thing. A lot in the same way as when Facebook later became popular, it did so on the backs of college universities

enabling exclusive access. College universities were enabling exclusive access to high-speed internet. You couldn't buy it, really. You'd have a 56K modem. That was pretty good, but you couldn't stream stuff. We couldn't use the internet like we experience it today. That was one thing. The second thing was the record industry really was at a crossroads. And I can certainly speak to this more authoritatively now because in between companies, I did a stint as CTO of Columbia Music, where they hired me because of my Napster experience to build a digital media distribution platform. So I got to see how it all worked on the inside too. But suffice to say, I'd hear a single and I'd want the single. And I'd have to spend $20 for a freaking CD.

And I was tired spending all that money. So actually, I would say there's three things. There was the broadband internet and universities growing residentially. There was this ever-increasing cost to CDs. So they were $10 and they were $19.99, which is 20. And sometimes there were 23 and like, stop screwing with us. And then the MP3 became really, really popular. And that was the unlock.

So those three things together, I think, created this opportunity. And I don't know, I really don't believe that when Napster was first written, that it was written with this intention to disrupt the music industry. I just reject that. I think that's historical revisionism that's very self-serving because it came out of the computer security underground

and the way we exchanged stuff back then was on IRC or Internet Relay chat and everybody had these little bots on the chat that would advertise files and a lot of them were password protected and we were all pissed up. It just should be easy. We should be able to share stuff.

But music was kind of the thing that we all bonded and connected on. So MusicNet, which is what it was originally called, came out of IRC and the computer security underground and the hacker underground as a way for us to share stuff with each other. And because it was just built for us, it didn't have limits.

It didn't have restrictions. The download wasn't even protected. So Fanning would give the client executable to somebody and that person would literally hand it to somebody else and that person wanted to hand it to somebody else. And it all just worked. Now, of course, the thing was crashing constantly in the background, but we fixed that.

But like, it made it so easy, mp3s broadband internet made it so easy to give people what they wanted now when you say it out loud like that you're like well that's dumb why didn't the industry do that to begin with why didn't they simply give people what they wanted that is the nature of being an entrepreneur is find the need find a way to deliver the need charge a margin there it is that's business but the recording industry didn't want to do it that's been litigated ad nauseum many many things there's no point talking about here but suffice those were the three things that really um unlocked that moment in time was the growth of broadband internet, the prevalence of MP3s,

and the increasingly easy ability to convert your CDs into MP3s, and then Napster shows up and makes it just easy to share that stuff and find that stuff. So basically, if I want to share a song with you, I can easily share it, which is something that didn't exist before. People today don't know that. Hey, just send me the file. And we're like, yeah, do you want me to text it to you? Do you want me to email it to you? Do you want me to file share it to you? None of that existed back then, right? So it's really hard to put that in the context for people who didn't live through that. Exactly. So I'm translating it a little bit. But so here it is, this thing is clearly taking off. But I think also sometimes when things are taking off, this is where the problems

also start. I want to talk a little bit about when it is working out. I think this is where it exposed a lot of the issues, right? It sounds like you worked your ass off. So I want to talk a little bit about it. Well, we were having fun, right? And so what is it? that saying? Love what you do and you don't have a work day in your life. There's this whole thing about 996 now, nine to nine six days a week. I never work the four hour work week. I'm sorry, Tim Ferriss. I'm sorry. That shit's not real. I apologize. I worked so hard. How is that happening? Okay. He does not work four hours a week. I can tell you that much. Anyway, in 996 was soft back then. You worked seven days a week, but you did it because you were doing something you love. We slept under our

desks. And that became this canonized thing of like, oh, well, let's get, and they were door desks. They weren't even real desk. They were doors. One end would be a bookcase and the other would be like two posts. That later got taken by Amazon and other larger companies and other bigger cultures to become like a thing. They didn't have to buy them. We did. We didn't have any money. Again, it's the 28612 problem versus having your 486 DX 401. It's like, no, it's the scarcity and the challenge to overcome really hard problems is where true, I don't like the word innovation. I think it's a nothing word like technology. The word I use is ingenuity. Ingenuity doesn't blossom without challenge. And real challenge, not fake challenge. Like, I'm

going to go sleep on the couch on someone's place because that's cool. Oh, you get a lot more creative when your back is against the wall. That's exactly right. And some of the best stories I've heard about other entrepreneurs. Another quick example. A buddy of mine worked for me at my last company at Augma AI. He was our head of design. And I found out his story. And I found out his stories in Israeli. He came over with literally nothing in New York, was sleeping on benches and in parts that had to figure out how to live off of $3 and something cents a day. He found a pizza place where he could get a slice of pie and a drink here reliably. He had to find a place where he could keep a sack of stuff safe. And from there, now he's a highly successful,

highly regarded, wonderful human being type of person, right? But who would he have been if he hadn't faced that level of challenge in adversity? Now, I'm not saying he should have, and I'm not saying he loved it. And maybe he wished it didn't happen. I'm not speaking for him. But I am saying that the outcome of that challenge, the outcome of being on a farm and not having much, the outcome of having nothing when you immigrate in the United States, which is a common trope, but a really meaningful one, is where a lot of ingenuity comes from that we sometimes label as innovation, but it isn't. And it's a lot of my story, too. But I think it's important, and the reason why I took you there, Jordan, is I think there's a little bit myth around the easy button.

especially in this age of AI. Right, right, right. There's a lot of that, right? And social media also makes it look so easy, right? So you see these things and you're like, why is it so hard for me? And that's why I want them to hear the stories of sleeping under the desk and hustling. Well, I'm making it sound too good, then.

I'm making it sound way too good. I made $60,000 a year. I live in Silicon Valley, guys. You can't live off of 60 kids. That was my first salary. So I get it. 33, working for Amp Incorporated, aeronautical machine parts in Pennsylvania, 33K. I was making 37 as consultant.

They made me a job offer for 33, thought they were doing me a favor. I said, no. Like, that's what people used to make back then, right? Wow, how things would change. There isn't a sense and easy button. It's called going to work for Google or Microsoft. That has kind of screwed up so many aspects of building companies. People come out of college expecting used to be a six-figure salary.

Now it's a $200,000 salary. And I'm thinking, like, good for you. America is a very diverse land of opportunity and you go get yours, right? But what I loved startups for, what I lived for was so rewarding because it was so challenging. And it is challenging. Building something from nothing is challenging. There is an easy button. It's just not building companies.

It's going, letting someone else experience the challenge and supporting them in their journey. That's the easy button. But if you want to be an entrepreneur, you want to build a business. something on your own or you want to be in part of something early because it's practically the same thing. There is so much misery. I actually talk everybody I possibly can out of it. I tell them everything that sucks, everything that hurts, all the soul-crushing pain. The highs are high and the lows are low. But the lows are really low. Oh, they're lower than the highs, for sure, and they're more frequent than the highs. So I really try to talk everybody out of it. And anyone who's still

sitting there going, then I'm like, okay, you should probably be an entrepreneur. But like everyone else who bails out, I'm like, I just did you a favor because this sucks. Because what no one tells you is that when you're at the top, when you're the CEO and you're in charge, it's actually the worst job. Success always belongs to your team. Failure always belongs to you. Shit flows uphill, not downhill. But there's no one above you. You have a board and their shit rolls downhill to you. are literally responsible for everyone. You are responsible for the success and failure of everything, but you don't get to reap the reward of success unless the end game is successful. Meanwhile, this entire journey is soul-crushing. And pretty lonely.

Extremely lonely. But you can learn a lot from it. You can push yourself. You can challenge yourself. And if you like personal development programs or you like learning new things, trying to master new things, joining a startup is actually a great way to grow yourself despite the challenge. Actually, not even in spite, because of the challenge. But let's talk about then Napster, because it does blow in your face a little bit. Maybe that's a nice thing to say about it. There's the whole thing of John Fenning taking, which is Sean's uncle, right, taking 70% of the company.

There's also lawsuits coming your way. So walk me through a little bit. Speaking of highs and lows, you see this thing. taking off, and then you see these things coming your way. Take me on Jordan's journey for a second. That frame now includes so many other experiences. I know. I'm generalizing here. Sorry. From a Napster standpoint, the juxtaposition of staying up all night till three in the morning and solving a really hard technical problem that no one had ever solved before, we had three specific moments of those in our lifetime.

We recently had a 25-year NAFTA reunion where I got up on stage and I enumerated all of them. It was a big to do. It was really well done by Chris Fenner, thanks to him primarily. But the juxtaposition of that experience and then going to get a drink and seeing a pizza get delivered,

watching it get open, and there being an eight ball of Coke in the center's support of it, and you're going, we're being sued by the federal government, what the fuck are you doing? Excuse my language. I'll try to dial it back.

What are you doing? And then waking up the next morning to a mass press conference out front where Lars Alrich was going to show up and hand-deliver printed names. There was the whole DMCA. If a copyright holder told us the name of the person to take down, we would take it down. They could have emailed it to us. They could have given us a CD-ROM, but they printed it out. And they printed it out landscape, not portrait.

So fewer names per page, one row. And he wheeled this thing up. It wasn't a wheelbarrow. It was one of those dock cart things in boxes. And then he had a big press conference. So like this is just insanity of like, you're being sued by the federal government. They're about to subpoena everybody's computers.

You just did something really freaking awesome. And this crazy bet, you know what bonkers thing is happening out front of the company. That was a level of insanity. I don't think I've ever experienced ever again in my career, but I've had a lot of insanity. But that one was a peak insanity moment. It's just like, how can all these things?

And then we would all walk to lunch and then go to the Japanese tea gardens and sit there and try to allow the insanity to seep out of us in this beautiful, serene, in this tea garden in the middle of San Mateo, of suburb. All of this stuff was crazy. Can you sleep at night at that point? Look, when you work not nine to nine, but like... You sleep because you are tired. Six to 12. You're exhausted and you don't have a choice. We had a network operations center presence down at AboveNet in San Jose, and I brought my jixir out,

and if servers crashed, I had to hop on that motorcycle and book it down 280 at, you know, 130 to get there as quickly to go reboot the router or, you know, the switch because it failed or whatnot. There was all these crazy experiences that I think people read about these things, and they're like, this would be really cool to go through it. And yes, it's really cool to be past it and telling this story, but in the midst of it, you're making 60K, you're feeling highly unappreciated. You're doing God's work, really, trying to make the impossible happen. And people are trying to sue you, people are trying to shut you down, people are trying to hold you up.

It wasn't all bad, but like, I don't know how best to describe it. We need to pause for a super brief break. And while we do, take a moment and share this episode with every single person who may be inspired by this, because this information can truly change your life and theirs. Now, every cool opportunity you will ever find is most likely from a hidden market. It's the people who think about you when you're not in the room and bring the right opportunities to you. This means that the people you hang out with truly matter. That's why we created our flagship live event in San Jose, California, in the heart of Silicon Valley.

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auto renew separately see terms on site. Did you know that you're changing an industry at that point? Certainly. One thing Parker was really good at was narrating from a salesy standpoint. And the narration that got seized upon was, yes, we're disrupting the industry. And it was true. It was true. It was absolutely true. That happened and it needed to happen. The problem with every single revolution is at the end of the revolution, they march the revolutionaries up against a wall and they shoot them. And then the big businesses come in, the Apple Musics and the Spotify's, while the Napsters bleed to death on the ground. Lo and behold, that's what happened. Kind of that happened. Yeah. It's just what happens. It's what happens. And you leave, right?

That was the first one to leave. Talk to me about that moment because that was your every day, right? Is there like a fear? There's like, oh, my God, who am I without this? I'll give the texture of the moment, and then I'll speak to that. We had relocated from our offices in San Mateo to this warehouse building on Veterans Boulevard and Redwood City. And it was a warehouse. It was a cube farm with a second story off to the side on the west part of the building that was on the second story.

So people in offices literally looked down at everybody else in the cubes. We move into this place, and I'm in the midst of this fight for all of us to get $90,000 salaries. I'm not fond of saying this out loud because everybody has a role to play, and everybody is important in some way. But if two of us had been hit by a bus, there wouldn't have been a company. The engineers were critical to the success of NAFTA because nothing else was going well. So the technology worked, and that's why Napster became what it was. And without it, it was nothing else. It was an idea that someone else would have seized upon.

So we move into this super depressing environment, and I'm having this fight for not just myself, but everybody on my team to get paid more. And it's a fight that I can't understand. They're individual cubes. So my team wants to make a pit, take down the walls of three of the cubes, so that the four of us are in a single cube, effectively. we're told no. Why? Go F yourself. Okay. We wanted to sit over there. We wanted this. We wanted that. In the grand scheme of things, we weren't asking for really anything. But the common experience was no, no, no, no, no. Now, back then, and I don't know if it's still

true today, but back then, the federal government considered email a legitimate way to notify people of things. And it's infinite incompetence. It thought that if they sent you something, that you had received it. That was the expectation. In other words, if someone sent you a take-down notice or this or that or a legal thing, but they misadressed it, it was still expected you would get it. Now, we know in today's day and age, get the email just wrong, it bounces right back and no one gives a shit.

But in this case, that was the real hard problem. So someone had to be postmaster. Now, I had, in addition to building the back end, I had done all the corporate security, I'd done all the IT until Hector Via Lobos took over. Who's freaking awesome. I got to see him earlier this year. He's an awesome guy. I was able to let that go,

but I still had pieces of the infrastructure still because I ran the back end. I was in charge of it. And so I was Postmaster. And my job was to make sure that finger fumbled email addresses, things got to where they were going. The moment that came for me was in the midst of, I think we had been shut down once already, but turned back on.

and I'm the one that did the shutdown. That's a thing that most people got wrong. I wrote the code. I'm the one that turned it off. But we're in this moment where we're trying to raise money from Bertelsman. Now, no one really knew the details of it. But John Fanning misadresses something to counsel with the company, and it comes to me. Now, I'm a computer security guy.

I take the trust seriously. I've always taken pride in being an honorable person. this was my one moment of failure. I'm like, this is from John Fanning, and this is about financing. I'm going to read it. So I read it all. In it, I read how we given this guy, Milt Olin, $150,000 salary, we're going to pay for all of his flights from L.A. to San Francisco. We were going to pay for a car, and we were going to pay for his apartment. Keep in mind, I'm having an argument to go from 60 to 90, and they're just throwing stuff at this guy. And a lot could be said about Milt, but my experience of him were never that pleasant. So I'm having that kind of experience. I'm watching

executives pop up like weeds and we're having this experience. We were just not valued. We don't feel valued. We don't feel taken care of. And there are other people who, you know, we had a VP of who's trying to assert his value over ours. And like, it is what it is. It all happens. It's water under the bridge at this point. But that put me in a very terrible place. So I decided I've had it up. I read this thing and I am just so shocked at all the benefits that are being thrown out by this company. Meanwhile, if two of us got hit by a truck, this company's over, I couldn't do it anymore. So I go into that VP of Engineering's office, and I tell him, I'm leaving. And he's like, I think you should wait a week. I knew what he was talking about. He thought I was going to be super

excited that Bertelsman was going to give us $50 million. In fact, it was 60, with a $10 million set aside for its own record label. But that was precisely the reason why I wanted to leave. I was like, this is not going to take us down the good path. This doesn't take us down a really terrible path. going to get sued. We're going to get ultimately shut down, and this is going to be a miserable nightmare experience. And even then, I'd still do it if I felt value, if I felt appreciated, but I didn't. So I said, sure, I'll wait a week. And that week came, and the deal was announced, not for 60, but for 50. And that was the final thing for me. It was like, you just lied to everybody. Like, you could have told us to keep our mouths shut so we wouldn't get sued again. That's fine. But

you just told us 50. The number clearly said 60. Like, it's fine. These people, I don't trust them. I don't trust them with my own health and mental well-being. I don't trust them with anyone else's. I got to go. It was brutal. So that's the texture. That was the context. Yeah, I thought to myself, who the hell am I?

I've been on such a whirlwind peak valley and peak high experience, peak low, peak high experience. Who the hell am I going to be when I leave this place? Because I very much was, you know, I had other responsibilities too. I ran the moderator group. It was a volunteer group of people who were on the chat forums, and I wrote code. to give them special capabilities, to manage unruly people or bad people. I got to spend my New Year's Eve 2000 Y2K online with the federal government, with the FBI, because people were making bomb threats and chat rooms.

And I had to be there to give them information on these people who were connected to the system because they were going to take all of it seriously. They weren't going to take any chances. I gave my heart and soul this thing, and that was who I was. And at that time, we still weren't rock stars. Fanning was, and Parker had become a rock star by association, but the rest of us were in the background and not really feeling valued by the company. So I just didn't know what I was going to do. It turned out I had this waypoint opportunity in between starting companies where I got to

go work for someone else's company and helped them turn it around. And they really leaned in on my background and used it as a sort of like, hey, listen to us, we have value, we have worth because we have this guy and a whole bunch of other reasons, too. They were really smart guys too. But that was a helpful sort of transitory thing where I had a place to sort of rest. And as it turns out in my career between every company I start, I go and work at someone else's company to turn around or fix it or do something without ever intending. That has become sort of a pattern for me where I get to recharge because I'm not the sole person responsible for success and failure and everything, but I get to lift someone else up in service to that. But yeah, I had a real

identity crisis for a significant period of time over that. The reason why I'm going there for a second, And first of all, because I've had my own identity crisis when I was kicked out of my own company. But I think there's something, I think a lot of our listeners are somewhat in an identity of what's next, right? Like I've maybe ticked some boxes of success and what else is there? What else can I be doing? And sometimes to reinvent yourself is really, really hard, right? And hopefully, Leap Academy helps some people, right? But I'm just like, you know, but I think these stories are.

really important, Jordan. So you go and work for someone, but eventually you are crazy. So you do decide to start another company. So talk to me about what gets you to start these things and maybe share some of the stories. I'll start by saying that I think AI has completely reset everything I'm about to say. I think we're all in an undiscovered country right now. And I don't think anyone is giving good advice right now because no one really knows what's about to happen other than there's going to be a lot of job loss and recreation in some other form. And the only thing I will say is that you'll need to reinvent yourself and leap again and again. That's the only thing that is conference.

No, no, it's a great pitch for Leap Academy because you need to think about what is the methodological process I'm going to follow to achieve this outcome, right? And I think you've got that. So the question is, why did I build what I built? And when I go back to start at Napster, I participate in that because that was something that was a value to me. And every company I built after that, Cloudmark, anti-spam, messaging, security. CloudCrowd and Servio, you know, crowdsourcing with a reputation system backed by it,

which is a form of AI colloquially. But CloudMark was absolutely an AI company. We were machine learning technology doing anti-spam and messaging security. Every little company that I built along the way, Atlas Informatics, Augment AI, I was building something that had value to me. And it wasn't my driving notion, but it was a reassurance in the back of my mind that if I built something that was of value to me, it was likely a value to someone else. And if it was a value to someone else, it was likely worth some money. That's it. It wasn't my driving force, but that was

the reassurance. So if I could build something that I would use every day that made me more productive, made me more effective, made me more efficient, made me more capable, good things were going to come of it. There's a lot of things that can go wrong in building a company, hire the wrong people, partner with the wrong investors, build the wrong product, right? The truth of being an entrepreneur, and I was just giving this advice today as well, is not having a plan. A plan is just a list of stuff that's not going to happen. The skill is an adaptability and perseverance. What do you do when your face meets a fist?

That famous Tyson quote, everybody thinks they've got a plan until they get punched in the face. That's entrepreneurship. It's not having the right plan. It's not building the perfect product. It's not having the perfect investor. It's what do you do with the on-the-ground reality when it's different from what you expected? How do you adapt? How do you shift?

How do you change? How do you keep going? When do you do it? When do you not do it? And some of that is experiential knowledge, which I call wisdom. You can't know. You can't read it in a book. But there's a lot that you can do to prepare yourself for those moments that you can read in a book or in a podcast.

The idea was I always built something of value. I had a spam problem. Everybody had a spam problem in 2002. Again, some millennials don't remember this. Zoomers definitely don't know this. we had a real spam problem back then, back when Bill Gates famously said it'd be a solved problem in two years. One of the few times he was wrong. But I was hot on the trail of it, and we built a great business. By the end of it, we were doing 40, 45 million in revenue a year. Is that when Bill Gates

was on your board? Or is that a different one? No, that's a different company. Oh, I want to hear that one, too. Okay. Yeah, Cloudmark, I'm most proud of for a couple different reasons. The one is the company still exists today. I founded it in 2002 with a co-founder of Vipa Wade Prokosh, who is I can't say enough great stuff about this guy. He is, my opinion, he has easily surpassed me, and I love that. When people that I raise up surpass me, it's just the best outcome ever. It's like a proud parent kind of thing, even though he owns his own success. It's not mine.

But anyway, it's done it with him, and I'm proud of it because I took one of my key insights at an Aster was that what made it successful was nothing that we just talked about, not a single thing. What made it successful was culture. The people that built the technology all belonged together. We fit together like pieces in a puzzle. Yeah, we had conflicts and issues, but we rocked. When it was time to get up on stage and play our instruments, we rocked this place out.

And it was because at the core, we shared the same values, we believed in the same things. We disbelieved the same things, right, the negative and the positive both. we were very culturally compatible. And so when I said about building Cloudmark, I had that same notion of, and granted, 2002, bust. Everybody was leaving the valley. I couldn't pay people.

I struggled to raise my first 50K, but I did. I paid people in equity only for a while. Why did they come to work for me for nothing? Because we belonged together. They believed and they fit. We all fit. We were a whole that was greater than the sum of its parts. And so that was another thing.

And I've used that insight in all my following companies, and it's a really strong piece of advice I give other entrepreneurs. And to would-be entrepreneurs who are doing the meetups, and you need to choose carefully. Picking the wrong people is the number one reason for any of my failures in anything that I've done, career or otherwise. I love people. I love seeing the best in people. And I still do.

I refuse to give it up. But like I've had to become more practical about it. And certainly in business, it's easier to be more practical and pragmatic about, here's what I need, here's who you are, here's who we are, here's why it's not a fit. Here's why I want the best for you. You should go somewhere else. And in that way, no one suffers. Because with the wrong people, you will suffer. In a startup, you're going to suffer anyway. With the wrong people, you will suffer mightily. But with the right people, you will suffer happily. There it is. I like that. With the right people. I gave a talk at Web Summit, like a 10-minute thing.

I remember, it's all about culture, yeah. It's all about culture, right? And so that was one of my proudest moments in Cloudmark and a recipe that I've tried to repeat in an ongoing fashion. I want to ask you something about culture. Actually, I'm fascinated. I love talking about culture. I know, I know, I know.

So culture is easier, to some extent, when things are going well. Is that culture? That's my question. How do you define culture? That's a great question. How do you cultivate it? I've written a little bit about this, and I'm always revising my perspective anyway. I think a lot of people get caught up in the definition of what culture is and they get attached to a, oh, it's a list of phrases. Oh, it's a series of words. Oh, it's a this. It's a that. It's a whatnot. And then there's all these problems, like how you come up with those values and you put them up on a wall and you put them in the employee handbook and you put them in the employee onboarding materials. And then it's not actually true. What does that do? You're trying to do your best. You are the best intention. Sometimes it's because the words are aspirational. They're not real. They're aspirational is what we want to be.

but we aren't. So how do cultures perpetuate, I think is probably the first important question. Cultures, in a broad sense, outside of the workplace, perpetuate by people living them and talking about them and being them. I think that's the critical first equation in defining a really good culture is, who are we? Yes, we know who we want to be, but who are we today? Why is it? I love sitting next to you. We are completely different. You're from a different country. You speak a different language, you're a guy, I'm a girl, like, whatever. How are we so different, and yet we enjoy each other's company so much? And I reflected on that so much. Why did I enjoy fanning? Why did I enjoy Ollie? Why did I enjoy Jority? And then my next company, like, what did I love about these people?

And I came up with this three dimensions of thinking about it. And yes, I think there's a value in having words that describe a culture, because words can be used, they can be repeated, they can be assigned and attributed. One of my favorite words is adaptability. It's always a core value for me. And so I can praise it. I can evaluate and critique using that word. That was very adaptable. Great job. I think you're very fixed in your thinking. We would be served better if you were more adaptable and you're thinking about that. It perpetuates through its use and its application and it's living. So words I think is one good dimension of that. The second dimension of it, I always felt was a little cheeky, but was super useful, was I gave myself permission to rethink what

values they were without me having to describe the definition of a value through sentences or phrases. One of my favorites is clean hands make you wrong. They need to be dirty. You don't know what you're talking about unless you've gotten your hands dirty. My most favorite is sooner as better now is best. Do you want to know who I am? Listen to these sentences, these phrases. Do you want to know what I'm about? Do you want to be able to evaluate whether you fit with it or not? Listen to what I'm saying and just try it on. Was that a value? As sooner is better and now it's best of value? I don't know. I don't care. I'm telling you who we are as a culture and then you can judge for yourself whether or not this

feels like your fam. So there was that. And then the third thing, and this came from an insight I had when I went through a culture definition exercise at Cloudmark. When I had handed the CEO reins off to another person, he put us through a culture definition exercise, which I think was wise, but it was also too late because we'd already grown too large without such a thing. And we had already culturally fractured, and this executive was implicitly operating against this set of values, and this other executive was implicitly, and we had our own sense of it. And so we were trying to heal that rift, and we ended up with the lowest common denominator. It wasn't great. But what I gained out of this experience as a useful piece of advice was people sometimes try to insert

traits of people in his values, self-reliant. You can say, well, that's a value because I value it. Yeah, that is a way to be. I'm not going to tell you you're wrong if you make it a value. But I'm going to say it's most instructive to say, this is the type of person we're looking for. Organized, disciplined, you could put discipline as a value. I just don't think it's that useful. Anywhere where you can't praise or critique someone with the word without making them feel wrong, I think it's a bad value. It's a bad word. It needs to be constructive.

So the intersection of those three things, traits, these sort of aphorismic phrases, and these words all combined to me to help give you a sense of what a culture is. Now, you could come over the fourth, you could use two, you could do, it doesn't matter, matter, right? I think the point is, if you want to communicate what a culture is, find all the things you love about it, and then categorize them. I only arrive at it by serendipitously experiencing an amazing, tight-knit culture. It wasn't actually that serendipitous. I think it actually came from Wu. We had this one rule in Wu. We had two rules. We had basically two governing rules and only two rules. You know what sounds like Spike's Club? Sorry. Well, hold on your pants here for a second. Anyone could invite anybody, and anyone could remove anybody. And what netted out

was a group of people who trusted each other, who shared the same values, the same ethos, the same mindset, the same principles, sooner's better, now as best, that's an ethos, that's a principle. And, you know, I don't know, Fight Club is the right way to arrive at the right answer, but that group of people synthesized what became Napster. Fanning, absolutely the originator of it, right? But we all sort of jumped on to help him when he asked for help. And that's how I got involved. And so I've been trying to repeat that sort of thing as like, yes, come as you are.

Here's who we are. And I take this so seriously that when I do interviews and I teach this to people, we're all taught. Here's a job wreck, need, need, need, want, one, nice to have, nice to have. And then here's a person, complicated human being. Yes, no, yes, yes, no. 80%. Great, let's hire them. Oh wait, wait, wait, wait, here's an 87%. Let's hire them. What does that mean? And I've learned that

the culture fit is the most important success factor in anything that you do. You can have the right business, the right product, the right this, right that, the wrong people, and it's done. It's never going to happen. You could have the wrong business, the wrong product, the wrong go-to-market strategy, the right people, and you might actually figure it out. Culture is the root of it. That's why I take it so seriously. So when I teach people interviewing, I teach them how to interview for culture first, not last. That's interesting. Let's go there for a second if our listeners here want to pass an interview, but they also

want to find the right fit, right? If it's going to be the wrong culture fit, it's not going to be a good fit. But how should they navigate that, do you think? Well, I don't know if you're the interviewee that you have much control over the interaction beyond your personality coming out. But for what it's worth, this is how I think about it. I call it the narrative arc interview or the white space interview. If I have your resume, my goal is not to ask you a single question that's on the resume.

My goal is to ask you about the white space in between the things on your resume, those transitory points. I could look at your resume and go, wow, you went from the Air Force to this, to that, to that. And you got bought by a company, but then you left. And that's all super-impresent. And then I would miss the story where you were kicked out. It's in the white space. It's in that transition where we have to reflect on ourselves. We have to look left, look right, say what's going on around ourselves, and that's where

the truth of our souls comes out. And the goal of establishing a culture fit is to understand who you are at a core level. What are your values? What are your principles and mindsets? What are these things that are important to you? But I can't ask you because there's a power imbalance in this particular situation and there's confirmation bias. You're going to tell me what you think I want to hear.

But I still need the answers. So how do I get to the answers? without ever asking the questions. Narrative Arc interview. I start very much the way you started this podcast. I'll go a little earlier, and my famous starting question is, what did you want to be when you were a little kid?

And I swear to God, 99% of the time, I can draw a line from something they experienced their family, their father was this, or they were really exposed to this, and they were really, and now look at them. There's some connection between being five or eight and wanting to be something and who they are as a person in their 40s or 50s today, 99% of the time, right?

But I will follow them, and then I will specifically focus on the white space. And I love that because I think what we say is that success leaves clues, right? You see the clues, you see the seeds. Ooh, I like that. But you've got to ask questions that find them. You can't ask them, what made you successful? You'll get the Instagram answer. You'll get the LinkedIn post.

The performative, oh, well, here are the three things that led to my success and the five strategies I use and the two things to watch out for. And like, no, that's not the truth of a person. You're not going to ever understand culture fit because you're right. It is about fit. If there's a fit, you will suffer happily. If there is not a fit, you will suffer mightily. That is very true. It is better to be alone than to suffer with fools. That is a core tenet of mine. I would rather suffer alone happily than to suffer miserably with fools. And I'm not being overly negative in that statement. It's just to say, like, I'm not a fit is a not a fit. we're doing each other a favor if we arrive at the end of a conversation saying this feels like a fit

or being honest with ourselves and like you're great i'm great this was great but it's not a fit and i think before we started recording we talked a little bit about starting a business and how hard it actually is and i think you also had some beautiful stories about bill gates or whatever but can you share a story that just gives an example and i know nepser is one example but gives an example of what it actually takes to build something from scratch because it is a lot harder than it sounds, but just give us a little bit of the lay of the land and the roller coaster example.

I can give several stories. Again, I will frame it in the context of the now that a lot of the non-human struggle has been automated. If I could give a plug that I have absolutely no incentive to make, Atlas Stripe will set up your company, incorporated, file the 83B paperwork, file all the state it's amazing. You used to be, you had

to figure all that stuff out on your own and that you had to get a lawyer who knew how to navigate that stuff and you had to get a this and get an accountant who understood this and now it's kind of just all been automated for you. So one whole chunk of the hard part has been taken care of for you which I really love. You still have to know what you're doing though. And you still have to know

what you're building and how to get it into people's hands and build something meaningful and useful and valuable in the world. In terms of story, gosh, Cloudmark was probably the hardest start of anything because we were literally at the peak of the first.com bust. You didn't build companies in San Francisco back then. This is going to shock anyone who didn't live through this period of time because San Francisco is where you build companies now. But no one who built technology companies lived in San Francisco in the late 90s in the early odds. Nobody. They lived in San Jose. They lived in the peninsula. They lived in the

peninsula. They lived in the East Bay sometimes, Oakland, but nobody lived in San Francisco. Then the jobs, then the bust, and with the bust economic activity. So even though the people who lived in San Francisco didn't work at these companies, the economic, the revenue, the city, county, state revenue all went through the floor. And nobody had spending money. And so everything took a dump. And everybody left San Francisco. There's a really interesting time to be walking around that town. Even the dangerous parts weren't as dangerous, because there weren't as many people. It's just not many people.

South of the market used to be a terrible place to be. Another good friend of mine, Adrian Scott, used to live in a loft in the worst part of town, and you could walk there because no people, no crime. Anyway, I built this piece of software. So engineers are not famously known for being clever with naming. So I name this thing spilter, spam filter. Okay. And also being a little bit of a tongue-in-cheap type of person.

and our logo at the time was this dog with a very worried look on his face and a hand with a sick shooter to its head. Oh, God. And it said, stop the spander, we'll shoot this dog. I'm a dark humor person. Suffice to say, that logo didn't last long, but that was the ethos at the time. Stop the spammer, we'll shoot this dog. And I had written this open source software.

And at the time, I was married to a person who was a recruiter, tech recruiter, so she understood some stuff about tech. And she put her hand on my shoulder one summer afternoon and said, yes, so what is that? And I'm like, oh, it's this amazing thing. It's using machine learning. No one uses machine learning. It's super cool. It's going to be amazing.

Great. I'm going to give it away for free. Everybody's going to use it. And my ego is going to grow two inches bigger. She's like, uh-huh. So like, do you think people would use it? Yeah, that was the second question. She was like, you think people would pay for it?

And I'm like, yes. And then her grip on my shoulder tightened. I'll never forget the moment. And she's like, and she too is somewhat of a tongue-in-cheep person. She's like, you need to make some money, bitch. And I was like, and in every turn, I sort of resisted it. But then I went and spoke with another friend of mine, an ex-Green Beret, Dave, David, who was, you know, a VP of BizDev type of person. And I'm bouncing it off him.

And he's like, yeah, no, I think you can build a business out of this. And so I sat to building this business off of open source software that I then closed source. I met my co-founder who had built a very complimentary piece of technology that put together really made a difference. He was down in Los Angeles doing nothing. I think he just finished his last contract. When I went down to visit him, he was in an apartment that had no furniture. He had a bed mattress on the floor, maybe some Cheetos or some stuff at the head of it. And this is the way it was back then, right?

When you're off trying to build something and you ain't got any money, you just make it work. You're not couch surfing, you're floor surfing, you know. Brought him up with me back to stay with me in San Francisco and we built this company. The first offices, I deliberately went back to where we built Napster for West 4th Avenue, Union Bank of California building, which is no longer, it's been bought and renovated. It's a different bank now. But I built Cloudmark in the same offices we originated NASDAO. That's so symbolic. It was pretty cool. That's all symbolic. It was symbolic, right? And so we're in these offices.

But I was out there on the shoe leather express, beating the pavement, trying to find money. How do you not give up at that moment? There was something in me. that was worried that it wasn't going to work, specifically the technology. And because of that, nothing. None of it was going to work. If the technology didn't work.

But there was also an intuition that I thought, if I have the right people, we'll figure it out eventually. And man, what a gamble that was. Man, what a gamble it is, just to say, if I find the right people, we can solve any problem. He's become a mantra of mine now.

But back then, I'm 22, something like that, and everybody's lost tons of jobs, millions and millions and millions of dollars have been lost in companies that just evaporated overnight. And let's not forget what precipitated the dot-com bust was two airplanes flying into a building. So everybody pulled back, everybody went to ground. A lot of harm was felt everywhere. And here I am going like, yeah, I need to make some money. I think this is valuable. I think it could work, but I'm worried it might not. But if I find the right people, I think we can figure it out together. Like, I don't have to be responsible for all of the answers. And when I met Vipple, when I met the right co-founder, the right partner,

I really felt like, okay, I hate doing these things alone. To this day, I built Atlas Informatics as a sole founder, and it was an incredibly challenging experience because of that. I had great executives by the end of it that I could rely on and delegate to quite well, but boy, being the sole person responsible, like it was still me. By having Viple and a partner who was smart in an entirely different ways than I was. Very complimentary. I think we were able to do things that no one had really been capable of doing yet. And I would say the same of Napster. It was the same thing. I'll just about some quick technical things. Back then, we were using a version of Linux that everybody was using. I think it was Linux 2.0. Its TCP stack was written in such a way is that it could take

over 32,000 connections, but it could only ever service a thousand of them. So we had these piece a crap commodity PC hardware. We did it three years before Google popularized it, but we had these crappy PC hardware terribly racked by yours truly in our above-net knock, plugged into a link-sysk consumer-grade router because I couldn't get the dang Cisco thing to work. No one understood why it wasn't working. You could see these clients connecting, but it literally wasn't moving data between them. And it took me like a week, and I figured it out, and I've submitted a kernel patch for it, and we rebuilt all of our kernel for all our service, and it worked. So we did all these things that you may or may not heard of only because we were a great team,

capital G, capital T, and the root of it was culture. And so how did I feel about it in that circumstance, despite these great odds? There weren't many people to hire. I just stuck to my guns of trying to find my people and bring those people with talent together, and then we would figure it out together, and we did. Amazing. And what is it, six startup or whatever later? Yeah, with more than one billionaire.

Yeah. What would be one thing that you wish somebody told you earlier in your career based on everything that you see today? And obviously culture is one of them, but what else? I mean, that would be the one, the criticality of that. You better love it or else you're really going to hate it. Don't do it out of curiosity. Do it because you're building something you believe.

even because it's that belief and that commitment and that dedication that will carry you through it. If it's a good idea, if it has money-making potential, you may still fail at it. Because the amount of misery and suffering you're going to go through to get to that outcome is going to really challenge you in ways that can't be solved if you don't fundamentally want it. I absolutely agree. And I'll compliment what you say. I think I hear from 10 of time people that are saying, oh, it's so hard to find a job these days, I'll start a company. Please don't. Like, it is always going to be easier to find a job than to start a company. I agree with you, except with one exception. Culturally, I would love to fit in to a larger organization. And I still look forward to a day

where that might actually be true. But I don't. All the things I believe in, all the ways I think, all the ways I operate are ideal for building something from nothing. But for some reason, constantly tissue rejected by other companies, other non-startups, right? So yeah, I think one of the reasons I start companies is because there's the easiest hard thing to do. I know. I'm sorry, I just contradicted you on that. But like I said, I build the things I believe in. And so it works out. I'll close with this final thought for folks that are later in their career. I have done so many things and the story is not about me. The story is about me and other people

who helped me do it. And the thought process in my mind is I would build something and then I would reach out and try to find these other greats. These people who in my mind I placed above me. Maybe the inverse was true in their minds.

And they somehow some way came and worked with me and helped me raise this thing up. And I've only gotten to where I got to because of that. And I've been thinking like, maybe it's time for me to play the other role. to help someone else lift them up in pursuit of their journey. I've done a lot on my own, and I could continue to do more on my own.

But there's this notion of giving back and helping the next generation be a service to them and building something great and big. So that's where my head is at right now. Jordan, thank you for this beautiful conversation. My pleasure. It was great to be here. Remember this episode. It's not just for you and me. You never know whose life you are meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or download button for the show and give it a five-star review. This really means the world. Join me in helping tens of millions of individuals reinvent their career and leap into their full potential. Look, getting intentional and strategic with your career is now, more important than ever. The skills for success have changed. AQ, adaptability, reinventing, and leaping are today the most important skills for the future of work. Building portfolio careers,

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