The Untold Story of Napster's Success, Collapse & Hard-Won Lessons | Jordan Ritter | E138

Summary

Episode Overview

Episode Title: The Untold Story of Napster's Success, Collapse & Hard-Won Lessons
Podcast: Leap Academy with Ilana Golan
Guest: Jordan Ritter (Original Co-founder of Napster)
Date: December 16, 2025

In this episode, host Ilana Golan sits down with Jordan Ritter, one of the original minds behind Napster, to explore the gritty, high-stakes reality of building revolutionary startups. Together, they trace Ritter's journey from rural Texas to the heart of Silicon Valley, delve deep into the untold stories behind Napster's meteoric rise and fall, and extract invaluable lessons on culture, perseverance, and the challenges of entrepreneurship. The conversation busts myths about the ‘easy button’ in tech, reflects on culture as the root of company success, and offers practical wisdom for those seeking to "leap" in their careers.

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Key Discussion Points & Insights

1. Early Life: Seeds of Ingenuity and Hard Work

• Scarcity breeds ingenuity:

  • Growing up on a farm with limited resources taught Jordan to optimize, problem-solve, and embrace challenge.
  • [02:24] “The scarcity of resources… is actually what drove me to optimize, to really drive an engineering mindset…I wrote my own mouse driver.” – Jordan Ritter

• Musical roots and parental influence:

  • Musical talent and exposure to entrepreneurship from parents (who ran small businesses) laid an unexpected foundation for his future path.

• No label for entrepreneurship:

  • “No one was called an entrepreneur... They were small business people... I didn’t know until later that I was actually the son of two entrepreneurs.” – [04:25] Jordan Ritter

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2. Napster’s Origin: Chance, Community, and Timing

Surrounding oneself with like-minded, driven people is critical.

• [09:46] Ritter details being pulled into the Boston hacker and computer security underground, where networking and serendipitous meetings drove innovation.

• Napster emerged from hacker culture:

  • "Napster came out of the computer security underground…We were all piling in to help Fanning." – [12:35] Jordan Ritter
  • The group "Woowoo" proved to be a breeding ground for several future tech billionaires.

• Right people, right place, right time:

  • "Who you surround yourself with will dictate a lot of where you’re going." – [11:42] Ilana Golan
  • Importance of proximity to smart, ambitious people.

• Observing the rise of broadband and MP3s:

  • "The growth of broadband… universities were turning on their dorms with broadband... The MP3 became really, really popular and that was the unlock." – [20:53] Jordan Ritter

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3. Napster’s Meteoric Rise — and the Reality Behind It

• Explosive growth through confluence of technology and unmet demand

  • Factors: Broadband internet in universities, soaring prices for CDs, the advent of MP3 files, and user frustration over music access.

• Napster was not built to disrupt, but disruption followed:

  • “I don’t really believe that when Napster was first written, that it was written with the intention to disrupt the music industry. …It was a way for us to share stuff with each other.” – [23:36] Jordan Ritter

• Myth of the ‘easy button’ for startups:

  • “There is, in a sense, an easy button. It’s called going to work for Google or Microsoft. That has kind of screwed up so many aspects of building companies.” – [27:43] Jordan Ritter

• Startup life: Highs, lows, and suffering:

  • “If you want to be an entrepreneur… There is so much misery. I actually talk everybody I possibly can out of it. ...with the wrong people, you will suffer mightily. But with the right people, you will suffer happily.” – [29:08 & 50:18] Jordan Ritter

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4. Napster’s Downfall: Lawsuits, Leadership Issues, and Leaving

• Legal and internal challenges intensified with success

  • The company faced lawsuits, including from Metallica/Lars Ulrich, and executives who did not value engineers.
  • “The juxtaposition of staying up all night… and then waking up the next morning to a mass press conference out front where Lars Ulrich was going to hand deliver printed names…” – [30:52] Jordan Ritter

• Culture and appreciation matter:

  • Engineers were not valued, and despite their critical role, the company failed to retain loyalty with its best talent.

• A personal breaking point:

  • “I was having this fight for not just myself, but everybody on my team to get paid more... Meanwhile, if two of us got hit by a truck, this company’s over.” – [37:09] Jordan Ritter
  • Ritter leaves after realizing executives are not transparent or supportive, leading to an acute identity crisis.

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5. Reinvention and Lessons Learned

• Recharging between startups:

  • “Between every company I start, I go and work at someone else’s company…without ever intending. That has become a pattern where I get to recharge.” – [43:52] Jordan Ritter

• Building for oneself, but not just for oneself:

  • “If I could build something that I would use every day… good things were going to come of it.” – [46:03] Jordan Ritter

• Adaptability trumps having a perfect plan:

  • “A plan is just a list of stuff that’s not gonna happen. The skill is adaptability and perseverance.” – [46:49] Jordan Ritter
  • Cites Mike Tyson: “Everyone has a plan until they get punched in the face.”

• Culture > Everything:

  • “What made [Napster] successful was culture. The people that built the technology all belonged together… At the core, we shared the same values.” – [47:56] Jordan Ritter
  • “Picking the wrong people is the number 1 reason for any of my failures… With the wrong people, you will suffer mightily. But with the right people, you will suffer happily.” – [50:13 & 50:18] Jordan Ritter

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6. Defining and Interviewing for Culture

• Three dimensions of culture:

  • Words (core values), aphorisms (“sooner is better, now is best”), and traits/behaviors.
  • “Anywhere where you can’t praise or critique someone with the word without making them feel wrong, I think is a bad value… it needs to be constructive.” – [54:51] Jordan Ritter

• The right fit is everything:

  • “If there’s a fit, you will suffer happily. If there’s not a fit, you will suffer mightily… It is better to be alone than suffer with fools.” – [59:29] Jordan Ritter

• Interviewing for culture:

  • Focus on the “white space” between resume lines—the stories of transition and adversity.
  • “My goal is to ask you about the white space... those transitory points. That’s where the truth of our souls comes out.” – [57:10] Jordan Ritter

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7. Hard Truths About Starting Companies

• Startups are NOT the fallback for failure elsewhere:

  • “It is always going to be easier to find a job than to start a company.” – [68:51] Ilana Golan

• Don’t do it out of curiosity. Do it because you believe:

  • “Don’t do it out of curiosity. Do it because you’re building something you believe in. Because it’s that belief…that will carry you through.” – [68:16] Jordan Ritter

• And sometimes, it’s time to help others leap:

  • “Maybe it’s time for me to play the other role, to help someone else lift them up in pursuit of their journey... there's this notion of giving back and helping the next generation.” – [70:22] Jordan Ritter

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Notable Quotes & Moments

• The misery of entrepreneurship:

  • "If you want to be an entrepreneur... there is so much misery. I actually talk everybody I possibly can out of it." [00:00] – Jordan Ritter

• Ingenuity and adversity:

  • “Ingenuity doesn’t blossom without challenge. Real challenge, not fake challenge... That’s where a lot of ingenuity comes from that we sometimes label as innovation, but it isn’t.” [26:06] – Jordan Ritter

• On leaving Napster:

  • “I gave my heart and soul to this thing… and that was who I was. I had a real identity crisis for a significant period of time.” [43:09] – Jordan Ritter

• On culture:

  • “With the wrong people you will suffer mightily. But with the right people you will suffer happily.” [50:18] – Jordan Ritter

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Timestamps for Key Segments

• Early influences and coding on the farm: [02:24–06:40]
• Meeting Sean Fanning and Parker; hacker culture: [06:40–13:56]
• Napster’s founding and first investment: [13:52–16:23]
• Startup life, suffering, and scarcity: [24:48–29:08]
• Legal troubles; the highs and lows: [30:50–33:52]
• Culture as the secret ingredient: [47:56–50:38]
• Culture fit, interviewing, lessons for job seekers: [56:53–59:29]
• What to know before building a company: [68:01–69:10]
• Reflecting on giving back and next steps: [70:22–70:44]

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Final Takeaways

• Entrepreneurship is not easy or glamorous. It requires passion, resilience, and the right team.
• Culture is foundational; it determines success more than product or market.
• Adversity fosters ingenuity and grit.
• Build for yourself, but ensure what you build solves a real need.
• Success is rarely solitary—find your people and you’ll “suffer happily.”
• When contemplating a leap, understand your motivations and the realities of startup life—and know it’s always okay to help others leap too.

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This episode is a masterclass in authentic startup storytelling and honest, hard-won wisdom. Anyone contemplating their next leap—into a new career, a new company, or a new personal challenge—will find clarity and inspiration here.

Transcript

[Jordan Ritter]

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.

[Leap Academy Host]

Jordan Ritter was one of the original minds and co founder of Napster, which revolutionized the way we think about music.

[Jordan Ritter]

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 gonna suffer anyway. With the wrong people, you will suffer mightily. But with the right people, you will suffer happily.

[Leap Academy Host]

What it actually takes to build something from scratch because it is a lot harder than it sounds.

[Jordan Ritter]

One of the reasons I start companies is because it's the easiest hard thing to do.

[Leap Academy Host]

What would be one thing that you wish somebody told you earlier in your career?

[Jordan Ritter]

Don't do it out of curiosity. Do it because.

[Leap Academy Host]

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 were 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 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 multiplex. It has endless insights and I can't wait to just dive in. Jordan, thank you for being on the show.

[Jordan Ritter]

Great to be here.

[Leap Academy Host]

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 the way from where you were a teen.

[Jordan Ritter]

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, 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 spaced to 40. The interesting thing about this experience and having originally a 2400 baud modem, then a 14 4, 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 CDoc serial interface layer driver, which is how BBSS used to talk to com ports back in the old days.

[Leap Academy Host]

But wait, you're on a farm. How do you even know about these things?

[Jordan Ritter]

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 school. So 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 Malakoff. I learned flute, which is probably the worst instrument to learn, except I was sitting in band surrounded by all these cute girls. And so I thought I was very, very smart and probably was actually very, very smart. 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 whatevers. And I legit thought that I was going to go to college and become a musician. So I started looking. But I was also an IB and I took AP and IB Comp Sci. And it was just mind numbingly 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 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 race. I had all the C 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 BBS's 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 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 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.

[Leap Academy Host]

How do you then eventually meet the Sean's? Sean Fannings and Sean Parker.

[Jordan Ritter]

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 I 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 enjoyed it and. 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 netact, like Detect, but with an N. 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 2600, the old hacker magazine. But 2621 was 2600 for 21 and over. 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 won would get dinner for free. And this had the loft and it had New Hack City and had CDC and 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 Woowoo, 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. Woowoo 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 Koum 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 Comp Sci 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 with what he had. But his software was written by a 16 year old.

[Leap Academy Host]

What year is that roughly? Jordan?

[Jordan Ritter]

This was 98. 98 was when he and I first met. The web was taking 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 biz. 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, which I thought was fun. Just because once you're a large commercial, public company, you don't want to rock the boat on anything like that.

[Leap Academy Host]

So that was the end of that one.

[Jordan Ritter]

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. Lindo 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 he 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. They're all mixing ideas around the latest and greatest AI space.

[Leap Academy Host]

It 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.

[Jordan Ritter]

So we were talking about chance, right? And being lucky. I think though, Chance favor is 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 chances are 90% of the people there are just pedestrians just kind of gazing and looking at things. But there's 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 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 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 Woowoo 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 code. So I'm like, all right, if I send it this, it crashes. And if I do it, this is 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 just take it over and let me focus on the client and you do the server? And I'm like, sure, 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 vc, pretty much all of them were tempestuous characters in one form or another.

[Leap Academy Host]

Are you still working at the time or did you already leave?

[Jordan Ritter]

So, interesting. September, I think maybe it was late August. Fanning came over. I'd 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 in super late. I guess it was 11, 11:30 or whatever. What I didn't know was that he brought another really good friend of ours, Larry, whose online handle was Lime Fest. We call him Larry Lime Fest. And Larry was the guy that did the website, needed a bunch of other stuff, done 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 F this up. You got to come in and stay down there while I go up and talk to Jordan or 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. You know, he's like, this is going to turn into thing. And I didn't know. I really didn't know. 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 he said something to me, the effect of 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 Gixxer 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 la. I just ended up not in la. 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 and 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?

[Leap Academy Host]

I mean you kind of couch surf your way into it.

[Jordan Ritter]

And it wasn't like I live in a 10 story loft with all these little toys and gadgets and stuff, but I choose to go couch surf. No, we were broke. We were broke. And back in those days you made 60k a year. That was the starting salary. Like, 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 Gantt chart. They 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 of 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 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 there was Parker and Fanning and John Bodanza was to me like the quintessential client team. And then there was me, Ali Aydar 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. Fanny 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?

[Leap Academy Host]

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, who may be inspired by this. Because this information can truly change your life and theirs. Now I want to check in with you. Yes, you. Are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be, do you secretly feel you should have been further along in your income, influence or impact? Do you ever wonder how to create not just a paycheck. But the life you want with the paycheck, the thought leadership, the legacy, the freedom. Because that was me. And that's exactly why I created the Leap Academy program which already changed thousands of careers and lives. 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, multiple streams of income and ventures are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com training. Check out this completely free training about ways to fast track your career and you'll even be able to book a completely free strategy call with my team. That's leapacademy.com training. You know you want to start a business. What you may not know is how to make it a reality. GoDaddy Aero got you. It uses AI to help you find the domain name that is right for you. Next answer. Just a few prompts and with a couple of clicks Aero will design a professional looking website or storefront in minutes. Aero can even help you stay engaged with your customers. Just just attach a professional email that matches your domain. With GoDaddy Aero you can build a business without having to know a thing about this stuff. So just visit GoDaddy.com to get started. That's GoDaddy.com premium feature required. Pay subscription See terms on site and sure enough in 1999 this is taking off like crazy and I think my shared with you before we started recording I'm like NAFTR is a story I have to tell because this is such a pivotal moment. I was in intel at the time and we were hearing about these crazy growth things and we were like what is going on? So talk to me about it. Why did it take off like this? What happened?

[Jordan Ritter]

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 and I want to go.

[Leap Academy Host]

There in a second for sure.

[Jordan Ritter]

Yeah, if it's possible. It is what it is. It's long ago 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 fricking CD and I was tired of spending all that money. So actually I would say there's three things. There was the broadband Internet in universities growing residentially. There was this ever increasing cost of CDs so they were $10 and they were 15, and they were 1999, 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. Every 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 like pissed off. 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 then that person would literally just hand it to somebody else and that person would 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 nauseam. Many, many things. There's no point in talking about it here. But suffice to say those were the three things that really 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.

[Leap Academy Host]

So basically if I want to share a song with you, I can easily share it, which is something that didn't exist before.

[Jordan Ritter]

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.

[Leap Academy Host]

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.

[Jordan Ritter]

Well, we were having fun, right? And so what is that saying, Love what you do and you don't have a work a day in your life. There's this whole thing about nine, nine, six now. Nine to nine, six days a week. Yeah.

[Leap Academy Host]

Four hour work week. I never worked the four hour work week. I work.

[Jordan Ritter]

I'm sorry, Tim. Tim Ferriss. I'm sorry. That shit's not real. Apologize.

[Leap Academy Host]

I worked so hard. How is that happening?

[Jordan Ritter]

Okay, he does not work four hours a week. I tell you that much. Anyway, 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 desks, 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 286.12 problem versus having your 486 DX4100. 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 from someone's place because that's cool.

[Leap Academy Host]

Oh, you get a lot more creative when your back is against the wall.

[Jordan Ritter]

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 Ogna AI. He was our head of design and I found out his story. He's an Israeli. He came over with literally nothing in New York, was sleeping on benches and in parks and 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. And 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 and 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 is 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.

[Leap Academy Host]

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.

[Jordan Ritter]

Especially in this age of AI.

[Leap Academy Host]

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.

[Jordan Ritter]

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 Silicon Valley.

[Leap Academy Host]

That was my first salary.

[Jordan Ritter]

That's when I was 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. Yeah, like that's what people used to make back then, right? Wow, how things have changed. There is, in a sense, an 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 something on your own or you want to be 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.

[Leap Academy Host]

Are low, but the lows are really low.

[Jordan Ritter]

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. 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, 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.

[Leap Academy Host]

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.

[Jordan Ritter]

That frame now includes so many other experiences.

[Leap Academy Host]

I know I'm generalizing here, sorry.

[Jordan Ritter]

From a Napster standpoint, the juxtaposition of staying up all night to until 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 Napster 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 then and seeing a pizza get delivered, watching it get open and there being an eight ball of Coke in the center 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 Ulrich 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. 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 it's 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 fricking awesome and. 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. 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, a suburb. All of this stuff was crazy.

[Leap Academy Host]

Can you sleep at night at that point?

[Jordan Ritter]

Look, when you work, not nine to.

[Leap Academy Host]

Nine, but like you sleep because you are tired.

[Jordan Ritter]

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 had brought my Gixxer out and if servers crashed, I had to hop on that motorcycle and book it down 280 at 130 to get there as quickly as to go reboot the router or the switch because it failed or whatnot. There's 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 pass 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.

[Leap Academy Host]

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. It's February 26 to 28 and is the number one conference for reinvention, leadership and careers in the United States. It has speakers like the former president of Starbucks and many other leaders, including yours truly, myself and and I'd love to personally welcome you, give you a hug and hear what you think about the podcast. We'll have many networking opportunities, photo opportunities, and we already know every single person after this event will go supersonic on their reputation and career. So grab your tickets quickly because this event always sells out. So go to leapacademy.com leapcon or you can search on Google Leapcon2026. It's L E A P C O N. Don't miss out where the most impactful leaders hang out in February. So go to leapacademy.com leapcon I will see you there. Hey, are you running a business online or creating an impressive portfolio career? Look, you're going to have to build trust with your customers and with your network. And you can only do that by using a professional looking domain and a professional email. By far the easiest way to get your domain is with GoDaddy and there's never been a better time. Visit GoDaddy.comGdnow and you can get a domain and professional email plan for just 99 cents a month for a year. That's such a tiny investment for a lot of credibility. So choose a domain that's right for you and for your brand and align a professional email to match. Go to GoDaddy.com GDnow and seriously look legit. That's GoDaddy.com GDnow new customer purchases only products Auto renew separately See terms on site. Did you know that you're changing an industry at that point?

[Jordan Ritter]

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.

[Leap Academy Host]

It was true.

[Jordan Ritter]

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 Spotifys while the Napsters bleed to death on the ground. Lo and behold, that's what happened.

[Leap Academy Host]

Kind of that happened.

[Jordan Ritter]

Yeah, it's what happens. It's what happens.

[Leap Academy Host]

And you leave. Right?

[Jordan Ritter]

I was the first one to leave.

[Leap Academy Host]

Talk to me about that moment because that was your everyday, right? Is there like a fear? There's like, oh my God, who am I without this?

[Jordan Ritter]

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 Napster 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 its infinite incompetence. It thought that if they sent you something that you would receive it. That was the expectation. In other words, if someone sent you a takedown notice or this or that or a legal thing, but they misaddressed was still expected you would get it. Now we know in today's day and age, get the email address 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 Villalobos took over. Who's fricking 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 backend, 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 Bertelsmann. Now, no one really knew the details of it, but John Fanning misaddresses something to counsel at 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'd given this guy, Milt Olin, $150,000 salary. We're going to pay for all of his flights from LA 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 can be said about Milt, but my experiences with 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 where we're 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 Engineering who's trying to assert his value over ours. And like, it is what it is, it all happens. 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 Bertelsmann 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 is going to take us down a really terrible path and we're going to get ultimately shut down and this is going to a miserable nightmare experience. And even then, I'd still do it if I felt valued, 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. 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. 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 gotta 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 gonna be when I leave this place? Cause 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 in 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 to 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 help them turn it around. And they really leaned in heavily on my background and used it as a sort of like a, hey, listen to us. We have value, we have worth, because we have this guy. And. 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 it 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.

[Leap Academy Host]

The reason why I'm going there for a second, 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.

[Jordan Ritter]

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.

[Leap Academy Host]

And the only thing I will say is that you'll need to reinvent yourself and Leap again.

[Jordan Ritter]

That's exactly right.

[Leap Academy Host]

That's the only thing.

[Jordan Ritter]

No, no, it's a great pitch for Leap Academy because, like, 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 and start at Napster, I participated in that because that was something that was of 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 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 of value to someone else. And if it was of 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 gonna 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 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, 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.

[Leap Academy Host]

Is that when Bill Gates was on your board or is that a different company?

[Jordan Ritter]

No, that's a different company.

[Leap Academy Host]

Oh, I want to hear that one too. Okay.

[Jordan Ritter]

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, VIPA Wade Prakash, who is incredible. I can't say enough great stuff about this guy. He is, in 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, I found it with him and I'm proud of it because I took one of my key insights out of Napster 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. The negative and the positive both. We were very culturally compatible. And so when I set 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 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 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.

[Leap Academy Host]

I like that.

[Jordan Ritter]

With the right people. I gave a talk at Web Summit, like as a 10 minute thing.

[Leap Academy Host]

I remember 350 people.

[Jordan Ritter]

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.

[Leap Academy Host]

I want to ask you something about culture. Actually, I'm fascinated.

[Jordan Ritter]

I love talking about culture.

[Leap Academy Host]

I know, I know, I know. So culture is easier to some extent when things are going well.

[Jordan Ritter]

Is that culture?

[Leap Academy Host]

That's my question.

[Jordan Ritter]

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 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. It's 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, 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 Ali? Why did I enjoy Jordi? And then My next coming, 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. Or I think you're very fixed in your thinking. We would be served better if you were more adaptable in your thinking about that. It perpetuates through its use and its application and its living. So words, I think, is one good dimension of that. The second dimension of it I always thought was a little cheeky but was super useful, was I gave myself permission to rethink what values there 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 is better, now is best. 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? Sooner is better, now it's best to value it. 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. 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 as 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 is 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 combine to me to help give you a sense of what a culture is. Now you could come up with a fourth. You could use two. You could do it doesn't 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 arrived at it by serendipitously experiencing an amazing tight knit culture. It wasn't actually that serendipitous. I think it actually came from Woowoo. We had this one rule in Woowoo. We had two rules. We had basically two governing rules and only two rules.

[Leap Academy Host]

It almost sounds like Spikes Club. Sorry.

[Jordan Ritter]

Well, hold onto 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 is better, now is best. That's an ethos, it's a principle. And 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 is 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, want, nice to have, nice to have. And then here's a person. Complicated human beings. Yes, no, yes, yes, no, 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 could 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.

[Leap Academy Host]

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 at the wrong culture, that's what it's about. It's not going to be a good fit. But how should they navigate that? You think, well, I don't know if.

[Jordan Ritter]

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 impressive. 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 the, 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. And they really 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.

[Leap Academy Host]

And I love that because I think what we say is that success leaves clues. Right? You see the clues, you see the seeds.

[Jordan Ritter]

Ooh, I like that. But you 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 used. 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.

[Leap Academy Host]

That is very true.

[Jordan Ritter]

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, not a fit is 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.

[Leap Academy Host]

And I think before we start 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 Napster 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.

[Jordan Ritter]

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. It used to be you had to figure all that stuff out on your own and that would. You had to get a lawyer who knew how to navigate that stuff. And you had to get a this and an accountant who understood this and that. 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 peak of the first dot 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 and the early aughts. Nobody. They lived in San Jose, they lived in the Peninsula, they lived in 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. It was 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.

[Leap Academy Host]

There weren't many people.

[Jordan Ritter]

It's just not many people. South America 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 named this thing Spilter Spam Filter. Okay. And also being a little bit of a tongue in cheek type of person, our logo at the time was this dog with a very worried look on his face and a hand with a six shooter to its head.

[Leap Academy Host]

Oh, God.

[Jordan Ritter]

And it said, stop this band or we'll shoot this dog. I'm a dark humor person. Suffice it to say that logo didn't last long. But that was the ethos at the time. Stop the spammer and shoot this dog. And I'd 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, yeah, 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 2 inches bigger. She's like, 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? I'm like, yes. And then her grip on my shoulder tightened. I'll never forget the moment. She's like. And she too is somewhat of a tongue in cheek 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 a VP of Biz dev 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 set to building this business off of open source software that I then closed sourced. 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 I said 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. 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. 4 West 4th Avenue, Union Bank, 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 Napster out of.

[Leap Academy Host]

That's so symbolic. That's so symbolic.

[Jordan Ritter]

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.

[Leap Academy Host]

How do you not give up?

[Jordan Ritter]

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. It'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 and companies have 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 Vibpel, 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 vipple and a partner who was smart in 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 spot 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 IP stack was written in such a way as that it could take over 32,000 connections, but it could only ever service 1,000 of them. So we had these piece of crap commodity PC hardware. We did it three years before Google popularized it. But we had this crappy PC hardware terribly wracked by yours truly in our above net noc plugged into a linksystem 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 submitted a kernel patch for it and we rebuilt all of our kernel for all our servers 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.

[Leap Academy Host]

Amazing. And what is it, six startup or whatever later?

[Jordan Ritter]

Yeah. With more than one billionaire. Yeah.

[Leap Academy Host]

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?

[Jordan Ritter]

I mean that would be the one, the criticality of that. You better love it or else you're really gonna hate it. Don't do it out of curiosity. Do it because you're building something you believe in. Cause 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.

[Leap Academy Host]

I absolutely agree and I'll compliment what you say. I think I hear from time to time people that are saying, oh, it's so hard to find a job these days. I'll start a company. Please don't. It is always going to be easier to find a job than to start a company.

[Jordan Ritter]

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 it'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 I 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 of service to them and building something great and big. So that's where my head is at right now.

[Leap Academy Host]

Jordan, thank you for this beautiful conversation.

[Jordan Ritter]

My pleasure. It was great to be here.

[Leap Academy Host]

Remember, this episode is 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, multiple streams of income and ventures are no longer a nice to have you. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com training check out our completely free training about ways to fast track your career. You'll even be able to book a completely free career strategy call with my team. So go to leapacademy.com training.