How I Built This with Guy Raz - Craigslist: Craig Newmark — The Forrest Gump of the Internet

Episode Date: September 29, 2025

What if the founder of one of the internet’s most enduring brands… never wanted to run a company?In 1995, Craig Newmark was a 42-year-old computer programmer in San Francisco who simply wanted to share local tech meetups with friends. He started an email list that became Craigslist—a website that reshaped how we find jobs, apartments, and community.In this conversation, Craig opens up about how not having a grand vision (or a taste for power) led to one of the most popular platforms in the world. With fewer than 50 employees, Craigslist still generates hundreds of millions in revenue—while looking like a website frozen in 1996.This is the story of an “accidental entrepreneur” who built a global brand by being in the right place at the right time—and why he now calls himself the Forrest Gump of the Internet.In this episode, you’ll learn:Why keeping things simple is often the smartest design choice.How knowing your weaknesses can be the ultimate superpower.Why community beats marketing every time.How to monetize minimally—and still build a wildly profitable company.Why luck and timing matter more than you might think.Timestamps:07:10 Craig’s childhood struggles with social situations—and how local Holocaust survivors shaped his worldview16:15 Discovering the early internet and becoming an “evangelist” at Charles Schwab20:07 The simple email list that broke at 240 addresses—and became “Craig’s List”29:16 Why Craig refused banner ads and said no to early monetization35:00 Handing the CEO role to Jim Buckmaster—and how that decision led to Craigslist’s success49:44 eBay buys a stake in Craigslist, then launches a competitor—sparking a messy legal battle53:46 Was Craigslist really responsible for killing newspaper classifieds? Craig reveals his opinion58:08 Why Craig gave hundreds of millions of dollars to support journalism, veterans, and… pigeons1:03:10 Craig on money, meaning, and why billionaires are often miserableFollow How I Built This:Instagram → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.com This episode was produced by Chris Maccini with music composed by Ramtin Arablouei.It was edited by Kevin Leahy with research by Sam Paulson. Our engineers were Patrick Murray, Maggie Luthar and Robert Rodriguez.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Your place, with all of its personal touches and its amazing location, could make someone else's vacation even better. Your home might be worth more than you think. find out how much at Airbnb.ca.ca. I figured I'd start a very simple mailing list, where maybe I would tell 10 to 12 people about stuff going on. And it kept spreading word of mouth. More stuff started appearing there. I said, hey, apartments are getting harder to find,

so people can send me that. Other people wanted me to put job postings on there, so I did that. in the middle of 95, at about 240 addresses, the CC list broke. Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz, and on the show today, how Craig Newmark's email list turned into one of the most popular online classified ad sites in the world. Craigslist. Okay, imagine pitching investors on a startup.

You tell them that it's an internet marketplace, but you're not going to worry about design. The site won't look all that good. Oh, and you won't spend a dime on marketing or sales. And the founder, he doesn't even want to run the company. He just wants to do customer service. Sounds like a pretty disastrous pitch, right? You would be laughed out of the room.

And yet every single one of the... things is true about Craigslist and its accidental founder, Craig Newmark. By the way, that pitch scenario, it never happened because Craig didn't want investors in the first place. He'd ever set out to build a business. He even admits that he was in the right place at the right time. The place was San Francisco and the time was 1995. And the internet was just beginning to take off. Craig was a somewhat awkward 42-year-old computer programmer. He struggled to fit in most places, but in San Francisco, in the mid-90s, he found his people, the kinds of people who were gathering at informal tech meetups around the city.

And at those meetups, you didn't have to be a good dresser or popular or funny. You just had to have ideas to share. And Craig saw a need. maybe other people would want to know about these meetups as well. So he solved this challenge in the simplest way possible by creating an email list. But that list grew so fast that Craig decided to build a website. And he called it craigslist.org. And soon, people wanted to post jobs and apartments and cars for sale as well.

The design was about as basic and straightforward as it gets, and it still looks pretty much the same today, nearly 30 years later. But here's what makes the story even more unusual. Craig knew from the beginning that he wasn't a CEO type. So just a year after incorporating, he stepped back. He handed control to a guy named Jim Buckmaster, and that turned out to be a brilliant decision.

By 2006, Craigslist had spread to 190 cities in 35 countries. 10 million people were visiting every month, all with fewer than 50 employees. Even today, with competition from Facebook Marketplace and others, Craigslist still brings in hundreds of millions of dollars a year. In 2024 alone, analysts estimated around $300 million in revenue. Now, over the years, Craigslist has faced plenty of criticism. Some blame it for the decline of classified ads and newspapers, and we'll talk about that in the interview. But Craig himself, he says he never meant to get rich, though of course he did. And now he's committed to giving almost all of it away. Craig Newmark grew up in Morristown, New Jersey.

His mom was an accountant and his dad, who was a salesman, died when Craig was just 13. Academically, Craig thrived, but socially, he struggled. And in the years that followed his dad's death, Craig noticed something about himself. A pattern he's still relevant. He's still wrestles with today. As a kid in grammar school, I remember having friends, but something happened as I became an early teenager because I was academically bright, and I would be the kid eager to show off in class,

and I lacked the ability to perceive social cues, so I didn't know what a nerd I was being, and by the time I hit high school, I was pretty well isolated. I had a few friends, also nerdish, and we had science and engineering and sometimes high school debate in common. I wore thick black glasses taped together, seriously.

I wore a plastic pocket protector, and I had no idea how off-putting that kind of stuff was to everyone around me. You know, Craig, anyone over the age of, let's say, 50 or 45 remembers when they were children, there were always kids, maybe us too, who were different or awkward or weird. And today, it's different, right? I mean, kids get all kinds of support. But when you were a kid in the 50s and 60s, there was no, nobody was saying, oh, he has a social anxiety disorder or he has, he has challenged. with social skills, right? Nobody saw it that way, right? It's hard to say how people perceive things. I wasn't a good public school system in Maristown. They did send me to the school psychiatrist. They decided that I might be salvageable, and so they got me some help. And I guess I turned out to be salvageable, but I have very

little understanding how that happened. I mean, clearly, you, you know, you have enough sort of self-awareness to know that this is something that was a challenge. I'm curious at a certain point, because I'm sure you've been to therapists and psychologists and maybe even psychiatrists, were you ever diagnosed on the spectrum or did anybody ever talk to you about that at all? The only formal intervention I had was, well, it was during sixth grade when they did send me for regular sessions. nothing beyond that. And I assumed that I was on the spectrum towards Asperger's for some years until I chatted with a neighbor who turned out to be a specialist. She told me, not on the spectrum.

I was just poorly socialized and needed to work on that. And now, as needed, I can fake social skills for as much as 90 minutes at a time. Wow. All right. Well, that's, I mean, it's really, this is fascinating because I think the fact that you recognize this and you knew it and you wanted to change it is really interesting, right? I mean, it was, it sounds like you, as far as you can remember, this is a frustration of yours, that you couldn't, I don't know, be one of the guys or blend in. It was a problem for me. It continues to be a problem for me. I've made peace with my issues. and try to channel them into constructive stuff. I was one of those kids, though, that loved being in a library. And to their credit, Maristam, New Jersey has a great old library. I hung out in young adults finding whatever science fiction I could find.

So you really found solace in books in science fiction. Like, that's where you kind of escaped to. I did escape into it on the upside, though, reading science fiction by technologists, engineers, and so on. That's how we learn to invent the future. Sometimes it's delusional. Sometimes it's real. It's all a real mixed bag. So when you were growing up in Morris 10, New Jersey, this is the 50s as a kid or 60s as a teen,

there were a lot, from what I've read about you, there were a lot of Holocaust survivors who lived in your area, some of whom taught at your Sunday school, your synagogue. Is that right? There were a number of them that made it visible. The mother of one of my classmates had her serial number quite visible. Her tattoo. A tattoo.

Yeah. And she did explain what that was about without getting. gruesome about it. So I was very aware of the situation. Only a few years ago did the folks at the Ford, a prominent Jewish newspaper, they actually dug into the past of my principal Sunday school teachers, Mr. and Mrs. Levin, and they found that Mr. Levin was a survivor, the relatively easy way, He left out of a speeding train on his way to a death camp, injured himself, but he wound up rescuing his wife and daughter. And maybe this is why he had such a big influence on me. But he never talked about that.

I'm pretty sure he never talked about it. He had a injured finger, bent at a bad angle, never explained it. He just encouraged me to be a really good. student. But he and Mrs. Levin taught me the big stuff that I should treat people like I want to be treated. I should know when enough is enough. And I should really take the Ninth Commandment about not lying, about bearing true witness. I should take all that seriously. And that determined my moral compass to this day. All right.

So after high school, you went to Case Western Reserve University in Cleveland, and you studied computer science. And this is in the early 70s because you graduate in, I think, 1975, I think. So computer science, very different than what it is now. I read that you wanted to study, and that was blown away by this, large language models in the early 70s. I didn't even know, when you think of LLMs today and AI, right? think of generative AI. I didn't even know that that was something you could study in the early 70s. They didn't use the term large language models. I was influenced by the people looking at neural networks, which are the basis of large language models. The deal is I got real interested in that.

I got interested in the idea of natural language processing, thinking that was a core to understanding consciousness. Because I had been very influenced. by a lot of science fiction. But the idea is that I was studying this in 73. I remember back then taking an AI course writing a theorem prover in a language called Lisp. I don't recall what a theorem prover is anymore. And all I remember about LISP is that it stands for lots of irritating stupid parentheses, which is what you see when you look at LISP code.

Okay. You graduate from Case Western and like a good computer science graduate and responsible young man in the mid-70s, you go and work for one of the biggest companies in the world, IBM. And I think initially you're in Boca Raton for some time,

you're in Detroit for part of the time. What were you doing for IBM? Well, in IBM Boca Raton, which was not very fancy at that point, I went to work

on a forgotten mini computer called the Series 1. I did some good work there, did some good software development, but the, you know, it was never taken

really seriously by the whole industry. The only thing I did, which I thought was really good, was I was a member of a team building a series one as a card that would fit inside of a PC. My big mistake was not getting more and more involved with the PC back then, but I got a good education. I made the right mistakes, and it's worked for me.

Yeah, and you somehow end up moving to San Francisco in the early 90s. Tell me, Was it, I'm assuming it was for a job? Well, 17 years at IBM, a Boca Raton, Detroit, a year in Pittsburgh. But I got tired at the East Coast, so I wanted a change. I checked out Seattle and San Francisco, interviewed with a number of companies like Charles Schwab. And the folks at Charles Schwab made me a good offer. They moved me out to San Francisco. I did some good work there, but my best work was volunteer.

I was one of a few people evangelizing the Internet at Charles Schwab in 94. I was one of three people saying, this is how we're going to do business. All right. You get to Charles Schwab, and this also coincides with the beginning of what we now know as the Internet, because the World Wide Web, basically, mosaic browsers, Netscape browsers are kind of floating around. and people start to use it. You're in San Francisco, which is going to become, you know, the most important tech city in the world. And you're at Charles Schwab where it's still probably a lot of paper memos and file cabinets and, you know, manila envelopes. And you're seeing this internet thing and you're getting excited about it. Tell me what was exciting about it to you. Well, the internet realized a vision that I had read about for decades in science fiction. I had used the early internet, the ARPANET, at college, and I kind of got it. And I was in San Francisco, right time, right place. I evangelized the internet at Charles Schwab.

I would go around teaching brown bag luncheons. I would show people use net. I would show myself logging in usually with a dial-up modem. I guess by being prepared through science fiction and so on. When I saw it, I got it. And the folks at Schwab started getting it pretty early. All right. So you're in San Francisco working at Schwab, getting excited about the Internet.

Tell me, what were you using it for me? Were you using it for fun stuff to learn about what was going on? Like, what was 1993, 94, what was the typical way you would use the Internet? I used it to find people of like-mind who were doing stuff that I might enjoy a lot. I went to the virtual reality special interest group that was at the old Exploratorium. And through that group, I learned about something called the Anon Salon, which was a fundraiser monthly for climate theater. and from there I learned about Joe's Digital Diner

where people sat around eating spaghetti and meatballs, but other people showed off early multimedia technology, and that's what the kind of community that I looked for. It sounds like for the first time in your life, right? Now you're in your late 30s, early 40s, you finally found a group of people who were like you. Yeah, I found people of like mind, met to more of them. I was still not real well socialized, but I was beginning to change.

And I got a lot of help from folks. And that changed me in really good ways. All right. So you are in San Francisco. You're going to these meetups where people are talking about multimedia technology. People are having conversations about the future of the Internet. And now looking back on it 30 years later, I mean, these are, I just imagine how these conversations were going. People were just talking about the possibilities and there was a lot of optimism and excitement.

And I guess around this time, so like the 95, 96, you started to send an email to a small group of people, like three, four people about what? Like tell an email saying, hey, this is going on or that's going on? That's the gist. I would hear about events usually involving arts and technology, like Joe's Digital Diner, like Theonanon's Salon. And I figured I'd start a very simple mailing list, where maybe I would tell 10 to 12 people about stuff going on. They told me about more, and I shared that. And through word of mouth, more people asked me to put them on this CC list. And CC, obviously, carbon copy.

So you're just carbon copying a bunch of people. And sending out a list every, what, presumably every week. Hey, here's what's going on this week that I know about. That's it. And this was early 95 after leaving Schwab. But sorry, why did you leave Schwab or were you laid off or what? I was downsized to use the terminology of the time. And I was lucky because beginning of 95 was when.

the dot-com boom was starting. And I was working at a boutique web design startup. That may not have ever gotten anywhere, but I was learning stuff. And I was doing this mailing list, and it kept spreading word of mouth. More stuff started appearing there. I said, hey, apartments are getting harder to find, so people can send me that. other people wanted me to put job postings on there so i did that in the middle of 95 at about 240 addresses the cc list broke and i had to use a list serve right okay you could and so

you had too many email addresses but now people are saying hey and more people want to join this list and people are saying i not only do i want to know what's going on can i post a job here, can I, I've got an apartment or room for rent. So it just kind of naturally becomes this thing. You're not, you're not necessarily architecting that. It's just, you've got a list. People are reading it. And then other people like, oh, can you add this thing to your email list this week? That's it. I had caught the vibe of the time, as the kids might say. And in the way I started, Craigslist, I created its own vibe where user-generated content became a genuine community thing. And my problem was that it was becoming a little too successful, too fast.

I got lucky. A guy named Eric Thice offered me the use of his list serve. He had a real server, which was an astounding 1.5 megabits. And the dilemma I had was when you're using a list server, you had to give the thing a name. As a nerd, I'm literal. I wanted to call it San Francisco events, but there were people around me who were much smarter than me, like a guy named Anthony Batt. He told me people were calling my mailing list, Craigslist.

He told me that I had created a brand. He was a guy. It was right. I had created something called Craigslist. When we come back in just a moment, Craigslist goes from a side project to a full-fledged company. But every company needs a leader, and Craig's not sure he's the right man for the job. Stay with us. I'm Guy Raz, and you're listening to How I Built This. Hey, welcome back to How I Built This. I'm Guy Raz. So it's 1996, and Craig Newmark's little San Francisco mailing list is really taking off.

And what began as a way to share local events is turning into something much, much bigger. And now, people are sending Craig all kinds of posts, jobs, apartments, services, even items for sale, which is making it messy to manage by email alone. In 96, I remembered that I'm a programmer. I can write code, which would take an email and make a webpage out of it. I have no design skills, so I'll just put up the simplest site I can. In retrospect, I realize, oh, I do have one really good design skill. I keep things simple and fast.

I'm one of those people who love to get to the point and then to stop talking. And that works in so many ways for so much of human beings. needs. So, all right, it sounds like it was already, you know, by the time you, Craigslist.org up online in 96, it's evolving naturally. People want to post all kinds of things. And what? Are you, you're managing this thing? You're taking in all the ads and literally putting them up there or how is it working? Well, the idea is people email me ads. I have written code. which turns those emails into classified ads on a site. Things work smoothly.

And whenever a task started to take too much time, like an hour a day, I wrote some code, so the task took me five minutes. And that was just me for the first few years. By the end of 97, we hit about a million pages per month. which was a lot then, and some folks wanted to help me run this site on a volunteer basis. So just to be clear, I mean, in 1997, by the way, Craigslist, I don't think it looks that different today than what it looked like then, right? Correct. Okay, so it didn't cost anything to put anything up there at all, right?

Was there any revenue at all, or was it just people posting and that was it? That was it. There were folks from Microsoft, Microsoft Sidewalk, who wanted to put up Banner ads. But I'm thinking Banner ads are usually stupid. I don't need the money. I'm doing well enough. So I said no Banner ads. But in 98, the site didn't do very well.

There were always problems. This was being done on a volunteer basis. So, okay, so you have this site, people are posting ads and you're managing it. You mentioned that there were some problems with it. What were the problems? Like it wasn't getting updated regularly. There was, there was, what, it wasn't managed well. What were some of the, tell me what some of the problems were.

Mostly, since the processes were still somewhat manual, ads didn't go up on the site in a timely way. It could take hours or days. That wasn't okay. And when there was a problem, well, sometimes to recognize a problem and to know the next steps, you had to be technical. And I was basically tech support also. So those were just, nothing about that was any good,

except for the spirit of some of the volunteers. So at the end of 99, people were telling me, hey, make it into a real company, charge people for it, pay people's salaries. Okay, before we get there, because I know 1999 you decided to incorporate as a company. But this was craigslist.org. And most people assume that dot org means your nonprofit organization. It doesn't, not legally, you don't, anybody can be.org. It doesn't mean you have to be. This is just a designation that the internet kind of, but there's no legal requirement to be

not-profit, but you were craigslist.org and still are. Yes. The deal is that back then in the community spirit or vibe. Dotorg was actually used for anything which put the community first, anything with that spirit of user-generated content. And so when somebody did that domain registration, they did craigslist.org. They also did craigslist.com and dot net. But given our spirit and intent, we stuck with dot org, because that reminded us and everyone else.

Something was very different about what we were doing. We were, I committed to a philosophy of monetizing the site. minimally. Well, I mean, just to push back a little bit, I mean, I think, and again, I'm not criticizing you. I think it's a smart move, but having it as a dot-org designation also creates a halo effect. It lets people think, oh, this is different. I mean, look, at the end of the day, you're a business, even if you weren't charging everybody, the site was, and eventually did make, was going to make money. It was going to charge people. Well, it helps signal what we were about, genuinely speaking. And I guess the dot-org thing in a way reminded ourselves that there is something different about us. And a lot of it is going to be minimal monetization.

Okay. This is 99. You incorporate as Craigslist as a business for profit. And you decide this is going to become my thing. And I guess you're convinced by. friends and other people that you should have a pricing model, right? And so I guess the model, which is still more or less the same today, is you would charge for job ads, some real estate listings, and a few other things, but most things would be free, right? And again, in 1999, you're still manually put, like people are emailing into the email address and somebody you or now you're paying people are manually taking that ad and put. putting it up? Well, at some point in the evolution, I don't recall when, we automated a lot more in terms of posting, and we relied on the community to let us know when there was a problem,

but we still needed a substantial team. For example, we had a technology team, we have a customer service team, we had billing very, very briefly, I think in 2000. we tried a little marketing, put a couple of job ads up in HR magazines that lasted maybe a month. So we ran very lean, and that was through 99. But towards the end of 99, I had hired a guy named Jim Buckmaster to take over technology. No one needed me to do technology anymore, but I was CEO. and I was a customer service rep. Just to clarify, I think you had about by April of 2000, about nine employees total that's maybe in addition to you.

And you hired Jim that year, but you were the CEO for the first year. And as you've already intimated in this conversation, and as I've read about, you felt like you were not good at being a manager of people. Tell me where your failings were. Well, I was generally bad at making tough decisions, including hiring and firing. I lacked boldness of vision, for example, to incorporate some new categories and to start expanding throughout the whole country. And I just wasn't emotionally predisposed to lead, at least not from the top down. So that first year, I mean, one of your hires that you make is this guy, Jim Buckmaster, and you recognize, I guess, by towards the end of the year that, hey, he was doing IT,

and you sort of think maybe he should be running this company, and I should take on a different role. Frankly, and as I like to put it, as a manager, I suck. And when I realized that, I realized, oh, I had hired Jim Buckmaster. and it appears that he would not suck in the manner which I did. And frankly, my suckage was kind of brutal, made him CEO, committed to him that I would not interfere with what he was doing. I would leave him to do his job. Jim not only has the tactical skills, socialization,

but also he intuitively understands the vibe of the community. That's one of the big reasons he had joined. And over the subsequent 25 years, Jim has maintained and amplified that vibe. And this was good because as a manager, I'm not good. But I'm a great customer service rep. So that's what I did really heavily

for about another 15 years or so. So Jim becomes CEO in November of 2000. And by the way, I'm totally on board with this. I don't ever understand why people let their egos get in the way of decisions like this. If you know that your business that you started is going to be more successful, with somebody else running it and you still playing a critical role like that's, that makes a lot of sense to me. I agree. Accidentally, I did the right and smart thing. You say accidentally. Yes. Why accidentally? I was just winging it. I was operating off my instincts, my gut. But I do realize that all of my success has to do with accidentally being in the right time, right place, accidentally making the right decisions, which makes me the farthest gump of the internet. Yeah. Craig, I mean, it's kind of remarkable because Jim is still. the CEO today. How did you, I mean, look, when you started Craigslist, there wasn't a ton of money coming in. I think by year three, you were bringing in around $7 million a year. So that was

definitely great. But in the first year, like, how did you incentivize somebody like Jim to become the CEO? How did you have the money to pay him? Or did you say, hey, I'll give you a big chunk of this business? We had the cash flow to pay the whole team reasonably well, including myself. And the decision was made. Again, he had the right philosophy. It didn't bother him that he wasn't going to get wealthy, or so we thought this way. And I did, as a purely symbolic gesture, gave him and others big chunks of equity,

not thinking that it might be worth a lot of money someday. for me the thinking is that money is important, but the philosophy, the approach, the vibe, that was the important thing. And he's done well. Yeah, for sure. Okay, so you have a competent, strong partner now running the business, and you've got cash flow coming in. And this is really, I mean, still 90% or more of the ads were free, but you were making enough money on the ads that weren't free. People would pay, what, $25 to $50 for a job posting, for example? That was it.

The philosophy, which was first articulated by the people who used the site, they were saying, hey, charge people who normally pay a lot more money for less effective ads. and that meant charging the people who put up a job, not the people who put up a resume. We would charge apartment owners, homeowners for their ads when they wanted to rent stuff out. We would not charge the people who were looking. And that's the philosophy to today. The deal is that Craigslist has done better than anyone expected.

our business model is, in a way, it's doing well by doing good. We've avoided becoming gentrified, like so many sites. Jessica Linga in her book, The People's Internet, said that we're one of the few remaining ungentrified sites. And I love that because I look at neighborhoods, which were only partially gentrified. or not at all, some of which are really successful, some of which are really about community. And I like that. I like that in neighborhoods. I like it in websites.

Yeah. I mean, Craigslist, I cannot imagine, will ever win any design awards. It is not. It is not. I mean, it is literally like you're going back in time. You're going to 1999 when you go on it. it's kind of amazing that it is exactly the same, which I want to talk about a bit. How did you decide to start to expand other cities, to go to L.A. and New York and then all around the world? Jim did. I was not bold enough to do that expansion. Jim was, and he took the site tech architecture that I had started on. he made it happen and he did so while maintaining the vibe we talk about

and it's the right thing and it turns out to be the successful thing. And you basically decided to take over our customer service. That was going to be the role you were going to play. No. No. I did not take over customer service. I acted as a customer service rep.

My agreement with Jim was that I would not be management in any role and I would leave him alone to make those big decisions. So I was a regular customer service rep. Okay. You step away and let Jim run the business. You don't want any direct reports because you recognize this is not a strong suit of yours. And you don't want to deal with that. I totally respect that.

But it doesn't mean that you're out of the picture, right? I mean, I'm assuming Jim is consulting with you about big decisions around the business. You're having regular meetings. Is that fair to say? I am asked occasionally when it makes sense to ask me because I'm really smart about some things and really dumb about other things. But the principle is that I'm not going to interfere and I have no influence or decision-making capability. You know, because Jim needs to be left alone to do what he's really good at. I have a number of lessons where people interfere with things, often pushing towards failure.

I suddenly, when I watch TV about Hollywood, I keep hearing about producers, giving directors what they call notes, which are usually a bad idea. I am a guy who rarely gives notes or they're equivalent. I got to focus on what I do well. I got a focus on building networks. I got a focus on supporting them. That's working. When we come back in just a moment, that hands-off style allows Craigslist to thrive

and puts Craig's ideals to the test in an uncomfortable partnership with a tech behemoth. Stay with us, I'm Guy Raz, and you're listening to How I Built This. Hey, welcome back to How I Built This. I'm Guy Raz. So it's the early 2000s, and Craig Newmark has handed the reins of Craigslist to a new CEO, Jim Buckmaster. And all around them, tech companies are collapsing. The dot-com bubble has burst and the stock market is plummeting. But meanwhile, Craigslist is stronger than ever, largely because it never took on any outside investors.

What I find so remarkable and brilliant about this business, whether this was intentional or not, and it sounds like it wasn't, is that the costs, overhead for this business were very low. And the margins were really high. Well, the cost part, the lien operation, we thank Jim for that. We do run lean, and that's well known. the amount of profit the company makes, no one outside of the company knows that. There are people who will fabricate numbers to fill out an article,

but the rule of thumb is that if somebody's telling you how much Craigslist makes, you might want to disregard that. Okay, let me ask you one question about estimates. Is it true that Craigslist today has only about 50 employees? last guy asked we had around 40 or so but I'm actually not current on our numbers this is remarkable because a business that is generating let's just say the numbers are wildly off okay let's say you're only generating 50 million dollars a year with 40 employees that's a pretty healthy company you're probably generating i mean there there there there were you know depending on the year some you years, it was like apparently a billion dollars in revenue, some years 500 million, some years 200 million, but still, with such a lean operation, I mean, it's a, it's remarkable that you can

have such a significant business with such a small number of people. It is remarkable, no matter what the revenue numbers are. Jim does a great job of running the company. And my concerns are that when I, uh, receive some of the byproduct of that, I have now committed all of that revenue to the charity world. Yeah. And I want to ask you about that. But going back to the sort of the beginnings here, so you are, I mean, Craigslist is really, it's growing organically. What is amazing to me, even in the first three, four, five years, when it's already bringing in, you know, tens of millions of dollars, there were no credible competitors. No one in the first three, four years was trying to do what you guys were doing in a credible way. What explains that in your mind? Because then VCs and bankers were funding people to make a lot of money. And there's not the kind of money that they're talking about in classifieds.

there was money though there was money to be made uh there was money substantial money sometimes but not the multiple billions that the vCs and bankers wanted okay 2004 eBay which at that at that point giant right obviously PayPal they don't PayPal and they they approach Craigslist to acquire it they want to outright buy it and And I guess Jim may be in consultation with you says no, but we'll sell you a stake, a minority stake. No. No. That's not what happened.

The deal is that I had given big chunks of equity to people, including one guy who decided he wasn't about the community mission. He wanted to sell equity, which did require the concurrence of people including Jim and myself. eBay told us that they had the same community mission, the same vibe that we did. We were convinced of it. So we authorized that guy to sell his equity to eBay. They wanted to buy as much as they could. And the only way they could do it was to buy it from somebody who was a shareholder. Yes.

Meg Whitman, who was the eBay chief CEO at the time, she said we were interested in making an acquisition of Craigslist. We would have loved to have bought the whole thing, but we knew that there was no path to control it, so we, you know, unless they sold some shares. So you guys had to approve that. They come in in 2004. They paid $32 million for 28% of the company. So eBay got a board seat, basically, on Craigslist. Okay. a board seat meant that eBay was now privy to confidential information about the business,

about Craigslist. But initially, it didn't matter, right? It sounds like for the first year or so they were a board member and that it was what it was. Yes. Okay. The reason why I asked that is because I know that things took a left turn in 2007 because eBay that year launches its own competitor, a classified advertising site called Kilji or Kijiji. Kijiji.

Kijiji, yeah, Kijiji. When you and Jim found out about this, did you, what was your, how did you react? I wasn't overjoyed, but thinking about it only took time and bandwidth away from things that I had to do. So I focused on what I had to do and just listened to Jim and counsel. Yeah. In part, I don't perceive them being a competitor because they don't have the same vibe, the same mission that we do. And, you know, you got to stay focused on what matters and ignore a lot of the rest. So this is a really interesting case because basically what your lawyers, what Craigslist lawyers and Jim decide to do was to dilute eBay's share.

They were able to dilute it to the point where the company could no longer have a seat on the board thinking, hey, if they're spying on us, we don't want them to have a seat on the board. That, of course, pisses eBay off and they sue you guys, then there's a counters suit. And this is 2008. And this is not going to be resolved, by the way, for anyone listening, until 2015 where eBay agreed when they were spinning out a bunch of their brands like PayPal to sell back the shares to you guys, to Craigslist. I don't know if that was their rationale, but that did happen. Got it. Okay. In the meantime, a couple things are happening.

We should mention this. the context, I think. By 2008, 2009, 2010, the classified ad business for newspapers is just collapsing. The year 2000, the year that Jim becomes CEOs, also unbeknown to you at the time or anyone, was the peak of advertising for papers for classified ads. It was $20 billion. It's estimated that that's how much newspapers brought in ad sales that year. and over the next few years they would see like a 70, 80% drop in ads.

And a lot of the, let's say, attention is being focused on Craigslist and online advertising, that a lot of the money has shifted there. And you're starting to really see the collapse of the newspaper industry. So of course, what does the newspaper media industry love to cover more than anything else? Itself, right? So a lot of attention is being focused on Cravenors. and how it's responsible allegedly for the collapse of local newspapers. Did you feel like you were being personally targeted by critics of Craigslist for the alleged or what would become the demise of newspapers?

I, in the past, felt that Craigslist did have a substantial effect on newspaper's survival. but until 2018, no one had done any of the numbers. I'd spoke to industry analysts like Ken Doctor and Rasmus Nielsen, who said it was ridiculous to think Craigslist had that big of an effect, and they had intuited that the cause of the newspaper's problem goes back to the 50s and 60s. TV news interfered with newspaper revenues, because they've replaced display ads and so on.

But I really didn't ever see the numbers until Thomas Bechtel published some serious research in 2018, showing that newspapers started suffering in the 60s. He ran all the numbers, found that there's just continuous straight-line decline with newspapers until around 2008, at which point Facebook and Google started getting a lot of that revenue. And that trend has continued. He tells me that if I feel Craigslist had that big of an effect, I'm diluting myself. What really hurt newspapers was TV news, followed by Facebook and Google. But, and this is something that I find very frustrating,

Whenever an article is written about this, the reporters never look up the research. They just start with the conclusion and continue with the conclusion that they've already made. Okay. Let's dig into this. You said it was really only in 2018 that you were convinced that actually Craigslist was not, quote-unquote, responsible for the demise and classified ad revenue. for newspapers and or and the collapse of the newspaper industry, which I broadly agree with. But you, but it sounds like until that point, you were, you did see the possibility that maybe this thing you created did do that. Is that what you're saying? That's correct. At that point, the discussion was more like, we don't know the real numbers, but that there's no reason that any newspaper couldn't have done exactly what I did.

Remember that the stuff I was doing, the coding that I was doing, was fairly simple from my point of view. I mean, I am a really good programmer, not a great one. But as a really good programmer, I was able to do this. I wrote code which got to the point and got stuff done. And that takes no genius. So, okay, so Craig, I mean, it doesn't take a leap. to make a connection between this, you know, sort of view that you held or that you believed, that maybe what you built was partially responsible for the demise of the newspaper industry

and decisions you made as a philanthropist because you made a lot of money. Again, I have no problem with people making a lot of money, right? I think it's important for people to be motivated by, you know, by certain things in order to contribute. But your philanthropy, a lot of your philanthropy, was and maybe still is, focused on journalism. You have a whole school named after you at the City of University of New York. You've given to Columbia Journalism School to New York Public Radio. Is it a leap for me to assume that some of that it comes out of penance or sense of guilt? That would be false.

Okay, explain. Here's the motivation. In high school, I had a great U.S. history and civics teacher, a guy named Anton Shulski. He taught us a lot of things, like the importance of due process. You got to follow the Bill of Rights. He also taught, like I say it, is that a trustworthy press is the immune system of democracy. And you protect the country. by supporting a trust-rary-free press.

I put a couple hundred million into it, and that's helps them. My two focus areas in the press now are the CUNY J-School, in part because CUNY is about giving people opportunity who never got much opportunity, and I support Wikipedia, which is where facts go to live. So obviously, you know, your time is sort of managing Craigslist ended early in that period. And your philosophy was, hey, get out of the way, let the most competent people run this thing, which you did.

And smartly so. And again, it's a private business. So nobody knows exactly how much money it's generated. There are all kinds of estimates. But I would think, and I don't think this is good or bad, I would just think this is the reality of the nature of the beast. There's a lot more competition now. There's Facebook marketplace and there's other places where people advertise next door. If you look at every business that's on how I built this, right, that we interview.

Every founder is thinking about the future, right? They want their businesses to be 100-year businesses. So they're constantly thinking of new ways to acquire customers, to market, to grow. And in the case of Craigslist, I wonder if you feel like that matters. I mean, in other words, what happens to Craigslist in 50 years? Like, is there a plan to keep it growing and to keep it robust? Or is it okay if it just fades away at some point? Our orientation is different.

The question is, does Craigslist serve the community? Does it continue to maintain that genuine community vibe? I do want it to survive and thrive. So I do think about Craigslist's future. But if a community service fails in its mission to be a community service, maybe it's time to go. Okay. So now here you are. You have done very well.

I mean, this was, you've even said, like I never anticipated being wealthy or having money or even this email list turning into a business apparently worth potentially billions of dollars. You never anticipated that. This was not in your, this was not in your in your horoscope. Yeah, I'm struggling with this even now because it's been pointed out to me that arguably, maybe I have elite levels of money, but simultaneously, I have the taste and attitudes of a peasant. I mean, it looks like you're wearing a Brunello Cuccinelli shirt right here on the screen. That's an $800 shirt you're wearing there, Craig.

I'm just kidding. Frankly, my wife is still telling me that I could do, I should do better than buying $15 henlies from Amazon. Well, you know, listen, to each his own. And I think that's great. What do you, I mean,

you say that it makes you uncomfortable to be in this position. Why? Well, the Sunday school values I got had to do with balance. I like living comfortably. I like helping my family

live comfortably. but how much do you need? At that point, you start to give it away to protect the country, sometimes to feed people. This is not a difficult decision. I don't need homes across the world. I don't need a private jet. And, you know, I know some of these billionaires a little bit,

and some of them are not miserable, but the majority are miserable. So what is your plan? I mean, you have quite a bit of life left to live. You've said publicly you want to give virtually all your money away. That's a lot harder to do than people think. Like, you literally have to deal with requests for proposals and look at what the request is and who the nonprofit is

and what they want and what they're doing. and it's slow. I have a good foundation for my decision-making, and a lot of it's become, we should protect the country, and to protect the people who've protected the country, and pigeon rescue. That's a separate one.

But the deal is that I'm very aware that I don't have the social skills to make good decisions in these areas. So I did a lot of research, made some good decisions like 10 years ago, and then I started building networks of networks of people who are really good in these areas and have funded people in these networks

to continue doing really good work. So what, besides, you know, supporting journalism, what's your focus? What's the thesis of where you want to put your money? Well, I feel that, you know, that we should support vets who've sacrificed a lot to protect us all. What I've done is located Bob Woodrow Foundation. They run this Got Your Six Network, which is a collection of nonprofits that are good at helping vets.

Military families sacrifice a lot to have their active service members help protect us all. And the Blue Star Families Organization, they are running network. of chapters and outposts who help military families with what they really need to do to live okay and to support their service members. And you mentioned pigeons. You actually do literally support a pigeon philanthropy, like a pigeon rescue. I love birds, and I have a sense of humor. So I do support a few. pigeon rescue groups like Wild Bird Fund in the Upper West Side and in the Bay Area it's called Palomacy. But I do indulge myself in other ways. For example, Mr. and Mrs. Levin taught me Sunday school at the Jewish Community Center in Maristown, New Jersey.

They've never been honored until I did something at the Community Center to honor them. and that involved also funds to restore a Torah damaged in the Holocaust. Do you think that you'll be able to actually give away all of your money or most of it by the time you die? I have it that in motion right now. I'm planning five to 20 years out. I have a pretty good idea of how I'll be doing that. my only issue is how am I going to do due diligence if all the money is not given away about the time I pass. So I figure I will exercise due diligence via a combination of seance and haunting people.

So, I mean, you've called yourself the Forrest Gump of the Internet, right, which is that you were at the right place or the right time, right? because he always seemed to be at the right place, Forrest Gump, and then made a lot of money in the shrimp business eventually. But you obviously are saying that because you were in the right place, the right time. It was like San Francisco. It was the late 90s. It was community. And then it became a brand. And then it became the cool brand that everybody went to.

And then it just became a brand. Like even to this day, if I want to find, I don't know, like secondhand. skis, which I actually did buy on Craigslist, I still go to Craigslist. I'll still check it. People, you know, people still go to it. So it is kind of amazing because you, you know, you could make the argument that there was a lot of luck involved there. It was just the right place and right time. Yes. And I think I already have the answer to this question, but I'll ask anyway, because I always ask, how much of where you got to you to tribute to luck and how much to hard work any? of it to hard work? I don't know how to figure the proportions. I've worked every day, literally, for the last 30 years. Some days are lighter than others. So I guess the work is hard, but it feels good.

It's a matter of purpose. So I just plug away. I get done what I need to get done. But I try to maintain my values. And again, the notion is how much is enough. You decide for yourself, how much is enough, and then you practice what you preach. And, you know, sometimes it works. It's working for Craigslist.

And some things in our world are good. That's Craig Newmark, founder of Craigslist. By the way, aside from the fact that you can find just about anything on Craigslist, They have some pretty bizarre ads, and there's even a page on Craigslist dedicated to the funniest and weirdest ones. It's called Best of Craigslist. And it includes ads like, this is a long shot, but any chance I can get my rock back or haunted Thai puppet available for sale. Or I need someone to retrieve a hidden obelisk. It goes on and on.

It's absolutely amazing. You should check it out on Best of Craigslist. Hey, thanks so much for listening to the show this week. Please make sure to click the follow button on your podcast app so you never miss a new episode of the show. And as always, it is free. And if you're interested in insights, ideas, and lessons from some of the world's greatest entrepreneurs, sign up for my newsletter at guyraise.com or on Substack. This episode was produced by Chris Messini with music composed by Ramtin Arablui. It was edited by Kevin Leahy with research help from Sam Paulson.

Our engineers were Patrick Murray, Maggie Luthor and Robert Rodriguez. Our production staff also includes Alex Chum. Carla Estevez, Casey Herman, Katie Seifer, Carrie Thompson, Ramele Wood, Neva Grant, Andrea Bruce, and Elaine Coates. I'm Guy Raz, and you've been listening to How I Built This.