← How I Built This with Guy Raz
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- [00:00]
Guy Raz
Wondery subscribers can listen to how I built this early and ad free right now. Join Wondery in the Wondery app or on Apple Podcasts. I love traveling with my family. We did an awesome trip this summer and one of the things that made the trip so special were the Airbnb experiences we did immersive tours, cooking classes, a chance to get coffee with a world class barista. I had so much fun on those experiences that I decided to host my own Airbnb Original Experience in San Francisco designed to help you think about how to unlock your next big move in your career or even in your life. To learn more about my Airbnb Original experience, head to airbnb.com guy this episode is brought to you by Klaviyo, the only CRM built for B2C and the key to making Black Friday and Cyber Monday your best biggest wins yet. When the holidays hit, your competition only gets louder. That's why the most successful brands use Klaviyo to cut through the noise and build personalized relationships that drive more revenue. With Klaviyo, you get marketing, service, analytics and all your customer data together on one AI powered platform. It's everything you need to build lasting customer relationships. Send exclusive email offers to your VIP customers. Deliver perfect, perfectly timed text to high intent shoppers. Maximize your ad dollars with precision. Join the more than 176,000 brands including Away, Patrick, TA and Dollar Shave Club already growing with Klaviyo. Make this holiday season your best yet at k L-A-V I-Y-O.com shopping for eggs should be simple. A happy hen makes a happy egg and that's why eggs from Happy Egg are so delicious. Happy Egg partners with family farms across the Midwest to raise happy hens outdoors. The proof is inside the shell. A tasty orange yolk. It's the difference you can see and taste. I just made an incredible omelette with eggs from Happy Egg. It was delicious and so fresh. Once you crack open a happy egg, you can see right away it's obvious. Visit www.happyegg.com built to find happy Egg near you.
- [02:51]
Craig Newmark
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 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.
- [03:33]
Guy Raz
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 those 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 never set out to build a business. He even admits that he, 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 this 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 in 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 still wrestles with today.
- [07:25]
Craig Newmark
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.
- [08:20]
Guy Raz
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 challenges with social skills. Right? Nobody saw it that way. Right.
- [08:54]
Craig Newmark
It's hard to say how people perceive things. I wasn't a good public school system in Morristown. 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.
- [09:17]
Guy Raz
I mean, clearly 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?
- [09:38]
Craig Newmark
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 neighborhood 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.
- [10:17]
Guy Raz
Wow. All right. Well, that's. I mean, it's really. It's just 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 sounds like you, as far as you can remember, this was a frustration of yours that you couldn't, I don't know, be one of the guys or blend in.
- [10:40]
Craig Newmark
It was a problem for me. 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, Morristown, New Jersey, has a great old library. I hung out in young adults finding whatever science fiction I could find.
- [11:09]
Guy Raz
So you really found solace in books and science fiction. Like, that's where you kind of escaped.
- [11:17]
Craig Newmark
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.
- [11:39]
Guy Raz
So when you were growing up in Morristown, New Jersey, this is the 50s as a kid or 60s as a teen, there were a lot from. 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, at your synagogue. Is that right?
- [11:57]
Craig Newmark
There were a number of them that made it visible. The. The mother of one of my classmates had her serial number quite visible.
- [12:08]
Guy Raz
Her tattoo.
- [12:08]
Craig Newmark
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 Forward, 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.
- [13:01]
Guy Raz
But he never talked about that.
- [13:04]
Craig Newmark
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.
- [13:44]
Guy Raz
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 then than what it is now. I read that you wanted to study and I was blown away by this. Large language models in the early 70s. I didn't even know you think of LLMs today and AI, right? You think of generative AI. I didn't even know that that was something you could study. In the early 70s.
- [14:15]
Craig Newmark
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 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, proverbs 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.
- [15:13]
Guy Raz
Okay, you graduate from Case Western and like a good computer science graduate, a 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?
- [15:37]
Craig Newmark
Well, in IBM Boca Raton, which was not very fancy at that point, I went to work on a forgotten minicomputer called 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, was really good was I was a core member of a team building a Series 1 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.
- [16:30]
Guy Raz
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.
- [16:41]
Craig Newmark
Well, 17 years at IBM, Boca Raton, Detroit, a year in Pittsburgh. But I got tired of 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.
- [17:27]
Guy Raz
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 a 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.
- [18:02]
Craig Newmark
Well, the Internet realized the 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 Usenet. 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.
- [18:54]
Guy Raz
All right, so you're in San Francisco working at Schwab, getting excited about the Internet. Tell me, what were you using it for? I mean, 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?
- [19:11]
Craig Newmark
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.
- [19:50]
Guy Raz
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.
- [20:04]
Craig Newmark
Yeah, I found people of like mind, met 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.
- [20:22]
Guy Raz
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 where the future of the Internet. And, you know, now looking back on it 30 years later, I mean, these are. And 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.
- [21:02]
Craig Newmark
That's the gist. I would hear about events usually involving arts and technology, like Joe's Digital Diner, like the Anon 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.
- [21:30]
Guy Raz
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.
- [21:43]
Craig Newmark
That's it. And this was early 95 after leaving Schwab.
- [21:49]
Guy Raz
Sorry, why did you leave? Did you leave Schwab or were you laid off or what?
- [21:53]
Craig Newmark
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 listserv.
- [22:45]
Guy Raz
Right, okay. 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, 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 a room for rent. So it just kind of naturally becomes this thing. 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?
- [23:17]
Craig Newmark
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 Theiss offered me the use of his listserv. He had a real server, which was an astounding 1.5 megabits. And the dilemma I had was when you're using a lisp 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 right. I had created something called Craigslist.
- [24:32]
Guy Raz
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. If you've been listening to the show these last couple of episodes, you've probably heard me mention the Airbnb original experience that I'm hosting. And I'm so excited to have a chance to connect with listeners in a completely new way. It's called the Reinvention Lab, and it's designed to help you think about how to unlock your next big move in your career or even in your life. I'll help you discover your own story in ways I do on this show with my guests. And attendees will get a chance to take a deeper dive with me on so many lessons I've learned from this show, lessons that have transformed how I work and think about the future. All proceeds from the event will go to support the Ronald McDonald houses that helps families stay near their children who are being treated at nearby hospitals. It's going to be really fun and I can't wait to meet you. So come join me in San Francisco and take your idea to the next level to Grab your spot. Visit airbnb.com guy it's gonna be great. Ever had one of those afternoons where your brain just quits on you? You're sluggish, hangry, maybe even a little foggy. What if it's your glucose? See, glucose is an energy currency for your mind and body. When it's stable, you're on point. When it crashes, so can you. That's why Lingo is so interesting. Lingo is a glucose wearable designed to help you connect the dots between your glucose and what you eat, how you move and how you feel. It shows your glucose data in real time. Instead of guessing, you see the impact of your choices. Maybe that healthy snack is actually sending your glucose on a roller coaster. Or that afternoon walk is the perfect stabilizer. It's about unlocking your consistent best all day long by truly understanding your body's unique responses. Get to know your glucose and learn about how to build healthy habits that work for you with Lingo, designed for you by Abbott through November 30th. Use code GUY10 on hello Lingo.com to get 10% off a lingo plan. Purchase one use per customer. This offer cannot be combined with other offers, US Puerto Rico and UK only. The Lingo Glucose system is for users 18 years and older, not on insulin. It is not intended for diagnosis of diseases, including diabetes. Individual responses may vary. AI companies have unique business models, each with distinct billing needs. Stripe is the go to choice for AI leaders from early stage startups to scaled enterprises. Whether it's OpenAI offering tiered plans based on user needs or cursor implementing flexible billing structures for code access, redefining the future requires sophisticated business models. With Stripe billing, you can support any business model from credit based to sales, negotiated contracts, and easily align your monetization strategy with customer value. Join the ranks of 78% of the Forbes AI 50 and millions of businesses worldwide that trust Stripe to help them build more profitable, scalable businesses. Discover more@swepe.com 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.
- [28:43]
Craig Newmark
In 96 I remembered that, oh, I'm a programmer, I can write code which would take an email and make a web page 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 a 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 needs.
- [29:24]
Guy Raz
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 you're managing this thing, you're taking in all the ads and literally putting them up there, or how is it working?
- [29:47]
Craig Newmark
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.
- [30:29]
Guy Raz
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?
- [30:38]
Craig Newmark
Correct.
- [30:39]
Guy Raz
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?
- [30:48]
Craig Newmark
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.
- [31:18]
Guy Raz
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, wasn't managed well. Tell me what some of the problems were.
- [31:38]
Craig Newmark
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 salaries.
- [32:26]
Guy Raz
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.org means you're a nonprofit organization. It doesn't. Not legally you don't. Anybody can be dot 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 a nonprofit. But you were craigslist.org and still are.
- [32:54]
Craig Newmark
Yes. The deal is that back then in the community spirit or vibe.org 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.net but given our spirit and intent, we stuck with.org because that reminded us and everyone else something was very different about what we were doing. I committed to a philosophy of monetizing the site minimally.
- [33:42]
Guy Raz
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 and the site was and eventually did make a was going to make money, it was going to charge people.
- [34:11]
Craig Newmark
Well, it helped signal what we were about, genuinely speaking. And I guess the.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.
- [34:28]
Guy Raz
Okay, this is 99. You incorporate as Craigslist as a business for profit and you decide that 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 putting it up.
- [35:11]
Craig Newmark
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 a billing very, very briefly. I think in 2000, we tried a little marketing, put a couple 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.
- [36:15]
Guy Raz
Clarify, I think you had about. By April of 2000, you had 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 has been, as I've read about, you felt like you were not good at being a manager of people. Tell me where, where your failings were.
- [36:43]
Craig Newmark
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.
- [37:08]
Guy Raz
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.
- [37:26]
Craig Newmark
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 technical skills, socialization, but also he intuitively understands the vibe of the community. That's one of the big reasons he joined. And over the subsequent, 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.
- [38:35]
Guy Raz
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.
- [38:59]
Craig Newmark
I agree. Accidentally, I did the right and smart thing.
- [39:04]
Guy Raz
You say accidentally.
- [39:06]
Craig Newmark
Yes. By 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.
- [39:32]
Guy Raz
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? Did you. Did you have the money to pay him? Or did you say, hey, I'll give you a big chunk of this business?
- [40:03]
Craig Newmark
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.
- [40:48]
Guy Raz
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 bucks for a job posting, for example.
- [41:15]
Craig Newmark
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 adults 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.
- [42:41]
Guy Raz
Yeah. I mean, Craigslist I cannot imagine will ever win any design awards. It is not. I mean, it is literally like you're going back in time, 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 LA and New York and then all around the world?
- [43:08]
Craig Newmark
Jim did. I was not bold enough to do that expansion. Jim was. And he took the site tech architecture that I'd 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.
- [43:34]
Guy Raz
And you basically decided to take over our customer service. That was going to be the role you were going to play?
- [43:39]
Craig Newmark
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.
- [43:57]
Guy Raz
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?
- [44:20]
Craig Newmark
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 their equivalent. I gotta focus on what I do well. I gotta focus on building networks. I gotta focus on supporting them.
- [45:21]
Guy Raz
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. If you've shopped online, chances are you've bought from a business powered by Shopify. You know that purple shop pay button you see at checkout? The one that makes buying so incredibly easy? That's Shopify. And there's a reason so many businesses sell with it. Because Shopify doesn't just make amazing buying experiences for customers, they're also the experts in helping small businesses grow big. Stop seeing carts going abandoned and turn those sales into Sign up for your $1 per month trial and start selling today at shopify.combilt go to shopify.combiltine shopify.combilt as a founder, you're moving fast toward product market, fit your next round or your first big enterprise deal. But with AI accelerating how quickly startups build and ship, security expectations are higher earlier than ever. Getting security and compliance right can unlock growth or if you wait too long, stall it. With deep integrations and automated workflows built for fast moving teams, Vanta gets you audit ready fast and keeps you secure with continuous monitoring as your models, infrastructure and customers evolve. Fast growing startups like LangChain, Rider and Cursor trust Advanta to build a scalable foundation from the start. I love that over 10,000 companies, from startups to huge enterprises, trust Vanta because it makes me trust them. Go to vanta.combilt to save $1,000 today through the Vanta for Startups program and join over 10,000ambitious companies already scaling with Vanta. That's v a n-a.combilt to save $1 thousand for a limited time 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.
- [48:46]
Craig Newmark
Well, the cost part, the lean 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.
- [49:16]
Guy Raz
Okay, let me ask you one question about estimates. Is it true that Craigslist today has only about 50 employees?
- [49:24]
Craig Newmark
Last I asked, we had around 40 or so, but I'm actually not current on our numbers.
- [49:33]
Guy Raz
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 a year with 40 employees. That's a pretty healthy company you're probably generating. I mean, there were, depending on the year, some 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 remarkable that you can have such a significant business with such a small number of people.
- [50:11]
Craig Newmark
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 receive some of the byproduct of that, I have now committed all of that revenue to the charity world.
- [50:32]
Guy Raz
Yeah. And I want to ask you about that. But, but going back to the, 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 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?
- [51:05]
Craig Newmark
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.
- [51:19]
Guy Raz
There was money, though. There was money to be made.
- [51:22]
Craig Newmark
There was money, substantial money sometimes, but not the multiple billions that the VCs and bankers wanted.
- [51:32]
Guy Raz
Okay, 2004, eBay, which at that point giant. Right. Obviously PayPal, they don't PayPal. And they approach Craigslist to acquire it. They want to outright buy it. And I guess Jim maybe in consultation with you says no, but we'll sell you a stake, a minority stake. No, no, that's not what happened.
- [51:59]
Craig Newmark
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 his 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.
- [52:34]
Guy Raz
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.
- [52:42]
Craig Newmark
Yes.
- [52:44]
Guy Raz
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 us 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. Right. Okay. So having a board seat meant that. 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 is. 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.
- [53:50]
Craig Newmark
Kijiji.
- [53:51]
Guy Raz
Kijiji. Kilgiji. When you and Jim found out about this, did you. What was your response? How did you react?
- [54:03]
Craig Newmark
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. 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 gotta stay focused on what matters and ignore a lot of the rest.
- [54:44]
Guy Raz
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 countersuit, 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 spitting out a bunch of their brands like. Like paypal, to sell back the shares to. To craigslist. To you guys, to Craigslist.
- [55:29]
Craig Newmark
I don't know if that was the rationale, but that did happen.
- [55:33]
Guy Raz
Got it. Okay. In the meantime, a couple things are happening. We should mention this, the context, I think by 2008, 2009, 2010, the, the classified ad business for newspapers is just collapsing. The year 2000, the year that Jim becomes CEO is also a. Unbeknownst to you at the time or anyone, was the peak of advertising for papers for classified ads they made 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 Craigslist 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, for the alleged or what would become the demise of newspapers?
- [56:57]
Craig Newmark
I in the past felt that Craigslist did have a substantial effect on newspaper survival. But until 2018, no one had done any of the numbers. I spoke to industry analysts like Ken Docter 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 Bechdel 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 deluding 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 their. With the conclusion that they've already made.
- [58:49]
Guy Raz
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 in classified ad revenue from newspapers and the collapse of the newspaper industry, which I broadly agree with. But it sounds like until that point you did see the possibility that maybe this thing you created did do that. Is that what you're saying?
- [59:18]
Craig Newmark
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.
- [59:57]
Guy Raz
Okay, so, Craig, it doesn't take a leap to make a connection between this 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 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 City of University of New York. You've given it to Columbia Journalism School, to New York Public Radio. Is it a leap for me to assume that some of that comes out of penance or sense of guilt?
- [60:57]
Craig Newmark
That would be false.
- [60:59]
Guy Raz
Okay, explain.
- [61:00]
Craig Newmark
Here's the motivation. In high school, I had a great US History and civics teacher, guy named Anton Schulsky. He taught us a lot of things, like the importance of due process. You got to find, follow the Bill of Rights. He also taught, like I said, is that a trustworthy press is the immune system of democracy. And you protect the country by supporting a trustworthy free press. I put a couple hundred million into it, and that's helps him. 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.
- [61:57]
Guy Raz
So obviously your time sort of in 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 hundred 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 does it, is it, is it okay if it just fades away at some point?
- [63:14]
Craig Newmark
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 serve, survive and thrive. So I do think about Craigslist future. But if a community service fails in its mission to be a community service, maybe it's time to go.
- [63:45]
Guy Raz
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 horoscope.
- [64:11]
Craig Newmark
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 tastes and attitudes of a peasant.
- [64:29]
Guy Raz
I mean, it looks like you're wearing a Brunello Cucinelli shirt right here on the screen. That's an $800 shirt you're wearing there, Craig. I'm just kidding.
- [64:39]
Craig Newmark
Frankly, my wife is still telling me that I should do better than buying $15. Henley's from Amazon.
- [64:51]
Guy Raz
Well, you know, listen. To each His Own. And I think that's, that's great. What do you. I mean, you say that it makes you uncomfortable to be in this position. Why?
- [65:04]
Craig Newmark
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 I know some of these billionaires a little bit, and some of them Are not miserable, but the majority are miserable.
- [65:50]
Guy Raz
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 they're doing. You know, the request is and who the nonprofit is and what they want and what they're doing, and it's slow.
- [66:18]
Craig Newmark
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.
- [67:05]
Guy Raz
So what. So besides, you know, supporting journalism, what's your focus? What's your. What's the thesis of where you want to put your money?
- [67:13]
Craig Newmark
Well, I feel that we should support vets who sacrificed a lot to protect us all. What I've done is located Bob Woodruff Foundation. They run this Got yout Six network, which is a collection of. 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 networks of chapters and outposts who help military families with what they really need to do to live okay. And to support their service members.
- [67:59]
Guy Raz
And you mentioned pigeons. You actually do literally support pigeon philanthropy, like a pigeon rescue.
- [68:07]
Craig Newmark
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 Morristown, 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.
- [68:56]
Guy Raz
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?
- [69:02]
Craig Newmark
I have 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 by the time I pass? So I figure I will exercise due diligence via a combination of seance and haunting people.
- [69:33]
Guy Raz
Okay, so, I mean, you've called yourself the Forrest Gump of the Internet, right? Which is that you were at the right place at the right time. Right. He always seemed to be at the right place, Forrest Gump, and then made a lot of money in shrimp, 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 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. 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. 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, the right time.
- [70:28]
Craig Newmark
Yes.
- [70:29]
Guy Raz
And I think I. I already have the answer to this question, but I'll ask anyway, because I always ask. And how much of where you got do you attribute to luck and how much to hard work? Any of it to hard work?
- [70:43]
Craig Newmark
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.
- [71:33]
Guy Raz
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 lessons from some of the world's greatest entrepreneurs, sign up for my newsletter@guyraz.com or on substack. This episode was produced by Chris Masini with music composed by Ramtin Arablouei. It was edited by Kevin Leahy with research help from Sam Paulson. Our engineers were Patrick Murray, Maggie Luthar, and Robert Rodriguez. Our production staff also includes Alex Chung, Karla Estevez, Casey Herman, Katie Cipher, Kerry Thompson, Rommel Wood, Neva Grant, Andrea Bruce, and Elaine Coates. I'm Guy Raz and you've been listening to How I Built this. If you like How I Built this, you can listen early and ad free right now by joining Wondery plus in the Wondery app or on Apple Podcasts. Prime members can listen ad free on Amazon Music. Before you go, tell us about yourself by filling out a short survey@wondery.com survey not great with finances? That's okay. Experian is your big financial friend. Explore credit card offers, some labeled no ding decline, which means if you're not approved, they won't hurt your credit scores. See experian.com for details. Applying for no Ding Decline cards won't hurt your credit scores if you aren't initially approved. 2025 Experian Experian.