The deal is that people see that we're for real. Craigslist is about helping people get through the day to put food on the table. In the longer run, Craigslist helped tens of millions of Americans realize that the internet is actually useful for something, that it's reasonably easy to use. And any luck I've had with Craigslist or anywhere has been by accidentally being in the right time and right place, which kind of makes me the Forrest Gump of the internet.
Welcome to the Lay of the Land podcast, where we are exploring what people are building in Cleveland and throughout Northeast Ohio. I am your host Jeffrey Stern and today I had the genuine pleasure of speaking with Craig Newmark, the founder of Craigslist and someone who has shaped the modern internet as we know it. Long before Craigslist became one of the most enduring, important, and frequented platforms on the internet, long before the internet even connected us at all, Craig was a computer science student here in Cleveland at Case Western Reserve University, tinkering with early programming languages, studying neural networks and artificial intelligence at the time and exploring the frontier of software engineering. The rest is history, as they say, an amazing history which we will cover in our conversation today. How Craig became the accidental entrepreneur behind one of the most legendary companies of our time and driving forces behind the internet itself. Our conversation spans his path to Silicon Valley, the creation and stewardship of Craigslist, the moral compass that has guided his decision-making along the way, and his growth personally as an entrepreneur and leader, the implications and consequences of building one of the largest platforms of all time and the work he's doing today to help make the internet and country better through his philanthropic initiatives with veterans, with journalism, with cyber security, and lots more. This was truly a special conversation and I'm very grateful to be able to share it with you today. So, please enjoy this awesome discussion with Craig Newmark, founder of Craigslist. Lay of the Land is brought to you and is proudly sponsored by Roundstone Insurance. Headquartered in Rocky River, Ohio, Roundstone shares Lay of the Land's same passion for bold ideas and lasting impact from our community's entrepreneurs, innovators, and leaders. Since 2005, Roundstone has pioneered a self-funded captive health insurance model that delivers robust savings for small and medium-sized businesses. They are part of the solution to rising healthcare costs, helping employers offer affordable, high-quality care while driving job creation and economic growth throughout Northeast Ohio. Like many of the voices featured on Lay of the Land, including Roundstone's founder and CEO, Mike Schroeder, Roundstone believes entrepreneurship, innovation, and community to be the cornerstones of progress. To learn more about how Roundstone is transforming employee health benefits by empowering employers to save thousands in per employee per year healthcare costs, please visit roundstoneinsurance.com. Roundstone Insurance, built for entrepreneurs, backed by innovation, committed to Cleveland.
Long before the internet connected all of us, long before I think Craigslist would be cited as one of the prime examples of how it's connected us, you know, you were tinkering with software and computers and technology. You studied computer science here in Cleveland at Case Western Reserve. And I'd love to start with, had you ever imagined that those technologies you were playing around with and studying then might one day bring together people really at the greatest scale in history and that you would be such an important contributor to that kind of historic development?
I had very little clue about how any of this would turn out. I should have known better. In particular, at Case there was a node of the ARPANET which was the predecessor to the internet and I kind of understood what it might be good for but I barely touched it. That was a mistake on my part. And mostly I was focused on learning all the programming that I could because I realized I was good at it and I might wind up with a good career out of it.
When you reflect back on that time and really your journey and just kind of trace your path back, what do you feel were the formative moments for you when you were younger that laid this foundation that sparked your curiosity in technology and the possibility for software?
Well, as a kid, somehow I wound up being good at math and science. I don't really know how or why. I do know that by the fourth grade or so, I was interested in dinosaurs and rocks. Now, lots of kids are fascinated by dinosaurs. That's been pretty true for decades now, but when I got interested in that, this was 60, 65 years ago. And my interest was academic as well as playing with what I thought were cool scary toys. I remember reading paleontology, whatever suitable for a kid and that was a lot of fun and I could imagine myself heading out to the desert to find fossils. However, that only lasted a few years. Then I got interested in physics, nuclear physics, even a little bit of quantum, you know, the reality underlying everything. And that sustained me kind of through high school. But by the time I got to college in my first year at Case, I realized that jobs in that kind of physics were really scarce. You had to be well within the top 1% and I just wasn't that smart.
Did you ever think about entrepreneurship or was that really beyond the scope of your interest?
Frankly, I never thought about entrepreneurship at all until I found myself by accident being one.
So, I'm sort of embarrassed to say this, but it never really dawned on me until I was actually preparing for our conversation that Craigslist was literally Craig's list, like your list at the beginning of this. It never just unpacked the word itself. So as an accidental entrepreneur of sorts, you know, making this transition from longtime software development to curating, you know, your own list and starting a Craigslist, obviously, what was the journey to becoming an entrepreneur and how did you navigate that having never really thought about it prior?
Well, I'm going to be bouncing back and forth in time as I talk about this. In college, after realizing that I just wasn't smart enough to go into quantum physics, I thought AI looks pretty cool. I had read all that science fiction talking about machine consciousness, not that we know what consciousness is. And I considered that fairly seriously for a year or two. And then I started reading about it, reading up on neural networks for language understanding, in its current form that's large language models. And I took a look at that and it was fascinating. There was a book I think by Terry Winograd on this subject. And after a while I realized this is really cool and important and there wouldn't be any jobs available for decades. So I better get into more mundane aspects of programming, either systems programming or application programming. So I learned everything that I could about that. I basically turned my time at Case into a vocational training, the vocational matter being software engineering, even though that was the infancy of software engineering. And I learned a lot about it. Unfortunately, I didn't get a well-rounded education. I took very little liberal arts which I regret but I got a really good education in software work and I just started plugging away doing that. I got a job at IBM in Boca Raton. I should have been more patient and see where else I might have gotten work. So I spent six years at IBM in Boca Raton. I figured I'll take a job not far from the beach. And it took me a long time to realize it, but I'm not a beach guy. I learned scuba diving and I realized, well, this is fun. It's kind of like my own Jacques Cousteau special, but it didn't really sustain my interest. And I started going to science fiction conventions, which were great for me. And I still think about them a lot. I went to a whole bunch starting in the late 70s and then I moved to Detroit. There was opportunity there and I thought I might like the people in Detroit better than South Florida. I guess I did. Kept going to a lot of science fiction conventions. Worked for IBM in the Detroit area doing factory automation work. You know, I was working for IBM but with GM, General Motors. And I acquired a lot of skills there. But frankly, through none of this did I acquire really important skills, just getting along with people. Frankly, as a nerd, I was oblivious to social skills. And as a result, I would occasionally be a jerk, by which I mean an asshole. And I was pretty bad in some respects. I was learning a lot of technology. I was acquiring a lot of technical skills, but I was really remiss in terms of learning how to work with people. And I spent 17 years at IBM then and I really learned no entrepreneurial skills. I learned some business skills like the idea of leading by example because I have no real top-down leadership skills. And my only hope for me, as one of my managers pointed out, I had a sense of humor and people seem to like that even when they really didn't want to work with me. So after 17 years at IBM, after a couple of rounds of downsizing where I got laid off from work twice, I wound up getting myself a job in San Francisco at Charles Schwab. But the deal is through none of that time was I really an entrepreneur in any sense. Not accidental, just nothing. No luck.
Yeah. Well, and so what was it about being in San Francisco that you feel then unlocked the entrepreneurial inclination?
Well, there was something happening in San Francisco about using new technologies in a way that gave everyone opportunities. There were new ways of telling stories, new technologies which promised to be open and available to everyone. We talked back then about democratizing the internet. And as I was at Charles Schwab, that's when the internet became a real thing. I started using it frankly towards the end of my time in Detroit and through a brief year in Pittsburgh, IBM Pittsburgh where I accomplished nothing. But I started learning about the internet and taking it seriously. And because I had read so much science fiction, frankly, I kind of intuited that the internet was going to change everything. So when I was at Charles Schwab, I went around the company teaching lunchtime brown bag lunches and I said, 'Hey, this is how Charles Schwab is going to operate someday.' I was lucky because of my work. I was exposed to the internet at that point. There was a guy named Derek Malamud who brought in the first web server and the first graphical browser within the company and looking at that and looking what was going on outside of Schwab. I'm thinking then this is how the world will work and specifically this is how Schwab is going to work. I wound up working with a marketing guy named Alan Nathan saying hey this is how everything is going to work. Pretty much no one got it at that point. I was part of another downsizing effort because I was still kind of a jerk. But I was really lucky because Schwab was generous. IBM had been generous as I left and I wound up doing work with web design people and I was prepared for when I got a good opportunity at Bank of America. I was doing contract work for them. But the deal was that I was not an entrepreneur through any of this. I started what other people called Craigslist because kind of after my time at Schwab, I started a simple mailing list where I would tell people, hey, here's what's going on in town that I heard about involving technology and arts. I started a simple mailing list and it spread word of mouth and so by accident I started something which turned into Craigslist but I had no clue to that effect.
So today I think it's something most probably take for granted, this idea that you can have trust at all on the internet. You know, certainly that you would put your credit card information and purchase things from people you've never met and so many of the just online interactions that we have today and how dependent they are on a baseline level of trust. I don't know that it was obvious that we'd be able to establish all that in this virtual world. Certainly, you know, at the time that you were building it, how did it evolve at that point in time from just a list that you were sending out into really what has grown today into what we think about as, you know, online communities?
Well, my deal was that in the middle of '95, again, trying to work in the area of web design, my mailing list, which was a CC list, had grown to maybe 240 addresses, at which point the CC list part broke. I had to use a list server, you know, and a guy named Eric Theise volunteered the use of his Majordomo installation. He had a web server at the time. He had a 1 megabit line to his server which at that point in time was really high speed, high bandwidth. And I had to give the thing a name because list servers need names. You had to distinguish one from the other. And as a nerd, I'm a pretty literal guy. I was going to call it San Francisco Events since at that point it was still mostly events. People around me though told me they already called it Craigslist. In particular, it was a guy named Anthony Bat who told me that's what people called it and that I had inadvertently created a brand. He explained to me what a brand is because I didn't know because I was that far removed from the business. He was right. I called it Craigslist signifying it would be personal and occasionally quirky and I just kept plugging away with the thing. It was just me for a few years. In '96 I realized, oh, I'm a programmer. I can write code which turns web pages into HTML and I could write the code and do it more or less for free. So I had instant web publishing around mid-'96 or so. And then by the end of '97 I realized that my website, the first Craigslist site, was getting about a million page views per month. Back then that was pretty good. Also, people who were putting jobs on the site wanted to pay me to do that. And then people started coming to me to help run this site on a volunteer basis. And that made sense because I needed some help. For the most part, when something took more than an hour every day, I would just write some code to greatly simplify whatever I was doing. And that meant that what took me an hour or more would only take me minutes. There's a lesson there about writing code and productivity. But in '98 I tried running things with volunteers and frankly that failed pretty badly. So by the end of '99 a lot of the people who wanted me to succeed told me I had to become a real entrepreneur. I had to start charging people to post jobs and so on for sure not just in a half-assed way. And I had to make a decision about monetizing the site. So I figured I would charge people who were already paying way too much for less effective ads and that I didn't need to make a lot of money doing this. I remembered my teachers in Sunday school, Mr. and Mrs. Levan, telling me, you know, that I should know when enough was enough. So I monetized minimally. So that wasn't an altruistic decision. That was just me remembering what I learned in Sunday school because around this point through '98, I would go to industry events and parties. And the bankers and venture capitalists were telling me I should monetize everything as much as I could the usual Silicon Valley way. Sure, they would throw billions at me. And a guy recently estimated I could have made around 11 billion. His estimate jives with my guesswork. But again, I decided I would remain true to the moral compass my Sunday school teachers taught me. And so I made one really big decision because I had accidentally started a business up, but I did so in a way consistent with what I believe in. And since I wasn't taking investment money, and I never have, I could make these decisions on my own. I got lucky timing wise because the most I ever spent on the site was 35 bucks a month for web hosting services and that's kind of nothing then and nothing now. '99 that year I rewrote the code. I used a real database engine called MySQL. And after finishing some coding and then hiring some programmers, I stepped down from any coding responsibilities. Tech was led by a guy named Jim Buckmaster. He was running things. I was both being CEO and doing a lot of customer service. And this is through '99. But towards the end of '99, I realize I'm not an entrepreneur. I'm really bad at tough decisions like hiring and firing. Looks like Jim would be good at this. So around the end of '99 or so, I realized that I should step down as CEO, make Jim the CEO. He would do a better job. But while I kind of suck as a manager, I'm a great customer service rep. So, starting end of '99, maybe beginning of 2000, I'm not sure, I would just do customer service. And I did that and nothing but customer service until sometime in 2018 at which point I retired. The deal is that Jim has done a better job than I could. And any luck I've had with Craigslist or anywhere has been by accidentally being in the right time and right place, which kind of makes me the Forrest Gump of the internet.
Sure. Forrest Gumping around. Well, there are a lot of threads there I want to pull on. I mean certainly if you just kind of consider Craigslist in the context of the tech world today, we're in this era of social media dominance, algorithms controlling the feeds, now this whole frenzy around AI. And to me and particularly hearing you just reflect on the journey and I think the humility with which you approached your own leadership as part of it. I mean, Craigslist is kind of the antithesis to all of that. We talked about the discipline with which you approached the business model, you know, kind of grounded in your values and I feel that kind of permeates to design as well, which is something I want to talk about. But to kind of frame a few of these topics, there's this picture on the internet that maybe speaks to that 11 billion left on the table that shows the homepage of Craigslist and overlays a bucket of categories of startups over time that have been tailored specifically to unbundle specific sections of Craigslist and you can go, you know, Nextdoor, Tinder, Reddit, Zillow, Airbnb, and the list, it literally goes on. And I kind of wanted to understand, I imagine the pressure, it would have been very easy over the years to succumb to expanding beyond traditional classifieds into other verticals or to lean more heavily into ads. But what do you feel has kept Craigslist as one of the top sites on the internet today? Basically 30 years later, you know, users still love the site despite an entire industry of venture-backed companies that have been started and have been largely successful in their own right playing in the same space that Craigslist has. I'm just curious how you think about that.
Well, my deal is that we kept things simple. I built this philosophy of minimal modernization into the DNA of the company. Chose Jim because he believed in the same thing. He's kept the faith over all these years. It's been 25 and I said I could just focus on customer service. And then when the customer service team no longer needed me, I was able to go full-time in philanthropy in a way where my faith was rewarded. And starting in 2015, I started doing more and more philanthropy. Retired at the end of 2018, went into philanthropy full-time, and that's worked out for the Craigslist community, but it's also worked out fairly well for the country because my focus has been on good stuff for the country, for example, in cyber security and also to support military families and vets.
Yeah. And I certainly want to unpack the philanthropic work you're doing. Maybe one of the ways to broach that is, I mean a lot of things become very obvious in retrospect but in the moment maybe aren't so obvious at the time and as you began to build what ultimately is an online classifieds site, had you thought about kind of if at all the state of traditional classifieds in the world of newspapers and kind of the fundamental disruption at that time that Craigslist kind of played in the real fundamental disruption of an alternative industry in the transition to the era of internet.
I was thinking a lot about classifieds, mostly how to do it better way back. I realized that Craigslist would have an effect on newspaper classifieds. They were slow to catch up, but newspapers did start doing some of the same, but maybe too late. So, I've always assumed that Craigslist had a substantial effect on newspaper revenues. I thought that way until 2018 when an industry analyst named Thomas Beal actually ran the numbers and he tells me that he can understand how maybe my ego might play a role in thinking that Craigslist had an effect but he tracked it all the way back to, he tracked newspaper revenues back then and he's saying that TV news had a major effect on newspaper revenues starting in the 60s and continued on a straight line down until 2008 or so at which point Facebook and Google started consuming a lot of newspaper revenues. He tells me that he couldn't measure any effect from Craigslist. No blips. So all my concern was well-intentioned but wasted because the problem that newspapers had looks like it was all TV news until 2008 when Facebook and Google somehow around then became a problem. Why around then I have no idea. I don't think Thomas has ventured an explanation, but I thought about it. I didn't think of them as competition because the idea was just to do a good job serving the community and that continues to be the right idea. That's my idea of entrepreneurship. Do something real that benefits community and that works.
What did you learn from your time in the customer service part of the business? What sticks with you from that era doing customer service?
Well, I would see what a lot of people in the country were doing online and I saw that everyone everywhere in the country people operate out of goodwill for the most part. They want to get through the day. They want to put food on the table. And now and then they want to help each other out. There are bad actors out there, but the role of bad actors has been greatly sensationalized by people looking for clickbait. And now we have perception problems where again people are overwhelmingly good both online and in real life. However, there are bad actors who exaggerate the prevalence of bad behavior, of crime. They usually do so to make a profit and they don't care who they hurt.
How did your thinking on those kinds of adversarial actors online evolve over time? You know, I imagine when you had started, you know, just from your own list did not maybe think about or envision at scale, but inevitably with a free public online platform. I mean, we're seeing this obviously across many platforms today. This sort of unbeatable problem of anonymous adversarial people online and just the way that changes people's behavior. But just how your thinking on that evolved.
I've been thinking about it a lot for 30 years. In part my thinking was affected by my high school history and civics class which was really good. Basically, I learned that, hey, you want to help the cops fight the bad guys. But in our country, we have this constitution and the bill of rights and other amendments which basically say that the accused have rights. They're innocent until proven guilty. And there's all this due process stuff like search warrants and subpoenas. And that stayed with me until around when I started Craigslist. I also met up with folks from the Electronic Frontier Foundation, which had just started around the same time, and they were trying to figure out what rights do people online have, and how do you fight for those rights while helping out the cops? And that started my thinking out. So from the very beginning I was talking with people who were genuine smart people about rights online. From kind of the beginning I was starting to talk with cops about what they needed to do to help fight crime online. And I've never stopped having those conversations. And the deal is that on the one hand you want to fight bad actors. You want to fight crime. On the other hand, I'm very committed even on an emotional basis to protecting the rights of the accused, to the idea of innocent until proven guilty. And our constitution as amended particularly with the Bill of Rights. The founders of this country did a really good job with some mistakes which have been fixed in large part and that shaped my thinking and I've stuck to it. I preach this, I practice what I preach and that's been pretty good. In the last couple months, I've realized that I need to renew my commitment to fighting crime online and in particular I need to do more work on fighting scams online as part of my cyber security efforts. The problem has been that with Craigslist, the most crap I've gotten from people have been when the company does a good job of fighting crime online. Because while you're doing that, while law enforcement operations are in progress, you can't talk about them because when you talk about them, the bad actors, the crooks, see what you're doing and figure out how to work around that. Unfortunately, while you're being discreet about this, different bad actors find that they could run different scams, often fundraising scams, that kind of thing. And then they start talking about crime fighting operations. And once they start doing that, the cops start saying, 'Hey, these things are growing less effective.' And at some point they say, 'Thanks, but it's not worth it anymore.'
Yet, I think despite perhaps the misguided perception one way or the other, it's still one of the most trusted platforms in the country, you know, for connecting people even today.
Yeah, thanks. The deal is that people see that we're for real. Craigslist is about helping people get through the day to put food on the table. And that's it in the day-to-day sense. In the longer run, Craigslist helped tens of millions of Americans realize that the internet is actually useful for something, that it's reasonably easy to use. As a company, we don't have to squeeze every dollar we could out of the site. I do want to give special credit to one other site which has maintained a great moral compass, specifically Wikipedia, which like I say, Wikipedia is where facts go to live. And Jimmy Wales' vision of a free site for knowledge for everyone. He stayed true to that and now the people who run it, the Wikimedia Foundation are keeping the faith and I help out however I can both with contributions and funding things like Wikipedia classes for beginners.
Yeah. It's certainly a kindred adherence to principles. The lore of Craigslist is also pretty legendary. I mean, I certainly remember growing up and going through people's compiled best Craigslist listings of all time. Hilarious ones, misconnections, famous ones like the yoga mat for sale, used ones. There are just a lot of legendary moments out there. Are there particular ones that you find yourself reminiscing on, you know, over the years?
In terms of ads, not as much as you'd imagine because I've always felt like there's a bit of a conflict of interest. I just wrote about this on the theme of this Craig used Craigslist and I sold my next to last car ever, a Saturn, through the site. And I'm careful about that. And frankly, I'm lucky that my wife, Mrs. Newmark, has taken on all the Craigslist duties for the last 10 or more years. When we want to give something away free, she handles it. When we want to sell something, which is rare nowadays, she'll do it. Maybe more importantly, she will use Craigslist to buy stuff a lot for our family because people in our family, they don't want anything that we would buy new for them. But if Mrs. Newmark can get a really good deal by buying something on Craigslist, she'll do that. And I think she's gotten a lot of really good vintage furniture on the site and that works out pretty great, which means I don't have to think about that kind of ever. And our last car, because I don't drive anymore, we just gave away to people in the family because there's a lot of kids who are now driving age. And they need the car which I bought like 20 years ago.
Yeah. Oh, that is pretty interesting. So, you found yourself not so much as a user of the platform itself.
Yeah. The deal is that I've always wondered what would be ethical, what would not be ethical, and I've never resolved that. Although my friends and advisers tell me I thought about it too much and we should just use it. And Mrs. Newmark didn't ask for permission. She just did what was useful. And in my case, I thought I might have to beg for forgiveness, but that never became a thing.
Yeah. So, if you were to go to your own website, you know, today, if you went to Craigslist, it's kind of astonishing because it's simple, it's fast, it's still text-based, and I think most interestingly, it's largely the same minimalist simple aesthetic that it's been. Much like you resisted maybe the pressure on the business model and monetization side. Just what's been your philosophy on design and aesthetic of the website?
Well, in '96, remember that's when I realized, oh, I'm a programmer. I can write code and get web publishing for free. I was thinking about the site and maybe it should be fancy and I realized I have no skills for making it fancy. All I know is to keep it simple and to the point and fast. That's how we started. That's the design philosophy that Jim maintained. And over the years I've realized that fancy doesn't usually do people any good. It usually means that things are hard to figure out and slow and buggy. Like I use one particular airline site a lot. They got fancy and they are buggy and they don't seem to be able to ever modify the site without introducing newer bugs as they fix them. So simple, fast, to the point. That's a good approach well to everything.
