He turned down $11 billion, here’s why | Craig Newmark (Craigslist Founder)

Craig Newmark (00:00:00):
VCs and bankers were telling me, "Hey, Craig. Do the usual thing. Monetize everything. We'll send billions in your direction." Recently, the only estimate with any reasoning behind it was done and they tell me that I turned down about 11 billion. That doesn't bother me because my moral compass was set in Sunday school. They told me that you should treat people like you want to be treated. You should know when enough is enough.

Eric Ries (00:00:38):
Welcome to this episode of The Eric Ries Show. Recently, I had the privilege of speaking with Craig Newmark, the founder of Craigslist. One of the most iconic and widely used online marketplaces in the world. What started as a humble email list in San Francisco almost exactly 30 years ago has evolved into a global platform serving over 550 cities. Helping millions of people find jobs, housing, and community. Craigslist, in many ways, has become so much a part of the Internet's infrastructure, so ingrained in our daily lives that we sometimes forget how revolutionary it truly was. I think some of us even forget that it had to be created in the first place.

(00:01:15):
In this conversation, Craig shares insights that I think every founder could learn from. We discuss his unconventional path to entrepreneurship, rooted in his deep commitment to community. He's not about chasing wealth. He actually talks about turning down an estimated $11 billion for Craigslist. He talks candidly about resisting the pressures of commercialization and how his moral compass has guided Craigslist's longevity. Why he believes knowing when enough is enough is a principle more of us should embrace.

(00:01:46):
But that's not all. Craig also opens up about his passion for cybersecurity and the ongoing threats to our national infrastructure. As well as his extensive philanthropic work supporting journalism, veterans, and even pigeon rescue efforts. In an era where exploitation and the accumulation of wealth at all costs are being valorized every day, it's really refreshing to hear from someone whose goal is just to build something with lasting impact, who stayed true to his values in a world obsessed with other things, and whose unique path, I hope, will inspire some of you to do things a little differently. Here's my conversation with Craig Newmark.

(00:02:24):
So Craig, thank you very much for doing this.

Craig Newmark (00:02:27):
Hey, it's my pleasure. I'm glad to be here.

Eric Ries (00:02:30):
Okay. So let me take you back. Because Craigslist, that's the thing that you will be most famous for, I think, forever, will be the site that is named after you. And I get the sense now that the story of how Craigslist came to be is not as well known as you think it would be. In fact, when I talk to people about it, they act like it's always been there. It's like a piece of infrastructure that just... How could it not have existed and how could we not live without it? And it's really remarkable that it's been a very consistent part of people's lives now for decades. Just go back in time, tell me a little bit about how it came to be. You couldn't be more different than the typical stereotype of a founder. Young founder drops out of college to do their venture-backed thing. Craigslist, it's got a totally different origin. So tell us that story.

Craig Newmark (00:03:18):
Yeah. I'm, at best, an accidental entrepreneur around 30 years ago and the 30th anniversary is soon, like March-April timeframe. I was in San Francisco, a lot of people helped me out. We were talking over the net and they tell me about what neighborhoods are like, places to eat are like, people who might be happy to socialize. Particularly with someone with the limited social skills I maintain. So I was part of a community and I figured, "I should give back to the community."

(00:04:00):
So I started... I would post events I heard about, which usually involve the technology, maybe arts, maybe technology used to express new art forms. That worked out really well for me. People started asking me to add them to the little mailing list I had. And it wasn't a Listserv then, it was just a CC list in the Pine email tool-

Eric Ries (00:04:28):
Oh, yeah. Taking us way back.

Craig Newmark (00:04:30):
Pine is the very, very old email tool. If you know what it is, you're probably an old guy, but not as old as me. But anyway, I just kept plugging away-

Eric Ries (00:04:41):
It's like an email equivalent of us having to have walked uphill both ways to get to school.

Craig Newmark (00:04:46):
That's exactly right and I am an old-timer. I'll credit you with that too.

Eric Ries (00:04:51):
Oh, for sure. I used Pine in my shell. I remember it very fondly.

Craig Newmark (00:04:56):
It's fun.

Eric Ries (00:04:58):
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Craig Newmark (00:06:43):
It spread word of mouth. People told me about more things. It spread word of mouth, spread more word of mouth. And in the middle of '95, the email tool I was using, Pine, for a CC list, broke maybe about 240 addresses. And then, I had to ask around for a Listserv. A guy named Eric Theis said, "Hey, you could use mine. You got to give the thing a name." And I was thinking, "It's still mostly events. We'll call it SF Events." I'm a nerd. I'm very literal.

(00:07:20):
People around me told me, "Hey, we already call it Craig's List. Craig, you've invented a brand and Craig, here's what a brand is," because I didn't know. They were right. That's what people wanted to call it and with my name on the thing, it meant that I would take it personally and commit. So again, just kept plugging away. Sometime later, maybe '96, it's still me. I remember, "Oh, I'm a programmer. I can write some code to take email which has a predictable format. I could turn that into instant web pages and I had instant web publishing for free." So that's the first site around '96.

(00:08:10):
And then, people were suggesting more categories and so on. Just kept plugging away. Just kept growing. Both delivered via email on the web. '97, I remember the end, a few milestones. In about a million page views per month, which was good then. People who post a job said, "Hey, Craig, let us pay you," and some volunteers approached me saying, "Let's make this a volunteer thing," and we tried that in '98. But towards the end of 98, some of the old timers on the list who had been there a few years told me, "Volunteer stuff doesn't work. Things aren't getting done." I had to make it into a real company. I had to make some decisions about that.

(00:09:05):
For example, what was the business model? Because VCs and bankers were telling me, "Hey Craig, do the usual thing. Monetize everything. We'll send billions in your direction." Recently, the only estimate with any reasoning behind it was done and they tell me that I turned down about 11 billion. That doesn't bother me because my moral compass was set in Sunday school. They told me that you should treat people like you want to be treated. You should know when enough is enough. And I was doing really well as a contract programmer. And I figured I could at least recover the costs with Craigslist if I adopted the monetization policy, that we would charge people who already were paying too much for less effective ads, so the policy of minimal monetization was adopted.

(00:10:11):
Looking ahead towards the here and now, that's still the Craigslist policy and that may be the core of a minimal or even no enshittification. I'm skipping ahead there, but the message is that, "I decided on this. It is not altruistic. It is not pious. This is just how my moral compass was set around 65 years ago. And I just stuck with it, embedded it into the code, the DNA of Craigslist."

(00:10:51):
In that timeframe, it took me about a year. But people helped me understand that as a manager, I suck. But I had already hired a guy, Jim Buckmaster, better at it than me. He kept the face, minimal monetization. He added a whole bunch of new cities, added new categories, kept the spirit. And that's why to this moment, I feel we have minimal monetization and while we've prevented serious enshittification. Me, I became full-time customer service rep and I did that for a very long time until, depending on how you count, let's say, eight years ago. And that's when I started doing philanthropy seriously. And I retired six years ago to do full-time philanthropy.

Eric Ries (00:11:52):
Well, congratulations. It's been quite a run and I want to get to the philanthropic work that you've done, because it's super interesting. But what I think what's so striking about that story is you tell it in such a matter of fact way and I've heard you tell it many, many times over the years. But you make it sound almost obvious that it just was a very natural thing to do, but almost every part of that story is very unusual. And so, I want to know if you just will go back in time with me and look at some of those moments. I actually hadn't really processed until you're just telling me the story just now. It wasn't even a website for more than a year, but you were a professional programmer. That surprised me. Why didn't you make it into a project right away?

Craig Newmark (00:12:36):
I just didn't think of it. Email is a great tool. It was great then. It's great now. And having something like a party invite or a job or an apartment that may have just gone on the market, email is the best way to get it to you. You would subscribe to what you want. If there was something that you were interested in but not in real-time, you would subscribe to the digest. So it met real human needs and that was a big design feature. The idea is what people wanted, and this is guesswork at my point, people want something which is fast and simple and obvious. And that's the site design, which I started in '96. And what we have now is basically a straightforward evolution of what I started in '96, but the philosophy is ordinary in terms of how we're taught to be people-

Eric Ries (00:13:44):
Yeah. And more about-

Craig Newmark (00:13:46):
... when we go to Sunday school-

Eric Ries (00:13:48):
Say more about that. Yeah.

Craig Newmark (00:13:49):
When we go to Sunday school in whatever form, no matter what your religion is, people are generally taught to treat people like you want to be treated. People may be normally taught, "Know when enough is enough. You don't have to be all about money and sometimes you should be your brother's keeper or your sister's keeper." That comes out in all the major religions in some form or another. And I'm a nerd. I'm a rule follower. That was pretty much made part of my core moral compass. And without thinking about it, I just followed through and I guess I got lucky.

Eric Ries (00:14:43):
Well, there is certainly, as in any entrepreneurial success, there's a lot of luck there. But also, it really strikes me... And of course, this was so much part of your story, from playing the role of customer service and even in the way that the thing started, this was always very closely connected to the social community in which you were embedded. Starting in San Francisco and then being part of all these other communities.

(00:15:03):
And that's the other thing I wanted to ask you about. Again, that's so different. We're living now, 30 years later, through an era defined by social media. And a lot of people have been talking about how anti-social, social media actually is. How destructive of community it's turned out to be, how out-ofistic, how individualistic. And you can see the founders of those companies have also... Some of them have gone, basically, very visibly crazy despite all of their wealth and power. And so, I wonder how you think about that. Craigslist is like the original social technology. One that stayed close to what people actually wanted, that turned out to be promoting of community rather than destructive of it. Was that an intentional choice?

Craig Newmark (00:15:44):
That wasn't an explicit, conscious spoken out kind of choice. That was me just operating both from my moral compass with what I saw from other people. The first virtual community that I seriously joined was something called The Well-

Eric Ries (00:16:03):
Oh, yeah.

Craig Newmark (00:16:03):
Whole Earth Electronic Network and I saw people treating each other with great respect and help. People would sometimes contribute really expensive consulting, medical help as needed. That worked out really well for people. Through that group, I think I heard about the virtual reality special interest group which met monthly at The Exploratorium in San Francisco. Now, VR back then was about 25 years premature. The vision was great, the community was great, but the theme was that people could actually help out people and that... Oh, that was all pretty consistent and fed into my moral compass, so I decided to practice what I preached. And I just didn't know any other way of doing things. This was frustrating to the VCs and the bankers who wanted to make a lot of money from this kind of thing, but I am a pretty stubborn nerd.

Eric Ries (00:17:08):
So talk about what that was like. Because I mean, I have worked with so many founders over the years. And for most people, the siren song of world historical, generational wealth and the allure of working with these bankers and VCs and famous people, there's a siren call to that, that has pulled many, many, many people down that path. And they don't even view it as a choice. For them, it's just an inevitable thing. Of course, it's what you do. Just talk about what that was like and why you think you didn't go down that road.

Craig Newmark (00:17:38):
Well, everyone has their own personal value system. Everyone wants to do what's right for them and maybe they're thinking about other people too. And I'm not going to judge anyone else's moral compass. It's just that something about the net, starting in the mid to late 1990s... Well, people got attracted to all the money and power they might've accumulate. And the buzz in the press was that lots and lots of people are making lots and lots of money and that was the norm.

(00:18:17):
And a lot of people are interested in luxuries and stuff like that, fancy cars and fancy places to live, private jets, and all that. And due to my nerdly dysfunction, I'm not interested. I do like my own idea of luxuries. Like I buy all the books I want. I have all the streaming services I want. I have small homes in both New York and San Francisco, since I'm connected to communities in both places. Also, our family is very large and likes to visit. A lot of that happens, so that works out. But again, the question from Sunday school is know when enough is enough. And at some point, it's more satisfying to change the world maybe. And somehow without conscious thought, I've stumbled into a number of areas which is helping a lot of people.

Eric Ries (00:19:25):
Well, that's what I think is so interesting about it and you went through this phase of thinking about maybe it was going to be a volunteer thing. And I think a lot of people hearing you talk would say, "Oh, it's about Sunday school. It's about moral compass. It's a nonprofit. Sure. Why not?" And you went down that road, you explored that a bit and you decided, nonetheless, to make it a for-profit company.

(00:19:43):
And I really wanted to single in on that decision, because so many people assume that once you become a for... I can tell you. Many people have told me this verbatim. Once you decide to become a for-profit company, it's just a matter of time before you sell out to investors, before you become about maximization of money and putting profits over people. And as you said in Cory Doctorow's famous phrase, "Enshittification follows next," so like as if it was not a choice but a gravitational pull. You nonetheless decided to be a for-profit company anyway and resist that pull. So did that seem like a strange or a difficult choice to you at the time or what were you thinking-

Craig Newmark (00:20:22):
When I made that decision, I winced a little thinking that maybe I'm cheating myself, maybe I'm missing out on something. But what I did just felt right. It felt completely right. And I was lucky in that when I did that, that was the beginning of the transition for most of the industry to the high-profit model. Out of some combination of stubbornness and dysfunction, I decided to stick with what felt was right. I got lucky. Very lucky in the sense that I was able to do things for essentially no money. I mean, the coding and maintenance, especially in the first few years, was all my time and my time only. I know I wasn't paying much for hosting costs, because this was a very low volume site for years. And I do remember paying something called Best Communications, maybe 35 bucks a month, which of course is noise level, particularly for someone who's beginning to make a consulting piece.

Eric Ries (00:21:35):
Sure. But again, the fact that it was so inexpensive was itself a choice. I mean, there must have been people who came up to you and said, "Well, you got to have a fancy design. You got to have a more elite brand. If you want to change the world with this, you're going to be left behind by all these venture-backed competitors who are doing all this fancy stuff that you're not doing." Tell me if people said that stuff to you.

Craig Newmark (00:21:58):
People said all that to me. I guess I just didn't care. Status stuff, prestige stuff, generally doesn't matter to me. Again, I can be self-indulgent at times, but not in the way that you'd expect me to be. Maybe it's limited imagination on my part. I knew what I was doing. It felt right. And when I did start acquiring substantial money, all still very surreal. And I figured, "Well, I'll do enough to provide for family and I have to keep Mrs. Newmark happy." And beyond that, I have discretionary cash and there are problems in our country that need help. For example, I started supporting vets' groups, figuring that they gave up so much, they sacrifice so much to protect us. They were giving up a lot, risking their lives to protect me, so I should do something about it. Then, I realized active service military families, they're giving up a lot to protect people-

Eric Ries (00:23:07):
Yeah. For sure.

Craig Newmark (00:23:08):
... so I should help them out. And then, I more and more realized the country is under attack using what the Russian military call hybrid warfare. I should do what I can to help out. The people I support are way braver than I am. And so, this is my pale echo to what they do.

Eric Ries (00:23:31):
Mm-hmm. So yeah, skipping ahead. So the other thing I think is really interesting about your story, because again, I counsel so many entrepreneurs, so I really have this in mind. People have this idea that if they go into entrepreneurship and they're a success and they make all this money and they do all this stuff, one of the rewards of that is getting to become a philanthropist. Getting to have influence in the world and get to do good stuff.

(00:23:53):
And yet when I tell them... If I tell them a story like Craigslist, they'll say, "Well, that's not going to work. I don't want to be a nonprofit. If I give up my chance to make money, then I'm not going to get to do all that cool stuff." And again, you have found this middle path where... I guess I don't want people to think you've taken a vow of poverty, like you've nonetheless been able to be [inaudible 00:24:13]. Craigslist is a very successful thing and I think about all the competitors that have come and gone, venture-backed and banker-approved and prestigious or whatever, over all these decades. That maybe made some money in the short-term but did not have anything close to the world-changing or sustainability aspects of Craigslist. You've been able to [inaudible 00:24:33] source of consistent income for you too. Just talk a little bit about that like, how do you make money from Craigslist and how have you been able to say, "That's enough. I don't need $11 billion, but I do want to make some money."?

Craig Newmark (00:24:49):
The deal is that we charge people who normally would be paying for those ads, charging a lot less. Like a car dealership should pay, apartment brokers should pay, people posting job ads should pay, and it's not a lot but that's what works. Sometimes we've charged people in response to, "Well, if you charge people a few bucks that way, that category doesn't get enshittified." And as I say that, I realize that 15, maybe 20 years ago, we did have an enshittification problem that New York City apartment brokers, where that was free to post, they would just post the same apartment ads multiple times a day and those categories just grew way out of control.

(00:25:40):
We decided the only way to limit that was to charge apartment brokers a very small fee. Because that way, if you have to pay something to charge it, you're going to post less. But we wanted to do what was fair. I actually came to New York. I spoke to apartment brokers, asking them what their financial situations were and I found that a new apartment broker would only make like 20,000 a year. That's the kind of job that you need four or five of to break even in New York. So we decided to charge people very little money for that. So that fixed that enshittification problem.

(00:26:30):
Other than that, I'm not current with what's happening on the site, because I have retired. But the philosophy is that, "Oh, do what your community wants and needs." Sometimes it's hard figuring that out and what we did find was a good hybrid of nonprofit or for-profit. B Corporations happened after the fact. Maybe that would have been an answer, but I guess we created our own. It works great. And sometimes if it works, don't fix it.

Eric Ries (00:27:08):
I wish more companies would learn that lesson. And I always ask people to think about it from the point of view, we're all customers of technology and how it feels like whenever your favorite app has an update. How long has it been since you had an update for some piece of technology where like, "Oh, goody. I'm so glad they changed the interface. I'm sure they made it better." And yet, we have these companies that have thousands and thousands of people working on them, trying to figure out how to make the product better, and they can't leave well enough alone. Often, because they are chasing after financial performance goals that are unrealistic, but are designed to drive a chair like this. They're a part of this whole gravitational dynamic that you were able to opt out of.

Craig Newmark (00:27:47):
Yeah. We got lucky in some ways. Since we're not advertising supported, we have no need or Craigslist has no need to artificially create engagement, where the purpose of engagement in that sense is not community. And so, they have more space to throw ads up there. Often, the algorithms on some social media sites, they are focused on driving engagement even if they're engaging with people who are lying to them, if they're trying to radicalize them. And that's not only bad for the country, but it's really hurting us as a country. I don't have any broad ideas, because solving that is going to require social skills. And like, have you met me?

Eric Ries (00:28:40):
Well, it's funny you say that. And yet, again, by contrast to social media, the business model alignment that Craigslist has with its actual customers allows them to use Craigslist to build community in the real world. Whereas, engagement based algorithms necessarily take people away from the real world into the virtual world in order to generate more engagement, even if that's destructive of community so-

Craig Newmark (00:29:03):
Yeah.

Eric Ries (00:29:03):
Yeah. I mean, I see you're self-deprecating, want to talk about that as being antisocial. But I would say, in some ways, that's having tremendous respect for people's social reality.

Craig Newmark (00:29:15):
Both are true. Well, let's say my social skills still need considerable improvement and I'm a man of 72, it's about time. But somehow in the process of being better socialized, I started a tool which people use to connect for real community. Now, maybe there are some better tools these days, but Craigslist accomplished that in a great deal, maybe in its first 20 years. I think it still does now. And the idea is that, well, we as a company have a mission and keep on it. Again, I did retire from the company, but I'm still connected, if nothing else, through board membership, that kind of thing. I still do a few things, but we do operate and we're structured very differently than anyone else. Everything works out oddly. And it's odd, the reporting on Craigslist, which I sometimes refer to as us. Sometimes it's right, sometimes it's wrong. Anything you read about financial numbers, revenue, you want to assume that's wrong, because people don't have access to the internals and the internals, you may not be able to guess them very well.

Eric Ries (00:30:40):
Yeah. Do you want to say anything about the size and scale of Craigslist, just for people who don't realize how big and impactful it is?

Craig Newmark (00:30:47):
Well, the size we have, I think, like 550 cities, that kind of thing. Although we're mostly a US site, a number of people, maybe about 40 or something like that, were making a fair amount. Maybe not as much as we used to. But again, given our objectives, we don't need to make a lot of money. We don't need to make VCs and bankers happy, which is good because they can tell you what you need to be doing. And if it means spreading misinformation, if it means hurting people, the VCs and the bankers, shareholders can do that. And that is a real thing on some big sites.

Eric Ries (00:31:36):
So I know you've done a lot with cybersecurity. And I just had to ask you because it's in the news right now that there's been this massive alleged Chinese hack of all of our mobile phones and mobile phone data. And I don't know, it struck me like when there was those NSA revelations about American government spying on Americans. It was mass outrage. Somehow, this story seems like it's totally passed under the radar and the fact that we're being spied on by foreign adversaries, no one seems to be paying attention to. Just... Yeah. What do you think about that?

Craig Newmark (00:32:07):
A lot of people in the cybersecurity community and the military are paying a lot of attention because the Chinese military has been attacking our infrastructure for some time. The two programs you hear about are Volt Typhoon and Salt Typhoon. Volt Typhoon has me really worried. They're talking about compromising our infrastructure like water, power, hospitals. So that in the case of a shooting war, they can turn off our water and electrical grid at home. That's bad. They could also screw around with our telecom services. Not only spying on us, but shutting it down selectively. And if you're trying to get hold of a first responder, because something bad has happened, if you can't get to them, that's also going to be a real problem for you.

(00:33:04):
So we do have real problems right now. The regular press needs to get a lot louder for a longer time about this. But meanwhile, there are cybersecurity people acting in goodwill to help better protect the country, so that our infrastructure and telecoms can take a punch. And even if they're knocked down, they can get back going again. Because if your water is shut off for an hour, you want it to be able to come back up in another hour. That's what people are working on.

Eric Ries (00:33:38):
How did you get interested in cybersecurity as an issue?

Craig Newmark (00:33:42):
I got interested in it when I was back in college for my thesis work. This is about 1975. My interest has come and gone over the decades. But now, I've seen, just by observing, that our country is under attack and it's up to regular people to do what they can to help out. Just like we all try to help out, Americans tried to help out, during World War II. I mean, I don't know what role I'm going to play. Maybe I'll be like Paul Revere alerting everyone. What we need is a General Eisenhower or General Washington to rally everyone. And for sure, that's for a person who has a lot more skills, a lot more social skills than I have.

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(00:35:30):
So let me go back again to this question of how Craigslist is structured. Because the other thing, I think, is really fascinating about this story... We're living in a moment where founder mode is a whole meme going around now. There's been this anti-manager push like, "Managers are bad and founders should be getting rid of all the managers they, themselves, hired. And cutting through all the stuff that they themselves set up," which maybe that's a conversation for a different day.

(00:35:55):
Another thing that's very unusual about this story is you took yourself out of a management role early on. Turned the company over to a really competent CEO. And a lot of times when people hear a story like that, that's the prelude to them talking about how the company lost its direction, lost its soul. Brought in professional management and then things went haywire. Again, one thing that's so interesting about Craigslist, how consistent it's been now for... I can't believe it's 30 years now. It's just incredible. What do you attribute that to, the fact that you've been able to keep the values and the moral compass of this organization over such a long time?

Craig Newmark (00:36:33):
Well, Jim shares the same values that I started with for the company and we make more than we need. Jim, himself, is not motivated by money all that much. So we just keep doing what we're doing. We don't pay much attention to what competition does, unless they try to pull a fast one. From-

Eric Ries (00:37:00):
Do you have any funny war stories about that?

Craig Newmark (00:37:06):
I have more confidentiality agreements than I have war stories. And right now, I'm just trying to track down an article which disappeared, but it's in the Wayback Machine about some companies which did try a dirty tricks campaign and I have to see what happened there. It's possible the newspaper or a magazine that ran the story, maybe they misplaced it because they had some really good reporting on something. We'll have to check that out later.

Eric Ries (00:37:41):
I see.

Craig Newmark (00:37:41):
The deal is that in the dot-com world, sometimes bad things happen. Sometimes bad things are exaggerated to make a competitor look bad. A lot of things do happen, but our focus is on going straight ahead, observing the community, and seeing what happens.

Eric Ries (00:38:04):
You never worried about your employees, like... So you're not motivated by money. Maybe your CEO is not motivated by money, but you still have people working for you. You were never worried about hiring somebody who seemed like they shared your values and then turns out that they start making decisions to move the site in a more exploitative direction? How did you prevent that from happening?

Craig Newmark (00:38:24):
Well, remember, I stepped down from management very early. One of the reasons is that I really dreaded the whole hiring or firing process. The deal is what Jim did is he just hired people who really seem committed to the value system. But on top of that, paid really fair salaries with really fair benefits. So I guess we had both belief system and good rewards to make things happen. Me, things have worked out better than I thought, that's why I'm giving so much of it away.

Eric Ries (00:39:04):
Yeah. You mentioned competition and I really want to ask you about this, because it was this... In the venture community, there was this big meme... Gosh. This is in the Web 2.0 era. That massive amounts of money were going to be made by slicing off pieces of Craigslist and building whole venture-backed companies out of every little piece of it, as if Craigslist was this free market research tool. Do you remember this?

Craig Newmark (00:39:29):
I do remember it. That theme, the meme itself, the visual, pops up about once every four months, six months, something like that. And some people doing that kind of thing, it's worked out real well for them. I wish they hadn't done bait and switch on our site, because that was quite a problem for a while and may still be. I don't know. But there are sites which are helping people. They're creating jobs. Those are good things. But if you begin your existence doing deceitful things like bait and switch, that may have implications which people haven't figured out yet.

Eric Ries (00:40:16):
Yeah. It didn't bother you, all the billions that were being made off the back of your work?

Craig Newmark (00:40:23):
I don't think it was off the back of my work. People did something which helps people. They had a different philosophy and I'm not going to go all judgey on anyone. Oh, this is funny. Sometimes it's funny. But normally, I try not to do that.

Eric Ries (00:40:40):
You know, I'm asking these questions. I feel bad like here you are a living what seems to be a very centered life. You have a lot more equanimity and sense of contentment than many of the billionaires that I know. And I guess what I want people to... I think there's so many people who are going to be watching this and they're like, "But that's not for me. I can't have that." But then, they take a path that they think is going to make them happy that winds up making them miserable. So I wonder where you think that sense of centeredness comes from?

Craig Newmark (00:41:13):
I don't know. Perhaps it lies in being particularly unimaginative. Part of it is that Sunday school thing. And then, part of it is knowing that I have much of what I want. I still need to get a lot better at communicating for very large numbers. And now and then, again, I can indulge myself. I sometimes just can't help tinkering with my technology. Like I might replace a long messy cord with a short cord that just fits. And I'm afraid I'm being quite serious when I say that I am motivated that way.

Eric Ries (00:41:55):
Yeah. Sure.

Craig Newmark (00:41:56):
But more importantly, I've met really rich people, sometimes billionaires. They are no happier than anyone else. I mean, once you satisfy basic needs, maybe for yourself, your family, maybe more, once you do that, then what's the point of all that? Yeah. Again, little luxuries are just fine, but decide what really matters to you.

Eric Ries (00:42:23):
Mm-hmm. Zooming out a little bit, what I think is so... The reason I wanted to have this conversation is there's this category of organizations, companies... We don't even really have good language for it. I call it civic infrastructure. You got the Wikipedia slogan right behind you on your desk. So yeah, Craiglist, Wikipedia, these are organizations that once they exist, people can't imagine how we ever lived without them.

(00:42:47):
And they play this really important role in our society, usually in governing or structuring large swaths of cultural or economic activity. And if you study them, they tend to be really different than your typical company. I've tried to build companies like that in my life and help other people do it. And one of the things I think is really interesting about it is that the typical company building advice we give people in the venture-backed startup community doesn't seem like it works real well for companies that are actually truly, genuinely designed to change the world in that way. And so, I just having... You've been involved in Wikipedia. You've been around other founders who've done things like this. If someone has that ambition, that like changing the world is not a joke, they really... It's not just a slogan, but they really believe in it. They want to use a for-profit company to do that. What advice would you give them?

Craig Newmark (00:43:42):
I guess people need to ensure that they're in touch with what's real. You have to feel the realness of the thing and talk to people. Because a lot of what's come and gone in the dot-com world have been ideas that sounded great, but they didn't connect with people or sometimes they were just too early. And so, you do need to do something that's real, that people want or might want when you tell them about it. And a lot of the things that I've heard about over the decades have sounded like nice shiny ideas that no one really wanted.

Eric Ries (00:44:24):
I don't want to name any names, so I'm not going to take the bait. I have so many companies I would love to ask you about, but I know it's not fair to dunk on individual things that have come and gone. Because of course, people have made a lot of money from those things. And as you say like, "Who are we to judge?" I don't know. I've helped so many people start companies and make so much money doing this now for [inaudible 00:44:46]. See, I'm getting a little old myself. And I don't mind. I don't begrudge people, their wealth, and power and status that they've gotten through that, through... I think it's wonderful. I just begrudge how miserable so many of them are.

Craig Newmark (00:44:58):
Yeah. It seems that the richer you are, the fewer your chances are for happiness. Among the big billionaires, that's what we see. There are ones who are quiet about things. And maybe, they actually are doing what they need to be happy. I don't hear much publicly about Larry and Sergei, so I think they are probably doing great in this sense. But there are others that you hear about and they just don't seem to be happy. And sometimes, they're getting even less happy.

Eric Ries (00:45:35):
Yeah. Well, and I think for those of us who are builders, and company builders in particular, there's this sense of the constant sacrificing and compromising of your core values that is necessary to be successful, that I really think grinds on people, really wears on them. And it's part of this mental health crisis that we're seeing and I almost think it's too painful for people who've made those sacrifices and compromises to be told that it doesn't have to be that way. So this is real narrative. I feel a lot of people spend a lot of energies is talking about how things like enshittification in Cory's wonderful phrase. But even if you don't buy into that framework, the way things are is basically inevitable. Once you go down this road, it has to happen that way. And so, yeah, you're around people who are the living proof that it doesn't have to be that way. I'm just curious, what's your perspective being outside that whole system?

Craig Newmark (00:46:29):
Well, for me, personally, again, all very, very surreal. And people have asked me this a lot and I think my experience is possibly unique. Because in the time and place I started, I had the... Well, I could build a low volume site, because everything was so new then. I didn't need to take money to do that. I'm, in some respects, stubborn and unimaginative, and then I can do that. Meanwhile, 5 or 10 years after that, if you're going to build something, it's going to require a lot of infrastructure which is going to require a lot of VC or banker money. So that means that to some large extent, they are the boss and they are going to insist on a payback after so many quarters and not many of them are willing to take the long view. So yeah, who pays the piper tells the tune. And by luck, I was able to avoid that.

Eric Ries (00:47:38):
I do think it's one of the things that's really interesting about the new generative AI, which is not without its problem. So one of the things, I think, that's really interesting about it is the possibility of recapturing some aspect of that era. The amount that an individual person at low cost can create is about to be really different than it was even a few years ago and I'm curious if you've given that any thought. Do you think that might allow people to recreate the experience that you had in some way?

Craig Newmark (00:48:03):
Well, in terms of building generative AI in large language models, the infrastructure for that is very expensive. But maybe-

Eric Ries (00:48:17):
I mean, those [inaudible 00:48:17] using it. Sorry.

Craig Newmark (00:48:16):
The people who use-

Eric Ries (00:48:17):
Using that infrastructure to build something new. Yeah.

Craig Newmark (00:48:20):
Yeah. The people who use it for things, I hope the whole thing unleashes a lot of creativity of an unpredictable nature. We are talking about technological discontinuities. You could call it singularities, if you wish. And the part of me that's always read too much science fiction hopes that people will find ways where we surprise ourselves and do things which are seriously new that no one would've imagined. I'm hoping for that. But more specifically, for example, I'm hoping we find new ways to both do drug discovery. And maybe, we even find ways to do enhanced or accelerated drug testing.

(00:49:05):
That smoke that may be just idle fantasy on my part, people are talking about it. No one knows. I'm hoping, but also fearing that we could develop artificial general intelligence, serious reasoning. But I do hope that doesn't... Well, let's say it's tough to consider. Maybe that'll turn into... From artificial general intelligence, it could erupt into sentience or self consciousness, self-awareness. But now, we are in the area of science fiction which is one actually that I like a lot. Because then, you get to ask... Well, if a machine becomes self-aware, I would argue it's become a person and it's qualifies for what we think of as human rights. But that's a matter of science fiction. So far.

Eric Ries (00:50:05):
So far. Are you in the fast you take off or the slow take off camp? Do you believe this is imminent?

Craig Newmark (00:50:12):
I plain don't know. The arguments are balanced. My only hard concern is that when you're training a large language model, don't train it on a source that you know is going to lie to you. Because that way, you're deliberately embedding a lying into your chat system and lying is a bad thing. Something I learned in Sunday school, although maybe a few years later in Hebrew school form, is that it is wrong to bear false witness. Usually translated, "Thou shall not lie." And you really don't want to program a large language model to lie to people. That is not good for anyone.

Eric Ries (00:51:05):
The other thing I wanted to ask you about is some of your philanthropic causes, I feel like... I wonder if they're related to experiences that you had that you encountered over the years of building Craigslist. And the one, of course, comes immediately to mind, you've been a tremendous backer of journalism and helping to seek out new models for journalism and new [inaudible 00:51:26]. We live in an age where that's obviously super important. There was a whole period of time where people were blaming Craigslist for the demise of the newspaper business model. I mean, now, we've forgotten how recently it was that newspapers used classified ads as a source of revenue. I'm just curious if that's related to that, if that's how you got to that topic area.

Craig Newmark (00:51:46):
Oh, the reason I got into journalism, ultimately, had to do with at high school US history class, that's where I learned and committed to things like the Constitution Bill of Rights due process. And as I'd like to put it, a trustworthy press is the immune system of democracy. I supported that with pretty large numbers, pretty large contributions. That hasn't worked as well as I hoped, but I love what the CUNY Journalism School does. Because CUNY in New York has been, for a couple hundred years, a way for a person who's growing up with nothing, of any background, they could wind up getting a good education leading to a good job and maybe to a good career. And I took advantage of that not at CUNY, but at Case Tech of Case Western Reserve in Cleveland where I went through on a full scholarship and I've done okay for myself. So a lot of people do okay for themselves through CUNY.

Eric Ries (00:52:58):
I wonder... I love your idea of journalism as the immune system of democracy. When we talk about civic infrastructure, journalism is one of the most important such forms of infrastructure and I think a lot of people have this sensation that it's been breaking down. Our immune system is being defeated right now by all these new pathogens. You've been around people who are trying to fix that problem. What gives you hope or what's got you excited about the possibility of making fixes there?

Craig Newmark (00:53:27):
Nothing is getting me excited right now. There's a lot of people doing great, trustworthy journalism that no one cares about because the people doing it haven't figured out how to do the right audience development. Because you might have a subscriber base of 100,000, which in local journalism might be good. But we need subscriber bases collectively in the hundreds of millions telling people what's really going on and that's not happening. And it's going to take people who are a lot smarter than I am. But meanwhile, I love the idea that people attending the CUNY J School will be able to do so tuition-free and we're moving in that direction right now.

Eric Ries (00:54:21):
That's really great. Another thing that you've done a lot of philanthropy round is education, and I remember, speaking of social media for a long time now, you're a very consistent poster of the requests on DonorsChoose and sites like that who need stuff for their classrooms. That's been such a notable part of my social media experience now for so many years having followed you. How did that get started and why is that important to you?

Craig Newmark (00:54:45):
I forget how the DonorsChoose thing started for me. I think the guy running it at the time just said, "Hey Craig, take a look at this." It made sense immediately because I did know even then that teachers aren't paid enough and I had a hint. They had to buy stuff for their kids out of their own pocket. That stuff might be paper and pens. That stuff might be snacks for kids who aren't getting enough food at home. So the idea of DonorsChoose, people funding things 5 bucks at a time, maybe 500 bucks at a time, that's easy for me to understand. And so, I'm still involved in it. Seems to be working. And sometimes, there's a guy I drag down to their board. I'm not on it. Maybe I need to bug this guy because he's the late show. And I told Mr. Colbert when he interviewed me on the old show and I saw him talk at one of the DonorsChoose get-togethers not long ago.

Eric Ries (00:55:58):
That's really great. It has that Craigslist feel to it of something that's obvious once you know about it and it's very tangible and simple, easy to understand, and very direct. No complicated 12-dimensional chess about how to make impact or whatever. It's very much like, "Here's a very defined need." Do you ever-

Craig Newmark (00:55:58):
Yeah.

Eric Ries (00:56:18):
Yeah. Do you ever worry about... I think a common criticism of stuff like that is that by addressing the symptoms of the problem, we divert energy away from solving the systemic injustice, that is why teachers are underpaid or why their classrooms don't have what they need. Did you come across that criticism ever?

Craig Newmark (00:56:34):
I do have that concern. I do hear it, let's say, relatively frequently. But there's no answer. We do need to fix that part of our system. And yet, meanwhile, teachers and their kids are suffering. So sometimes, while you're looking for a real cure, a Band-Aid is just what you want.

Eric Ries (00:56:58):
Mm-hmm. Are there other philanthropy things that you want to make sure we get a chance to talk about?

Craig Newmark (00:57:05):
I think I've completed the list. I do support other people in other areas and I do seriously support pigeon rescue-

Eric Ries (00:57:15):
Ghostface Killah, right?

Craig Newmark (00:57:16):
Yes. The deal is-

Eric Ries (00:57:17):
Explain Ghostface Killah for those that don't know.

Craig Newmark (00:57:20):
Well, Ghostface Killah is a pigeon who routinely visits our garden in New York. He runs the pecking order. And he won't come over every day, but he was here a few hours ago insisting on being fed. He had a couple of his buddies with him and we are fond of the guy. He's a tough old bird. We observe that... I think he's looking for his fifth wife now and a lot of the pigeons around our block seem to have some of his plumage. So he seems to get around and it's personally very distressing that this pigeon, his social skills are far better than mine.

Eric Ries (00:58:05):
So many people see pigeons as a nuisance. Why do you see it differently?

Craig Newmark (00:58:09):
Oh, I love birds and they are a very successful species, so I respect that. I mean, I am excited that today, a cardinal couple showed up. I'll be posting that later-

Eric Ries (00:58:25):
[inaudible 00:58:25].

Craig Newmark (00:58:24):
... [inaudible 00:58:24] mail and that's pretty exciting. And over the past few days, we've seen a Northern Mockingbird and a Red-tailed hawk and this is all in Lower Manhattan.

Eric Ries (00:58:38):
Okay. I got to get off the bird train of questions, because I feel like we... So many people are like, "Don't ask him about birds. Ask him about his advice for things." Okay. Sorry. I have so many bird related questions, but I'll save that for another time. Let me just get back to the advice for entrepreneurs, if you don't mind. Just I want to get your take on a couple of things. Is that all right?

Craig Newmark (00:58:57):
Yes.

Eric Ries (00:58:58):
Yeah. Okay. So many people starting out see what you've done as almost like an unattainable goal. So I'm curious like I know that the specific circumstances that gave rise to Craigslist were unique. Yet, there must be people right now who are sitting on an email list or sitting on the prototype of something cool or a classic MVP that's starting to get some energy. And people are starting to tell them, "Oh, you got to do this. You got to do that. You got to invest in design. You got to invest in marketing. You got to raise money. You got to do that..." People are getting caught up in all that churn. And I wonder, if someone like that came to you right now, what advice would you give them?

Craig Newmark (00:59:35):
The advice I routinely give is that, while the technology is exciting, the hard part is audience development or marketing or whatever you like to call it. It has a whole bunch of names, but people need to get excited about using your stuff. And then, they need to use it and become a normal part of their day-to-day living. And you may have a great idea and you may implement it really well, but the philosophy of, "If you build it, they will come," rarely works. Sometimes it does, but that's probably because somehow you got good word of mouth and that kind of accidental audience development can work. It worked for me with a little help. I may have talked about it in parties in the late '90s and so on. But for the most part, Craigslist sold itself.

Eric Ries (01:00:41):
Well, and it was also your classic overnight success that was many years in the making. You had to be comfortable-

Craig Newmark (01:00:46):
I guess so.

Eric Ries (01:00:46):
... with being relatively small for quite a long time. If you'd raised a seed round and had to make it viable in 18 months, it wouldn't be here right now, right?

Craig Newmark (01:00:55):
Well, you're right in that we just grew slowly and slowly and slowly and that worked out well for us. That may not be a possible approach for anyone anymore. I just don't know.

Eric Ries (01:01:10):
Mm-hmm. The other thing, I think, is interesting about your story is people often tell me that it's too late for them. Almost like Darth Vader at the end, right? "It's too late for me." And sometimes they tell me that after they've built a billion dollar company and they have lots of investors and it's really, there's a lot of momentum. But I hear that from people even who've raised only a small amount of money or who've just gotten started actually, already feel like it's too late. That they've lost control of the situation. They won't be able to resist these negative forces. And I'm curious, now, there's a whole trend of people who have gotten off that train even though they began it. I'm curious if you have advice for people who are in that feeling like, "Oh, it's too late for me."

Craig Newmark (01:01:47):
Well, sometimes it is too late. They didn't do their audience development. They didn't build a customer base ahead of time or maybe there's just too much competition, so there's no market niche for them. Yeah. The deal is that I do speak with a lot of people in business or in the nonprofit world. People who do have something great, but they've neglected to build an audience for it. And sometimes, there's still a window of opportunity. And sometimes, it really is too late and they need to have the acumen and strength to know when it is too late and then to give up before they waste more time and money.

Eric Ries (01:02:34):
Yeah. But I think it's something interesting also. You've said this a bunch of times and I'm also only registering. I guess I'm a little slow today. It's only registering to me now. Whenever I ask you this question about how to resist in enshittification or how to keep the soul of the company or how to do almost anything I've asked you, you always come back to closeness with the customer, the audience.

(01:02:55):
And it's almost like... Am I getting this right? I hear you saying that that ultimately is the counterweight, to the extent that you are embedded in a community, you are serving people, you are their customer service agent. You have an opportunity to resist people who are trying to get you to do something that is bad for those people. Because ultimately, the power that you have as an organization, that's where it stems from.

Craig Newmark (01:03:18):
Well, sometimes one's moral compass can waver and engaging with the people you're serving tends to rejuvenate that compass. And I guess that's what works for me. Even when attacked for serving the community in high-risk ways, somehow I was still talking to people and they reminded me that I needed to do what's right. And that's hard to do at times if you're being hit by a dirty tricks campaign saying some of the obvious. Yeah. And when you're in business, if you're successful enough, you will encounter situations wherein you see people doing things that are a little bit shocking. Because sometimes people do stuff which you just wish didn't happen and it has damaged some of my optimism about the internet. My optimism was formed around 1995 when everyone thought we were going to make the world a lot better. Now, we have made the world a lot better. But also, in other respects, we've made the world worse and I help fight back. But we need people who have serious leadership skills. And of course, leadership skills are social skills. And again, have you met me?

Eric Ries (01:04:56):
Yeah. Okay. But let me ask you one more question about that, because a very common narrative is that exploitation and ruthlessness are a form of competitive advantage. So a part of the investor-driven company building playbook is you get monopoly or a monopsony power, use that to raise prices. If you don't act ruthlessly, a competitor will and it will drive you out of business. And what I think is so interesting is many of people who have taken that approach, at least as it relates to competing with Craigslist, have come and gone. Either the company is long gone or it's descended into something that's quite dark.

(01:05:35):
Meanwhile, Craigslist has had this very consistent staying power over a really long period of time. So much so that you might even say that avoiding exploitation is part of its competitive advantage. And I'm curious what you think about that, the idea that doing right by your own customers and making the product actually better, or at least not degrade, that's a source of competitive advantage. That being trustworthy is a source of competitive advantage. What do you think about that?

Craig Newmark (01:06:01):
I really want to think that's true and I think I've seen it elsewhere, maybe with Wikipedia. I don't know, because I haven't looked at the numbers. I haven't surveyed the whole industry. That would be a big distraction. I will just keep my rather naive face on the business model which, in a way, is doing well by doing good. I'm not in Craigslist anymore, but that's the philosophy the company has maintained and continues to do so. And it's worked out pretty well in unexpected ways. Craigslist helps people get through the day, helps people put food on the table. But also, has shown tens of millions of Americans that the internet is useful and is reasonably easy to use. I say tens of millions of people, I have no idea how many Americans have actually used Craigslist. I'm guessing it's somewhere between 100 million and 200 million, but no one knows.

Eric Ries (01:07:07):
That's incredible. Before we wrap up, can I just do a quick lightning round?

Craig Newmark (01:07:11):
Sure.

Eric Ries (01:07:12):
Okay. One of my favorite things in preparing for these interviews is just getting to read things that you've written before or other interviews that you've said and it... I write down quotes I think are funny as I go through my research and I got to ask you about a couple of them. My-

Craig Newmark (01:07:27):
Sure.

Eric Ries (01:07:28):
Definitely my favorite, you said, "Any success I've had in my life has been accidentally being in the right time and right place. That makes me the Forrest Gump of the internet."

Craig Newmark (01:07:39):
That's true. I stand by it.

Eric Ries (01:07:40):
What did you mean? Explain.

Craig Newmark (01:07:44):
I got lucky starting my thing in the time and place of a San Francisco mid-'90s, a time which can't be reproduced, I think. Not for this kind of stuff. So hence, I was lucky. I naively did something good, committed to it, and didn't stop just like Mr. Gump.

Eric Ries (01:08:09):
You said that you were committed to customer service for the rest of your life and that death is your exit strategy.

Craig Newmark (01:08:17):
The joke is is that I'm seriously committed. I plan to do it forever. After that, it's over or is it? I am thinking that for my philanthropic work, I may perform due diligence via seance.

Eric Ries (01:08:38):
Well, I think it's pretty clear that Craigslist will outlive us both. I guess I... We won't get into the supernatural implications of what that might be beyond. Yeah. That's really great. And last one I wanted to ask you about. You said just to do something real and keep it simple. And of course, that's so much the essence of what Craigslist is all about. What does that mean to you?

Craig Newmark (01:08:59):
Yeah. Do something that matters to people. Like on Craigslist, we help a lot of people just get through the day. Sometimes it's running a small business with ads that are free or cheap and that, alone, ain't bad right there. So address real human needs. Like again, getting through the day, maybe getting rid of a big piece of furniture, maybe buying a big piece of furniture, maybe finding a place to live where you stick that piece of furniture. These are human basics. Maybe we don't need a new computer game. But again, now and then you need a new sofa.

Eric Ries (01:09:41):
Well, Craig Newmark, thank you so much, obviously, for taking the time to have this conversation. But I really appreciate your humility and the commitment to serving people that you've had now for quite a few years. And Craigslist has been such a part of my life and so many people's lives. So just on behalf of all the people that you've touched, thank you.

Craig Newmark (01:10:00):
I appreciate it. And it's not humility, it's just being real and that works.

Eric Ries (01:10:08):
Amen to that.

(01:10:11):
You've been listening to The Eric Ries Show. The Eric Ries Show is produced by Jordan Bornstein and Kiki Garthwaite. Researched by Tom White and Melanie Rehack. Visual designed by Reform Collective. Title themed by DP Music. I'm your host, Eric Ries. Thanks for listening and watching. See you next time.