Craig Newmark on Institutional Maintenance, Giving Away Control, and the Internet We Were Promised (Live at 92NY)

Craig Newmark's career, in retrospect, looks like a series of deliberate subtractions: he kept Craigslist plain, stepped aside as CEO early on, gave his equity to his foundation, and now funds people and gets out of their way. His theory, arrived at gradually, is that recognizing your limitations and relying on your network is how you get more done. Tyler and Craig discuss why webpage design has gotten worse for 30 years, what Craig's "obsessive customer service disorder" taught him about human nature, why trusting people and maintaining a nine-second rule for scams aren't as contradictory as they sound, why roommate ads are a better way to find love, why Craigslist never added seller evaluations, why Leonard Cohen speaks to him more than Bob Dylan, what William Gibson's Neuromancer got right about the internet, why Jackson Lamb is now one of his role models, why large foundations lose accountability, what two painful Ivy League grants taught him philanthropy, what he gets from rescuing pigeons, the hard lesson he learned about confronting people who lie for a living, his favorite TV shows and movies, the one genuine luxury he can't go without, what he still needs to learn, and much more. Read a full transcript https://conversationswithtyler.com/episodes/craig-newmark/ enhanced with helpful links, or watch the full video https://youtu.be/pZMuKkH92fo on the new dedicated Conversations with Tyler channel. Recorded April 14th, 2026. Other ways to connect Follow us on X https://twitter.com/cowenconvos and Instagram https://www.instagram.com/cowenconvos/?hl=en Follow Tyler https://twitter.com/tylercowen on X Follow Craig https://x.com/craignewmark on X Sign up for our newsletter https://mercatus.tfaforms.net/5060931 Join our Discord https://discord.gg/JAVWP7vTxt Email us: [email protected] mailto:[email protected] Learn more about Conversations with Tyler and other Mercatus Center podcasts here https://www.mercatus.org/podcasts. Timestamps: 00:00:00 - Intro 00:02:41 - Stepping Aside as CEO 00:04:20 - Customer Service and Social Skills 00:16:27 - Restaurants 00:18:06 - Music 00:19:27 - Science Fiction 00:20:14 - TV Shows 00:26:03 - Philanthropy 00:30:20 - Journalism 00:31:55 - Pigeons 00:32:50 - Entrepreneurship 00:35:09 - Craig's Personal Philosophy 00:37:37 - Major Regrets 00:39:17 - Audience Q&A 00:46:23 - Outro

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Tyler Cowen?

  Conversations with Tyler is produced by the Mercatus Center at George Mason University, bridging the gap between academic ideas and real-world problems. Learn more at mercatus.org. For a full transcript of every conversation, enhanced with helpful links, visit conversationswithtyler.com.

• 0:28Tyler Cowen?

  Craig, hello, welcome.

• 0:30Speaker 01

  Good to meet you.

• 0:31Tyler Cowen?

  As founder of Craigslist, I have a very simple question for you. Why does it seem as if webpage design has just gotten worse for 30 years running?

• 0:41Speaker 01

  In my ignorance, when I first put up the first Craigslist site, I just kept it simple, knowing I have no design skills, except simplicity and speed is a design criterion, and people haven't gotten the message. I've seen designers do some very attractive work that no one has asked for, and I appreciate it. And since I relinquished any management control of Craigslist in 2000, Jim Buckmaster has kept the design clean. Sometimes I like seeing, "Oh, fancy design, but as a general rule, I just want to get the thing done." And on any site, I want to get the thing done and get on with my life.

• 1:20Tyler Cowen?

  And how do you stop them from adding bells and whistles and making it complicated?

• 1:25Speaker 01

  Them at Craigslist, no need. Jim is committed. Throughout the whole world, I just struggle like anyone else. Like when I want to cancel a streaming service, it is never straightforward.

• 1:39Tyler Cowen?

  But what then was wrong with the 1990s web? Because people did move away from it. There's now so many walled gardens, so many complex websites. I react with horror when I have to buy a ticket and then upload it into an app, and it feels it could all be simpler. Why didn't things stay with where they were? What's your account of that?

• 1:58Speaker 01

  The big problem is that people, to do successful sites, as time went on, had to compete more and more. That meant they had to attract a venture capital, I guess, who made more and more demands of them. So, the first thing I did was to go to the website and go to the website. Where people had to extract whatever dollars they could out of their site. And then I guess that began a process of what Cory Doctorow calls "enshitification." He captured the process much better than I just articulated it. He's also a bit of a hero of mine in that he's more articulate about our rights online. He's also braver than I am because he's okay with putting a target on his own back. Oh, and he writes good novels.

• 2:41Tyler Cowen?

  I have a question. This is from GPT, and I quote, "Your biggest decisions all look subtractive. You monetized as little as possible, stepped aside as CEO, kept doing customer service, and now in philanthropy, you prefer to fund people and get out of the way. What are you subtracting from yourself that other founders are addicted to?" Pretty good at GPT, isn't it?

• 3:03Speaker 01

  Yeah, that's a valid perspective. I think of it differently, mostly because as I age and have grown a decrepit, I've realized my limitations and that I'm not good at things. I realize that accidentally I've built networks of networks, and it's the networks of networks that get stuff done. And sometimes I can find network builders who can do the stuff I want to on my behalf, and they get it done. The best examples, Blue Star Families for military families, Bob Woodruff Foundation for vets. And so I'm

• 3:43Speaker 01

  not subtracting things. I'm just becoming much more effective overall by sharing power and money. That seems to be working. Also by building networks of networks, that's a kind of, just in the past week or two, I've realized that's the most effective form of estate planning I'm doing, because as I become elderly, I have to wonder how my work is going to survive me, and that I could create Craig GPT, or I could just come back and haunt people for due diligence purposes. But the networks of networks have a life of their own.

• 4:20Tyler Cowen?

  What is scarce in your life then? You're giving away money, right? You don't have to run the company on a day-to-day basis. We'd all like more years to live. But what is it that if you had more of it, you could be more effective with?

• 4:33Speaker 01

  I guess ideally, I would have more social skills, meaning some.

• 4:39Tyler Cowen?

  But we're simulating social skills just fine here, right?

• 4:42Speaker 01

  That's the phrase I use. At least on my part, what looks like social skills is just fakery. And I can do it for short amounts of time, maybe 90 minutes. And I've given up, though, on actually accumulating social skills, getting better at it. But more to the point, I try to get into positions where other people can show social skills.

• 5:03Tyler Cowen?

  One journalist once described you as having, quote, "obsessive customer service disorder", unquote. Isn't that a social skill?

• 5:10Speaker 01

  That's more obsession, so it's pathological.

• 5:13Tyler Cowen?

  But a good one!

• 5:13Speaker 01

  Well, I believe that you should treat people like you want to be treated. So think of the many times that you needed customer service. Sometimes you can get good customer service, but that's the exception. That's no reason for us not to provide good customer service. Like earlier today, someone sent in a grant proposal and I had to tell them that they forgot to sign the thing. A very minor thing. But more importantly, I'm telling people they need to do some planning for good communications because their work is much less valuable if they can't talk about it effectively.

• 5:51Tyler Cowen?

  According to Susan Fries, who wrote about you, in one year, you answered 40,000 customer service emails. Is that possibly true? And if so, what did you learn about humanity doing that?

• 6:03Speaker 01

  I have the vague memory of being asked and then counting the number of emails I had sent that year. It's hard to believe, but I work every day, so I guess that's 10 times that's 365. That's like maybe 4,000. So I don't know if I got the number right, but it's too much. The thing is, well, like I say, a nerd's gotta do what a nerd's gotta do. What I learned about people doing customer service at Craigslist was that people everywhere are kind of the same. We want to get through the day, which is sometimes tougher than other days. And that one thing I noticed in New York is that New York is a collection of small towns, not so much a big city.

• 6:47Speaker 01

  So New Yorkers aren't all that different than people anywhere. For the most part, New Yorkers want to get through the day. It may be harder to get an apartment. And rent stabilization is a passion. But otherwise, people everywhere are kind of similar. And the amount of bad actors is actually very tiny.

• 7:04Tyler Cowen?

  So you became more trusting as people, helping them?

• 7:07Speaker 01

  Oddly enough, I did become more trusting. Unfortunately, during those years, at first, I became less prepared to deal with bad actors. And I learned the hard way that if you're basically honest, if you believe in the ninth commandment, you will never be able to confront successfully someone who lies for a living. And that was a painful lesson that took a couple of years to sink in. And it wasn't a good year or two.

• 7:36Tyler Cowen?

  So I think of much of Craigslist as saying you can trust other people if the incentives and institutions are correct. And your nine-second rule, you know, wait for nine seconds and think before clicking on something you get, say in your email or on a social network site, is a kind of lack of trust. Is it that your views have changed? Or how does the whole picture fit together?

• 7:58Speaker 01

  Just, I have learned something, and my team has learned something from real life. The notion is that a normal, a very common technique of scammers is to rush you into something, to convince you of the scam by making it sound urgent. And if you wait a little while, stereotypically nine seconds, you can reconsider what they're doing. And then you can evade certain kinds of scams. I screwed up in that respect about 10 years ago, but in a small way, I just lost a credit card number. I realized it not long after and, you know, changed it. But that's kind of stupid.

• 8:39Speaker 01

  I'm trying to learn other things as well, working potentially with the AARP. Because if nothing else, my wife has to monitor her mom's credit card purchases because there's often issues there.

• 8:52Tyler Cowen?

  So if I do this, what should I be thinking between second eight and second nine? I get what I should be thinking in the first two seconds, but at seven, eight rolls around, what am I doing?

• 9:02Speaker 01

  If something still smells bad to you, I would either not do it or go right to the source. If they say they're pointing you to, let's say, Amazon for something, I would say type in Amazon directly because a common technique of scammers or fishers is to get a domain name that might look like Amazon but isn't. Like if you use a font where you use an R followed by an N, some fonts kind of make the RN together look like an M. So you'll go to what looks like Amazon and they will capture your user ID and password. Then they'll get you to Amazon and you won't know that they just stole your credentials.

• 9:48Speaker 01

  So that's actually an illustration of a common technique for which solutions exist. A long story, there's a cat and mouse game involved, but I'm trying to figure out what institutions to fund to stop that from happening.

• 10:05Tyler Cowen?

  What is it that you understand about used goods that others do not?

• 10:09Speaker 01

  Probably nothing. The only thing is I want as few of them as possible because I worry about having too much stuff. And whenever I buy technology, knowing that I will replace it eventually, I try to get something that will be, even used, will be a good acquisition, typically by one of my nephews or nieces. My collection is 24 of them and counting.

• 10:35Tyler Cowen?

  Now, missed connections used to be a feature. Oh, I saw you on the subway. You seem so smart. You were reading Catcher in the Rye, whatever. What happened to that?

• 10:44Speaker 01

  I think it's still there, but in a different category altogether. And it, over the years, over the decades, oh, it does work now and then. I've been invited to weddings where they met each other through the site or where people had good relations. We all have had experiences where we meet someone and there's some chemistry. And neither party gets contact data. And it's kind of sad. I've thought about that for a long time, but Jim just decided to put it up after he became a CEO sometime in the middle of 2001.

• 11:19Tyler Cowen?

  Why don't dating apps work better? If we mostly can trust people, right? The first day you spend more than nine seconds with them. There's many marriages from missed connections where you've even officiated perhaps. Yet everyone says dating apps are terrible.

• 11:34Speaker 01

  I don't know, because to have a gut feeling of them, I'd have to use them. And let's say that they hit their stride after I had gotten involved with the future Mrs. Newmark. I sense the opportunity for comedy coming on that will get me in trouble. And even alluding to that will probably get me in trouble after Eileen watches this.

• 11:55Tyler Cowen?

  But you know, many smart people who articulate their concerns to you. I hear from people all the time. Dating apps are terrible. Why dating apps are terrible? Oh, there's gender imbalance if it's New York City or people just want something other than a long-term relationship. You don't have an implicit mental model of what's going wrong?

• 12:14Speaker 01

  My gut tells me with no evidence.

• 12:17Tyler Cowen?

  Yeah.

• 12:17Speaker 01

  Is that people aren't genuine, aren't real on dating apps. The only basis for this thought is about 25 years ago, before Craigslist had dating sections. I met several women who told me they used the roommate ads for dating because in a roommate ad, a guy would be relatively honest.

• 12:40Tyler Cowen?

  And not married, one hopes.

• 12:41Speaker 01

  Uh, well, yeah, actually, I didn't think of that, yes.

• 12:47Speaker 01

  So that's very good. I'll have to steal that for the repertoire. But this is serious. That's what women told me way back in the past. And this had to be a man right around, well, probably late 90s. I really am old.

• 13:03Tyler Cowen?

  That seems to me Craigslist is especially strong in job ads, services and automobiles. Do you have any sense why those areas or maybe you think it's something different?

• 13:12Speaker 01

  I don't know. The deal with Craigslist in general is that it's for real. People are really putting stuff up there. You generally know what you're getting. You have no illusions about, oh, what's going on? At some point in the past, other sites where you build up a profile, they look like you're actually dealing with a real person. And maybe that was true for a while, but now it's very easy to use generative AI to build up a profile which looks real, but it's fake. And if you're going to buy something from that person, having some confidence that they're real, you may have a problem. That's the kind I think of a great deal these days. And how do we warn people adequately about it?

• 13:57Speaker 01

  We really do need to launch a much bigger public service campaign about problems with scamming, problems of cybersecurity, and what regular people can do to prevent them.

• 14:08Tyler Cowen?

  But even before generative AI, you didn't have seller evaluations the way eBay and Uber have, right? Uber, oh, this driver is a 4.98, you assume it must be okay. And Craigslist didn't do that. Why not?

• 14:22Speaker 01

  I can't speak for Jim, because at that point I had given all management to Jim. But even before him, I vaguely speculated on things like user reviews of any sort, like Yelp style. And I was thinking, it will be really easy to game that kind of thing. Frankly, even then, I was reading science fiction, which looked into the future, about how online media and the internet would be gamed. I'm even thinking back to 1984, William Gibson Neuromancer, which affected me and a lot of people in the field, and I'm hoping will be a really good Apple TV show. Yeah, I'd like it to be better than Slow Horses. Jackson Lamb is now one of my role models. I can tell you later why, not for his hygiene, but the deal is that, and I've lost track

• 15:07Speaker 01

  of the question, because I wanted to say why Jackson Lamb is now my role model, which you can feel free to prompt when you're in the mood.

• 15:15Tyler Cowen?

  But seller evaluations, right? You've never evolved them. Podcasts get evaluated on Apple, right? This gets so many stars.

• 15:24Speaker 01

  But it's just too easy to game those systems now. What I'm hoping for are user authentication systems, not state or government instituted ones exclusively, because I worry about governments. A lot in life is based on who you trust, and you want to be able to know who you're talking to. But I don't want to turn over a lot of this to the government because of some of my political biases. So I'm looking for balance. If you can identify yourself to other parties in a way that kind of shows you are who you claim you are, that can be good. And you know, the credit card companies working together may have a solution. Driver's licenses may be in part a solution.

• 16:08Speaker 01

  And you know, ninety percent of Americans have phones with digital wallets. Maybe there's something there. But I need to run this by the Electronic Frontier Foundation. Because they think of things that I will not think of. And they may tell me why my idea is terrible.

• 16:27Tyler Cowen?

  What do you think of the simple model that institutions get gamed and they deteriorate over time? If there's a new restaurant in New York City, it will be great for the first six to nine months. Then too many people want to come. The people who come after that are less informed. They slack on quality. There's always a line out the door. Just everything becomes a bit worse. And the way to live life is to find the peaks of things in early times and then move on. Correct or not?

• 16:53Speaker 01

  That sounds like too much work for me. And I might accidentally go to a hip hopping in places, happening places, which is not my thing. So I just look for the mundane, the ordinary.

• 17:06Tyler Cowen?

  So say you're choosing a restaurant. What's your algorithm?

• 17:09Speaker 01

  My algorithm is, well, does it look like a hole in the wall?

• 17:13Tyler Cowen?

  And that's a good thing.

• 17:14Speaker 01

  Actually, quite seriously, my deal is in the last year or two. I've realized that I have the tastes and attitudes of a peasant. I'm a peasant with money. Nevertheless, like if somebody wants to take me to fine dining, if they're treating, I'll try it. Otherwise, I'll not look for an expensive place. Like yesterday, I had a slice, well, actually two, small slices. And that was ten bucks. You know, two slices, ten bucks at the place. They like me, so, and that was lunch.

• 17:51Tyler Cowen?

  I like restaurants where there are non-US citizens screaming at each other and none of them look happy. Then I feel the food will be good.

• 17:58Speaker 01

  That sounds like a comedian speaking. And I kind of like that, except for the yelling part.

• 18:06Tyler Cowen?

  What's your favorite Tori Amos song?

• 18:08Speaker 01

  Oh, I used to have a much better idea of what that would be, but I've forgotten. These days, I focus mostly on my rabbi, Leonard Cohen. Like I delve dive more into You Want It Darker. I've also become a Swiftie, but since I haven't listened to her last album enough, I have to reserve judgment.

• 18:28Tyler Cowen?

  I like Silent All These Years by Tori Amos, especially the live version.

• 18:32Speaker 01

  That's very good, and I think I did hear it live when I spent a year in Pittsburgh in 1992.

• 18:42Tyler Cowen?

  And for you, what makes Leonard Cohen deeper or more interesting than Bob Dylan?

• 18:46Speaker 01

  It's hard to say, but the bottom line gut level is that with Leonard's help, I kind of feel God speaking to me.

• 18:54Tyler Cowen?

  But not from Dylan?

• 18:55Speaker 01

  I've listened to him more, and one problem is sometimes it's with my hearing issues, it's hard for me to make out his words. But for whatever reason, Leonard just speaks to me more. That's a very individual idiosyncratic thing. So I, I don't know. I should say Taylor Swift does not make me feel like God has me on speed dial.

• 19:22Speaker 01

  But I do like her stuff, and I do live near Cornelia Street.

• 19:27Tyler Cowen?

  What in science fiction has influenced you and how?

• 19:30Speaker 01

  There's the William Gibson stuff. I remember reading in 1984, his seminal work, Neuromancer, which he wrote knowing nothing about computers, and yet it's influenced a great deal of how the internet has evolved. Right now, I'm going through a lot of the stuff by KJ Parker, whose novels are about a kind of different earth with a different history that parallels ours. And his novels, a lot of them about our characters who are faking their way into positions of responsibility, who turn out to be really good at those jobs under pressure. They're a kind of competence porn. Much like The Pit is.

• 20:14Tyler Cowen?

  Why was Seinfeld so popular? I long have found it puzzling that people who don't really know New York might even like the show. Sometimes they like it without understanding that some of the characters are in New York or perhaps might be Jewish. That always struck me as bizarre.

• 20:29Speaker 01

  I don't know. I just felt that those characters were, in some respects, a version of me despite their exaggerated bad tendencies. Maybe that's it. I do, you know, George Costanza, Jason Alexander, I've always felt is one especially attractive man. A short, balding, kind of chubby, Jewish. And I do see a lot of the Larry David coming through there. Like, I see, we see more Larry David on, oh, on Curb. And I do like that a lot, even when I'm cringing.

• 21:03Tyler Cowen?

  So I think Curb, your enthusiasm is funnier than Seinfeld. It's more willing to be dark. And Jerry is a character, I think he's a good straight man in the Al Dabedin-Castella sense, but I don't find him funny, in fact.

• 21:16Speaker 01

  It's mixed. And I, I don't think about the funny part, I just try to enjoy it. And, oh, if you try too hard to understand something, sometimes that makes it, well, it's like explaining a joke doesn't make it funnier. So I just enjoy the thing. It only, it took me a long time to enjoy Monty Python. And I just, even on the way here, I saw, I think, a vertical format video from, I think it's Monty Python and the Holy Grail. And a peasant woman was explaining to King Arthur that just because some quote-unquote tart threw him a sword, that didn't make King Arthur divinely appointed.

• 21:58Speaker 01

  And that was, in retrospect, really funny, not necessarily topical.

• 22:05Tyler Cowen?

  Often the best parts of Monty Python I've never understood. So you hear Tony Jackman golf clubs. I'm like an 11-year-old, I have no idea.

• 22:13Speaker 01

  Yeah.

• 22:13Tyler Cowen?

  And it's funny.

• 22:14Speaker 01

  There's a lot of things I don't get ever. Some things I get years after. That's, I guess, comedy. I wish I was as good at it as Jackson Lamb, who's, you know, one of my role models now because of something he said in the latest book.

• 22:31Tyler Cowen?

  Which is?

• 22:33Speaker 01

  He said that small talk is just bullshit leaving the body. And speaking as someone with very limited social skills, that's a way of life for me. I don't quite have the personal hygiene issues he has, although as I get older, I use aging as an excuse for issues.

• 22:54Tyler Cowen?

  But I want to push back on this to you, that you don't have social skills. People came to see you, they're laughing. You started a company, you got other talented people to work there, you were meta rational, you knew when to give up control on which issues, but to spend a lot of time doing customer service and respond to all those emails, right? You visited realtors who broke the rules of Craigslist. You seem to have extraordinary social skills, albeit unusual ones.

• 23:20Speaker 01

  That's a kind way of saying it, and I think I can accept it. Let's say in my naivete, well, sometimes naivete and being honest about it is a kind of social skill, so maybe I'll accept that. I guess a lot of social awkwardness is a part of my branding. I do know that I lack the kind of social skills that you need to be comfortable in Washington, and that's why I have layers of insulation whenever I go there, through consultants, through some of the think tanks I support. Like, I'm thinking of one who I recently gave a substantial grant to, who's doing good work, particularly in protecting U.S. infrastructure, starting, for the most part,

• 24:05Speaker 01

  with water supplies and sanitation and going to hospitals. They are working with people like the Water Information Security Action Center. They can talk to people in ways that I can't relate. Kathy Roth-Duquette from Blue Star Families is really good at Congress and news people.

• 24:27Speaker 01

  And she's much better than I ever could. And so I'm happy that she just does it. Sometimes she will trot me out as useful. I'll be doing that again in a few weeks. For at Bloomberg News for Vets in Tech. They train vets in technology jobs, particularly cybersecurity.

• 24:46Tyler Cowen?

  When you visited those realtors who broke the Craigslist rules, were you nice to them?

• 24:50Speaker 01

  Always, because this is like 20, 25 years ago.

• 24:54Tyler Cowen?

  That's the best social skill.

• 24:56Speaker 01

  Well, I just would wander in. I would introduce myself. They would panic.

• 25:04Speaker 01

  Then there would be introductions and photography. The deal is, I wasn't out there to bust their chops. I just figured I needed to learn more about what was going on. Because while those ads were free, at one point, they started posting the same ads over and over and over again. So that those sections were just unusable. I spoke to a lot of new apartment brokers. And they said that they didn't want to have to post the same ads over and over again. And that if we charged a few dollars for those ads, that would solve the problem. And to charge them 10 or 20 bucks for them is nothing. But it would be a rate limiter.

• 25:46Speaker 01

  And, and we've settled on 10 bucks. Because I realized that a new apartment broker would be making maybe 20,000 a year in New York. And if you're doing that, you have to have one or two other jobs to get through the day.

• 26:04Tyler Cowen?

  Is it still true that Craig Newmark Philanthropies has no formal employees?

• 26:08Speaker 01

  That's correct. I'm a contractor. And we have others.

• 26:12Tyler Cowen?

  So even you are not an employee?

• 26:14Speaker 01

  Yes, that's the way Mabel ranges it. Mabel is my bookkeeper and financial person. She is very scary. I'll see her next week. I think I'll tell her I said that. She's also the bookkeeper and so on for Craigslist. Because she's very committed and she's learned a lot on her own. She has a lot more practical legal knowledge than the lawyers. And she's a refugee from Myanmar, which is pretty impressive.

• 26:41Tyler Cowen?

  Sure.

• 26:41Speaker 01

  She's taught herself a lot of this stuff. And I don't know what I'd do without her, but she does frighten me.

• 26:47Tyler Cowen?

  As you know, many other foundations have large staffs, right? And multiple layers of decision making. What are they getting wrong?

• 26:54Speaker 01

  I don't really know. And I'm trying to judge.

• 26:57Tyler Cowen?

  But you have some theory of why you didn't do that, right?

• 27:00Speaker 01

  Tangentially, I'll say, I'm trying to judge less and less. I've been so wrong and unfair at times. What I find problematic is that when they have layers of management and too much spread out responsibility, there may not be enough accountability. Multiple levels of sign offs slow things down. They operate very responsibly with annual budgeting and so on. And they do so in a way often that's too rigid. Plus, when they reach a certain size, like 150, I think it's Dunbar number. Then one part of the nonprofit doesn't know what the other part is doing. And me, I have the advantage of ignorance, not knowing what I'm doing, having limited objectives, but getting a lot of help.

• 27:45Speaker 01

  I rely on the kindness of strangers. I've made mistakes, but not too bad. I've never made a really big mistake. It's that sometimes the money hasn't been used effectively. Like, I'm afraid I've lost my confidence in Ivy League schools.

• 28:00Tyler Cowen?

  How did that happen?

• 28:03Speaker 01

  Two substantial contributions to Ivies were fairly ineffective. I should have made those contributions instead of big checks. Should have made them big checks, but given out multi-year based on milestones. So that's a lesson, a little painful, but the money wasn't wasted. It just wasn't used as well as I'd like.

• 28:24Tyler Cowen?

  So the main initiatives, such as supporting veterans, those are your idea, right?

• 28:28Speaker 01

  That is an idea I came up with in response to, maybe 15 years ago, I was at a luncheon at Colonial Williamsburg, put on by PBS NewsHour. And I sat next to a guy from Iraq and Afghanistan, Vets of America. And they explained to me what the situation of vets was in America. They were not treated very well. Veterans Affairs needed work. And I figured, well, this is something I can understand. And having grown up in the capital of the revolution, Morrisville, New Jersey, growing up during the Vietnam War, when returning soldiers were treated badly, I had some idea of the need to help out.

• 29:11Speaker 01

  Several years ago, the need to help out military families, active service sunk in. When I was doing a photo op at God's Lovely Deliver, I didn't know I would be packaging food. And that's been the first and only time I've had to wear a hairnet. They told me I didn't need to wear one, but I thought it was funnier to wear one. And talking to Kathy from Blue Star, I understood that active service military families get moved around a lot every year. And when you're moved around, you lose all your connection to community. You don't know where good childcare is. You don't know the schools or places to buy food. And given the current payment model for families,

• 29:54Speaker 01

  you may not have enough money to feed your family. That's one reason why we sponsored a food pantry at Fort Wadsworth in Staten Island. And so I was there for the inauguration, which was the only time I've ever been in Staten Island. And my image of it was based on that story arc in Sex and the City. I didn't like the sequel very much, by the way, but I still watched it.

• 30:20Tyler Cowen?

  Have you become somewhat disillusioned with journalism, the way you've become disillusioned with the Ivy League?

• 30:26Speaker 01

  Let's say that I've gotten a lot of training in journalism ethics.

• 30:31Tyler Cowen?

  The hard way?

• 30:32Speaker 01

  Let's say a mix of ways, because I've met people who do it great. And I've met people who say they do it great and don't. And people, some people don't even try. So let's say that in some cases, I'm not trying anymore in most respects, because it's just too frustrating. I do have a lot of confidence in the CUNY Journalism School, and that's the one I put my, other people put my name on. And I like it a lot, because CUNY, the whole school's been about opportunities for New Yorkers who are growing up with no opportunities. They're growing up with little or no money. The graduates are being trained in trustworthy journalism. They're actually getting journalism jobs that pay okay,

• 31:16Speaker 01

  and they're graduating with little or no student debt. The other journalism thing I support is Wikipedia, because they're learning over time, and with a lot of pain sometimes, how to get it right. Knowing that sometimes articles will get things wrong, but they get corrected. They're still learning. But I realize that when they have an article up there, it will get corrected over time. And when something is in the New York Times, they make a good faith effort to get things right, but they still get things wrong now and then, and they generally don't fix them.

• 31:55Tyler Cowen?

  Why rescue pigeons?

• 31:56Speaker 01

  I love birds, and I admire pigeons. And I guess I need a pet. I need a comfort animal. And Hatbird, or other Hatbird, aren't enough. But I hang out in front of the coffee shop, and then they'll see me, I'll wave around my bag of bird seed, the good stuff. And then they'll come and they'll rest on my arm. And then they'll eat right from there. And that makes me happy. And the people walking by will look at me, and some find it entertaining. And I really should get a dog. I travel a bit much, but if I got a nice portable lapdog, maybe a Doxy,

• 32:37Speaker 01

  or I've now read about Dox and Corgi hybrids called Dorgies. It would sound like my speed, and I could call mine a Dorky. And we would be happy.

• 32:50Tyler Cowen?

  One big question I have about your career. So you worked, I think, seventeen years at IBM, which we all think of as the establishment in some way. This is a while back, of course. And then you become a highly successful entrepreneur. What is it that changed in you or snapped, or something gave you more ambition, or it was all just accident? Seventeen years is a long time. How is it you're such a late bloomer? What's your account of that?

• 33:15Speaker 01

  It's a combination of accident and realizing that things were not right. I realized around age forty that I really had problems with socialization.

• 33:27Tyler Cowen?

  You weren't funny back then.

• 33:28Speaker 01

  Not at all. And I got Charles Schwab to move me out to San Francisco. I started using the Internet. A lot of people kind of like me helped me settle in. I saw a lot of people who were kind of my people and learned that I had to, you know, meet people halfway or more. I started realizing, for example, that a lot of my behavior, particularly in the IBM field, frequently I was a jerk, by which I mean asshole. I needed to listen people more and to be somewhat empathetic. It was needed for me to change. Doing customer service, you know, when I reached San Francisco and started doing Craigslist, doing that

• 34:11Speaker 01

  kind of customer service where you're directly interacting with people on a grassroots level, that can change your guy for the better, and that worked out for me.

• 34:20Tyler Cowen?

  And what did you learn about yourself doing that?

• 34:23Speaker 01

  That I didn't have to be a jerk and that I just had to think, you know, am I being a good person for the other person? I mean, sometimes when you're stressed or impatient or the person just isn't listening, you strain it. Like when you're talking to someone else's customer service and you tell them something, explain it, and then later on they ask you to tell them the same thing, that will tax my patience. Or I will ask some questions and then they answer half of them and then I have to repeat that. That will irritate me a little, and yet I have to realize that they're just another person struggling to get through the day.

• 35:07Speaker 01

  And I should be the nice Craig.

• 35:09Tyler Cowen?

  And do you think the personal philosophy you've brought to philanthropy is simply copying the philosophy you had at Craigslist or still have? Or it's somehow a transformation or evolution of it?

• 35:20Speaker 01

  On a gut level, it's kind of the same as Craigslist. Because again Craigslist is just about helping people get through the day. And as a byproduct, showing people that the internet can be useful and relatively easy to use. And in terms of the philanthropy there that I've done, I look for the mundane, for the down-to-earth stuff that people need that may not be addressed well enough. For example, vets and active service military are treated better after nine eleven than they were before. The VA has gotten its act better together somewhat. Still, families need to be treated better.

• 36:01Speaker 01

  Meanwhile, someone needs to take a stand against scams on an ongoing basis forever to make suggestions for regular people as to what they could do. And a lot of what we all can do also prevents cybersecurity incidents like where you work. Everyone is responsible for keeping it safe because if a bad actor, say stereotypically in North Korea, manages to crack your company's system, if they manage to install ransomware, grabbing your mission-critical data and encrypting it, scrambling it, that can bring your whole thing down.

• 36:42Speaker 01

  That's kind of like in recent episodes of The Pit where another hospital was brought down by ransomware and they kind of prematurely brought down all their own computer systems. But this is a big, serious national security issue, which I'm working with on the civilian side. And you'll hear people like me talk about resilience. Like I funded something called the Cyber Resilience Corps, which is volunteers, again, starting by helping small water suppliers get their act together because very few of them have the staffing to protect their systems.

• 37:22Speaker 01

  And the new breed of AI systems are going to be really good at bringing down stopping water supplies in a lot of our country, which is something that the Chinese military are actively working on already.

• 37:37Tyler Cowen?

  Do you have any major regrets from your Craigslist efforts?

• 37:40Speaker 01

  Well, I really needed to learn that lesson I mentioned earlier about knowing that as a ninth commandment kind of guy, I will never be a match for someone who's lying about things. And for various reasons, I thought I, in my, in some arrogance, thought I could constructively confront a person like that, but I don't have the skills. And even more so, they were trying to get me to spill the beans on ongoing criminal investigations. And the cops had told me, because I was helping support a whole bunch of investigations across the country led by the FBI.

• 38:24Speaker 01

  They told me, don't spill the beans, don't talk about actually anything going on. They were right. But after the whole thing was over, I could have spoken about that, but I was still being paranoid because I'm such a rule follower. And that provided an opportunity for bad people to run their own kind of scams. It's all very painful and I'm still under a doctor's care, but that's the big mistake I made, acting in some arrogance, not listening to people who said, okay now, and then getting professional help in terms of being a much less bad communicator.

• 39:06Speaker 01

  The downside of this is that if you're applying for a grant from me, I will be really annoying about how well you're doing in communications.

• 39:16Speaker 01

  I'll be very annoying.

• 39:17Tyler Cowen?

  This brings us to our audience questions, and the first one is, how helpful is the FBI and how can we scale law enforcement?

• 39:25Speaker 01

  The FBI, when it comes to these areas that I'm talking about, fighting scams and so on, is actually pretty good about it. I've actually been chatting with them for some years about various efforts, sometimes supported by nonprofits, which actually go after bad guys and scan the internet looking for sites which are trying to do things like download malware onto your systems when you visit them. I got their advice when it came to funding something called Shadow Server. It's not as exotic as it sounds, but they actually scan the net and they run honeypots, which are sites

• 40:07Speaker 01

  that look like vulnerable companies that the bad guys will try to load ransomware on. And in the whole process, the Shadow Server people can figure out what's going on. The FBI also needs to launch a new program alerting people to the dangers of scams, but that's a program that's not fully announced yet.

• 40:27Tyler Cowen?

  What propelled you to become a Swifty?

• 40:29Speaker 01

  For some reason, her music is very accessible. There are unexpected depths to it. It's snappy in a way that no one else's music is otherwise. And it just generally have a sense that I have to like more than Jess Leonard Cohen.

• 40:44Tyler Cowen?

  You once sold part of Craigslist to eBay and then bought it back. Will you ever sell it all? What will Craigslist be in 50 years?

• 40:52Speaker 01

  Well, personally speaking, I've put all of my Craigslist ownership into a nonprofit foundation, a 501(c)(4). So all dividends, all sales of equity go in there. The way Craigslist runs is very unconventional. Jim's the boss. Now and then if I say something smart, I can influence things. But basically, I'm at that phase in my life where I'm giving away money. And that act of putting all the equity into that 501(c)(4), I called a septuagenarian fund, because I turned 70 then. And that's where the money has gone. I had to run it by Mrs. Newmark, of course. She might have liked me to tell her that I was calling it the septuagenarian fund,

• 41:37Speaker 01

  because that's when I turned 70. And oddly, I made the decision to do that just after, I think it was the Patagonia guy, decided to do the same thing. Or he announced it on the day that I made the decision, which was kind of funny.

• 41:52Tyler Cowen?

  Why is strong water pressure so important in a shower? And it is, I fully agree with you on that.

• 41:59Speaker 01

  Well, let's say that there are some luxuries I enjoy. All the books I want, all the streaming TV I want. And my real idea of luxury is a really good shower. For me, a really good shower has good pressure. Doesn't have to be strong, but it needs to be strong enough. It has to be a walk-in shower, because of my previously mentioned decrepitude. I don't want to fall. And also not wanting to fall, I want a grab bar. I'm afraid having grab bars everywhere is now becoming a household design criteria for me. And I wish that was a joke.

• 42:38Tyler Cowen?

  What's something you try to do every day that you really love?

• 42:41Speaker 01

  That I really love, I'm afraid, is some combination of getting stuff done. Food, and unfortunately, I practice the seafood diet. And then I'll do some reading, generally a trashy science fiction or spy novel. And then I'll watch some TV, sometimes TV that I'm not proud of watching.

• 43:00Tyler Cowen?

  Here's one for both of us, I'll try it first. What are your favorite movies and why? I love Bergman films, Smiles of a Summer Night, Scenes from a Marriage, Devil's Eye, many others. Hitchcock films, maybe my favorites are Rear Window and Vertigo. And most recently, I like the movie Serat and the drama. But Craig, what are your favorite movies and why?

• 43:21Speaker 01

  Blade Runner.

• 43:21Tyler Cowen?

  The director's cut, right?

• 43:23Speaker 01

  I'm not sure which, because I do like voiceovers. It's the hard-boiled tradition. Beyond that, I like long-form TV. And again, there's like For All Mankind on Apple TV now, Severance, Slow Horses, with my role model, except for the hygiene part.

• 43:42Tyler Cowen?

  You like Westworld?

• 43:42Speaker 01

  I loved Westworld, particularly the first season.

• 43:45Tyler Cowen?

  Yes.

• 43:45Speaker 01

  Since in decades of reading science fiction, it offered the first reasonable explanation of how artificial consciousness could come about, and that's a big deal for me. There's so many others, yeah, it's hard to think of them because once I finish watching a series, I move on to the next one. I loved My Mother's A Car, but that was about 60 years ago, and I have no idea why that occurred to me. That may have been before your time.

• 44:13Tyler Cowen?

  It was. Since you're from Morristown, New Jersey, is The Sopranos too foreign to you or too close, or does it make sense?

• 44:21Speaker 01

  It kind of made vague sense in terms of milieu, but my brother lived in that milieu, and we drove through it a few times, and The Sopranos perfectly captures it. Also, in the same milieu, there's The Real Housewives of New Jersey, and he says it is perfect. I've never watched it, and just last week, the New Jersey state guy in charge of computer security said that he loved The Sopranos intro, because as Tony drives out of New York, he passes by a lot of critical infrastructure, even refineries, all of which it is his

• 45:05Speaker 01

  job to worry about.

• 45:07Tyler Cowen?

  Very last question. What is it you want to learn about next?

• 45:10Speaker 01

  Basically, I need to learn better skills in terms of understanding the social impact, or not, of the people I provide grants to. This is a big problem in philanthropy. It's related to the whole giving pledge thing, because there's a lot of stuff that's not effective at all. There's a lot of stuff that's so-so, and then there's stuff which actually does make a difference. I need to better learn to tell the difference. A lot of this revolves around communications.

• 45:45Speaker 01

  Because a lot of people who do great work, because they're skilled in the work, are not skilled in terms of communications. I'm now considering two big grants, both at the same major university in the neighborhood. And I need to help them understand that they can't rely on university marketing communications to do a good job. They'll have to do it themselves. I should add that neither of them are Ivy League.

• 46:16Tyler Cowen?

  Craig Newmark, thank you very much. Thanks for listening to Conversations with Tyler. You can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. If you like this podcast, please consider giving us a rating and leaving a review. This helps other listeners find the show. On Twitter, I'm @TylerCowan, and the show is @CowanConvos. Until next time, please keep listening and learning.