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

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. Yeah. And it's funny. 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 is one of my role models now, because of something he said in the latest book. Which is? 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 but i want to push back on this view that you don't have social skills.

22:57Tyler Cowen:People came to see you. They're laughing. You started a company. You got other talented people to work there. You were metarational. 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. You visited realtors who broke the rules of Craigslist. You seem to have extraordinary social skills, albeit unusual ones. 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.

23:40I 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 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-Duket from Blue Star Families is really good at Congress and news people, and she's much better than I ever could.

24:29And 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. When you visited those realtors who broke the Craigslist rules, were you nice to them? Always, because this is like 20, 25 years ago.

24:54Tyler Cowen:That's the best social skill. Well, I just would wander in. I would introduce myself. They would panic. 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.

25:44but it would be a rate limiter. And we settled on$10 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.

26:03Tyler Cowen:Is it still true that Craig Newmark Philanthropies has no formal employees? That's correct. I'm a contractor and we have others. So even you are not an employee. Yes. That's the way Mabel arranges 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. Sure. She's taught herself a lot of this stuff.

26:44Tyler Cowen:And I don't know what I'd do without her, but she does frighten me. As you know, many other foundations have large staffs, right? And multiple layers of decision-making. What are they getting wrong? I don't really know. And I'm trying to judge. But you have some theory of why you didn't do that, right? 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.

27:23And 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. 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. How did that happen? Two substantial contributions to Ivy's were fairly ineffective.

28:07I should have made those contributions instead of big checks. I 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. So the main initiatives, such as supporting veterans, those are your idea, right? 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.

28:51They were not treated very well. Veterans Affairs needed work. And I figured, this is something I can understand. And having grown up in the capital of the revolution, in Maristam, New Jersey. Growing up during the Vietnam War, when returning soldiers were treated badly, I had some idea of the need to help out. 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.

29:33And 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, 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.

30:16I didn't like the sequel very much, by the way, but I still watched it.

30:21Tyler Cowen:Have you become somewhat disillusioned with journalism, the way you've become disillusioned with the Ivy League. Let's say that I've gotten a lot of training in journalism ethics. The hard way, 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 has been about opportunities for New Yorkers who are growing up with no opportunities.

31:06They'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, 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.

31:50But they still get things wrong now and then. And they generally don't fix them. Why rescue pigeons? 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 birdseed, 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, or I've now read about dachshund-corgy hybrids called dorkies, 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, 17 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? 17 years is a long time. How is it you're such a late bloomer? What's your account of that? It's a combination of accident and realizing that things were not right. I realized around age 40 that I really had problems with socialization. You weren't funny back then. Not at all.

33:30and 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 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 kind of customer service where you're directly interacting with people on a grassroots level, that can change your guy for the better.

34:19And that worked out for me. And what did you learn about yourself doing that? 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.

35:01And yet I have to realize that there's just another person struggling to get through the day, 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? 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 9-11 than they were before.

35:55The VA has gotten its act better together somewhat. Still, families need to be treated better. 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.

36:41that'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've 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. 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.

37:37Do you have any major regrets from your Craigslist efforts? 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 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, They told me, don't spill the beans, don't talk about actually anything going on.

38:28They 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 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. 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.

39:16Tyler Cowen:I'll be very annoying. This brings us to our audience questions. And the first one is, how helpful is the FBI and how can we scale law enforcement? 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.

39:59It's not as exotic as it sounds, but they actually scan the net and they run honeypots, which are sites 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. What propelled you to become a Swifty? 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 has a sense that I have to like more than just 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? Well, personally speaking, I put all of my Craigslist ownership into a non-profit foundation of 501c4. 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 501c4, I called a septuagenarian fund because I turned 70 then, and that's where the money has gone.

41:31I 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 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. He announced it on the day that I made the decision, which was kind of funny. Why is strong water pressure so important in a shower?

41:57Tyler Cowen:And it is. I fully agree with you. 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. What's something you try to do every day that you really love.

42:41That 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, or Rear Window and Vertigo. And most recently, I liked the movie Sirot and the drama. But Craig, what are your favorite movies and why? Blade Runner. The director's cut, right? 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.

43:42You like Westworld? I loved Westworld, particularly the first season. Yes. 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 car, but that was about 60 years ago, and I have no idea why that occurred to me.

44:11Tyler Cowen:That may have been before your time. It was. Since you're from Morristown, New Jersey, is the Sopranos too foreign to you or too close, or does it make sense? 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 loves the soprano's 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 job to worry about.

45:07Tyler Cowen:Very last question. What is it you want to learn about next? 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 because a lot of people who do great work, because they're skilled in the work, are not skilled in terms of communications.

45:53I'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. Craig Newmark, thank you very much.

46:24Tyler Cowen: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 at Tyler Cowan, and the show is at Cowan Convos. Until next time, please keep listening and learning.