E550 Craigslist Founder Craig Newmark

Craig Newmark is an American internet entrepreneur and philanthropist best known as the founder of the classifieds website Craigslist. Theo is joined by Craigslist founder Craig Newmark to talk about how he started the legendary website, his philosophy on the internet and personal freedom, how he’s utilized his fortune for good, and what he saw while moderating the dark side of Craigslist. Craig Newmark: https://www.instagram.com/craignewmark/ ------------------------------------------------ Tour Dates! https://theovon.com/tour New Merch: https://www.theovonstore.com ------------------------------------------------- Sponsored By: Celsius: Go to the Celsius Amazon store to check out all of their flavors. #CELSIUSBrandPartner #CELSIUSLiveFit https://amzn.to/3HbAtPJ Shopify: Go to http://shopify.com/theo to sign up for a $1-per-month trial period. ShipStation: Get a 60-day free trial at https://www.shipstation.com/theo. Thanks to ShipStation for sponsoring the show! Valor Recovery: To learn more about Valor Recovery please visit them at https://valorrecoverycoaching.com/ or email them at [email protected] ------------------------------------------------- Music: “Shine” by Bishop Gunn Bishop Gunn - Shine ------------------------------------------------ Submit your funny videos, TikToks, questions and topics you'd like to hear on the podcast to: [email protected] Hit the Hotline: 985-664-9503 Video Hotline for Theo Upload here: https://www.theovon.com/fan-upload Send mail to: This Past Weekend 1906 Glen Echo Rd PO Box #159359 Nashville, TN 37215 ------------------------------------------------ Find Theo: Website: https://theovon.com Instagram: https://instagram.com/theovon Facebook: https://facebook.com/theovon Facebook Group: https://www.facebook.com/groups/thispastweekend Twitter: https://twitter.com/theovon YouTube: https://youtube.com/theovon Clips Channel: https://www.youtube.com/c/TheoVonClips Shorts Channel: https://bit.ly/3ClUj8z ------------------------------------------------ Producer: Zach https://www.instagram.com/zachdpowers Producer: Nick https://www.instagram.com/realnickdavis/ Producer: Cam https://www.instagram.com/cam__george/ Producer: Colin https://instagram.com/colin_reiner Learn more about your ad choices. Visit megaphone.fm/adchoices

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

• 0:00Theo Von?

  I have some new tour dates to let you know about. I'll be in East Lansing. I'll be in Toledo, Ohio, Roma, Ontario, in the Canada. Pittsburgh, PA, Eugene, Oregon, Kennewick, Washington, Seattle, Washington, Victoria, BC, in the Canada. College Station, Texas, Belton, Texas, San Antonio, Durant, Amarillo, Oxford, Mississippi, hadda, hadda. Fayetteville, Arkansas. Hee hooey. Tuscaloosa, Alabama, rollin' ahead. And Tallahassee, Florida. Rosemont, Illinois, Winnipeg.

• 0:43Theo Von?

  Um, and Calgary in the Canada. Get all your tickets at theovon.com/TOUR. Thank you so much for your support. And thank you to the fellow in Montana that gave me this jacket. Got some Indian artifacts on the back.

• 0:58Theo Von?

  And just want to say thank you. I really like this jacket. We've also got some new merch, some new Gang Gang tees. Um, in pepper and ivory. And we've got a new Gang Gang hat. That giga deh. Uh, check those out and more at theovonstore.com. Um, happy holidays to everyone. Today's guest is an entrepreneur and a philanthropist. He worked at IBM, he worked at Bank of America. But most people know him as the founder of Craigslist. A site that has given so many unique experiences to the world. We're so happy to get to spend time today with Craigslist's own Craig Newmark.

• 1:58Theo Von?

  And just want to let you know, like, we're just excited you're here and we don't have any, this isn't like a, like a got you podcast. We're not trying to do anything uncomfortable. You know, obviously you've had a very unique life and we just wanna, I think we're curious about it, you know?

• 2:13Speaker 01

  Well, two episodes ago, you had Ryan Martin.

• 2:16Theo Von?

  Yeah.

• 2:17Speaker 01

  And I learned one big thing on, on thinking about what he had said. So I'm, I'm prepared to even mention that because he made me realize something, which I won't be able to do anything about, but at least understanding helps.

• 2:34Theo Von?

  Oh, about anger?

• 2:35Speaker 01

  Yes.

• 2:36Theo Von?

  Yeah. Yeah. He's a, yeah, I thought Ryan Martin was really interesting. He's a professor over in Green Bay. Because I think anger is something that's kind of enveloping people a lot these days, you know? I find it a lot in myself and you almost get in, I mean, obviously it's, it's kind of embarrassing. You know, it's a weird feeling that's like, you know, it can lead to a lot of negativity, can lead to, you know, dangerous activities, but it also you, I feel that you get embarrassed of it, you know? And it kind of just takes you over.

• 3:01Speaker 01

  Well, in my case, it's tied in with some traumatic stress. And my deal is I learned the hard way that no good deed goes unpunished. I learned that a person who's basically honest will never be able to successfully deal with a person who lies for a living.

• 3:21Speaker 01

  That's very frustrating because I have to keep it in. Someday, somebody may be able to do, to deal with it, maybe with some help from me. Someday, some situations may turn into some real drama, possibly criminal referrals. But I'm the kind of guy who people for years have been told, have been telling me that some areas, I just don't have the skills and I contribute by not talking.

• 3:51Theo Von?

  Hmm. So do you feel like you're kind of a quiet guy sometimes?

• 3:56Speaker 01

  Generally quiet, generally restrained, except for reasons of comedy.

• 4:03Speaker 01

  I know, I know that I'm not as funny as I think I am. And yet, like, I tell my philanthropic grantees that I would like for them to tolerate my sense of humor, but not encourage me.

• 4:19Theo Von?

  Okay, nice.

• 4:20Speaker 01

  And so far, that's worked out well, particularly last night, the Bob Woodruff thing. I did briefly hang out.

• 4:28Theo Von?

  What was it last night, just so we can tell our listeners now?

• 4:30Speaker 01

  Yeah. Last night, there was a fundraiser for the Bob Woodruff Foundation. They run a network called Got Your Six.

• 4:40Theo Von?

  Got Your Six?

• 4:41Speaker 01

  Got Your Six, like in the military sense.

• 4:43Theo Von?

  Right, Got Your Bet.

• 4:44Speaker 01

  Yeah. And about 350 organizations who are actually good at helping. And many philanthropic organizations are challenged when it comes to actually helping. But these guys are good. They need a lot of money to help out, help out vets and their families. And this was both a comedy concert and a music concert. The guys, I think it was Mike, Mark Norman.

• 5:09Theo Von?

  Oh, Mark Norman was there?

• 5:10Speaker 01

  Yeah.

• 5:11Theo Von?

  Yeah, he's great. We're both from New Orleans.

• 5:13Speaker 01

  Well, starting from there, there's Jim Gaffigan.

• 5:18Theo Von?

  Wow.

• 5:19Speaker 01

  Joey Seinfeld, and Jon Stewart on the comedy side, which was great for me.

• 5:26Theo Von?

  Yeah.

• 5:27Speaker 01

  And then on the music side, Norah Jones, and then there's this guy, Springsteen.

• 5:34Theo Von?

  Yeah.

• 5:35Speaker 01

  I had spoken to him before.

• 5:36Theo Von?

  Yeah.

• 5:37Speaker 01

  And I told him that, as a nerd, I understood that he was very popular, but that I don't know his music. And he reacted quite satisfactorily. His jaw dropped. His wife, this was a few years ago, but his wife got the joke immediately. The better part of the joke is I was being literal. I really am a nerd.

• 6:03Theo Von?

  Yeah.

• 6:04Speaker 01

  I'm the kind of guy in the late 60s in high school. I wear a plastic pocket protector, thick black glasses taped together, no social skills.

• 6:15Theo Von?

  So you really, you, did you kind of embody that nerd vibe? Like you were like, you saw nerd and you were like, I'm gonna be over here, I'll be there.

• 6:22Speaker 01

  I had to originate the thing.

• 6:24Theo Von?

  Wow, this you right here?

• 6:26Speaker 01

  You found the, the store of old photos.

• 6:30Theo Von?

  Oh wow, yeah.

• 6:31Speaker 01

  That's me in high school.

• 6:32Theo Von?

  That's net.

• 6:33Speaker 01

  Those are the thick black glasses.

• 6:34Theo Von?

  Oh yeah.

• 6:35Speaker 01

  Not taped together at the time. Now see, I can simulate or fake normal human social behavior now, but it is a simulation. I have to, I have to work hard on it all the time. And after a while, I will start getting, start getting cranky.

• 6:54Theo Von?

  Okay.

• 6:55Speaker 01

  But the nerd cliche originated right around when I was around, so I do take credit for it.

• 7:01Theo Von?

  Well, we're glad to have one of the most nerd-torious humans, Craig Newmark. Thanks for hanging out, man. I appreciate it. You know, we're in, we're in the Chelsea Hotel number two. Do you know that? I know you're a Leonard Cohen fan.

• 7:15Speaker 01

  Yes.

• 7:16Theo Von?

  And this is, he had songs based that were based out of here. I think he spent time with Janis Joplin here.

• 7:21Speaker 01

  He did.

• 7:22Theo Von?

  Yeah, allegedly.

• 7:23Speaker 01

  And well, I'm, uh, near where I live, in the, uh, in the village, not far away, walking distance. I have a friend, my comedy consultant, and he lived here during that heyday. He knew both of them and others. He was intimidated by, uh, by Leonard Cohen. See, this friend was in the process of transitioning from music to comedy, which turned out to be easier for him to do. He was really big in the seventies and eighties. He may not have invested well.

• 7:58Speaker 01

  Cause I saw him, uh, saw him yesterday. But he's much funnier than I am for real.

• 8:05Theo Von?

  Yeah, okay.

• 8:06Speaker 01

  And that's why I know that I'm not as funny as I think I am.

• 8:11Theo Von?

  Very fair. You look, you got, you're doing okay with me so far.

• 8:15Speaker 01

  Thank you. If I knew you better, I'd, I believe comedians indulging indulging a practice called breaking balls.

• 8:24Theo Von?

  Oh, yeah.

• 8:25Speaker 01

  I will introduce my friends sometimes as a guy who used to be funny. I will tell him, oh, yeah, comedy requires actually funny material.

• 8:35Theo Von?

  Yeah, yeah, that's a good, that's a good starting, that's a good starting point.

• 8:38Speaker 01

  But he's, he's given me a couple jokes to use, reminding me that at my, at his age and my age, when you get down to tie your shoes, you look around and you think, what else can I do while I'm down here? And unfortunately, that's turned true. When I do get down, I'm, I'm, I have some worries about being able to get back up again.

• 9:01Theo Von?

  Yeah, yeah, yeah. Once you get down to the ground floor again, sometimes you kind of want to stay down there. I, um, I used to, we used to listen to Leonard Cohen when I was a kid. My mom would put it on when we would, uh, when we would have to clean the house on Saturdays and my mom would put it on, um, that I remember that song, uh, when the walls came down.

• 9:20Speaker 01

  Okay, that's, uh, older school even for Leonard.

• 9:24Theo Von?

  All the way to hell. And we'd be like, all right, I'll, I'll clean.

• 9:28Speaker 01

  Yeah, I vaguely remembered, uh, him, well, in like eighty-eight or so, uh, I'm Your Man premiered, and I love that. And first we'll take Manhattan, and then I found, uh, various positions.

• 9:43Theo Von?

  What is that first? We'll take Manhattan and with?

• 9:47Speaker 01

  Then we'll take Berlin.

• 9:48Theo Von?

  And then we'll take Berlin. Yeah, dude, that's crazy. That, those lyrics have mildly been in my head over the years, and I didn't even know that that's where they were from. They were from Leonard Cohen.

• 9:57Speaker 01

  Yeah, he influenced a lot of musicians after. Uh, he's my favorite to, uh, in an obsessive way.

• 10:06Speaker 01

  And now and then, when I'm in the right mood, I will listen to him. He's not cheerful, by the way, most people will think about him.

• 10:15Theo Von?

  He's a little dark.

• 10:16Speaker 01

  Yeah, but he's uplifting if you're into it.

• 10:19Theo Von?

  Yeah, he reminds me of a kind of a darker Anthony Bourdain of music in a way.

• 10:24Speaker 01

  I haven't thought about that, but I'm trying not to think too much about food.

• 10:30Theo Von?

  Okay, okay. Well, you have a...

• 10:33Speaker 01

  Well, my problem simply is that since I've been on the run all morning, I did pass a place which had what looks like a good slice of pumpkin pie.

• 10:43Theo Von?

  Oh, yeah, brother.

• 10:44Speaker 01

  I, however, may have been disappointed. So I'll think of something later this afternoon.

• 10:51Theo Von?

  Something a little less risque, huh?

• 10:52Speaker 01

  Well, my problem is that food is just too delicious. And it's hard to know when to stop.

• 11:00Theo Von?

  Yeah, well, it's funny because they don't put a stop sign at the bottom of a dessert or something.

• 11:05Speaker 01

  That may or may not be helpful. I will face the challenge in roughly two hours.

• 11:12Theo Von?

  Okay, there we go. Well, we have you for a limited time today. I do want to talk. You are the Craig from Craigslist.

• 11:19Speaker 01

  Yeah.

• 11:19Theo Von?

  That is true.

• 11:20Speaker 01

  Yes.

• 11:20Theo Von?

  Okay. And how did Craigslist start? Like, just, I know that's a basic question, but it's, you don't even think about it as a regular human. We don't even know that you're a real, we just, you don't even know.

• 11:32Speaker 01

  Yeah, and I occasionally tell people that Craig is fake, like Betty Crocker. My deal is that I moved to San Francisco mid, well, mid 93.

• 11:44Theo Von?

  Okay.

• 11:45Speaker 01

  And I saw there were a lot of people helping each other out on the net, sometimes doing so, giving away expensive consulting time.

• 11:55Speaker 01

  And I took advantage of that. People helped me settle in, told me about neighborhoods and restaurants and events that I might get interested in.

• 12:03Theo Von?

  So you're communicating on the, on the internet, just with people looking for information about being, living in a new area?

• 12:09Speaker 01

  Yeah, a lot of this was from the well and early virtual community, some from Usenet news groups, which were the first big deal discussion boards. And there is this spirit that we were all going to use the net to help each other out.

• 12:24Theo Von?

  Yeah.

• 12:25Speaker 01

  So I thought I should get back, started a simple CC list, telling people about what I thought were cool events, usually arts and technology, like Joe's Digital Diner, or the Anon Salon, which was a party fundraiser for a local theater, highly entangled with the very earliest Burning Man. And I, I never got involved with that because I realized that I'm not a burner at heart.

• 12:54Theo Von?

  Yeah.

• 12:55Speaker 01

  But this mailing list started growing via word of mouth. And I started asking for more stuff than just events, like if people wanted to sell something, if people had a job or an apartment.

• 13:10Theo Von?

  So that's how it started. You started just emailing people just with information about things to do in the area. It started to grow. And it was just an actual list of people you were sending a message to.

• 13:19Speaker 01

  Yeah, it was literally an email CC list, and that broke at 240 addresses. I had to use a listserv. I had to give the thing a name. I was, I'm very literal as a nerd. I wanted to call it San Francisco Events, since it was still mostly that. Yeah, I, yeah, I don't have much of an imagination.

• 13:41Theo Von?

  Well.

• 13:42Speaker 01

  But then I, I was going to call it S of Events. People around me told me they had given it a name, Craigslist. They told me I had accidentally created a brand. Then they explained to me what a brand is, because I was that naive. They were right. Called it Craigslist, just kept growing increasingly. For the first three years, just me.

• 14:07Theo Von?

  And how often was the, was the list going out?

• 14:10Speaker 01

  Whenever somebody had something, I would send it out.

• 14:13Theo Von?

  Okay. So is that once a week or twice a month?

• 14:16Speaker 01

  If I was lucky, it could be, let's say, something worthwhile a few times a day.

• 14:21Theo Von?

  Oh, nice. Okay.

• 14:23Speaker 01

  The deal is not that big, but let's say high value. And I was being careful. I didn't want to spam anyone. And it just kept growing via word of mouth. And we've never really done any advertising.

• 14:37Theo Von?

  Yeah.

• 14:38Speaker 01

  Yeah, I should be careful. I'll wrap around to it, but I'm not involved with the thing nowadays. I'm retired, busier than I've been, but retired. But yeah, the deal is it's just me for a few years.

• 14:50Theo Von?

  And you're the only staff member?

• 14:52Speaker 01

  Yes.

• 14:52Theo Von?

  And what were some of those early high value items? Like, what was something that would come across? Are we talking like, kind of like a, like a painting? Are we talking like a little catamaran? What are we talking?

• 15:03Speaker 01

  Mostly I was thinking about jobs.

• 15:06Theo Von?

  Okay.

• 15:06Speaker 01

  Because one of the best things you could do for someone is to help them get a job. Sometimes then help them, well, find a place to live.

• 15:17Speaker 01

  What Craigslist is about in a lot of ways is helping put food on, helping people put food on the table.

• 15:22Theo Von?

  Right, you were, yeah, that's a great point. If you can help somebody get a job, it's such a, that's residual.

• 15:28Speaker 01

  And it was completely free the first three years. But the people who were putting jobs on there wanted me to charge them for, to post for jobs.

• 15:39Theo Von?

  Because they felt some like indebted in some way?

• 15:42Speaker 01

  Well, they felt that they were paying a lot more money for job ads in other places with fewer results, less quality results. So they said, charge us a little bit, that'll pay the bills. And they were right. Experimented a little bit with volunteers and charging for jobs in 98. But I got the idea from people in 97. Running with volunteers didn't work.

• 16:11Theo Von?

  What do you mean running with volunteers? You mean to help you?

• 16:13Speaker 01

  Yes.

• 16:13Theo Von?

  Okay, and at that point, you're just doing it out of your home?

• 16:16Speaker 01

  Exactly right.

• 16:17Theo Von?

  First three years off of your home computer?

• 16:19Speaker 01

  Yeah.

• 16:19Theo Von?

  And how big, how big did the email list get? Sorry, Craig.

• 16:23Speaker 01

  You know, I don't really know how big it got through that time. Because in 96, I remembered that I'm a programmer. I can write software which turns emails into webpages. And so I started doing that, which gave me web publishing for free.

• 16:41Theo Von?

  Okay.

• 16:42Speaker 01

  And I, when something started taking too much of my time, I wrote some more code, which reduced what might take an hour a day to a few minutes a day.

• 16:51Theo Von?

  Got it.

• 16:51Speaker 01

  And that happened a number of times. But ninety-eight tried running it with volunteers. The people who cared for the thing, who were doing job postings in particular, said volunteer thing isn't working. Sometimes things would take a while to get posted. So I had to make the thing into a real company.

• 17:12Theo Von?

  Right. So at that point, you're like, if I wanted to keep this going, it's gotta, there needs to be some checks and balances. And obviously salaries help help create that.

• 17:20Speaker 01

  Yeah, I need to hire other people to do coding, customer service billing. And that meant making it into an actual corporate structure.

• 17:33Theo Von?

  Was that scary to think about that?

• 17:35Speaker 01

  Very scary. But the hard part was, at that point, you know, at events, parties, I would talk to bankers and venture capitalists who wanted me to do the usual Silicon Valley thing.

• 17:47Theo Von?

  Yeah.

• 17:48Speaker 01

  Monetize everything. And they would throw billions at me. And I was thinking, I don't need billions. I don't understand why people would do that. Speaking, and that has to do with in Sunday School, Mr. and Mrs. Levin, they taught me that you should know when enough is enough. They taught me to treat people like you want to be treated. So nothing altruistic. This is just a return to Sunday School values, literally. And so we Craigslist philosophy is to monetize only those ads for people who are paying more money for less effective ads.

• 18:33Speaker 01

  So not an altruistic decision.

• 18:35Theo Von?

  Right.

• 18:36Speaker 01

  Just basics.

• 18:38Theo Von?

  Yeah, but also a little bit of barrier to entry, which not in a negative way, because you still, everybody needs to hire someone or has the opportunity. And maybe they can't afford the ad, but, but it provides a little more structure too. Even just some basic.

• 18:53Speaker 01

  Yeah.

• 18:53Theo Von?

  It does provide some structure, right?

• 18:55Speaker 01

  Well, that's useful in the sense that.

• 19:00Speaker 01

  Well, everyone is struggling trying to get through the day.

• 19:03Theo Von?

  Right.

• 19:04Speaker 01

  And some people are selling, doing things for profit like brokering apartments in New York City. And with, sometimes with questionable ethics. And I found one year that new apartment brokers might make like 20K in a year, which even 15 years ago, you had to work two or three other jobs. So I said, how do you balance the idea that you want to give everyone a break? And I was able to suggest stuff to the people running the company at that point. Because also in, again, I made Craigslist into an actual company in 99.

• 19:45Theo Von?

  Okay, so that's when it became an actual company in 1999?

• 19:48Speaker 01

  Yeah.

• 19:48Theo Von?

  And at that point, you guys have an office? You guys have?

• 19:52Speaker 01

  We turned it from running it in a room in my house into a room in a commercial strip way out in the neighborhoods of San Francisco.

• 20:03Theo Von?

  Wow, that's cool.

• 20:04Speaker 01

  And the other hard decision I had to make that year, 99, was that I started to realize with help that as a manager, I suck.

• 20:15Theo Von?

  Oh, yeah. It's hard to be a manager, isn't it?

• 20:17Speaker 01

  Very hard.

• 20:18Theo Von?

  You don't realize when you're gonna go, when you're gonna, once you start to have employees and stuff, you're like, suddenly I'm a boss. And if you never wanted to be a boss, it's a very precarious situation to be in. I've been there, man. What, what were some of the things that you noticed you were not good at?

• 20:33Speaker 01

  Well, mostly hiring and firing.

• 20:36Theo Von?

  Okay.

• 20:36Speaker 01

  As a nerd, I am not good at reading people. And I needed to promote someone who would be good at that. And I'd already stopped coding because I hired a bunch of people who are better than me.

• 20:50Theo Von?

  Okay.

• 20:50Speaker 01

  I stepped down to just do full-time customer service. I'm a great customer service rep.

• 20:56Theo Von?

  Okay.

• 20:57Speaker 01

  Not a manager of customer service, but I was a customer service rep and did that for maybe around 15 years.

• 21:05Theo Von?

  Okay, so you ended up just being a customer service rep at your own company?

• 21:08Speaker 01

  Yes.

• 21:09Theo Von?

  Wow, so if somebody had a customer service issue, they would contact you on the phone or email?

• 21:13Speaker 01

  Well, with some luck. They would contact someone else on phone first.

• 21:19Theo Von?

  Okay.

• 21:20Speaker 01

  I took that luxury for myself of not having to answer the phone.

• 21:24Theo Von?

  Okay.

• 21:24Speaker 01

  But they would generally email me because I was just Craig at craigslist.org. Easy to guess. So I spent a lot of time doing that kind of thing and got a lot of stuff done.

• 21:39Theo Von?

  And you found yourself effective there?

• 21:41Speaker 01

  Yeah, well, I saw, what I mostly saw was a lot of good. That is, people on the net are overwhelmingly good. The bad guys, bad actors, get a lot more press because sometimes mainstream media generates clicks by emphasizing the bad.

• 22:01Theo Von?

  Yeah.

• 22:01Speaker 01

  This is kind of a normal thing.

• 22:03Theo Von?

  Especially nowadays. What were some of the, what were some of the things you saw in there early that, that helped you to believe in the good and continue to make it go?

• 22:12Speaker 01

  Consistently, I saw people helping each other out. Consistently, I saw people give away stuff that they could have sold for some cash.

• 22:22Theo Von?

  Ah.

• 22:23Speaker 01

  Like sometimes you don't need the cash and then you would just give away something of actual value, like old computer equipment. That was pretty good.

• 22:34Theo Von?

  Oh, yeah. A lot of baby cribs on there, a lot of stuff like that.

• 22:37Speaker 01

  In fact, that's in particular, that's particularly true. Baby cribs, baby carriages.

• 22:44Theo Von?

  Oh, yeah.

• 22:44Speaker 01

  And moving boxes because.

• 22:47Theo Von?

  Which could also be a baby carriage, depending on, you know.

• 22:49Speaker 01

  Or a cat toy.

• 22:50Theo Von?

  Oh, yeah.

• 22:52Speaker 01

  But the idea is that when you move, you have a lot of boxes which are still really good. And the chances are nearly 100% someone not far away needs.

• 23:05Theo Von?

  Needs those boxes.

• 23:05Speaker 01

  Good boxes.

• 23:06Theo Von?

  Yeah. I used to live with a guy, I lived with this guy named Kenny for a bit, and he. Was a pretty big stoner, right? And I didn't know him. Met him on Craigslist, right? I get over there and I end up living over there and he would stack, he had a couple of cats and stuff. And at night, he was kind of like a, uh, I guess, kind of an avant garde, like circus-y, kind of an animal trainer guy. But he would stack all the boxes, these empty boxes in the room, and he would make the cats play on them. And he'd make me come out of my room to watch the show, you know? So it was crazy, but it was like, I don't know, it's something I still kind of remember about him. I kind of, I guess it was pretty, I thought it was interesting. But yeah, people use boxes. Yeah.

• 23:45Speaker 01

  Yeah. Well, the deal is that, uh, people everywhere in the country are, uh, okay. I, uh, when you're doing customer service at that deeper level, you see a lot of stuff and most of it is great. I did see some stuff I, uh, wish I didn't. And that's the problem with content moderation. It's a very tough job, especially if it's full time and you're not getting paid much. And so these people are only seeing questionable stuff and that can do some damage.

• 24:18Theo Von?

  Yeah. Were you, uh, so at that point, yeah, I guess, because Craigslist started to be this place. It kind of became everything really fast is what it felt like just as a user, right? It became like a first place where you could get a used, you know, you could get a blender, an air balloon or a roommate. But then it started to escalate too, where there was like, um, you know, people would buy drugs on there, you know? Or people, you'd see people like, um, I would do it, you know? And you would see people, but they also had code names for the drugs. So it made it to be this kind of like, um, it, it had a fun spot to it, you know? You'd be on there. I mean, they had like, I remember beef jerky was a code name. Um, those mini Bennys they had, that brain dander, that baby hay was one of them.

• 25:03Theo Von?

  Um, I'm trying to think of any other, that Pedrito Blanco was a spam, but you know what it was? That Dragon de Negro they had. Um, uh, I'm trying to think of that Whispering Mother. That was, that was a kind of a native one that they were, that was peyote.

• 25:18Speaker 01

  Well, I know that, uh, the mainstream press greatly exaggerated a lot of this. They didn't point out that what you see on the street always makes it online and online everywhere.

• 25:31Theo Von?

  You guys weren't producing it.

• 25:32Speaker 01

  Well, what they, what the mainstream press doesn't point out, that if you're a conscientious site. You keep around the digital forensics and because people leave a lot of trace evidence around CSI style.

• 25:47Theo Von?

  Wow.

• 25:48Speaker 01

  And that years and years ago, I talked with a lot of cops who were real pleased with the way that we kept around the forensics. And because of high school history, I learned the balance between fighting crime and the rights of the accused, what's in the Bill of Rights, what's in the Constitution.

• 26:10Theo Von?

  Wow, so you had to, so you took that upon yourself to, it must have been kind of a tough navigation. Was it tough to navigate that personally because you have this, this atmosphere that people can kind of, it's a, it's just a pathway, right?

• 26:23Speaker 01

  Well, what I did is I mentioned this to the boss and to the lawyers and said that we got to do this balance. We had the advantage of having the Electronic Frontier Foundation available because they're the big pioneers of all this stuff online.

• 26:39Theo Von?

  What does that mean, the Electronic Frontier Foundation?

• 26:41Speaker 01

  Well, what they did is they're a great voice in standing up for the rights of regular people. And that balance, you got to do the right thing to, for victims and cops, you got to do so in an American way, meaning looking at the Bill of Rights. And if a cop wants to see the forensics, there needs to be something like a subpoena or a search warrant. That's the way things are done in our country.

• 27:08Theo Von?

  There's the laws.

• 27:09Speaker 01

  That's judicial overview. And that's the ultimate purpose of that was to prevent the kind of abuse we saw under King George, literally speaking. I did have that really good high school history teacher. He taught the kind of civics that you don't have nowadays. But I took this in the, in 1970, I'm really old.

• 27:34Theo Von?

  You look great.

• 27:34Speaker 01

  Well, thank you. This teacher was great because he even took us once to a taping of a firing line, which was William F. Buckley Jr. He invented American conservatism, at least the modern form of it. And that really influenced me because at that point, I'm going off on a tangent, but at that point I was looking at that. I was starting to take a bit of a look at libertarianism, that kind of stuff. And this is more than 50 years ago.

• 28:05Theo Von?

  So it's funny because you kind of ended up in this space later on where you're like trying to look at the ethics of like, um, communication, who has rights, what the, how do you protect people, but also give people the freedoms that they are deserve under their own life? Is that what you're kind of saying?

• 28:21Speaker 01

  That's pretty much it. Um, these days, frankly, uh, I've given up on politics.

• 28:26Theo Von?

  Yeah.

• 28:26Speaker 01

  For some years, I now regard terms like liberal and conservative as kind of bullshit.

• 28:33Theo Von?

  Yeah.

• 28:34Speaker 01

  And I gotta, well, I gotta focus on helping people who protect the country. Like there's vets and their families. There's active service members in their families. Uh, and right now, uh, we're beginning to see battles on our soil, on our own systems, uh, as a precursor to a cyberspace warfare.

• 29:00Theo Von?

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• 29:40Theo Von?

  business and get the same checkout that Allbirds uses. Sign up for your $1 per month trial period at Shopify.com slash.

• 29:52Theo Von?

  Theo, all lowercase. That's Shopify.com/ Theo. Just go to Shopify.com/ Theo to upgrade your selling today. Shopify.com/ Theo. You know, since the last holiday season, things have changed, certainly. The world has gotten busier and different. Your life has changed. Maybe something you did last year, you don't do anymore and something you didn't do, now you do. Things evolve. Certainly, we have that with our online store. Different items. Switching to a new storefront. All those sorts of things come into play.

• 30:36Theo Von?

  ShipStation helps us achieve our shipping goals. That's right. Whether you're looking for better efficiency during the hectic holiday season or your business has outgrown your old shipping solutions, you need ShipStation to help you scale your business. I love the automation. I love the simplicity. I love being able to not only learn it for myself, but instruct a coworker easily. Scale your e-commerce business with the shipping software that delivers. Switch to ShipStation today. Go to ShipStation.com, use code Theo to sign up for your free 60-day trial. That's ShipStation.com code T H E O.

• 31:20Speaker 01

  Right now, people, well, like you, as an influencer, you're a target.

• 31:27Theo Von?

  Yeah, we get stopped for things and we have to take certain things down, things that we think are just fair speech, you know, we have to put it all through a filter, you know?

• 31:34Speaker 01

  Well, I'm more worried about our foreign adversaries. And I'm most worried about our foreign adversaries starting to compromise our utilities, water, power, and even our cars. Because that's a thing that's happening in the here and now.

• 31:52Theo Von?

  Really?

• 31:52Speaker 01

  You could do a search online for something called Volt Typhoon.

• 31:56Theo Von?

  How do you spell it?

• 31:57Speaker 01

  Volt, like electrical volt.

• 31:59Theo Von?

  Okay, Volt.

• 31:59Speaker 01

  Typhoon, like a big storm. And the FBI have been warning everyone that right now.

• 32:07Theo Von?

  Yep. What is a Volt Typhoon? A cybersecurity expert explains that Chinese hackers targeting US critical infrastructure.

• 32:14Theo Von?

  What is this? Can you tell me a little bit about it? Do you mind, Craig?

• 32:17Speaker 01

  Right now, what they're doing is they're infiltrating home systems to be used to attack other systems. What's worse is they're attacking the programmable controllers, which control the flow of water into our taps. They're controlling the flow of electricity into our homes. And a lot of those systems for much of the country are not protected. The deal is that most of the country, there are rural water systems, rural electrical systems. They don't have the resources to protect them. So a Chinese hacker, a Chinese military hacker could get in there.

• 33:02Theo Von?

  And sway our elections and stuff?

• 33:03Speaker 01

  Well.

• 33:04Theo Von?

  Sway our waterways, sway if we have access to water?

• 33:07Speaker 01

  Well, what they can do is turn off the water supply. And so if, let's suppose you wanted to invade a small island country, which was our ally. And if the other country, our adversary, wanted to discourage us from fighting on behalf of our ally, they could just started, they could start shutting off water and power. And, you know, if they did that where you're living, that would kind of ruin your day.

• 33:37Theo Von?

  Yeah, yeah, yeah, yeah.

• 33:38Speaker 01

  And for that matter, they could, they could compromise cars, which are internet devices.

• 33:45Theo Von?

  Oh, that's true, especially as cars become more electric.

• 33:47Speaker 01

  Yeah.

• 33:48Theo Von?

  And more like digital, really.

• 33:50Speaker 01

  Yes, they could shut off your car, stall it out in the middle of rush hour traffic. If they did that in a city like New York, if they could just do a hundred cars, that snarls traffic indefinitely.

• 34:03Theo Von?

  Wow. Yeah, you do that and then they shut the power down and now things are getting really weird.

• 34:07Speaker 01

  Yeah. And all they would have to do is show they could do it. And that would, that's where the military is headed these days. It is not replacing shooting wars.

• 34:19Theo Von?

  Yeah.

• 34:19Speaker 01

  But it's more powerful. Like in World War II, the war came to our shores a little bit. In whatever's happening next, it's going to be a much bigger thing. I'm planning to issue a national call to action wherein we tell everyone that we need to protect our homes. Utility companies need to protect themselves. We're trying to build the networks of networks where everyone can protect each other.

• 34:51Speaker 01

  I'm, I'm not the guy to really be Paul Revere.

• 34:55Theo Von?

  Right.

• 34:56Speaker 01

  Uh, cause that would require like social skills.

• 34:58Theo Von?

  Mm hmm.

• 34:59Speaker 01

  And remember, I'm a nerd.

• 35:00Theo Von?

  But you could be his horse, maybe.

• 35:02Speaker 01

  Well, I need to be something. But the deal is, is as I issue this call to action, as I point out that many utilities are not protected. I'm going to piss off a lot of people.

• 35:14Theo Von?

  You think so? Um, why would they be upset? I don't understand that part.

• 35:17Speaker 01

  Well, sometimes people kill the messenger. And I got, so I'll do it carefully. We're ramping up slowly. We have this pause, take nine campaign. So when you get a, like a suspicious email, that could be phishing. And our adversaries are really smart. They're as smart as our guys.

• 35:38Theo Von?

  Yeah.

• 35:39Speaker 01

  And, uh, we need to know how to fight back. I need to consider helping out a new group being funded at Vanderbilt.

• 35:48Theo Von?

  At Vanderbilt?

• 35:49Speaker 01

  Yeah.

• 35:49Theo Von?

  Oh, nice. That's where I live in Tennessee.

• 35:51Speaker 01

  Well, they've just, uh, started within the past couple of weeks, started a new facility, which is going to be led by, uh, General Paul Nakasone, who led, I think it was Cyber Command. And they have this, uh, philosophy of, uh, defense forward where they're, uh, not waiting for the adversary to come and get us. We're taking more active measures.

• 36:15Theo Von?

  And that's a big concern for you. So that's something you donate to, right?

• 36:18Speaker 01

  Well, that's the, a big area, like one big area in veterans and military families. And I've now committed to, uh, 200 million.

• 36:29Theo Von?

  Wow.

• 36:30Speaker 01

  And I've already spent more than half of it. For cybersecurity, I've also committed a couple hundred million. This is not altruistic. This is just, well, I was raised in the 50s to be a patriot. This is just me following through with basics. And I got the cash. I'm not much for luxuries. I do get all the streaming services I want. And I do have a larger TV than I should.

• 37:02Theo Von?

  Yeah, I won't say anything.

• 37:04Speaker 01

  And beyond that, well, again, back to Sunday School. You want to know when enough is enough.

• 37:13Theo Von?

  Right, you have to get back. Yeah, we talk about that on here sometimes. I wonder if there should almost be a law. I mean, you couldn't make it a law, but that at a certain point, people, somebody doesn't need any more money, you know, like, because then it becomes, you see some people, they just have so, it's like, what are you doing? Like, you know, it becomes almost this obsessive thing where, I don't know, it just, it seems scary to think that some people have so much money.

• 37:34Speaker 01

  Well, I don't judge any of that. Everyone decides what's right for themselves. And that's none of my business.

• 37:42Theo Von?

  Okay.

• 37:43Speaker 01

  I figure I should put my money where my mouth is. And then try to get some good stuff done, make the occasional mistake. And some of my decisions weren't great, but they weren't really mistakes.

• 38:00Theo Von?

  You mean like in what, investing and stuff like that, you mean?

• 38:02Speaker 01

  Well, I don't invest really.

• 38:04Theo Von?

  Okay.

• 38:05Speaker 01

  I do, I guess, yeah. What, in the libertarian movement and the related financial stuff, in the 70s, early 70s, there was this idea of capital preservation. Because inflation was really bad then. So people were finding assets which, where they could preserve their capital. Of course, I was in college, I didn't have much.

• 38:28Theo Von?

  Right.

• 38:29Speaker 01

  But I invest in the literal sense, very little. I just want to keep what I have for nonprofits and some for myself. And I want to keep that safe.

• 38:41Theo Von?

  Yeah.

• 38:42Speaker 01

  And, but that's the old libertarian background.

• 38:46Speaker 01

  Um, these days, my philosophy is much more mixed because I am, uh, you know, told in Sunday school and elsewhere that you do want to, well, now and then you go on to be your brother's or sister's keeper.

• 39:01Theo Von?

  Mm hmm.

• 39:01Speaker 01

  Now and then you want to help people out who need a hand.

• 39:04Theo Von?

  Mm hmm.

• 39:05Speaker 01

  How you do that effectively, no one knows the real answers for, but I can do a couple of things and not altruistic, it's just, uh, basics.

• 39:15Theo Von?

  Mm hmm.

• 39:16Speaker 01

  And I learned all that, uh, over 60 years ago. I mean, I realized recently how formative that was. That's when I started reading, uh, science fiction.

• 39:25Theo Von?

  Hmm. Yeah, it's funny how those young years, you, there are little things you'll keep. I still remember like certain things that I told someone I would do like 25 years ago. And every day, every couple of days, someone was like, hey, don't forget, you still have to do that little thing, you know? Um, it's funny how, how like those formative years and things that we hear when we're young, um, can have such an in, in, uh, such an effect on us even as we grow older. Um, I want to talk a little bit more about the actual site. So the company starts growing, right? And in addition to people helping each other get jobs, people were helping each other, people were starting relationships on there. I went on dates off of, um, Craigslist before, you know?

• 40:04Speaker 01

  Good.

• 40:04Theo Von?

  Did you yourself ever go? Did you?

• 40:06Speaker 01

  No, I, I always felt like a conflict of interest.

• 40:10Theo Von?

  Yeah.

• 40:10Speaker 01

  And, uh,

• 40:11Theo Von?

  That's true. You're like, hey, I'm Craig.

• 40:12Speaker 01

  Yeah. I got, I got lucky in a, uh, I got lucky in a, uh, local, uh, cafe.

• 40:18Theo Von?

  Oh, you met your?

• 40:19Speaker 01

  Wife.

• 40:20Theo Von?

  Your wife? Okay.

• 40:21Speaker 01

  And we've been together for over 20 years now.

• 40:24Theo Von?

  Wow. And if you have some social awkwardness, what was that like for you?

• 40:27Speaker 01

  Uh, I decided I would take a, a big chance.

• 40:30Theo Von?

  Yeah, I've been there, dude.

• 40:32Speaker 01

  And, uh, uh, told her that, uh, she's beautiful. The guy next to me, she tells me he rolled his eyes.

• 40:40Theo Von?

  Yeah.

• 40:41Speaker 01

  And because he rolled his eyes, that's why she started talking to me.

• 40:46Theo Von?

  Oh, wow. So there was a little bit of some empathy there, human empathy.

• 40:52Speaker 01

  Well, it could have been a pity discussion.

• 40:55Theo Von?

  That's another way of saying empathy.

• 40:56Speaker 01

  Obviously, I, obviously, I charmed her.

• 41:00Theo Von?

  Yeah, that's the spirit.

• 41:01Speaker 01

  So last night, we were at this fundraiser because I think she wanted to meet Jerry Seinfeld in particular, and I don't blame her. I had nothing to say. I was tongue tied. But that's how I normally act when I talk to celebrities, particularly if you're backstage and there's a show going on.

• 41:25Theo Von?

  Yeah.

• 41:26Speaker 01

  And having done a little bit of that, you got to get your head into the moment, and you don't want a distraction.

• 41:33Theo Von?

  Right. Yeah, that's a good point. You just want to kind of be a fly on the wall in some sense.

• 41:37Speaker 01

  Yeah.

• 41:38Theo Von?

  Wow. So you started off, said hello in a cafe, and then how long was that? Was your relationship, how long did that kind of dating life go for you guys?

• 41:50Speaker 01

  Well, after about nine years, I think, I brought her over to, I showed her Facebook on a screen. I don't really use it anymore, but I said, is it okay if I change my relationship status to engaged?

• 42:05Theo Von?

  Wow.

• 42:06Speaker 01

  And it took her a moment, but she said, oh, that's good, because I calculated at that point that parental pressure had grown significantly.

• 42:17Theo Von?

  From yours and hers?

• 42:18Speaker 01

  Hers.

• 42:18Theo Von?

  Okay.

• 42:20Speaker 01

  And that worked out pretty well.

• 42:23Theo Von?

  That's a pretty suave online move. That's almost the most online way you could ask someone to marry you, I feel like.

• 42:30Speaker 01

  Well, I hate to say it, but if you consider that suave, you may also be a bit of a nerd.

• 42:36Theo Von?

  I have, I think when it comes to, yeah, yeah, there's like, yeah, talking with women, it definitely, it's not my, you know, I wouldn't, yeah.

• 42:48Speaker 01

  Yeah, I uh.

• 42:49Theo Von?

  You're not, yeah.

• 42:50Speaker 01

  Yeah, I, okay, that's the nerd cliche again.

• 42:53Theo Von?

  I, um, yeah.

• 42:54Speaker 01

  I'm still socially awkward. Uh, sometimes I can disguise that.

• 42:59Theo Von?

  Yes.

• 42:59Speaker 01

  But that's still, uh, me and it's not going to change now that I'm in my, uh, sunset years.

• 43:06Theo Von?

  Yeah, yeah, yeah. Sometimes it doesn't go away. You kind of start to learn it. I think I just had the, I, I have the tough thing of asking a girl out. Like, sometimes I'm okay with talk. I'll, I'll, I'll get good with talking with a woman, but it's just that next part. And we'll just be standing there and we'll be like, well, somebody should ask somebody out or walk away from somebody. And then you're just still just standing there.

• 43:26Speaker 01

  Yeah. Well, that's the purpose of, uh, Miss Connections.

• 43:29Theo Von?

  Yeah.

• 43:30Speaker 01

  Which anecdotally, I know, uh, works once in a while because I've encountered, uh, over the years, a bunch of, uh, couples which had gotten, uh, married.

• 43:40Theo Von?

  No, off of Miss Connections.

• 43:42Speaker 01

  Yes. And, uh, I like that a great deal. It is, uh, romantic in a understated way.

• 43:49Theo Von?

  Oh, yeah. Well, how did that start? How did that Miss Connections start?

• 43:52Speaker 01

  Well, Jim decided he wanted to put it up. He was the boss then, so he did.

• 43:56Theo Von?

  Oh, Jim was the, um, guy running the company at that point?

• 43:59Speaker 01

  Um, when I realized that, again, I'm a terrible manager, I'd already hired Jim, who's a good manager.

• 44:06Theo Von?

  Jim, what's his?

• 44:07Speaker 01

  Jim Buckmaster.

• 44:08Theo Von?

  Jim Buckmaster, yeah.

• 44:09Speaker 01

  You'll see pictures of us, uh, together and if it looks like we're at, uh, eye level, it's because I'm standing on a box.

• 44:17Theo Von?

  Okay. He, he's a, he's a smaller guy?

• 44:20Speaker 01

  He's a big, uh, he's a foot taller than me.

• 44:22Theo Von?

  He's a taller guy. Okay.

• 44:23Speaker 01

  So it makes for, uh, good, there are.

• 44:26Theo Von?

  There you are. You actually do have your box.

• 44:27Speaker 01

  That's, uh, the old office space and I was the one who, uh, who, uh, suggested the, the gag there.

• 44:36Theo Von?

  Yeah.

• 44:36Speaker 01

  And, uh, and, uh, kudos to your guys for being really good at pulling stuff up.

• 44:42Theo Von?

  Craigslist.org. Yeah, man. When you guys were the first one to do.org, people were like, what is it? People thought I meant Oregon. People didn't even know what, you know, where is it?

• 44:52Speaker 01

  Well, it was an early use of it and our approach was to be this minimal monetization thing. And there's no category for that online. So that caught the spirit and worked.

• 45:06Theo Von?

  Yeah. And, um, and so missed connections, do you remember like the first missed connection that was ever put up or the first personal that was ever put up? I'm sure people ask you that a lot.

• 45:14Speaker 01

  Don't remember much of that at all. Um, I, everything is a blur. And unfortunately, I wasn't smart enough to keep a lot of records. And so a lot is, uh, lost. Like from the, uh, Internet Archive and the Wayback Machine, I could see the first site that I put up was mid or late 96. And that was pretty good. And I evolved that kind of minimal style. Like, right now, our site hasn't changed much in appearance in 30 years.

• 45:50Theo Von?

  Why is that?

• 45:51Speaker 01

  Well, I talked to a lot of people and they want it simple, fast, effective. They want, what you see is what you get. And we've heard from a lot of designers who want fancy.

• 46:04Theo Von?

  Yeah.

• 46:05Speaker 01

  And fancy may not be, uh, the answer for a lot of things.

• 46:11Theo Von?

  Yeah.

• 46:11Speaker 01

  Sometimes, you know, you do see something which is impressive, fancy and yet effective. But that seems to be the minority.

• 46:20Theo Von?

  Yeah. Yeah. Yeah. This is, you know what you want. What do you want?

• 46:24Speaker 01

  Yeah.

• 46:24Theo Von?

  You want heavy equipment outside of South Jersey? What do you want? You know, you want biotech out of, you know, in Mendocino? You know, you want legal issues? You know, you want rideshares? You want rodeo interests outside of Fort Worth? It's just, it's all right there, you know?

• 46:40Speaker 01

  Yeah.

• 46:40Theo Von?

  You can put it together quick, even a simple, even someone who isn't technologically advanced could go here. And even the, the, the terms you have on there, it's like childcare, right? Pets, rants and raves. It's like, it's just, it's every, anything you could need is kind of right here.

• 46:56Speaker 01

  And that means the site is always fast.

• 47:00Theo Von?

  And oh, because it's not a lot of big back, background. Wow.

• 47:04Speaker 01

  And See, we've helped people in the tens of millions or more put food on the table.

• 47:11Theo Von?

  With jobs, you mean, and selling things?

• 47:13Speaker 01

  Uh, exactly.

• 47:14Theo Von?

  Okay.

• 47:15Speaker 01

  And advertise their services. But also, we've, the site is so simple. We've shown tens or maybe hundreds of mil- millions of Americans that the internet could be useful and reasonably easy to use. And that meant a lot of people who may have been hesitate- hesitant to get on the net. They get on the net, and again, that's fairness for everyone. That's treating people like you want to be treated, and that ain't bad.

• 47:48Theo Von?

  Yeah. Fairness, that's an important word, huh? You, it's important to you?

• 47:53Speaker 01

  Uh, very much so, because, uh, you try. Sometimes it's hard. There are often tough decisions to be made. And, uh, but Jim, uh, took over that for the company. And, you know, maybe he's done a better job than I ever could. And I did make for a great customer service rep.

• 48:13Theo Von?

  What, how, what made you choose Jim Buckmaster? What was it about him when you interviewed him?

• 48:17Speaker 01

  Uh, he believed in the mission. And he was, uh, good on the technology side. Because he, in a way, had two jobs, a manager and programmer. Because getting good programmers is hard. And Jim, over time, hired a tech staff, everyone better at their job than I was.

• 48:41Theo Von?

  Wow. That's cool. It's also cool to hear you recognize that. Like, yeah, these people are better than I was, you know, to learn where your spaces were best.

• 48:49Speaker 01

  Uh, yeah, I'm funnier than any of them are.

• 48:52Theo Von?

  Of course.

• 48:53Speaker 01

  Uh, but that's a, uh, that's, uh, may not be a high bar. Well, they did sometimes did great things and like they would sometimes pull out great, uh, great ads of all sorts, particularly Miss Connections. And for a while ran a, uh, running Best of Craigslist, although I haven't looked at that in a while. You see with the philanthropy stuff I'm doing, that's consuming. I'm now working harder than I've ever been.

• 49:22Theo Von?

  Wow.

• 49:23Speaker 01

  Um, because I, I guess I am in a mission. Uh, you know, vets and their families need our help.

• 49:29Theo Von?

  So that's one of your important causes. I know independent journalism, veterans. Um, what is another philanthropic cause you enjoy?

• 49:36Speaker 01

  Specifically also active service members and their families.

• 49:40Theo Von?

  Okay.

• 49:41Speaker 01

  Without going on at length, I'm shocked that military families aren't paid enough to, uh, get both a good place to live and, uh, food.

• 49:52Theo Von?

  Yeah.

• 49:53Speaker 01

  And the model used to be the volunteer army would be single guys. Well, there's a lot of families. They're relocated about 600,000 times a year.

• 50:03Theo Von?

  Oh, yeah.

• 50:04Speaker 01

  And that's where Blue Star Families comes in. I can go on a great length and I think I'll stop there.

• 50:09Theo Von?

  But that's the name of an organization that you help support?

• 50:12Speaker 01

  Yes. Well, Bob Woodruff Foundation for Vets.

• 50:14Theo Von?

  Okay.

• 50:15Speaker 01

  25 million from last night.

• 50:17Theo Von?

  Wow.

• 50:18Speaker 01

  And I happen to have a meeting, an event with Blue Star Families, which could also use something like that, but which I won't pre-announce.

• 50:28Theo Von?

  A fundraising event? Well, if you guys ever need a comedian and want, I'd love to come. I can't believe it. I, I wish I'd have known last night. I would have gone. That would have been awesome.

• 50:35Speaker 01

  Well, the connection is through Caroline Hirsch.

• 50:37Theo Von?

  Okay.

• 50:38Speaker 01

  Who used to run Caroline's and now runs the New York Comedy Festival.

• 50:42Theo Von?

  Yeah, that's going on this week.

• 50:43Speaker 01

  Yeah, that's a world I know nothing about. Uh, I kind of would like to.

• 50:49Theo Von?

  Yeah.

• 50:50Speaker 01

  But, uh, people are, uh, busy. I should do other things. The, uh, Comedy Cellar is down the street from me.

• 50:58Theo Von?

  Yeah.

• 50:59Speaker 01

  I've never gone in.

• 51:00Theo Von?

  Really?

• 51:01Speaker 01

  Yeah. Well, they seem to be booked all the time.

• 51:03Theo Von?

  Yeah, they're pretty, and it's, it's limited seating too in there.

• 51:05Speaker 01

  Yeah. And they're supposed to open at least one more space. And, uh, Yeah, I should get off my butt and do something. But there's always lots more work. Not only my own work, but let's say my in-laws need some help.

• 51:23Theo Von?

  Oh, yeah, they always do.

• 51:25Speaker 01

  And fortunately, we can do a good job about that. But I got to stay focused on the areas where I'm doing some good.

• 51:33Theo Von?

  Right.

• 51:34Speaker 01

  The cybersecurity part is is part of that because we, you know, this is the new war.

• 51:41Theo Von?

  And did you start to learn that? Where did that interest come from? Did that or where did that realization that cybersecurity is going to be such a big thing? Was there a lot of like attacks on security at Craigslist? Like, did that happen?

• 51:54Speaker 01

  Well, there was always something, but we had a good team for that.

• 51:58Theo Von?

  Right. But did you have to have that? Like, what would say if someone was attacking Craigslist? This is what I'm asking. What would they be trying to get?

• 52:05Speaker 01

  Well, they would be trying to disrupt service.

• 52:08Theo Von?

  OK.

• 52:08Speaker 01

  They would try to, oh, try to steal proprietary information, which did happen.

• 52:15Theo Von?

  What does proprietary information mean? I'm sorry, Craig.

• 52:17Speaker 01

  Proprietary information at any company is like secret information, like payroll.

• 52:23Theo Von?

  OK.

• 52:23Speaker 01

  Client list. We didn't have much of that because we are a simple classified site. But people thought that we had some quote unquote, secret sauce.

• 52:34Theo Von?

  Yeah, some big fancy stuff.

• 52:36Speaker 01

  And the irony is that that was never the case. And yet people tried to do things. They there were some problems with leakages of that information. But the problem that I'm I'm not concerned with that at Craigslist now. I'm concerned, well, I've been reading about this for decades. And now I see that an adversary would do something like, well.

• 53:05Speaker 01

  You know, they would try to, a form of warfare would be to try to jam or hack a drone.

• 53:12Theo Von?

  Right.

• 53:13Speaker 01

  If they turn your drone against you.

• 53:15Theo Von?

  Wow.

• 53:15Speaker 01

  You're gonna have a bad day. If it's an autonomous drone, one that's figuring out where the enemy is for itself. If they could subvert it, they would turn our autonomous drone back against us. That would make for someone's bad day.

• 53:32Theo Von?

  Yeah, imagine if they, if we sent out a drone and it's supposed to get information, send it to a artillery unit or missile that's supposed to fire automatically from the information from that drone and they're able to hack it. We could, you could literally, our army could themselves, wow.

• 53:48Speaker 01

  There's a lot of mundane things like our, well, our hot water heaters at home are, you know, becoming internet connected. So sometimes they could diagnose it remotely, boilers like that in factories. There are painting robots and those things, if hacked, they could start running them at high. An oven could be just told to run at high.

• 54:17Theo Von?

  Yeah, grill.

• 54:17Speaker 01

  Until it burns, causes a fire. And if there's a few fires like that, your first responders can deal. But if there's a thousand, you have a problem.

• 54:28Theo Von?

  Yeah, if somebody hacks your oven, you don't even think about that. Somebody hacks your ovens, next thing you know, there's 1,100 fires in an area.

• 54:35Speaker 01

  Now, the deal is that there's room for optimism, for help, because there are already people who are really good at dealing with this. What I'm doing is gathering them together, funding them so that they could work together, starting to work with local governments everywhere, everywhere through the country.

• 54:56Speaker 01

  Starting to come up with, let's say, some best practices because we have some breathing space, we think.

• 55:01Theo Von?

  Got it.

• 55:03Speaker 01

  And the idea is that, you know, water supplies, power supplies, they also go down because of natural disasters. They need to be resilient. They need to be where you knock them down, they can come back up in a small amount of time.

• 55:19Theo Von?

  Well, it's even funny, like even with drones, like when I was a kid, you had to do a little bit of peeping, tomming, right? If you wanted to look into somebody's window, you had to go over there.

• 55:27Speaker 01

  I don't know anything about that.

• 55:28Theo Von?

  Yeah, I'm not saying you do. Yeah. And I, you know, and I'm not saying I do, you know what I'm saying? But I do, you know, but I do, I know. But yeah, somebody here does, and it's me. But what I'm saying is this, now as a kid, you can use a drone. And that's the laziest thing. We, you had to go risk getting beat up by a woman's husband to look in their window, even if they were just cooking or whatever, right? I'm not getting lewd with it. I'm just saying, you know, but now you can just get a drone and go do it. It's like, just breaks my heart, some of that kind of stuff.

• 56:00Speaker 01

  In Manhattan, apparently that's illegal. And like, oh, right now, I wonder, I like my tech toys.

• 56:10Theo Von?

  Yeah.

• 56:10Speaker 01

  I would get a drone and I would be bored with it after a few minutes.

• 56:13Theo Von?

  Yeah.

• 56:14Speaker 01

  My neighbor kids would enjoy it because they would learn how to use it really well. And their parents have vetoed the idea for the reason you mentioned.

• 56:23Theo Von?

  I'm sure. I didn't even think about that. Yeah, because I'm still like just squinting real hard and hoping I'm seeing something.

• 56:29Speaker 01

  Well,

• 56:30Theo Von?

  You know?

• 56:30Speaker 01

  It's a big problem in New York.

• 56:32Theo Von?

  I bet. That's awesome.

• 56:33Speaker 01

  Lots of big problems, lots of big cities all near each other.

• 56:37Theo Von?

  Yeah.

• 56:38Speaker 01

  And a contested airspace because we need the cops to have drones, you know?

• 56:44Theo Von?

  That's just getting cra- it, you know, yeah, I just, you don't think about all of those things. You don't think about all the ways that we could be hacked and the immediate effects of it, you know?

• 56:52Speaker 01

  Yeah. So we need to protect ourselves in all sorts of ways. And that's why, you know, the idea is to build networks of, networks of volunteers who are running, let's say, the nonprofit world, the NGO world. And that way, then they cooperate with other parties. But we do have to, well, it's like World War II. We looked out for each other. Everyone tried to play their part. And the looking out for each other in that positive way isn't bad.

• 57:27Theo Von?

  Yeah.

• 57:28Speaker 01

  And like, right now, if something starts happening weird with my baby camera equivalent, I would like to be able to get help from someone.

• 57:40Theo Von?

  Right.

• 57:41Speaker 01

  And even worse, if the oven started running away, I would want to know what to do about that.

• 57:48Theo Von?

  Yeah. When Craigslist, when you, at what point were there ever like categories that you wouldn't do? Were there ever?

• 58:03Speaker 01

  Right, very early on, we heard in large numbers that people didn't want gun sales on the site. And there I am thinking, because I still have some influence then, there are constitutional rights there. But one of them is property rights. So if you have a site, it's your property, you get to set the rules. So you decide what's right and wrong there. So I believe in property rights and freedom of choice, and that's what you exercise. And that's what people do through the net. It's your site, your thing, you decide what the rules are.

• 58:44Theo Von?

  So you were able to, so you actually got to decide that or not decided, or you and your team?

• 58:49Speaker 01

  Team.

• 58:49Theo Von?

  Okay.

• 58:49Speaker 01

  I had an opinion, but I wanted the team, as such as it was, to work it out. That was a little bit of good management, but I couldn't consistently deliver good leadership. And even now, I'm not a top-down kind of leader. Maybe I could lead by example. My frustration in a way is that I want to be able to lead by example when it comes. There's a lot of people with a lot of discretionary money, billionaires, who maybe could be doing really good stuff with that. And I'd like to have the skills to inspire them.

• 59:32Theo Von?

  Understood.

• 59:33Speaker 01

  I don't have those skills.

• 59:35Theo Von?

  Well, I don't even, I mean, I think even here in today, the things that you care about are things that sometimes I don't even think to care about in some ways, or fears that I don't think that, you know, you don't even think that, oh, somebody has to, we need to have. A person needs to donate to this because maybe our country isn't worried about it enough yet. You know, it's, you know, so I think it sounds like you're doing a good job.

• 59:58Theo Von?

  When you, um, did your company, because I'm trying to think like, so guns was a thing. Did you guys end up selling them on there or no?

• 1:00:05Speaker 01

  Uh, no, he said, uh, no guns.

• 1:00:07Theo Von?

  Uh huh.

• 1:00:07Speaker 01

  And, uh,

• 1:00:08Theo Von?

  Swords, anything?

• 1:00:10Speaker 01

  I, I have a feeling swords are okay, but I've never thought about it.

• 1:00:15Theo Von?

  Yeah. I'm trying to think of some, I mean, because he, I mean,

• 1:00:19Speaker 01

  Well, drugs are illegal, uh, they're off.

• 1:00:22Theo Von?

  So drugs were off, but people would try to skirt around that. But even then, some of that was sometimes also, now, were there ever caught, like, could the cops use your site as well if they wanted to, to like as, um, decoy type of stuff?

• 1:00:37Speaker 01

  Uh, I hear gossip about that. I don't know how true that really is.

• 1:00:41Theo Von?

  Right, because you don't know, right?

• 1:00:42Speaker 01

  I do know that the cops, uh, have used the site in different ways to, uh, fight crime. Sometimes, uh, let's suppose they think they see a stolen item being, uh, uh, being listed on the site. Then they would, well, this is true for anything on the net. If a cop sees something they think is wrong and they have a shot at doing something about it, they send a subpoena or a search warrant to the, uh, site. And then the site, uh, the operators usually pass it to their lawyers. And then the, uh, site operators provide the forensic evidence to the cops. Um, which again is like CSI and just fighting, uh, fighting crime there.

• 1:01:26Speaker 01

  The deal is in this country, we have these checks and balances, uh, in the constitution and bill of rights. And you know, the founders of the country did a really good job of that.

• 1:01:37Theo Von?

  Yeah.

• 1:01:38Speaker 01

  You know, there are amendments and so on, which we only thought of years after. But the, uh, the people who did the initial work did great work. And it, uh, for the most part stands up today.

• 1:01:52Theo Von?

  They, they built a good structure over there. Yeah, well, it's funny because you guys, there was, yeah, just like it's such a part of history, you know, it's such a, um, I mean, I went on dates from it. I remember I met a girl. We, I met a girl on, I mean, I would use casual encounters too, you know, it's like that was sometimes, um, I met a girl one time and we watched a Nets game and made love, honestly. And she let me sign her cast, right? And I was like, you know, and it was, we had a great time. I think we, I think we dated for.

• 1:02:23Speaker 01

  Well, there's, uh, there's no accounting for taste.

• 1:02:26Theo Von?

  Yeah.

• 1:02:26Speaker 01

  But I'm glad, I'm glad.

• 1:02:29Theo Von?

  Yeah, I know. Who wants to be a Nets fan?

• 1:02:31Speaker 01

  Yeah, your guys can remember that one for later use.

• 1:02:35Theo Von?

  Oh, they've been on there, dude. I think we accidentally met up once. Um, but there was a place, you know, I was like, I had such a tough time at a certain point in my life, dating. There was something that added a level of mystery about it that I really liked.

• 1:02:48Speaker 01

  I've never thought about that.

• 1:02:50Theo Von?

  Oh, yeah.

• 1:02:51Speaker 01

  Everyone works differently. Everyone does have different tastes and, uh, uh, that's, uh, none of my business.

• 1:02:59Theo Von?

  Yeah.

• 1:03:00Speaker 01

  You know, as long as it's legal.

• 1:03:02Theo Von?

  Oh, yeah, it was, it was legal. Did you, um, it's funny to say that people started marriages. So people even got married off of, um, putting out a dating, like I would like to meet someone.

• 1:03:13Speaker 01

  Yeah.

• 1:03:13Theo Von?

  Wow. Did you ever get invited to a wedding or anything?

• 1:03:15Speaker 01

  I have gotten invited a number of times. I'm not much for ceremonies or galas or anything like that. And my relatives know this very well. I have a dispensation to not go to some of the more obscure events on my wife's side.

• 1:03:33Theo Von?

  Yeah.

• 1:03:34Speaker 01

  And I'm, and I'm, on the record, I'm very grateful.

• 1:03:38Theo Von?

  Yeah.

• 1:03:42Theo Von?

  I think your comedy is getting better.

• 1:03:45Speaker 01

  I've promised to, if I'm offered open mic night, I will not do it.

• 1:03:52Theo Von?

  Is pornography causing a problem in your life? Do you find yourself watching porno for longer periods of time and having trouble stopping? Is porn affecting your relationship or dating life? Well, you're certainly not alone. Watching pornography has become so commonplace today and oftentimes, men use porn to numb the pain of loneliness, boredom, anxiety, and depression. Shame and stigma prevent men from talking about these issues and getting help for them. I want to introduce you to my friend Steve. Steve is the founder of Valor Recovery, a program to help men overcome porn abuse and sexual compulsivity.

• 1:04:36Theo Von?

  Steve is a long-term sexual recovery member and has personally overcame the emotional and spiritual despair of abusing pornography and has dedicated his life to empowering men to do the same. Steve is an amazing person and he is a close friend of mine. I mean that. Valor Recovery helps men to develop the tools necessary to have a healthier sex life. Their coaches are in long-term recovery and will be your partner, mentor, and spiritual guide to transcend these problematic behaviors. To learn more about Valor Recovery, please visit them at www.valorrecoverycoaching.com

• 1:05:19Theo Von?

  or email them at [email protected]. Thank you. When you guys, at what point did you realize, okay, I need to... Had you had enough of the day-to-day? What made you start to decide, I want to sell the company?

• 1:05:37Speaker 01

  I haven't sold the company.

• 1:05:39Theo Von?

  Oh, you haven't sold? Okay, sorry.

• 1:05:41Speaker 01

  Here's the, well, the history to prevent some confusion. I gave a guy some equity. I made it a gift on the expectation that he'd deliver. That may have not happened, but he wanted to sell, sold to eBay, didn't work out, and we bought that equity back from eBay.

• 1:06:02Theo Von?

  Nice.

• 1:06:03Speaker 01

  Now, what I've done is I had a chunk of equity stock and again, thinking, I don't need this. So I created a 501(c)(4) foundation.

• 1:06:16Speaker 01

  Put all the equity in there and that's what generates dividends and sales.

• 1:06:21Theo Von?

  Okay.

• 1:06:22Speaker 01

  And that's what I'm using to fund these things.

• 1:06:24Theo Von?

  Ah.

• 1:06:25Speaker 01

  So I now have a good idea of how much money I have to give away with in the rest of my life.

• 1:06:31Theo Von?

  Because you can look at the residual, the dividends and the earnings.

• 1:06:35Speaker 01

  That's that kind of stuff. And I figure I've got five to 20 years. And I know roughly how fast I should do it. And my trouble though is that I'm 72, 20 years out, I may have to conduct due diligence via a seance.

• 1:06:54Theo Von?

  Yeah.

• 1:06:55Speaker 01

  And Ouija boards don't have the bandwidth I need. So I may, I may just come back and haunt people.

• 1:07:04Theo Von?

  Yeah. Hey, that would be awesome. Yeah. Oh, I could definitely see a spirit looking for a place to stay, you know?

• 1:07:10Speaker 01

  You have an excellent point there, although computers don't operate very well in the, in the afterlife. Although I'm making an assumption. I don't know if that's true.

• 1:07:22Theo Von?

  So no, so you still own it?

• 1:07:25Speaker 01

  Oh, I, this is an important distinction. I now own no equity. It's in that foundation, 501(c)(4).

• 1:07:35Theo Von?

  Okay. So the company was transferred into a foundation or sold to a foundation?

• 1:07:38Speaker 01

  My parts of it. Other people do own chunks of the company.

• 1:07:41Theo Von?

  Got it.

• 1:07:42Speaker 01

  And they do what's right for them.

• 1:07:44Theo Von?

  Okay.

• 1:07:44Speaker 01

  Me, what's right for me is frankly to keep a little for myself.

• 1:07:50Speaker 01

  Because the wife insists that she needs to buy socks.

• 1:07:54Theo Von?

  Yeah. Oh, yeah.

• 1:07:55Speaker 01

  And so we have some leftover, which we do share with family. And, but the vast bulk of it is now for charity. I mean, just yesterday, a guy, I guess an economist analyzed what I would have made had I done the usual Silicon Valley thing. He said, now I'd be worth 11 billion.

• 1:08:19Theo Von?

  If you had saved the company and just sold it?

• 1:08:21Speaker 01

  Well, if I did the usual.

• 1:08:22Theo Von?

  Right.

• 1:08:23Speaker 01

  And maybe he's right. I don't understand the analysis.

• 1:08:26Theo Von?

  Right.

• 1:08:27Speaker 01

  But I don't know what I would do with that.

• 1:08:29Theo Von?

  11 billion dollars?

• 1:08:31Speaker 01

  Uh, yeah.

• 1:08:31Theo Von?

  Yeah. What would you even do it? How many, yeah. Cause how much money can you put in your bank?

• 1:08:36Speaker 01

  Well, I don't think about it. There are some luxuries I like, but I don't own a car.

• 1:08:44Theo Von?

  Really?

• 1:08:44Speaker 01

  Frankly, between the subway and Uber cabs or Lyft, that's what I need.

• 1:08:51Theo Von?

  Yeah.

• 1:08:52Speaker 01

  And again, this is not altruistic or anything like that. This is just being sensible.

• 1:08:59Theo Von?

  And altruistic, just so our listeners know.

• 1:09:01Speaker 01

  Altruistic means that you sometimes value helping other people more than yourself.

• 1:09:07Theo Von?

  Okay.

• 1:09:08Speaker 01

  It's the Bible thing.

• 1:09:10Theo Von?

  Right.

• 1:09:10Speaker 01

  And I agree. I just, my variation of have enough to be comfortable and to indulge your family, maybe friends sometimes, and then better to give stuff away. It's a difficult balance because the future is unpredictable, and I guess it's gotten more unpredictable. But there are people who need a lot of where I can help.

• 1:09:37Theo Von?

  Yeah.

• 1:09:37Speaker 01

  Without digging into my personal stuff.

• 1:09:40Theo Von?

  Yeah, understood. Yeah, I just wanted to know, because yeah, sometimes I forget and sometimes maybe some of our listeners forget. Did you ever feel like other tech companies, even though they were probably, I bet secretly jealous, looked down at Craigslist? Because it was this, like, what was that like? I just wonder.

• 1:09:57Speaker 01

  Oh, they've, they're, they're quite explicit. They don't, it's not a secret. They don't like this model we have of doing well by doing good.

• 1:10:09Speaker 01

  Sometimes, let's say they're not respectful of it, and that's okay.

• 1:10:14Theo Von?

  Yeah.

• 1:10:15Speaker 01

  The thing is, I remember what I learned in Sunday School, and people often forget. And again, not pious of me or anything like that.

• 1:10:24Theo Von?

  No, I think it's fair to stand up for also what you are aiming for.

• 1:10:27Speaker 01

  Well, I've met a bunch of rich people. None of them are that all that happy.

• 1:10:34Theo Von?

  Yeah.

• 1:10:35Speaker 01

  And, yeah, having too much money is a, is a big trap. And you get surrounded by people, by yes men. And you get insulated from the needs of, of regular people. And that does some real damage.

• 1:10:56Theo Von?

  How do you keep yourself balanced from that? Yeah, because it's interesting because you seem like someone who would have a fair answer to what are some of the side effects, the negative side effects of.

• 1:11:06Speaker 01

  Well, the deal is that it

• 1:11:09Theo Von?

  Of money, of having some money, you know, or coming into some money.

• 1:11:12Speaker 01

  Yeah, the deal is to be a little bit as cheap as I was when I grew up in the 50s. And to do things for yourself or by yourself, like especially going cross town. I don't need to take a car. The subway is usually better. And so I do that, although I did get here on a limo because someone else paid for it.

• 1:11:37Theo Von?

  Yeah.

• 1:11:37Speaker 01

  And they really wanted to.

• 1:11:40Theo Von?

  Good.

• 1:11:41Speaker 01

  So the deal is that, and I now and then I like will go to fancy dinner.

• 1:11:46Theo Von?

  Oh, yeah, that's nice. You have to treat yourself to good food.

• 1:11:49Speaker 01

  The thing is that you could find good food a lot more cheaply and with a little bit more fun. And so a lot of those things I just don't, I just don't get. And I wouldn't mind having a smaller house, but the wife's side of the family is very, very large.

• 1:12:13Theo Von?

  Yeah.

• 1:12:14Speaker 01

  I have a one nephew and one niece. The nephew just got married and I had to attend that one.

• 1:12:20Theo Von?

  Yeah.

• 1:12:21Speaker 01

  However, my, my, on my wife's side, we have 20 nephew and nieces.

• 1:12:27Theo Von?

  Oh, that's too many.

• 1:12:29Speaker 01

  Well, it mostly means that I've learned to control my language.

• 1:12:32Theo Von?

  Yeah.

• 1:12:32Speaker 01

  Because I don't want to, I don't want to catch shit from any of my relatives.

• 1:12:37Theo Von?

  Yeah.

• 1:12:38Speaker 01

  And it works out pretty well. Typically, I know, as they say, that when the kid is allowed to watch HBO, I'm allowed to use saltier languages.

• 1:12:50Theo Von?

  Oh, yeah, I hate that, buddy. Yeah, only salt in our languages.

• 1:12:56Theo Von?

  Yeah, I was just wondering, um, what was, was there one thing like it was whether it was a something like a, like a, like a specific Leonard Cohen piece, a record that he made and he'd autograph? Was there one nice thing you bought for yourself that, um, what was something that was meaningful to you?

• 1:13:13Speaker 01

  I bought some of the prints that he made.

• 1:13:16Theo Von?

  Oh, you did? Okay.

• 1:13:17Speaker 01

  He's an artist for real. The thing which I regret is that around here, there was an auction of a lot of his letters and stuff.

• 1:13:25Theo Von?

  Oh.

• 1:13:26Speaker 01

  And I should have, uh, I should have, uh, overindulged myself.

• 1:13:30Theo Von?

  Yeah.

• 1:13:31Speaker 01

  But I, it was the first auction I actually seriously participated in and I just didn't, uh, I just didn't get anything.

• 1:13:39Theo Von?

  Yeah, man.

• 1:13:40Speaker 01

  I don't recognize it. I didn't have anything in color. I did as a black and white prints. And you're heading into some of the ones that just passed. The ones in the middle right now, two of them, I think I have.

• 1:13:52Theo Von?

  Wow, that's cool.

• 1:13:54Speaker 01

  Yeah, especially the one, that's exactly what I have.

• 1:13:57Theo Von?

  Really?

• 1:13:58Speaker 01

  Yeah, and I may have that one on a T-shirt.

• 1:14:01Theo Von?

  Wow.

• 1:14:02Speaker 01

  Yeah.

• 1:14:03Theo Von?

  Yeah, something like, that's nice, man. Especially if it's art or something like that. It's like, you know, if I could go back in time, there was like a time, one time I was in, I was in Tanzania, you know? And I was doing, uh, Mount Kilimanjaro.

• 1:14:17Speaker 01

  Okay.

• 1:14:18Theo Von?

  Right? And we, and afterwards we went someplace and they had a piece of art in there and it was like $500, right? And I could spend like maybe $300, but I wished I'd have spent, cause going like, it was 15 years ago and it's like, you know, the $200 didn't, wouldn't have changed my life that much, you know? It was a lot of money at the time, but it's like, I didn't even think about it two weeks later or two months later, you know? So I just wished that I would have, cause I really liked the painting, you know? I was like, God, I just, and I, sometimes I wish, like every now and then there's little things like that. I wish I'd have gotten like a nice piece of art or something, you know?

• 1:14:53Speaker 01

  Yeah. And the, uh, let's see, on my side of the, uh, the house, that's the, uh, biggest investment I've made in art. Uh, my wife was an art major, so she knows this stuff and a lot of it these days is, uh, cheap at auction. And she's, uh, good at that. Yeah, she's gotten good at a number of things, including, uh, free upgrades while flying.

• 1:15:14Theo Von?

  Oh yeah, it's a deal.

• 1:15:15Speaker 01

  That's her new hobby.

• 1:15:16Theo Von?

  Oh, yeah.

• 1:15:17Speaker 01

  And she's good at it.

• 1:15:20Theo Von?

  I'm trying to think of something else. Were there other? So, so what, Craigslist was kind of the, the, the stepchild of the tech industry in a weird way? Was it looked at like that? Cause I could imagine how jealous, cause here's people putting billions and millions of dollars into building this thing, this new avenue and all these venture capitalists and stuff like that. And then they, all this advertising and here you are with this basic kind of peer to peer. How can I offer something that could potentially help my neighbor or connect two neighbors that could use something?

• 1:15:54Speaker 01

  Yeah, we've always been an outlier. As one person put it, we're one of the few ungentrified sites on the net.

• 1:16:02Theo Von?

  Yeah.

• 1:16:03Speaker 01

  And I guess we like it that way. Nothing has, not, not everything has to be expensive or fancy.

• 1:16:10Theo Von?

  Yeah.

• 1:16:11Speaker 01

  To give credit to a site I consider a ungentrified, that's Wikipedia. Wikipedia is where facts go to live. And in the long run, Wikipedia, I think is the most important of all sites. I work with him and even in New York, I'm working with their local chapter to give classes Wikipedia for beginners.

• 1:16:36Theo Von?

  Really?

• 1:16:37Speaker 01

  Well, when you get to write an article or change an article, that gives you a lot of power.

• 1:16:43Theo Von?

  Mm hmm.

• 1:16:44Speaker 01

  Well, in a small way to determine how people think of things, you get to write history.

• 1:16:51Theo Von?

  Oh, and some of it's not true. Like there's stuff on my Wikipedia, like attaching me to like a part of my family, like, um, like my, they have my fan, half my family members wrong on it and stuff and it like puts me in a, it's crazy. I'm like, all right.

• 1:17:04Speaker 01

  The deal, unlike newspapers, well, they don't correct themselves normally, especially not in a big way. But in Wikipedia, you can do that. And basically you can get a good citation.

• 1:17:19Theo Von?

  Oh.

• 1:17:20Speaker 01

  Some evidence of what's right and wrong, and then send it to someone who knows how to edit it and.

• 1:17:26Theo Von?

  And they can do it.

• 1:17:27Speaker 01

  They can do that.

• 1:17:28Theo Von?

  Oh dang.

• 1:17:29Speaker 01

  And

• 1:17:29Theo Von?

  I gotta get in there.

• 1:17:30Speaker 01

  Yeah, you guys know how to get hold of me.

• 1:17:33Theo Von?

  Okay.

• 1:17:33Speaker 01

  And then I I know I can get hold of someone who can who knows how to do the edits.

• 1:17:39Theo Von?

  At least how to do it.

• 1:17:40Speaker 01

  Gone to the class yet.

• 1:17:42Theo Von?

  Okay.

• 1:17:42Speaker 01

  And yeah, the deal is that the system isn't perfect. But it's better than anything anyone else has tried.

• 1:17:50Theo Von?

  Yeah, it's true.

• 1:17:51Speaker 01

  And things do get fixed. It may not happen as fast as anyone wants.

• 1:17:58Speaker 01

  But again, there's things, let's say in the newspaper of record. And things which I know are wrong and which have been presented to them. And they're just not going to fix it.

• 1:18:10Theo Von?

  Yeah. And that's And they don't want to?

• 1:18:14Speaker 01

  I don't understand the reason.

• 1:18:15Theo Von?

  They want to shape history sometimes, you think?

• 1:18:17Speaker 01

  Well, the deal is they some, you know, they were brought something which was wrong. It was proven to be wrong. And they they say they weren't going to be truth vigilantes. And I guess I disagree.

• 1:18:34Theo Von?

  Yeah. Yeah, that's interesting. Well, that's a big thing about information now. It's like it's something I worry about with AI because if there's. And even just the history of the web, like things in the history of the web, because people can alter that over time.

• 1:18:49Speaker 01

  There's big problems with that now. A number of AI systems are feeding on the output of other AI systems, which could be hallucinating. Or it could be if you

• 1:19:01Theo Von?

  Compromised.

• 1:19:03Speaker 01

  Uh, yeah, well, that's one way to do that. And I like the idea of really good AI replacing or supplementing search. But I I worry about that also because even if I just casually screw around. I can get the AI systems to produce wrong information.

• 1:19:27Speaker 01

  And I talk about it with some of the people at these companies and hope that they get it right. I do have a lot of hope for AI doing customer service because if it's done with commitment, if it's done right, it can be done much better because sometimes like you call up for a customer service, you get a call center someplace where they just don't know how to do it.

• 1:19:55Theo Von?

  They don't know.

• 1:19:56Speaker 01

  And I try to be kind to people who have been effectively sabotaged by their management. Sometimes I become less impatient than I should be.

• 1:20:09Theo Von?

  Yeah. Oh, yeah. Oh, you'll call up customer service and they're like, we don't even know what you're talking about, but they still answer the phone. I'm like, who are you?

• 1:20:17Speaker 01

  Yeah.

• 1:20:17Theo Von?

  Like, we don't even, yeah.

• 1:20:19Speaker 01

  Instead of complaining about that, I'm trying to talk about it and I am putting my money where my mouth is, like for Consumer Reports, which I'm involved with and working with a lot.

• 1:20:30Theo Von?

  With the magazine website?

• 1:20:32Speaker 01

  Yeah.

• 1:20:32Theo Von?

  Okay.

• 1:20:32Speaker 01

  Because they're trustworthy.

• 1:20:34Theo Von?

  Ah.

• 1:20:35Speaker 01

  And the idea is that, yeah, I would enjoy working with an AI system which would be responsive and give me good information.

• 1:20:45Theo Von?

  Mm hmm.

• 1:20:47Speaker 01

  And even if it can't, maybe it would kick it to a person who might have to do research, but at least they would be good at it.

• 1:20:54Theo Von?

  Ah, understood. Yeah, I have one more. I also have a question about that, but I want to remember to ask this. How did Craigslist make money?

• 1:21:01Speaker 01

  Like, oh, oddly enough, since we run very lean, Jim runs us very lean, and even though we minimally charge, that makes enough because we're not, we're not expected to produce great results for VCs.

• 1:21:19Theo Von?

  For venture capitalists.

• 1:21:20Speaker 01

  Yes.

• 1:21:20Theo Von?

  So you don't have these, you don't have these money guys like, I need my return.

• 1:21:24Speaker 01

  That's right. Yeah. If no one's invested millions in us, we don't have to go public. No one's looking to get billions.

• 1:21:32Theo Von?

  Mm hmm.

• 1:21:32Speaker 01

  And I'm happy with the current results.

• 1:21:37Theo Von?

  Yeah.

• 1:21:38Speaker 01

  The future is scary sometimes, but this works out pretty well.

• 1:21:43Theo Von?

  You've also talked a lot about, yeah, that's your water.

• 1:21:46Speaker 01

  Yeah, thank you.

• 1:21:47Theo Von?

  I have just like one or two more questions.

• 1:21:49Speaker 01

  Sure.

• 1:21:53Theo Von?

  Better, I can get it for you.

• 1:21:56Speaker 01

  I'm stubborn.

• 1:21:57Theo Von?

  Stubborn?

• 1:21:58Speaker 01

  I am stubborn.

• 1:22:02Theo Von?

  Oh my god, dude, you're crazy Craig, because I've never heard somebody...

• 1:22:08Theo Von?

  Imagine I'm trying to open a water, right? I can't open it.

• 1:22:14Theo Von?

  And then I say, "I'm stubborn." Like, "I'm stubborn." I don't know, it didn't even make sense. To me, it was very, that was very funny. You're like, "I can't open it," and I was like... I don't know if you could open it or not, I was just trying to, I don't know, but I was like, "Oh, can I help you?" And then you're like, "I'm stubborn." But to me, in my head, I was like, "He can't open it, but he just, the bottle's stubborn." Anyway, it doesn't make any sense.

• 1:22:41Speaker 01

  My, my deal is that, as an old man, I'm happy when I can still do some things.

• 1:22:46Theo Von?

  Oh, I see what you're saying. You've talked a lot about independent journalism, right?

• 1:22:52Speaker 01

  Okay.

• 1:22:52Theo Von?

  And that's something that, like, I've read anyway, is near and dear to your outlook in the world.

• 1:22:59Speaker 01

  Okay. Well, what we learned in US history, in this high school class, is that a free and trustworthy press is just required to keep a republic alive. And the whole media system is fractured in all sorts of unpredictable ways. You're part of that, I'm a lesser part of it. And I don't know what to do now, except that I try to support things that I know work. Like the Journalism School at the City University of New York.

• 1:23:31Theo Von?

  Okay.

• 1:23:32Speaker 01

  And Wikipedia is now a modern journalism. There are other things that I try to help. But I'm confused and I'm kind of paralyzed around a lot of this. So I did a lot in the past, but these days, I'm just trying to focus in those areas where I can help Americans defend the country, because that's a well-defined good, which we need in a big way right now. And like, service members, active or veteran, and their families have given up a lot for us, and we don't treat them right, so I can do something about that.

• 1:24:12Speaker 01

  Cyber warfare is a thing and it needs help because the government can do some stuff, but everyone needs to play a role like in World War II. Everyone needs to harden their systems a little bit depending on how much of a target you are.

• 1:24:30Theo Von?

  Yeah, it's funny. I didn't realize until you said some of those things like, what if suddenly all of our cars were compromised or half of them or all of our ovens were compromised to the point where they started fires in all of our homes, you know? I'm just kind of fascinating to me, you know?

• 1:24:45Speaker 01

  Well, it means also I've read too much science fiction in my time.

• 1:24:49Theo Von?

  Hmm.

• 1:24:49Speaker 01

  But if, uh, if 1% of those systems were compromised, that alone is a big problem.

• 1:24:57Theo Von?

  Yeah, and we don't even realize it. Were there other businesses that you tried to start before or after?

• 1:25:04Speaker 01

  Uh, no, I am not a real businessman. It's been a happy accident. I'm like, uh, any success I've had has been by accidentally being in the right time at the right place. And that makes me the forest gump of the internet.

• 1:25:21Theo Von?

  But also with the right attitude to bring one person to another, you know, try to keep the golden rule in your mind, things you learn from Sunday school. What about, are your parents pretty proud of you? Are your parents still alive, Craig?

• 1:25:36Speaker 01

  They passed long ago.

• 1:25:38Theo Von?

  Oh, they did.

• 1:25:38Speaker 01

  I'm sure they would be. I, uh, know that my high school history teacher, uh, learned about his contributions to all my stuff. He, uh, heard about it, uh, when he, while he was still around and that was a big deal.

• 1:25:54Theo Von?

  Oh, that probably meant a lot, huh?

• 1:25:56Speaker 01

  Yeah, and well, because teachers work hard for little pay.

• 1:25:59Theo Von?

  Oh, yeah.

• 1:26:00Speaker 01

  So anything, uh, anytime they have any long-term effect is a big deal.

• 1:26:05Theo Von?

  Yeah. Yeah, it's so funny. I like, I still keep in touch with a lot of my teachers, you know, it's important to me.

• 1:26:12Speaker 01

  I should, but at my age, there may not be many left.

• 1:26:15Theo Von?

  Well, that's why we gotta get that Ouija board going.

• 1:26:19Speaker 01

  Yes.

• 1:26:20Theo Von?

  You know, I think that's the next level. Um, what are some, what are some small, before you leave, Craig, what are some goals in your life like right now? I know you've talked about some of the kind of work oriented and giving back. Um, are there any kind of personal goals or are there anything like, um, I don't know, is there any kind of goals you have, even if they're just like human to yourself, things you still want to learn or do?

• 1:26:40Speaker 01

  Professionally, I want cybersecurity to be a household word that everyone takes seriously.

• 1:26:49Speaker 01

  Personally, uh, I'll be glad if the dentist tomorrow uses nitrous oxide.

• 1:26:55Theo Von?

  Yeah.

• 1:26:56Speaker 01

  And I will make the same joke over again. That is, can I take the bottle home? And he will refuse me.

• 1:27:05Speaker 01

  But we like to do that.

• 1:27:06Theo Von?

  No, we do like to do that. Um, I think that's good, guys. Pretty good. Is there anything else that you want to share that's important to you?

• 1:27:13Speaker 01

  I think you got it all. And I think people will be tired of hearing from me after 90 minutes.

• 1:27:19Theo Von?

  Well, look, I do know if you, if you, if you really want to get some nitrous oxide, you might be able to find some on Craig's list.

• 1:27:26Speaker 01

  I've, I've been advised by my medical team against it. Well, I can remember, well, for sure, is like the Batman says, I'm not the nerd you want, but I'm the nerd you got.

• 1:27:40Theo Von?

  Man, I don't know how somehow I almost get your sense of humor now, Craig. It's very interesting.

• 1:27:44Speaker 01

  That, uh, that might be tragic.

• 1:27:46Theo Von?

  Yeah. Well, thank you, man. Thank you for, uh, I like, I just like some, I like your initial goals of like, my goal is to help one person find something. This person's in need. This person might have this. How can I be of service there? Um, learning when you notice that I'm not a good manager of this, so I need to get some help here, right? It's not a strong suit of mind. Maybe this world, but the customer relations is a strong suit of mind, you know, and, and that's interesting just because, you know, sometimes we all feel like we have to do everything in, in different spaces. And then, um, yeah, and I'm glad you find a lady along the way. How long have you, how long's your marriage been now?

• 1:28:21Speaker 01

  Married 12 and together 20.

• 1:28:23Theo Von?

  That's great.

• 1:28:24Speaker 01

  And it's good that I'm better at remembering those dates than she is.

• 1:28:27Theo Von?

  Yeah. Amen. Um, Craig Nummer, thank you so much, man.

• 1:28:32Speaker 01

  Hey, it's my pleasure.

• 1:28:33Theo Von?

  I appreciate your time.

• 1:28:35Speaker 02

  Now I'm just floating on the breeze And I feel I'm falling like these leaves I must be cornerstone Oh, but when I reach that ground I'll share this peace of mind I found I can feel it in my bones But it's gonna take