Craig, hello. Welcome. Good to meet you. As founder of Craigslist, I have a very simple question for you. Why does it seem as if webpage design has just gotten worse for 30 years running?
In my ignorance, when I first put up the first Craigslist site, I just kept it simple, knowing I have no design skills, except simplicity and speed is a design criterion. And people haven't gotten the message. I've seen designers do some very attractive work that no one has asked for, and I appreciate it. And since I relinquished any management control of Craigslist in 2000, Jim Buckmaster has kept the design clean. Sometimes I like seeing fancy design, but as a general rule, I just want to get the thing done. And on any site, I want to get the thing done and get on with my life.
And how do you stop them from adding bells and whistles and making it complicated?
Them at Craigslist? No need. Jim is committed throughout the whole world. I just struggle like anyone else. Like when I want to cancel a streaming service, it is never straightforward.
But what then was wrong with the 1990s web? Because people did move away from it. There's now so many walled gardens, so many complex websites. I react with horror when I have to buy a ticket and then upload it into an app and it feels it could all be simpler. Why didn't things stay with where they were? What's your account of that?
The big problem is that people to do successful sites as time went on had to compete more and more. That meant they had to attract venture capital, I guess, who made more and more demands of them, where people had to extract whatever dollars they could out of their site. And then I guess that began a process of what Cory Doctorow calls enshittification, and he captured the process much better than I just articulated it. He's also a bit of a hero of mine in that he's more articulate about our rights online. He's also braver than I am because he's okay with putting a target on his own back. Oh, and he writes good novels.
I have a question. This is from GPT and I quote, 'Your biggest decisions all look subtractive. You monetized as little as possible, stepped aside as CEO, kept doing customer service, and now in philanthropy, you prefer to fund people and get out of the way. What are you subtracting from yourself that other founders are addicted to?'
Pretty good at GPT, isn't it? Yeah, that's a valid perspective. I think of it differently. Mostly because as I age and have grown decrepit, I've realized my limitations and that I'm not good at things. I realize that accidentally I've built networks of networks, and it's the networks of networks that get stuff done. And sometimes I can find network builders who can do the stuff I want to on my behalf and they get it done. The best examples, Blue Star Families for military families, Bob Woodruff Foundation for vets. And so I'm not subtracting things. I'm just becoming much more effective overall by sharing power and money. That seems to be working, also by building networks of networks. That's a kind of just in the past week or two, I've realized that's the most effective form of estate planning I'm doing because as I become elderly, I have to wonder how my work is going to survive me and that I could create CraigGPT or I could just come back and haunt people for due diligence purposes. But the networks of networks have a life of their own.
What is scarce in your life then? You're giving away money, right? You don't have to run the company on a day-to-day basis. We'd all like more years to live. But what is it that if you had more of it you could be more effective with?
I guess ideally I would have more social skills, meaning some... but we're simulating social skills just fine. That's the phrase I use. At least on my part, what looks like social skills is just fakery. And I can do it for short amounts of time, maybe 90 minutes. And I've given up though on actually accumulating social skills, getting better at it. But more to the point, I try to get into positions where other people can show social skills.
One journalist once described you as having quote obsessive customer service disorder unquote. Isn't that a social skill?
That's more obsession. So it's a pathological but a good one. Well, I believe that you should treat people like you want to be treated. So think of the many times when you needed customer service. Sometimes you can get good customer service but that's the exception. That's no reason for us not to provide good customer service. Like earlier today, someone sent in a grant proposal and I had to tell them that they forgot to sign the thing. A very minor thing. And more importantly, I'm telling people they need to do some planning for good communications because their work is much less valuable if they can't talk about it effectively.
According to Susan Freese, who wrote about you, in one year you answered 40,000 customer service emails. Is that possibly true? And if so, what did you learn about humanity doing that?
I have the vague memory of being asked and then counting the number of emails I had sent that year. It's hard to believe, but I work every day, so I guess that's 10 times 365. That's like maybe 4,000. So, I don't know if I got the number right, but it's too much. The thing is, well, like I say, a nerd's got to do what a nerd's got to do. What I learned about people doing customer service at Craigslist was that people everywhere are kind of the same. We want to get through the day, which is sometimes tougher than other days. And one thing I noticed in New York is that New York is a collection of small towns and not so much a big city. And so New Yorkers aren't all that different than people anywhere. For the most part New Yorkers want to get through the day. It may be harder to get an apartment. And rent stabilization is a passion. But otherwise people everywhere are kind of similar and the amount of bad actors is actually very tiny.
So you became more trusting of people helping them.
Oddly enough, I did become more trusting. Unfortunately during those years at first I became less prepared to deal with the bad actors. And I learned the hard way that if you're basically honest, if you believe in the ninth commandment, you will never be able to confront successfully someone who lies for a living. And that was a painful lesson that took a couple years to sink in and it wasn't a good year or two. So I think of much of Craigslist as saying you can trust other people if the incentives and institutions are correct.
And your 9-second rule, you know, wait for nine seconds and think before clicking on something you get, say in your email or on a social network site, is a kind of lack of trust. Is it that your views have changed or how does the whole picture fit together?
Just I have learned something and my team has learned something from real life. The notion is that a normal, like a very common technique of scammers is to rush you into something to convince you of the scam by making it sound urgent. And if you wait a little while, stereotypically nine seconds, you can reconsider what they're doing and then you can evade certain kinds of scams. I screwed up in that respect about 10 years ago, but in a small way, I just lost a credit card number. I realized it not long after and, you know, changed it. But that's kind of stupid. I'm trying to learn other things as well, working potentially with the AARP because if nothing else, my wife has to monitor her mom's credit card purchases. Because there's often issues there.
So if I do this, what should I be thinking between second eight and second nine? I get what I should be thinking in the first two seconds, but seven, eight rolls around. What am I doing?
If something still smells bad to you, I would either not do it or go right to the source. If they say they're pointing you to, let's say Amazon for something, I would say type in Amazon directly because a common technique of scammers or phishers is to get a domain name that might look like Amazon but isn't. Like if you use a font where you use an R followed by an N. Some fonts kind of make the RN together look like an M. So you'll go to what looks like Amazon and they will capture your user ID and password. Then they'll get you to Amazon and you won't know that they just stole your credentials. So that's actually an illustration of a common technique for which solutions exist. A long story, there's a cat and mouse game involved, but I'm trying to figure out what institutions to fund to stop that from happening.
What is it that you understand about used goods that others do not?
Probably nothing. The only thing is I want as few of them as possible because I worry about having too much stuff. And whenever I buy technology, knowing that I will replace it eventually, I try to get something that will be, even used, a good acquisition typically by one of my nephews or nieces. My collection is 24 of them and counting.
Now, missed connections used to be a feature. Oh, I saw you on the subway. You seem so smart. You were reading Catcher in the Rye, whatever. What happened to that?
I think it's still there, but in a different category altogether. And over the years, over the decades, oh, it does work now and then. I've been invited to weddings where they met each other through the site or where people had good relations. We all have had experiences where we meet someone and there's some chemistry and neither party gets contact data and it's kind of sad. I thought about that for a long time but Jim just decided to put it up after he became CEO sometime in the middle of 2001.
Why don't dating apps work better if we mostly can trust people? Right? You the first day you spend more than nine seconds with them. There's many marriages from missed connections where you've even officiated perhaps yet everyone says dating apps are terrible.
I don't know because to have a gut feeling of them I'd have to use them. And let's say that they hit their stride after I had gotten involved with the future Mrs. Newmark. And I sense the opportunity for comedy coming on that will get me in trouble and even alluding to that will probably get me in trouble after Eileen watches this.
But you know many smart people who articulate their concerns to you. I hear from people all the time dating apps are terrible. Why dating apps are terrible? There's gender imbalance if it's New York City or people just want something other than a long-term relationship. You don't have an implicit mental model of what's going wrong.
My gut tells me with no evidence, is that people aren't genuine, aren't real on dating apps. The only basis for this thought is about 25 years ago before Craigslist had dating sections, I met several women who told me they use the roommate ads for dating because in a roommate ad a guy would be relatively honest and not married. One hopes. Well actually I didn't think of that. Yes. So that's very good. I have to steal that for the repertoire. But this is serious. That's what women told me way back in the past. And this had to be right around well probably late 90s. I really am old now.
It seems to me Craigslist is especially strong in job ads, services, and automobiles. Do you have any sense why those areas? Or maybe you think it's something different?
I don't know. The deal with Craigslist in general is that it's for real. People are really putting stuff up there. You generally know what you're getting. You have no illusions about what's going on. At some point in the past, other sites where you build up a profile, they look like you're actually dealing with a real person. And maybe that was true for a while, but now it's very easy to use generative AI to build up a profile which looks real, but it's fake. And if you're going to buy something from that person, having some confidence that they're real, you may have a problem. That's the kind I think of a great deal these days. And how do we warn people adequately about it? We really do need to launch a much bigger public service campaign about problems with scamming, problems with cyber security and what regular people can do to prevent them.
But even before generative AI, you didn't have seller evaluations the way eBay and Uber have, right? Uber, oh, this driver is a 4.98. you assume it must be okay and Craigslist didn't do that. Why not?
I can't speak for Jim because at that point I had given all management to Jim. But even before him I vaguely speculated on things like user reviews of any sort like Yelp style and I was thinking it will be really easy to game that kind of thing. Frankly even then I was reading science fiction which looked into the future about how online media and the internet would be gamed. I'm even thinking back to 1984, William Gibson's Neuromancer which affected me and a lot of people in the field and I'm hoping will be a really good Apple TV show. I wish if Yeah, I'd like it to be better than Slow Horses. Jackson Lamb is now one of my role models. I can tell you later why. Not for his hygiene. But the deal is that and I've lost track of the question because I want to say why Jackson Lamb is now my role model.
Wish you could feel free to prompt me when you're in the mood. But seller evaluations, right? Never evolved them.
Podcasts get evaluated on Apple, right? Oh, this gets so many stars. But it's just too easy to game those systems. Now, what I'm hoping for are user authentication systems, not state or government instituted ones exclusively because I worry about governments. But, you know, a lot in life is based on who you trust and you want to be able to know who you're talking to. But I don't want to turn over a lot of this to the government because of some of my political biases. So I'm looking for balance. And if you can identify yourself to other parties in a way that kind of shows you are who you claim you are, that can be good. And you know the credit card companies working together may have a solution. Driver's licenses may be in part a solution. And you know, 90% of Americans have phones with digital wallets. Maybe there's something there, but I need to run this by the Electronic Frontier Foundation because they think of things that I will not think of and they may tell me why my idea is terrible.
What do you think of the simple model that institutions get gamed and they deteriorate over time? If there's a new restaurant in New York City, it will be great for the first six to nine months. Then too many people want to come. The people who come after that are less informed. They slack on quality. There's always a line out the door. This everything becomes a bit worse. And the way to live life is to find the peaks of things in early times and then move on. Correct or not?
That sounds like too much work for me. And I might accidentally go to hip happening places, which is not my thing. So I just look for the mundane, the ordinary.
So say you're choosing a restaurant. What's your algorithm?
My algorithm is does it well, does it look like a hole in a wall? And that's a good thing. Actually quite seriously, my deal is in the last year or two I've realized that I have the tastes and attitudes of a peasant. I'm a peasant with money. Nevertheless, like if somebody wants to take me to fine dining, if they're treating, I'll try it. But otherwise I'll not look for an expensive place. Like yesterday I had a slice and like well it's actually two small slices and that was 10 bucks, you know, two slices, 10 bucks at the place they like me so and that was lunch. I like restaurants where there are non-US citizens screaming at each other and none of them look happy. Then I feel the food will be good.
That sounds like a comedian speaking and I kind of like that except for the yelling part. What's your favorite Tori Amos song?
Oh, I used to have a much better idea of what that would be, but I've forgotten. These days I focus mostly on my rabbi Leonard Cohen. Like I delve deeper into You Want It Darker. I've also become a Swifty but since I haven't listened to her last album enough I have to reserve judgment.
I like Silent All These Years by Tori Amos especially the live version.
That's very good. And I think I did hear a live when I spent a year in Pittsburgh in 1992.
And for you, what makes Leonard Cohen deeper or more interesting than Bob Dylan?
It's hard to say, but the bottom line, gut level is that with Leonard's help, I kind of feel God speaking to me, but not from Dylan. I've listened to him more and one problem is sometimes it's with my hearing issues, it's hard for me to make out his words. But for whatever reason, Leonard just speaks to me more. That's a very individual idiosyncratic thing. So, I don't know. I should say Taylor Swift does not make me feel like God has me on speed dial. But I do like her stuff and I do live near Cornelia Street, not Magnolia, Cornelia Street.
What in science fiction has influenced you and how?
There's the William Gibson stuff again. There was I remember reading in 1984 his seminal work Neuromancer which he wrote knowing nothing about computers and yet it's influenced a great deal of how the internet has evolved. Right now I'm going through a lot of the stuff by K.J. Parker whose novels are about a kind of different earth with a different history that parallels ours. And his novels a lot of them are about characters who are faking their way into positions of responsibility who turn out to be really good at those jobs under pressure. They're kind of confidence porn, much like The Pit is.
Why was Seinfeld so popular? I long have found it puzzling that people who don't really know New York might even like the show. Sometimes they like it without understanding that some of the characters are in New York or perhaps might be Jewish. That always struck me as bizarre.
I don't know. I just felt that those characters were in some respects a version of me despite their exaggerated bad tendencies. Maybe that's it. I do, you know George Costanza, Jason Alexander, I've always felt as one especially attractive man, a short, balding, kind of chubby Jewish. And I do see a lot of the Larry David coming through there and that I do like, like we see more Larry David on Curb and I do like that a lot even when I'm cringing. So I think Curb Your Enthusiasm is funnier than Seinfeld. It's more willing to be dark and Jerry as a character I think he's a good straight man in the old Abbott and Costello sense but I don't find him funny. In fact, it's mixed and I don't think about the funny part. I just try to enjoy it. And if you try too hard to understand something, sometimes that makes it, well, it's like explaining a joke doesn't make it funnier. So, I just enjoy the thing. It only took me a long time to enjoy Monty Python. And I just even on the way here, I saw I think a vertical format video from I think it's Monty Python and the Holy Grail and a peasant woman was explaining to King Arthur that just because some quote unquote tart threw him a sword that didn't make King Arthur divinely appointed. And that was in retrospect really funny. Not necessarily topical.
Often the best parts of Monty Python I've never understood. So you hear Tony Jaclyn golf clubs, I'm like an 11-year-old. I have no idea. Yeah. And it's funny.
There's a lot of things I don't get ever. Some things I get years after. That's I guess comedy. I wish I was as good at it as Jackson Lamb, who's, you know, one of my role models now because of something he said in the latest book, which is he said that small talk is just leaving the body. And speaking as someone with very limited social skills, that's a way of life for me. I may have, I don't quite have the personal hygiene issues he has. Although as I get older, I use aging as an excuse for issues.
