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. 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. On any site, I want to get the thing done and get on with my life.
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. When I want to cancel a streaming service, it is never straightforward.
What then was wrong with the 1990s web? 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 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. Then, I guess, that began a process of what Cory Doctorow calls enshittification. 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 of GPT, isn't it?
Yes, that's a valid perspective. I think of it differently, mostly because, as I age, and have grown a decrepit, I've realized my limitations and that I'm not good at things. I realize that accidentally I've built networks of networks, and it's the networks of networks that get stuff done. 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. 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, 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. I could create Craig GPT, or I could just come back and haunt people for due diligence purposes, but the networks of networks have a life of their own.
What is scarce in your life then? You're giving away money. 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.
We're simulating social skills just fine here.
That's the phrase I use. At least on my part, what looks like social skills is just fakery. I can do it for short amounts of time, maybe 90 minutes. I've given up, though, on actually accumulating social skills, getting better at it. More to the point, I try to get into positions where other people can show social skills.
One journalist once described you as having 'obsessive customer service disorder.' Isn't that a social skill?
That's more obsession, so it's pathological, but a good one. I believe that you should treat people like you want to be treated. Think of the many times that you needed customer service. Sometimes you can get good customer service, but that's the exception. That's no reason for us not to provide a 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. 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? 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 maybe 4,000. I don't know if I got the number right, but it's too much. The thing is, 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 the same. We want to get through the day, which is sometimes tougher than other days. One thing I noticed in New York is that New York is a collection of small towns, not so much a big city. 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. Rent stabilization is a passion. Otherwise, people everywhere are similar. The amount of bad actors is actually very tiny.
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 bad actors. 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. That was a painful lesson that took a couple years to sink in. It wasn't a good year or two.
I think much of Craigslist is saying you can trust other people if the incentives and institutions are correct. Your nine-second rule—wait for nine seconds and think before clicking on something you get, say, in your email or on a social network site—is a lack of trust. Is it that your views have changed, or how does the whole picture fit together?
I have learned something and my team has learned something from real life. The notion is that a normal, a very common technique of scammers is to rush you into something, to convince you of the scam by making it sound urgent. 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 changed it, but that's 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.
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 few seconds, but at 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. If you use a font where you use an R followed by an N, some fonts make the RN together look like an M. 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. 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. Whenever I buy technology, knowing that I will replace it eventually, I try to get something that, even used, will be a good acquisition, typically by one of my nephews or nieces. My collection is 24 of them and counting.
Missed connections used to be a feature. 'Oh, I saw you on the subway. You seemed 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. Over the years, over the decades, 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 sad. I've thought about that for a long time, but Jim just decided to put it up after he became a CEO sometime in the middle of 2001.
Why don't dating apps work better? If we mostly can trust people, right? The first date, 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. Let's say that they hit their stride after I had gotten involved with the future Mrs. Newmark. I sense the opportunity for comedy coming on that will get me in trouble. Even alluding to that will probably get me in trouble after Eileen watches this.
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, that people aren't genuine, aren't real on dating apps. The only basis for this thought is, about 25 years ago, before Craigslist had dating sections, I met several women who told me they used the roommate ads for dating because, in a roommate ad, a guy would be relatively honest.
Actually, I didn't think of that, yes. That's very good. I'll have to steal that for the repertoire. This is serious. That's what women told me way back in the past. This had to be, man, right around probably late '90s. I really am old.
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, 'Oh, what's going on?' At some point in the past, other sites where you build up a profile, they look like you're actually dealing with a real person. 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. 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 cybersecurity, and what regular people can do to prevent them.
Even before generative AI, you didn't have seller evaluations the way eBay and Uber have. Uber, this driver is a 4.98. You assume it must be okay. 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. I was thinking, it will be really easy to game that kind of thing. Frankly, even then, I was reading science fiction, which looked into the future about how online media and the internet would be gamed. I'm even thinking back to 1984 William Gibson Neuromancer, which affected me and a lot of people in the field, and I'm hoping will be a really good Apple TV show. Yes, 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. I've lost track of the question because I want to say why Jackson Lamb is now my role model, which you can feel free to prompt me when you're in the mood.
Seller evaluations, right? You've never involved them. Podcasts get evaluated on Apple, right? This gets so many stars.
It's just too easy to game those systems now. What I'm hoping for are user authentication systems, not state- or government-instituted ones exclusively, because I worry about governments. A lot in life is based on who you trust, and you want to be able to know who you're talking to. I don't want to turn over a lot of this to the government because of some of my political biases. I'm looking for balance. If you can identify yourself to other parties in a way that shows you are who you claim you are, that can be good. The credit card companies working together may have a solution. Driver's licenses may be, in part, a solution. Ninety percent of Americans have phones with digital wallets. Maybe there's something there, but I need to run this by the Electronic Frontier Foundation, because they think of things that I will not think of, and they may tell me why my idea is terrible.
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. 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. I might accidentally go to a hip-hoppening places, happening places, which is not my thing. I just look for the mundane, the ordinary.
Say you're choosing a restaurant. What's your algorithm?
My algorithm is, well, does it look like a hole in the wall?
Actually, quite seriously, my deal, 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, if somebody wants to take me to fine dining, if they're treating, I'll try it. Otherwise, I'll not look for an expensive place. Yesterday, I had a slice. It was actually two small slices. That was $10. Two slices, $10 at the place. They liked me. 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. I 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. I dive more into You Want It Darker. I've also become a Swiftie, but since I haven't listened to her last album enough, I have to reserve judgment.
I like Silent All These Years by Tori Amos, especially the live version.
That's very good, and I think I did hear it live when I spent a year in Pittsburgh in 1992.
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 feel God speaking to me.
I've listened to him more, and one problem is sometimes, with my hearing issues, it's hard for me to make out his words. 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. I do like her stuff, and I do live near Cornelia Street.
What, in science fiction, has influenced you and how?
There's the William Gibson stuff. I remember reading in 1984 his seminal work, Neuromancer, which he wrote knowing nothing about computers, and yet it's influenced a great deal of how the internet has evolved. Right now, I'm going through a lot of the stuff by K. J. Parker, whose novels are about a different Earth with a different history that parallels ours. His novels, a lot of them are about our characters who are faking their way into positions of responsibility, who turn out to be really good at those jobs under pressure. They're confidence porn, much like The Pitt 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, version of me despite their exaggerated bad tendencies. Maybe that's it. George Costanza, Jason Alexander, I've always felt is one especially attractive man—short, balding, kind of chubby, Jewish. I do see a lot of the Larry David coming through there. We see more Larry David on Curb, and I do like that a lot, even when I'm cringing.
