In Search Of Excellence - Craig Newmark: Reinventing the Peer to Peer Transaction (Founder of Craigslist) | E59

Episode Date: May 2, 2023

My guest today is Craig Newmark – the Founder of the incredibly successful internet marketplace, Craigslist! Craigslist serves 700 cities in 70 countries and has 250 million users a month. In 2018, only four years after formation, Craigslist reached $1 billion in revenue.  During the last eight years, Craig Newmark has been one of our country's most active and generous philanthropist. During that time, he has given away more than $200 million. In 2022 alone, he gave away $81 million, which made him the 24th most generous philanthropist in the United States that year. (01:50) Craig's parentsGrowing up in a Jewish family in New JerseyHow his father's death impacted his futureStress of going to college from a young ageThe influence of Sunday school teachers(06:29) Craig's Education (Computer Science)Mastering quantum physics and computer scienceUsing the first computer for the first timeBeing a nerd in high school and collegeBeing bullied as a kid(12:14) Advice for people who don’t want to go to college63% of people graduating college on financial aidAdvice to those who don't want to goWhy 42 is not too late to start a companyAdvice to new foundersCraigslist started as a hobbyHow Craig became an accidental entrepreneur(18:53) Turning Craigslist into a real companyHow Charles Schwab got started on CraigslistTurning a hobby into a businessThe first dollar ad on CraigslistThe monetization philosophy of Craigslist(27:04) When is the right time to leave your job to start a company?When is the right time to leave a job to start a companyThe fear of failureWhy he didn't take money from CraigslistAdvice to other entrepreneursEvaluate and make judgments on the founderAdvice to those with founder syndrome(33:55) What went into the decision to hire Jim as CEOThe decision to hire Jim as CEOEarly on, Craig asked for the privilege of not being on the phoneTreating people the way they want to be treated(40:12) Customer service is a way to make more moneyThe CEO of Verizon (customer service is important)Dunbar's number and how it's been guiding principles at CraigslistNone of the figures can be relied onTop five elements of success(57:32) HumilityThe importance of being humble in search of excellence.One of Craigslist challenges.How Craigslist has dealt with these issues throughout the years.How craigslist dealt with the issues.(1:03:04) The downsides of having a lot of moneyNet worth is estimated to be between one and $3 billionThe downsides to having a significant amount of moneyHis obsession with pigeons(1:09:32) PhilanthropyCraig Newmark Philanthropies (CNP)Pigeon rescue vs other philanthropic giftsHow to get involved in philanthropyThe one piece of advice Craig would give his 21-year-old selfSponsors:Sandee | Bliss: BeachesWant to Connect? Reach out to us online!Website | Instagram | LinkedIn

The deal is that law enforcement asked Craigslist to do some things. Craigslist did it. This culminated in the FBI giving Craigslist an award for doing the right thing. Craigslist ran an extensive law enforcement operation. This is pretty much well known. It was not profitable in any regards, more the opposite. And that, you know, Craigslist worked with law enforcement. Welcome to In Search of Excellence, which is about our quest for greatness and our desire

to be the very best we can be. To learn, educate, and motivate ourselves to live up to our highest potential. It's about planning for excellence and how we achieve excellence through incredibly hard work, dedication, and perseverance. It's about believing in ourselves and the ability to overcome the many obstacles we all face on our way there. Achieving excellence is our goal, and it's never easy to do. We all have different backgrounds, personalities, and surroundings, and we all have different routes on how we hope and want to get there. My guest today is Craig Newmark. Craig is an entrepreneur and philanthropist who is best known for being the founder of

Craigslist, which serves 700 cities in 70 countries and has 250 million users a month, and which reached $1 billion in revenue in 2018, only four years after he started the company. During the last eight years, Craig has been one of our country's most active and generous philanthropists. During that time, he has given away more than $200 million. In 2022 alone, he gave away $81 million, which made him the 24th most generous philanthropist in the United States that year. Craig, it's an incredible pleasure to have you on my show. Welcome to In Search of Excellence. Hey, it's my pleasure. I'm glad to be here. I always start my podcast with our family because from the moment we're born,

our family helped shape our personality, our values, and the preparation for our future. You were born into a Jewish family in Morristown, New Jersey, and grew up with no money across the street from a junkyard. Your mom was a bookkeeper and your dad was an insurance and meat salesman. They met at a synagogue dance. And when your dad died when you were 13 years old, what were your parents like and how did they influence your future? And in particular, how did your dad's death when you were 13 years old influence your future? I never knew my parents very well at all.

Unfortunately, we weren't that kind of family, which may explain in part that I'm poorly socialized. And even now, I can simulate proper socialization for maybe as much as 90 minutes, but I'm faking it. Never really got to know my father at all. He was very distant. And my mother and I never grew really close. It is possible that my father's death caused me to grow injured on. And that may account for what previously was reasonable socialization. Maybe that was the cause of some problems. I don't know, and I never really will be able to know. When you were younger and you'd come home from school,

were your parents stressing education and said, hey, Craig, you got great grades, or Craig, I think you're doing great in school? Did they encourage you to be active in other things other than school? They kind of, at some point, took my academic performance for granted. They just assumed that it would be happening. They encouraged me to do other things. But as I recall, mostly for a college profile, it's shocking in some ways that they were thinking about it that much. This was the 50s, 60s. But I guess they had spoken to some

people, some parts of the family, which were much more successful, where the kids were already in college years ahead of where I would be. Did your parents go to college and did they stress college for you from the beginning when you were a kid saying you're definitely going to college, Craig, so don't think anything else? They never got to college and I think did complete high school. And I think from an early age, they took for granted that I would be going to college because I was academically intelligent, not emotionally intelligent, but academically. You know, I did well on standardized tests. So they kind of assumed that would happen. And in the 50s, 60s, and so on, people thought college was the only way to get to a better career in life.

So they really wanted me to do it. Was there a point in time, like there is for many successful people I know, when your parents gave you some kind of positive reinforcement mechanism and said, Hey, Craig, you're phenomenally talented, or you have a bright future, or you're going to be the best at whatever you do one day? Or did that come naturally to you at some point? I can't recall any encouragement of that sort from them. I think it was largely initiated by myself,

maybe including both public school teachers plus my Sunday school teachers. The Sunday school teachers were a major influence on me. You like going to Hebrew school on Sundays? It wasn't one of my favorite things. I did my best when I was a kid to try to get kicked out as much as possible, something I regret now, by the way. I was good at it. I was academically smart, again, not emotionally intelligent. And I guess I was very much a rules follower. And I had a feeling I would wind up committed to the substance of Judaism, even if I don't, even if I'm not observant in the usual senses. As a kid, you liked science fiction, comic books, and wanted to become a paleontologist.

Why a paleontologist? I guess kids love dinosaurs. And I figure if I love dinosaurs, I should study them. I have a feeling there is something more to it that I forgot. And I would have forgotten that like 60 years ago. At some point, you said, I don't want to be a paleontologist. And you wanted to do something in physics. And when you were 13, you formed a lifelong ambition, which was to do something in master quantum physics.

What is master quantum physics, and how on earth did you know what that was when you were 13 years old? Well, sometime in there, my teens, I wanted to study quantum physics. I guess you'd say I wanted to master it. And I kept studying physics throughout high school, landed in college, took a good physics course, and then I realized I just wasn't smart enough. To be in quantum physics or related fields, you have to be among the top percent or two of students,

and I didn't have it in me, so I went into computer sciences. Well, computer science is pretty difficult to go into as well. It's generally thought of, especially back then, very, very smart kids only went into computer science. You and I are from a different generation than most students today where you take computer science in high school. Back then, when you and I were growing up in high school, if you were in computer science, you were seeking it out. It didn't find you. And it was generally perceived to be only for the smartest kids

were interested in that. I did have to seek it out, but it wasn't for the smartest kids. There were a lot of us who realized that they could be good at computers and that would be a pretty good field to get a job in. How old were you when you got your first computer? Or used a computer for the first time? The first computer I used, I think I was 17 at high school. And I think I was using an IBM 1620.

And at that point, did you say, I mean, there was very little functionality on that computer back in the day. So what were you doing with it? Was someone showing you certain mathematical equations and tasks you could do? Were you trying to program it to create something? I was just fooling around with it. I remember computing, I think it was radius of gyverture back then as a class assignment, and I programmed it to play the game of NIM, which is a simple mathematical game, although I did program it to cheat if I flicked one of the sense switches. So you've described yourself even today as the ultimate nerd. You went to Morristown High School,

you wore taped together black rimmed glasses and a pocket protector. And in high school, I think your exact quote was your as possible nerd patient zero. You also sang in the school choir. You joined the physics club. You co-captained the debate team. What was that experience like thinking you were a nerd? And did you want to be a nerd or say to yourself one day I'm going to grow out of this and I'm going to have a different kind of a life. I never consciously realized that I was a nerd until years and years after high school. Had I realized it then and what it meant, my life would have been simpler. Maybe I would have gotten properly socialized, but I would have never gotten the path I have,

which has been very good for me, very good for my family, and arguably good for the species. Were you bullied as a kid because you were a nerd? I was very nerdy when I was a kid as well. Completely different person today. It kind of came out later in high school. I became more social. Certainly in college, it came out a lot. But were you, a lot of kids get bullied when they're nerds,

especially when they're not socially part of a more popular crowd and don't have a lot of friends. I don't recall being bullied very much at all. I would be left out of things, but I just can't remember any sense that I was bullied. So going back to education, you earned a bachelor's degree in computer science from Case Western Reserve.

And after you graduated, you briefly worked as a researcher before getting a master's degree in computer science, also from Case Western. In this day and age, is a college degree necessary to both our personal development as individuals and to our future success? I tend to think that in a lot of fields, particularly computer-related ones, you don't need a college degree for that. A lot of people teach themselves things. Some people do take formal coursework.

And I think the thing that's missing from college that people would need to reproduce in some fields is the ability to work in teams of people. So in computer sciences and maybe cybersecurity, I talk about the need for some education where people would be part of teams to set up and defend networks and then act as opponents to a different group. You would attack the networks that another team would set up. So teamwork is a big thing that needs to be taught. But aside from that, the value of college, let's say these days it's not very cost effective and people leave college owing a lot of money. They do.

I think the research shows roughly that 63% of people graduating college are on financial aid and the average debt is around $37,000. And this is a crazy statistic that the average loan takes 22 years to pay off. So the math there is very difficult to sort out. Yeah. I did take a loan. I left school with one, but it was pretty close to zero compared to what people have to deal with these days. So when people come to you for advice and they ask, Craig, should I go to college? I want to start my own company. I'm a programmer. I don't really need this. What's your advice to them?

I'd say learn what you can about computers, but more importantly, learn what you can about working with people, because pretty much nothing is done just by lone programmers, not in terms of large, complex requirements. And yeah, the idea is that even people like me need social contact. So I do think you need to study with other people now and then for that team experience that I cited. I'm not certain I answered your question. Did I come close? You came close. I'm curious what your thoughts are if you have no interest in going into computer science, programming, or technology. Someone comes to you and says,

hey, Craig, you're a super successful entrepreneur. You're an icon in the tech business. I'm not sure I want to go to college. I don't know if I need it. I'm going to start my own business selling widgets. And I think I'm really good at it. Do I need to go to college, Craig? Or should I? I don't think you do. Or don't I? I don't think you need to go to college if you already have the skills and relationships to make your business a success.

Some people are naturally good at that kind of relationship. There's not a lot of Some people are naturally good at that kind of relationship. There's not a lot of people who are naturally good at it. And for sure, I'm not one. So there will be people for whom college is a distraction and a waste of money they should be investing in their own venture. Your first job out of college was at IBM, where you worked for 17 years as a programmer. And then you worked for several more technology companies, including Charles Schwab. It's now 1995. And at this point, you're 42 years old. We're going to get a Craigslist in a minute.

But before we do, what's your advice to people in today's society when everybody thinks, I've got to start a company early before I'm too old, before I have golden handcuffs? Is 42 years old too late to start a company? 42 is definitely not too late. People are doing it well into their 50s and sometimes 60s. In my case, I didn't intend to start a company. It's just that I had started something. I've made commitments and I tend to follow through with my commitments. So starting it at 42, I guess, was a happy accident. We're going to talk about the happy accident in a minute. But many people

think, gosh, by 42, I have a house, I have a mortgage, I have kids. It's too much responsibility to take a risk. Yes, Craigslist wasn't intended to be a company when you started. We're going to talk about that in a minute. But there is some sense prevailing in the tech community, I got to do this early before I have all of those responsibilities. And a lot of the founders today have very little patience. I got to do it now. I want to do this as soon as possible. What's your advice to all of them, especially those... We know so many of these, Craig, who want to start a company right out of the gate. They're 22, 25 years old, no experience, have never managed anyone, no P&L responsibility. They say, I want to do this now.

I'd say for young people, if you have the tolerance for risk-taking, if this is something you believe in, then go ahead and really do. However, if you're in your 40s and have big responsibilities, including dependents, that calculation is somewhat different, and it's based on the individual. I spoke to a guy who didn't take his dream job because it would mean relocating his family in an area which would be hard to start again in because the cost of living would be higher, finding a place to live would be higher or harder, and even new schools would be challenging. Before Craigslist turned into a company, all those years you were working at these tech giants, did you say to yourself, I'm good with this, or one day I do want to be my own boss. I want to start a company. I

just don't know when. I may not try it. It may come to me. But were you satisfied with what you were doing? I was happy working for a company. That I started my own company, Craigslist. That was all just a happy accident. Again, I had started a hobby and it proved to have a lot of potential. And I felt obligated to follow through. So many iconic companies, some of the most successful companies in the world, like Facebook, Instagram, YouTube, and Twitter, didn't start out as companies. They started out as ways for people to network and share pictures and videos and as communication tools. Craigslist

falls into the same category. We've already talked about it briefly. Can you tell us how you became an accidental entrepreneur, how Craigslist started, and the point at which you realized you had a business there, particularly when the email program broke when you sent 250 emails out to people? Well, it was all just one tiny step after one tiny step. And again, I had no idea that I was creating a business in the first four years. It was a hobby. And then in one year, it was a hobby with volunteers. But people approached me towards the end of 98, telling me that if I wanted this thing to continue, if I was going to follow through, I had to make it into a real company.

And so I did. Well, let's go back to the very beginning. Take us through step by step. You created an email list for friends to make certain postings. What were the postings and what exactly was your initial idea when you were sending out these emails? Well, basically, I was inviting people to send me emails about interesting events or whatever they thought was important. For example, a job offer or something to sell. And people just started sending those things into me. I encouraged people to do that.

And then I would relay those to a CC list using my email program. As I think you've read, at some point, the CC list broke at around 240 email addresses. And that's when I had to use ListServer. I had to give the thing a name and I was going to call it San Francisco events since it was still mostly that I hadn't gotten many alternative postings in. And so again, the thing broke. I was going to call it SF events. People around me who are smarter than me told me that they already called it Craigslist, that I had inadvertently created a brand. They explained to me what a brand is, and then I just kept happily along my way. So at some point, people are using it,

and you're saying to yourself, wow, this is pretty cool. But you're still working. I think at Charles Schwab at the time. And you continue to work there for another year, two or three. What was happening during that time? And were you spending... How much time were you spending on Craigslist while you were working full-time? And during these two or three years, were you thinking, at some point I may leave if I can make money doing this and give up my day job? Well, as it turns out, early 95, Schwab had issues. And I was given a nice severance package, and I left, worked on this hobby of mine while I was still figuring out what to do. This was 95 during the rise of the dot-com bubble, so there was a lot of opportunity to learn and to do website work. And that kind of worked out for me, but even better sometime in early 96.

Oh, people encouraged me to go more freelance. I did so. But the idea is that I left Schwab, continued what was a hobby then, took a job as a freelance programmer, and that turns out to be pretty lucrative. So things were pretty good for me immediately after leaving the corporate world. And I just made better use of the programming skills I already had. I used teacher-self style books to learn even more. And I just kept on both with my hobby, but also my freelance programming work until at some point people helped me understand

that I needed to turn my hobby into a business. What was your work schedule like during this period of time? So many people I know, and this is true of me and most people I know who start companies, they have a full-time job and they're doing another job on the side. Startup on the side could be research. They do a bunch of research. Some do start companies, some don't start companies. But were you working 6am to midnight each day to get both done? Or what was the time like here for you?

I would work every day because I was freelancing and not going into the office every day. I would just intermingle things. I would work on my hobby in my spare time, and then I would work in my contracting job, billing hours and other time, keeping them very clean and separate and so on, encouraged, in fact, by my boss at the freelance job. And I just kept plugging away. I don't recall my hours very clearly, how I would spend things, since I'm a pretty fast worker and can get things done in small niches of time. Back then, everything was very crude, and it was actually fairly simple to keep maintained. What's more so is that when I found a task starting to become more burdensome, I would write some code and that would make the job easier. Do you remember if you were working until midnight some nights just to keep the thing alive and keep adding fuel to the fire?

Or because you had such flexibility, you weren't working 100 hours a week? Yeah. My total in that particular period, I was probably not working much more than 90 or 100 hours a week. And that just means working through the weekends, working into some evenings, not a big deal. The idea is that I was doing something I believed in and thought maybe it would be

lucrative someday. And do you remember what the first dollar customer ad was that you brought into the site? The site is free and then you charge certain people to post things on the site in certain categories. Do you remember what the first thing that somebody posted that you paid for was and how good was that feeling when that money hit that bank account? I don't remember much of any of the specifics there. I don't even remember our first ads, which is too bad. And they're lost to history. The earliest one I can remember was someone wanted to pay someone else for the someone else to take the CPA ethics test of the original someone. And that's both unfortunate, but also pretty funny. Do you remember how much that cost back then? Back then, that one would have been free.

For the first three years or so, pretty much everything was free. Started charging as an experiment in 98, and then making it into a real company in 99. That's when we started charging people more. But the monetization philosophy was basically like charge people much less than what they would be paying for less effective ads. Because I made a decision to monetize minimally for various reasons. What were those reasons? Well, basically, I was thinking about Sunday school, being told that i should know when enough is enough and that a person struggling to put food on the table you know they should be paid paying for food they should not be paying for an ad on craigslist So in a lot of cases, a lot of those things would be free. And even now, Craigslist tends to charge dealers of different sorts, people who are making serious

money for ads, and trying not to charge regular people who are just doing things like trying to sell an old car. So many entrepreneurs have a job. They have an idea. They plan to start a new company. At some point, they said, I'm going to go jump off and do this. They have a lot of fear when they go and start and leave a salary job. Suddenly, the money's not coming in anymore. And I'm talking about starting a company that's pre-revenue, so they have to have savings. What's your advice to people with respect to when is the right time to leave your job if you have a job to start a company in terms of where you are in your life,

in your career? We touched upon it a little bit, but can you talk about people's fear of failure and whether they should listen to that fear or when they should overcome that fear and jump off and go do it? I don't, I could have an answer for that. I can only speculate since the times when I really left the actual jobs I had, in both cases, both companies were suffering.

They really didn't know what to do about IT, and I was able to leave and get generous severances. The exception, I guess, is I did take on a small job during the Craigslist hobby years. And after people convinced me that Craigslist would only survive if I went full-time with Craigslist, at that point, I left an actual job that was fortunate because the startup I was with wasn't going to go anywhere. But I did take on the management of Craigslist at that point, only for a year, and built the beginning of a company. I wasn't too good at it, but I got a few good hires who made sure that the company runs well to this day.

Things took off. And like so many companies in the frothy market, this was part of the tech boom. There were companies created, including ours, Akamai, that had billions of dollars of value within a year or two. VCs pouring money into the tech space. And everyone wants to fund Craigslist. Throwing money at Craigslist, I'll give you tens of millions of dollars. All the best firms are knocking down your doors. You said no to all of them. In today's environment, there is some culture among founders for people to raise as much money as possible. These rounds are getting absolutely ridiculous. I'm seeing pre-seed rounds of $20 million. Why didn't you take the money?

And what's your advice to all of these entrepreneurs, 99% of whom I've ever met said, I'm going to raise a ton of money and I'm going to treat that as a mark of my initial success. In my case, my Sunday school teachers taught me to know when enough is enough. And I just followed through with what I learned there. I guess that helped set my moral compass. And that's what worked out for me. Personally, I don't understand the point of having enormous amounts of money and buying mansions all over the place and having a lot of cars. That just doesn't make sense to me, given my upbringing. Maybe that reflects poor socialization also. I don't know.

But that's what my values are about. Sometimes I talk about nerd values, meaning make enough to live comfortably and to help out family in particular, and then just move on from there. That's what's worked for me. That's how I continue to live, even though I'm far into my retirement now. So what's your advice to the founders out there, the majority of whom think they have to raise as much money as possible to start a company? It's so individual. So I'd say do what makes sense for themselves as individuals. It's a business decision first. It is an emotional decision second. Sometime you have to have enough cash to provide a runway while you're competing with people in the same space, sometimes the same hot new space.

When we look at funding companies, one of the things that we look at first and foremost, and probably the most important for me, is the founder, quality, experience, general feel and sense of the founder. We also evaluate and make judgments on, is this founder going to be the ultimate CEO of the company? Does this person know how to manage people, raise capital, motivate people? Have they ever done it before on a large, grand level? And often the case, they don't. In your case, you recognize early, which is rare among founders, that you are not the right person to run the company. Can you talk to us a little bit about founder syndrome, what you did at Craigslist, and what's your advice to those founders who stubbornly think they're the right person to manage their company until the very end, even if they're probably not. It's just an observation that in this industry, and maybe all industries, sometimes the person

who's good at starting something, who has that drive and that personality and other strengths, those strengths aren't the strengths required to continue the existence of an organization? And fortunately, I had seen big mistakes made earlier in my career in the industry. Saw people who started off with great software packages, which made them a lot of money, but they didn't realize when they needed to turn things over to someone who is good at running a business. Like one successful transition both ways were the guys at Google turning things over to Eric Schmidt, who ran things and taught them how to run things as serious managers. And then when they thought they learned enough, they took things back over.

Now things have moved again, but they did a good job building a good company. And what went into the decision for you? Can you talk about Jim a little bit and how you knew each other and what his skill set was before? And ultimately, did you guys have coffee one day and said, hey, Jim, I want you to run this. This is not the best job for me. The deal was that sometime towards the end of 99, people who were good at business,

people helped me understand that as a manager I sucked and again this was kind of late 99 right around the same time I hired Jim to be a technical lead and then

oh as I admitted to myself that I really didn't or shouldn't be CEO, that's when I realized that I had hired some people who were pretty skilled, pretty skilled in management. Jim was one of them. And I figured, oh, Jim will make a good manager.

I can step down. I left all management. I became a customer service rep. I didn't manage customer service. I became an individual customer service rep, which is a big, important thing because in most of U.S. computer industry, customer service isn't taken very seriously. Whereas in Craigslist, customer service was always taken very passionately. So what were the kinds of things you were doing in customer service? I think what you're talking about is fascinating.

Apple has great customer service. You call, you hit a button, someone calls you the minute you hit that button. Amazon, same thing. So many companies, you wait on hold for an hour. You get routed to call centers where people don't speak good English. It's frustrating. They hang up on you.

It's such an incredibly important job. And so few tech companies do it right. And I think it's amazing to have a founder of a successful company like Craigslist to actually be taking phone calls. So give us an example of the kinds of things you were doing in customer service where people writing in, hey, Craigslist, can you do this or that? And you would write it back. And did people know it was you actually writing back? My deal was that I did ask for the privilege early on of not normally being the person on the end of the phone. I did handle phone calls now and then, but mostly I was looking at emails coming in

and I would handle, you know, whatever problems articulated that way. I got emails sent to me by the bulk of the customer service leadership. But it wasn't hard to guess that my email address was craig at craigslist.org. That doesn't work anymore, but that was Craig at craigslist.org. And people ask me things like what category should something be in, or they ask me what needed to be paid for or whatnot. Sometimes people ask me if I could bend the rules for them, the answer always being no. People ask me for all sorts of things. Sometimes I was asked for help digging into a situation which was unusual. For example, people who were advertising for kidney donors. That turned out to be an unusual, unexpected, and successful thing.

I just saw an article on that a week or so ago because people were finding successful kidney donors on the site and somehow that worked well to complement whatever official mechanisms people have. So I would do actual customer service. I would also do some things running internal tools looking for issues, which I need to be vague about. But I was seriously an actual customer service rep until the, let's say, around seven years ago. At some point, I realized that I was still doing some customer service. The company needed me less and less. How important is it for companies to follow the principle of treating people how they want to be treated?

And where should this be in a company's ranking of goals and as a factor in their success? Well, we all learn and believe in the idea of treating people like you want to be treated. But as we grow up, we kind of forget that consciously. And maybe it's not. Maybe we haven't internalized it that well. When you're in a small company, 150 or less, then you can kind of operate on intuition. You get to know people, so you kind of remember treating people like you want to be treated. And so it's not that hard because it's internalized and you can follow through.

The problem is when companies get to be 150 people or larger, at that point then people forget what they learned. And companies start dividing into factions and cliques and all sorts. And it's hard to remember to treat people who are not your friends, who are not in the same clique. And as for that, I don't have a solution because I've never been in that situation where I'm in management. I could half-heartedly suggest that people keep talking about the golden rule,

keep telling people to treat people like they want to be treated, and just never stop saying it. You've got to stop short of spamming people. But maybe that can work. It's the only thing I can think of. And it's kind of half-assed suggestion, but it's what I would do. I would love for the CEO of Verizon to call the same number I have to call when there's a problem on my phone bill and sit and deal with people and wait on hold and try to explain things. And then it doesn't work and call back three or four months in a row,

which is one of the problems I'm having on my phone bill today. It's ridiculous. And it's frustrating. And it's funny, you're in the ivory tower up there and you're running a company with 10,000, 100,000 employees, I think people like the CEO of Uber did, got into Uber and drove people around for a couple weeks to actually experience what an Uber driver did and the experience of having customer service is as well. I think every CEO should put on a customer service hat and put on a client hat and experience their systems and experiences just like the rest of us do. I do agree wholeheartedly with that. The deal is that CEOs and people who are in high management need to have a real good sense of and commitment to customer service.

That can be done in a number of different ways, but the bottom line is they have to take customer service seriously. And I have seen companies who do take it seriously and some who don't. I'm an Amazon customer. They do seem to have fairly good mechanisms. They are flawed. But when you ask for a call, you generally get a call back fairly quickly. And maybe it doesn't work out perfectly, but it's a start

and you can actually get things solved that way. And it inspires customer loyalty. People want to keep coming back. It does. From my point of view, customer service is a way to make more money, to make a more successful company. But I have not been able to convince anyone in a big company of that. But I have not been able to convince anyone in a big company that. Sometimes I even volunteer to help fix some things, since that's in my skill set.

But I think I've been taken up on it very rarely. You talked about an organization with 150 people. You also, as a founder, know, as I do, when you start out as a smaller company, it's easier to keep the quality of employees higher. At some point, as you get larger and larger, you want everyone to be a superstar, but it's a lot harder to do. Can you tell us about something called Dunbar's number and how that's been one of the guiding principles at Craigslist over the years. Dunbar number seems to be an observation that when you get people working together, people can kind of know each other, rely on each other, trust each other, if the number of people involved is no more than 150. Once the number of people in the organization hits 150, then people stop knowing each other,

start forming their own cliques or factions or tribes. And then as soon as you get factions, factions are competing and wind up not trusting each other. The deal with Craigslist is that under Jim's leadership, we never even began to approach the Dunbar number. The deal is that Jim is real good at running the company lean so that there's not a lot of people in the company who aren't being really productive. And that way, keep the numbers small, tight, and lean, and you can do pretty well. And that does make for a lot of revenue per employee. I should clarify there that none of the figures which are public about Craigslist can be relied on. No one is actually publishing honest numbers.

Except maybe the page views, which people can somewhat, there are services out there to determine page views, visits, et cetera, et cetera. You're right. There are no reliable dollar figures out there. Typically, just people are making stuff. But one can look at page measurement services or traffic measurement services, some of which are reasonably accurate, some of which are free, because frankly, I'm not going to pay for it. And I am pleased to see Craigslist traffic still stays strong. Just to go back to Dunbar's number, we're talking about British anthropologist

Robin Dunbar, who Dunbar's name is, who the term Dunbar's number is named after. Does Craigslist still have fewer than 50 employees today? I think so, but I actually haven't asked in some years, and I didn't ask during the pandemic years because I didn't want to complicate Jim's life or for that matter, Mabel's life. She runs a chunk of the company. And sometimes you get curious about something, but why add one more task or a bit of homework to someone's job if they're already too busy? Let's switch topics and talk about elements of success, in particular, the importance of listening and patience. Can you tell us about a book you read 25 years ago by Deborah Tannen called You Just Don't Understand?

Well, that has to do a lot with gender communications and realizing that different people, between genders and otherwise otherwise too, people don't listen the same way. People don't make themselves known the same way. And that's just human life. I read the book. I now can remember to misunderstand less than I used to. For example, very often when my wife is telling me about something, specifically telling me about a problem, she is not asking me to solve the problem. She is just telling me about it. As a male and an engineer, I feel compelled to solve the problem. But she has explained to me a number of times, she doesn't need my help. She just wants me to listen. And frequently, but not always,

I can catch myself. How important are listening and patience to our success? You can't get anything done if you're not listening to people who are telling you what you need to know, particularly if they're telling you something you need to know that you don't want to know. Patience, the deal is, for whatever reason, things take time. I'm struggling to find enough patience in a number of ways, for example, regarding the delivery of a chair to replace a broken one. But also there's a lot of times when people in the nonprofit world are having difficulty articulating what they're doing because they're not good at talking about what they do, but they're good at doing what they do.

So I have to be patient to work with a person who's good at something, even if they're not good at talking about it. That is particularly important since in the nonprofit world, often people who are good at something, not good at talking about it. But in the reverse, there are a lot of people who are good at talking about what they I talk about a lot, which I'm known for, which is called extreme preparation. I'm talking about an entirely different new level of preparation. When someone prepares one hour for a meeting, I may prepare five or 10 for a meeting. Instead of preparing five hours, I may prepare 50 hours. We just did a presentation for Marriott around four or five months ago. I think we spent 80 hours on that thing. How important has extreme preparation been to your success? And can you give us one or two very specific examples where you killed it on the prep and said, I'm going to be the most prepared person for this project or this task or this interview or this product launch?

I don't think I practice what you'd call extreme preparation. I do some preparation work. I do bits of research as needed. I put together what notes I want to, but although I never put together a prepared talk and I make sure the things that are working that need to work for example if I'm going to demonstrate something and I need to spend some time getting my head into the right space

but I find that that works well perfectly for me. I can be spontaneous and do things that way, and that generally works for me. I also do believe that, oh, there's a number of ways of saying it. It's like no battle plan survives contact with the enemy. There's also a saying that man plans, God laughs, because I know that planning is often not resilient. So I try to stay resilient and be flexible as time goes on because sometimes no matter what you do, how well prepared you are, you get a surprise. And then if you're not prepared for a surprise mentally,

if you're not resilient, if you're not flexible, then you're screwed. So I guess I believe in a reasonable amount of preparation, but after that, it feels like too much preparation. I've always been coaching that when you prepare, part of the preparation is to prepare for the unexpected, and that includes logistical things which are easily solved, getting there two hours before if you're in traffic or not taking the last

flight out or laying out your clothes the night before or getting your dry cleaning done, all kinds of little things that people forget. And even during meetings, I don't know if this has been part of your career or not, I've seen the Wi-Fi go out. So we bring sometimes temporary routers to presentations. We bring presentations on USB sticks. We've seen all kinds of technical calamities. Even when we're pitching at Andreessen Horowitz or Benchmark or one of these other firms, things happen. And we want to be prepared to anticipate something going wrong. In this sense, I do agree with you pretty completely. I do contemplate

things going wrong. I will prepare the night ahead for a trip. If I have to give a demo or do something like that, I provide for some redundancy. And I even have a to-do list of things to do. For example, when I'm going to travel. For example, I carry a multi-tool with a blade, and then my to-do list is to always leave the multi-tool at home, since any blade is a problem bringing it onto a plane. So I do over-prepare in that sense. I over-organize at times. And I don't think I'm obsessive-compulsive. But now and then I find myself thinking I'm doing something that an obsessive-compulsive would do. I think I'm okay, but a professional might tell me I go over a limit. What are other elements of success?

If I asked you what are the five elements of success, what would they be? I would have to wing it and just remember what some of my values are, like treating people like you want to be treated, do customer service seriously. And I guess preparation, sometimes a little obsessive preparation, is required for the job. You know, I don't think about what it took for me because, you know, like I tell people, my success in work, a lot of it has to do with just accidentally being in the right time and place. And that makes me the Forrest Gump of the internet. Where does work ethic rank in terms of elements of success?

I guess I take work ethic for granted and shouldn't, because I just commit to something and I just do what I need to do to get it done. But you're right. I guess I could list that in my top five. So let's talk about some numbers that I think may be accurate about Craigslist and its huge reach. 700 cities and 70 countries, 250 million visits every month. I want to go to an article in the Guardian newspaper from February 2006 that said this. It wrote this, quote, it began with a single email to a few friends and has mushroomed into an international success to rival Microsoft and Google. Newmark deserves his place in the emerging pantheon of

technology pioneers joining Bill Gates, Larry Page, and Sergey Brin. Newmark, a man so nerdish, he makes Gates look like a flamboyant playboy, may even be the greatest of them all. Did you see that article? And what's your response to that? I believe I forgot about it long ago. It's flattering. I might enjoy it for a couple seconds. And then it's back to work.

I do like the comparison to Bill Gates as a flamboyant, flamboyant playboy. There are people who might argue some of that has happened. So I'll be amused by it. I'll be flattered. And then I got to get back to work when you reacted to this back at the time you said you weren't a celebrity and you said you want to assure all your readers that I don't exist and as a bonus joke for the physic nerds you said this you said I exist in a state of quantum superposition simultaneously existing and non-existing. What does that mean when you say

that? It means that I have a sense of humor and that as a nerd and someone who's read a little physics, I thought that was funny. The deal really is that there are people, still are people, who think that there is no Craig behind Craigslist, and that's funny. I think it's funny to encourage them for a while to think that, but I will generally admit my identity. But I do have a sense of humor. Oh, about lots of things. It's fairly surreal. It's fairly absurd. And that's what I was demonstrating in that comment. You are a celebrity in the technology world, and you are world famous in the technology world.

Do you ever stop and think about how people are comparisoning, have compared you to the likes of Bill Gates and Larry and Sergei? That must feel kind of good. I don't know if I believe I'm a celebrity. And I tell people that if you think that, you need to get out more often. It is flattering, and again, it feels good for a few seconds, and then I have to focus on what needs to be got done. How important is being humble in our search for excellence? I think humility is required because you have to have a realistic assessment of what you and your company can do.

If you start believing your own press, that's bad, and that's one form of dysfunction. Another one, well, somebody, maybe Scott Galloway pointed out that power corrupts and makes you stupid, or maybe he said money makes you stupid. The deal is that if you have power or money, that can isolate you from what's real. Like, it might isolate you from your employees, from your customers. At that point, you make stupid decisions. And at some point, if you don't recover, then you just become a matter of historical interest only. I had Tony Fidel on my podcast recently, invented the iPhone. That's a big deal.

The iPad, that's a big deal. And I said to him, Tony, do you ever stop to think about, close your eyes when you're sleeping or on a hike or meditating by yourself, all the billions of lives you've influenced in probably every country in the world? And I want to ask you a similar question. There's billions of transactions that have gone through Craigslist, trillions and trillions of dollars. I don't even know if you've ever tracked the number. I bet it's $100 trillion or more. How does it feel to influence the lives of billions of people around the world and make the world a better place by providing them a service that people obviously need and love? It feels pretty good to contemplate it, to think that one thing Craigslist did is it showed people,

a lot of people, that the Internet is actually useful for something and that it's reasonably easy to use. That's good to contemplate. It's good to reflect that Craigslist has helped people put food on the table. And then it's time to move on to the next thing that needs to be got done. Every company, every person has challenges. That's one of the reasons that I started my podcast was to inspire people by telling the stories and sharing the stories about how we all got there. And we've all had lots of challenges. I want to talk about one of Craigslist's challenges

with respect to erotic service ads. In 2010, attorneys generals in 17 states sent Craigslist a letter asking Craigslist to discontinue its adult services section, which was then called erotic services. It was hugely profitable, 7,000 ads in a single day back then. It still had a section called personals, but on March 23rd, 2018, Craigslist took down the personal

sections when Congress passed the Fight Online Sex Trafficking Act, which was meant to crack down on sex trafficking of children. But Craigslist still offers personal ads in other countries where the laws governing online content are different, such as Canada and the United Kingdom. How has Craigslist dealt with these issues throughout the years? The deal is that law enforcement asked Craigslist to do some things. Craigslist did it. This culminated in the FBI giving Craigslist an award for doing the right thing. Craigslist ran an extensive law enforcement operation. This is pretty much well known. It was not profitable in any regards, more the opposite, and that

Craigslist worked with law enforcement and followed the lead of law enforcement. Craigslist tended to focus more on what law enforcement required rather than what politicians said. So the idea is that any organization needs to work with appropriate law enforcement direction. Politicians have other ideas, and I guess one might argue that one should follow the lead of law enforcement, not politicians. And that's why Craigslist got that FBI award. When you say that it wasn't profitable, aren't all ads profitable? This was a very heavily trafficked part of your website at one point. All ads are not profitable.

Some are free. Some ads under direction of law enforcement might involve a charge, which doesn't go very far in terms of recovering the costs involved. And in fact, the attorney generals did tell Craigslist, this is very much on the record, did tell Craigslist to charge enough to recover costs. But Craigslist doesn't publish this, but it's very easy when you're running a very sophisticated law enforcement operation. Sometimes you can't charge enough to recover costs. So we've already talked about money a little bit in the show. And you don't like to talk about your net worth, but it's estimated between $1 and $3 billion. We've already said you don't own a car.

You prefer public transportation. You don't own a plane. You fly commercial. And you live with your wife, Eileen, in a small home in San Francisco's Coal Valley. You do have a three-bedroom apartment in Greenwich Village, which reportedly costs $6 million. Do you have other indulgences that you do personally? We're going to get into the philanthropy in a minute. But do you have other indulgences where you say, gosh, I have made a fair amount of money and

there's things that I wanted to treat myself to and I'm doing that? All estimates of my net worth are ridiculously overstated. I am not, nor have I ever been a billionaire, in particular since I've now given away so much. I do have indulgences. I have small homes in San Francisco and New York. They're bigger than I want because my wife's family likes to drop in. I do have some indulgences. I buy all the books I want. I do have all the streaming services I want. And whenever I want, I drink Mountain Dew, Diet Mountain Dew, which I'm doing right now. That's a cliche about programmers. But I don't indulge myself as much as I might want to. Again, I don't own a car because they're just a pain in the butt. And now and then I'll buy myself a treat. I might even engage in retail therapy.

For example, I'll buy a short cable to connect to things which will be so much neater than a long cable. And that's a little bit frivolous, but that's the kind of indulgence I enjoy. You're very unusual that way, I think, in terms of people that have made a lot of money. I think it's amazing what you're doing with philanthropy. We're going to talk about it in one second. It's truly incredible. But when you sat back and you said, all right, I've made a lot of money, Craigslist has been reportedly extremely profitable almost from the get-go and still is. Is making all that money all it is cracked up to be? And are there any downsides to having a significant amount of money?

Well, there's multiple questions in there. First, there are no accurate reports that have anything to do with how much money Craigslist makes. And I can only speak for myself about money. The deal is, again, from Sunday school, how much is enough? And once you get that enough and you help out family, for example, at that point, it's just more satisfying to change things. So that's what I'm doing. You're doing amazing things. Before we get there, can we talk about the painting of your beloved

pigeon, ghost face, kalah on your mantle? And what is your obsession with pigeons? Well, I love birds and I have a sense of humor and we observe them out here. It is fun watching them, just how they behave with each other and with us. For example, as soon as my wife or I come to the right window, Ghostface and others start congregating, assuming that we will feed them. And usually we will. It is interesting and sometimes entertaining to see pigeons fight for whatever food we put out there or might compete for dominance. I mean, you hear about pecking order, but every day we see pecking order in action. We are concerned that one of Ghostface's sons, we think,

we call Bigface. Bigface is making an attempt at displacing his father as boss. And we think Bigface is more stamina than Ghostface, but Ghostface is a more effective fighter. So it usually ends with Ghostface winning, and then he'll do his pigeon victory dance, which mostly consists of rotating in a circle and cooing menacingly. So it is pretty entertaining seeing this and educational as well. Most people don't know this, but there's actually 250 kinds of pigeons

and they're one of the smartest birds on the planet. They can find their way back to you from 1400 miles. But you said that one of the reasons you like pigeons is because they're the underdogs. Do you root for the underdogs? And how important has that been a theme of what you've done in your career and what you're doing right now? For whatever reasons, I tend to identify with people towards the bottom of the economic spectrum. That's how I grew up and identify. Recently, I realized that I grew up in a neighborhood full of junkyards, truck maintenance, and that kind of thing. I grew up as a peasant with no money.

And now on a gut level, I kind of feel like I'm a peasant with some money. And somehow I managed to reinforce that by virtue of the books I read and the movies I watch, and that feels about right. The principle is treat people like you want to be treated. And that works for me and reinforces that attitude that basically I'm a grunt. I've done well for myself, but I'm still a grunt and have the tastes of a grunt. I'm also though a nerd and that influences my taste. For example, I prefer science fiction over football. Do you watch any football at all? No, I'm a nerd. Let's talk about something I'm passionate about and you're very passionate about,

which is philanthropy. Can you tell us about Craig Newmark Philanthropies and Craig's Connects and what your goals are with those institutions? The Craig Connects things is obsolete. It was replaced by Craig Newmark Philanthropies. Craig Newmark Philanthropies is about my commitment to help and protect the people who help and protect the country. For example, I'm putting a lot of resources, time, influence, money into cybersecurity because when it comes to education or tool development, that's not something often done by the government, not done by industry. So it has to be done philanthropically to fill in those holes, some of which are really big. I'm also doing more, increasingly more, over time to support veterans and military families since, oh, let's say there are holes in those support networks that are not being addressed yet by government.

That's changing. The president is doing something about that, let's say for veterans and their caregivers. I think there's a big event tomorrow to that effect. So those are the things that Craig Newmark Philanthropies is about. Also, pigeon rescue. Is pigeon rescue an issue today? And why have you chosen pigeon rescue versus some of the other gifts that you've given to things like cybersecurity, journalism, election integrity? Let's say the amount of time, energy, and money I devote to pigeon rescue is very, very small.

It's zero compared to everything else. However, I do love birds, and I have a sense of humor, and I suspect that pigeons may be our replacement species. I mean, it's not like I, for one, welcome our pigeon overlords, but the deal is that I do love birds, and I do have a real sense of humor, and this seems to be a good way of doing it, which is genuinely compassionate. Why is it so important to you to support veterans and their families? I figure if someone's going to go overseas, risk taking a bullet to protect me. If the family is willing to sacrifice a lot so that their service member can do that, then I figure I, as an American, owe it to the veteran, to the active service member, to the families to do something about it.

I mean, we all do a bit of that with our tax monies, but it's not enough. I think there's a misconception out there about philanthropy that you have to be rich or have a lot of money to do good. What's your advice to founders about philanthropy in general and to all those people out there who are not founders, who are working at companies or 23, 25, 30 years old that want to get involved in something? Find something that you believe in. Find an organization which is vetted in the sense that they're really doing a good job

and not running a scam. And then make the modest contribution of your time or money to it. Like for teachers, there's DonorsChoose, which you can donate five bucks to help a teacher pay for a class project. Classrooms across the country are very underfunded, so sometimes the class project is just buying enough paper for their students. When it comes to vets, Bob Woodruff Foundation runs the Got Your Six Network, which is a network of, oh, a few hundred organizations that are actually good at helping vets. And a lot of organizations like that aren't. And then, you know, if you make small contributions now and then,

that helps people out. The same is true of organizations which feed people. Down the street from me is God's Lovely Deliver. They do a great job. They need cash contributions, and sometimes they need volunteers to help feed people. Those are the kind of things that regular people can do. Before we finish today, I want to go ahead and ask some more open-ended questions. I call this part of my podcast, Fill in the Blank to Excellence. Are you ready to play? Yes. The biggest lesson I've learned in my life is?

To treat people like you want to be treated. My number one professional goal is? To follow through with my commitments. My number one personal goal is? I'd like to be as funny as I think I am. Are you taking any comedy classes to be funny? I know people who actually do this. And I'll do a shout out to Joe Hart on this one who actually it helps them.

I do talk to a comic who lives around the corner from me. He recommends I keep my day job. My biggest regret is. Oh, not learning how to ride a bike. Is there a reason why you are not learning how to ride a bike. Is there a reason why you are not learning how to ride a bike? No, I just never learned how to ride as a kid. And I would be in better shape now. And maybe I'd be better socialized.

The one thing I've dreamed of doing for a long time but haven't is? I don't have anything like that. If you could go back in time, the one piece of advice you would give to my 21-year-old self is? Treat people like I want to be treated more proactively. I could be a jerk at times, and I should have made that a non-problem, but I didn't realize I was being a jerk. If you could be one person in the world, who would it be? I'm tempted to say Leonard Cohen, but that's a problematic thing because of the role he plays in my religious belief. He's my rabbi.

Right. And you have not met him? I met him once very briefly. I was too intimidated to get him in discussion. You've talked about him before in a lot of your other interviews. Is there a reason why you haven't reached out to him? I can see you're a little shy, but obviously if that's somebody you want to spend time with, I'm sure he would love to spend time with you. Well, the best reason is that he passed away about six years ago okay but before before that i was just too intimidated by the whole thing now as it turns out my comedian friend ann leonard cone lived in the chelsea hotel in new york the legendary chelsea in the 60s or 70s or something. So I'm very jealous about that. But time travel is hard to accomplish.

If you could be one person alive today in the world, who would it be? I don't know if I know anyone like that offhand. Maybe Taylor Swift. I am a Swifty, and I have a neighbor who would love me to drag her along to such a meeting, and it would be life-changing for her. So that would be a nice gesture, I guess. Have you been at a concert? No, that's too much work. Craig, this has been fantastic to have you on my show. I've been a huge fan for a long time. I was an early Craigslist user.

I grew up in the tech world as you did, really at the same time as you did. And it's been a true pleasure to have you on my show. Thank you for creating Craigslist and for serving the billions and billions of people over the years who have used Craigslist and continue to do it. And congratulations on the truly incredible things you've done with your philanthropy.

Thanks. And I just remember that a nerd's got to do what a nerd's got to do.