The deal is that law enforcement asked Craigslist to do some things. Craig's listed it. This call automated, culminated in the FBI giving Craigslist an award for doing the right thing. Craig's law Craigslist ran an extensive law enforcement operation. This is pretty much well known. It was not profitable in any regards more of the opposite. And that Craigslist worked with law enforcement.
Welcome to a 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 in which reach $1 billion revenue in 2018, only four years after
he started the company. During the last eight years, crack 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. Craig, it's an incredible pleasure to have you on my show. Welcome to a 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 do they influence
your future? And in particular, how did your dad's death it 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 really close. It is possible that my father's death caused me to grow indrawn. And that may account for what previously was reasonable socialization. Maybe that was
the cause of some problems. I don't know. And never really will be able to know
when you're younger, and you come home from school or 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 and 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 can 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're a kid saying you're definitely going to college cracks, I 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. 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 say 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 two that come naturally to you at some point.
I don't. 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 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 not emotionally intelligence. And I guess I was very much a rules follower. And I had a feeling of wind up committed to the, to the substance of Judaism, even if I don't, if even if I'm not observant, in the usual senses.
As a kid you like science fiction, comic books, I 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 was 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 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, you know, good physics scores. 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 as generally thought of, especially back then very, very smart kids only went into computer science, or 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 weren't computer science, you 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 use the computer for the first first?
Yeah, the first computer I used, I think I was 17. And at high school, and I think I was using an IBM a 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 to do where you're trying to program it to create something?
I was just fooling around with it. I remember computing I think it was radius of jog guy virture. 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 at the 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, he wore a tape together black rimmed glasses and a pocket protector. And in high school, I think your exact quote was your as possible in their patient zero. He also sang in the school choir, you join the physics club, your co captain, 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 want to grow out of this, and I want to have a different kind of life.
I never consciously realized that I was a nerd until years and years after high school. And I realized that that 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 are 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 kind of came out. Later in high school, I became more social, certainly in college, it came out a lot. But we're you. A lot of kids get bullied when they're, 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 wouldn't be left out of things. But I just can't remember any sense that I was bullied.
So going back to education, you earn 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 talked about the need for some education, where people would be part of teams to set up and defend networks, and then 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 it's yeah, the math 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 alone 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 that I come close. You came close.
I'm curious how 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, a 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 crag, or should I, I don't know. And I,
if they, I don't think you need to call to go to college. If you already have the skills and relationships to make your business success. Some people are naturally good at that kind of relationship. There's a lot of people who are naturally good at it. And for sure, I'm not one. So there will be people from college as 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 were for 17 years as a programmer, and then you work for AWS and any work 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 Craig's List 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 at 42, I guess was that was a happy accident.
We're going to talk about the happy accident in a minute. But many people think, Gosh, my 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 gonna 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. Is that in 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 are 20 to 25 years old, no experience have never managed anyone know p&l responsibility. They say I want to do this now. Okay?
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, we're 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're 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 what you were doing.
I was a happy working for a company that I started my own company, you know, 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 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.
But 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 post things and what exactly was your initial idea when you're sending out these emails?
Well, basically, I was inviting people to send me emails about interesting events, or whatever thought what they thought were was important, for example, a job offer or something to sell. And people just started selling those things into me. I encourage people to 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 the server, I had to give the thing
a name. And I was going to call San Francisco events, since it was still mostly that I had gotten many alternative postings in. And so again, thing broke, I was going to call this of events, people around me who were smarter than me, told me that they already called a 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, oh, 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 or two or three, what was happening during that time? And were you spending, how much time are you spending on Craigslist while you were
working full time. And during this, 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
was it turns out early 95, Schwab had issues. And I was given an ice 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.com, bubble. So there was a lot of opportunity to to learn and to do website work. And that kind of worked out for me. But even better, some time in, you know, 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 would, you know, I just made better use of the programming skills that I already had. I use Teach Yourself star books to learn even more. And I just kept on both this 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 I during this period of time, so many people I know, and this is true of me. And most people I know who start companies 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 where are you working 6am to midnight, each day to get both done? Or what was the what was the timeline here for you?
I would, I would work every day. And 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, oh, it was everything was very crude. And it was actually pretty simple to keep her 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
to remember if you were working until midnight, some nice 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, I 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 in the 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 able 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 had that bank account?
I don't remember much of any of the specifics there. I don't even remember our first eyes, which is to add, and their last 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 it
would have been 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 with a much less than the what they would be paying for less effective ads. Because I made a decision to minimize mine, 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 would be free.
Know, and even 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 gonna 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? Go do it?
I don't I have an answer for that. I can only speculate since the times when I really left the 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, they accepted 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 gonna go anywhere. But I did take it on. You know, 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 got a few good hires, who made sure the company runs well, to this day,
things took off. And like so many companies in a frothy market, this was part of the tech boom. There were companies created, including ours from occupy that that had billions of dollars of value within a year or two, feces pouring money into the tech space. And everyone wants to fund Craigslist throwing money at Craigslist, I'll give you 10s 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've seen pre seed rounds of $20 million. Why didn't you take the money? And what's your advice to all these entrepreneurs? nors 99% of whom I've ever met, said, I want to raise a ton of money. And I want 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 making enough to live comfortably, and to help out family in particular, and then just move on from there. That's worth 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 presents themselves as individuals, it's a business decision. First, it is an emotional decision. Second, some time. 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 and motivate people? Have they ever done it before? On a large grand level? And often the case they
don't. And your case, you 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 till 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 is good at starting something? Who has that drive, and that personality, and other strengths? Those strengths aren't these trends required to continue the existence of an organization. And fortunately, I had seen big mistakes made earlier in my career in the industry. So 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 Eau de to Eric Schmidt, who ran things and taught them how to run things as a serious managers. And then when they thought they learned enough, they took things back over. Now they are things have moved again. But they did a good job building a good company.
And what went into the decision for you. You keep talking 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 are 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 are pretty skilled, pretty skilled at 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 us computer industry, customer service isn't taken very seriously. Whereas in Craigslist, customer services was always taken very passionately.
So what were the kinds of things you were doing and 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. from Amazon, same thing, so many companies, you wait on hold for an hour, you get routed, the call center for people to speak good English is 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 and customer service were 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. My 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 [email protected]. That doesn't work anymore. But that
was Craig craigslist.org. And people ask me things like, what category should something be in? Or they asked me, you know, what needed to be paid for or whatnot? Sometimes people asked me if I could bend the rules for them. The answer always being No. People are asking 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 a 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 a, 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 than 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, and 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 grew up, we kind of forget that consciously. And maybe it's not, maybe we haven't internalized that, well, when you're in a small company, 150 or less, then you can cop but 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 internalize
and you can fall through. The problem is when companies get to be 150 people are larger. At that point, then people forget what they 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 have hardly suggest that people keep talking about the golden
rule. Keep telling people that treat people like they want to be treated and just Never stopped saying it, you got to stop short of spamming people. But maybe that's 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 an Uber, and drove people around for a couple of weeks to actually experience what an Uber driver did and a customer service. 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, oh, 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, 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 more successful company. 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 under Jim's
leadership. We never even began to approach the Dunbar number. The deal is that Jim is real good at running the country 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 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 that are public about Craigslist can
be relied on. No one is actually publishing honest numbers.
Except maybe the pageviews which people can somewhat there are services out there to determine pageviews visits etc, etc.
You're right. There are no reliable dollar figures out there telecom just people are making stuff. But one can look at page measurement services. Traffic measurement services, some of which are reasonably accurate, some of which are free, because frankly, I'm not going to pay you pay for it, you know, and I am pleased to see Craig's List traffic still stays strong.
Just to go back to Dunbar's number, we're talking about British anthropologist Robin Dunbar, who Denver's name is who the term Dunbar's number is named after this 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, Mabels 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 to people don't listen the same way. People don't make themselves known the same way. And as 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. Patients. The deal is for whatever reason, things take time. I'm struggling to find enough patients 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 just 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 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 do, but are terrible at it.
And in fact, maybe running scans.
Another element to success has been one of the core ingredients of my success is something which I talked about a lot, which I've known for which is called extreme preparation. I'm talking about an entirely different new level of preparation with similar prepares when our for meeting I may prepare five or 10. For 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 with 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 rights Bass, 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 a 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 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 and 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, I 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. Because, for example, I carry a multi tool with a blade. And then my to do list is to always leaves a multi tool at home. Since any blade is a problem, bring 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 but I can'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 one's 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, Twitter and 50 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 as mushroomed into an international success to rival Microsoft and Google knew Mark deserves his place in the
emerging pantheon. of technology pioneers joining Bill Gates, Larry Page and Sergey Brin, Newmark and 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 too 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 gotta get back to work.
When you reacted this back 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 nerves. You said this, you said I exist in a state of quantum superposition, simultaneous ly existing and non existing? What does that mean? When you say that,
it it means that I have a sense of humor. And that as a nerd, and someone who's got a little physics, I thought that was terrible. 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, how 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 comparison are have compared you to the likes of Bill Gates, and Larry and Sergey, that must feel kind of good.
I don't know if I believe if I believe I'm a celebrity. And I tell people that if you think that, you need to get 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 God 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,
or 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 and you're sleeping around a hiker meditating by herself 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 that 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 does help 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 story Whereas in 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 challenges with respect to erotic service ads. In 2010 attorneys generals in 17, States sent Craigslist a letter asking Craigslist to discontinue to adult services section which was then called
erotic services. It was hugely profitable 7000 ads in a single day back then. It still had a section called personals but on March 23 2018, Catholics 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, 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. Craig's listed it, this call automated, 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
of the opposite. And that, you know, Craigslist worked with law enforcement and follow the follow the lead of law enforcement, Craigslist tended to focus more on what law enforcement required, rather than what politician 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 they one should follow the lead of law enforcement, not politicians. And that's why Craigslist got that FBI word,
when you say that it wasn't profitable aren't all ads profitable. This was a very heavily traffic, 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. And in terms of recovering the costs involved. And in fact, the Attorney General's 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 one 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 cost $6 million. Do you have other indulgences that you do?
Personally, we're gonna get into the philanthropy in a minute. But 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 indoor I've ever been a billionaire. In particular, since I've now given away so much. I do have indulgences. And I have small homes in San Francisco in 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 I
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 then I'll buy myself a treat. I might even engage in retail therapy, for example, by 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 gonna talk about it in one second is truly incredible. But when you sat back, and you said, Alright, 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 that it's 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 Pichon ghost face collide 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 might compete for dominance. I mean, you hear about pecking order.
But every day we see pecking order and action. We are concerned that one of Ghostface sons we think we call big face, big faces making an attempt at displacing his father as boss. And we think big faces more stamina than goes face. But go fit goes face 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
queueing menacingly. So we are, it is pretty entertaining seeing this, and educational as well.
Most people don't know this, but there's actually Twitter 50 kinds of pigeons and they're one of the smartest person on the planet, they can find their way back to you from 1400 miles. But you said that you 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?
Nope. 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 cadex 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, you know, that's not something often done by the government, not by men, but 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 on 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 in 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 me 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 they are a 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 or working at companies are 2325 30 years old that wants to get involved in something,
find something that you believe in, find an organization which is vetted in the sense that they are really doing the job, and now running a scam. And then make the modest contribution of your time or money to it. Like for teachers, there's Donors Choose, which allow, 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 a few 100 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 love, we deliver. They do a great job. They need cash contributions. And sometimes they need volunteers to help
feed people. Those are the kinds of things that regular people can do.
Before we finished it. I want to go ahead and ask them our 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 quit 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?
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 he could be one person in the world, who would it be?
I'm tempted to say Leonard Cohen. But that's Oh, not 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 and a lot of your other interviews. Is there a reason? Why you haven't reached out to him? You you. 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 that, I was just too intimidated by the whole thing. Now, as it turns out, my comedian friend, and Leonard Cohen, 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 can make 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 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.
Greg, 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 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 nerds got to do what a nerds got to do.