Leap Academy with Ilana Golan
Craigslist Founder, Craig Newmark: How I Transformed a Simple Email List Into a Billion-Dollar Business
Tue, 11 Feb 2025
After Craig Newmark moved to San Franciso in 1995, he had a simple idea: a mailing list to share local events with friends. It wasn’t fancy and certainly wasn’t meant to change the world. However, as the list grew, people began calling it “Craigslist,” unknowingly naming what would become a billion-dollar digital marketplace. In this episode, Craig joins Ilana to share his journey, from creating Craigslist without VC funding to stepping down as CEO to focus on customer service. He also discusses how his moral compass continues to shape his work, including his mission in cybersecurity and his support for veterans and military families. Craig Newmark is an internet entrepreneur, philanthropist, and the founder of Craigslist, the online classified ads platform that transformed how people buy, sell, and connect. As a philanthropist, he supports causes related to veterans, journalism, tech ethics, and cybersecurity. In this episode, Ilana and Craig will discuss: (00:00) Introduction (02:01) The People and Moments That Shaped His Values (03:30) Navigating Social Skills as a Nerd (05:05) How a Simple Mailing List Led to Craigslist (08:23) Why Craig Rejected Billion-Dollar VC Funding (11:07) The Surprising Story Behind the Name Craigslist (12:46) His Slow but Steady Approach to Scaling (14:31) Fighting Fraud, and Dirty Tricks in Business (16:37) The Strategy Behind Growing Without Funding (19:02) Craig’s Pivot from CEO to Customer Service Rep (22:36) How Veterans Inspired His Cybersecurity Focus (29:51) His Pigeon Rescue Mission Craig Newmark is an internet entrepreneur, philanthropist, and the founder of Craigslist, the online classified ads platform that transformed how people buy, sell, and connect. As a philanthropist, he supports causes related to veterans, journalism, tech ethics, and cybersecurity. Craig also serves on the boards of several nonprofits and was named one of Time magazine’s 100 most influential people. Connect with Craig: Craig’s Website: craignewmarkphilanthropies.org Craig’s LinkedIn: linkedin.com/in/craignewmark Resources Mentioned: Craigslist Website: craigslist.org Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: Who is Craig Newmark and what is his impact?
A nerd's gotta do what a nerd's gotta do.
Craig Newmark, today we get to speak with the founder of Craigslist. He would say that he's a nerd and amateur philanthropist. I would say that Craig Newmark actually revolutionized how people buy, sell, and connect with their communities.
Chapter 2: How did Craigslist start as a simple mailing list?
Well, I had moved to San Francisco and I was starting to rediscover the internet and a lot of people helped me with everyday stuff. And then I decided early 95, I should reciprocate. So I started a very simple events related mailing list. We hit a million page views per month. And so in early 99, I turned Craigslist the hobby. into Craigslist, the company.
Chapter 3: Why did Craig Newmark reject VC funding for Craigslist?
The hard decision I made had to do with offers and so on from the bankers and venture capitalists. They told me that they wanted to throw billions of dollars at me. I would have to do the usual Silicon Valley thing, monetizing everything, and arguably selling out my community. So I decided...
Craig Newmark, today we get to speak with the founder of Craigslist. He would say that he's a nerd and amateur philanthropist. I would say that Craig Newmark actually revolutionized how people buy, sell, and connect with their communities. I think it's incredible. And Craigslist disrupted traditional, classified, and created a digital marketplace for billions of monthly page views.
So that's incredible. Now, Craig is involved with so many causes and we'll talk about it, but I want to take you back in time if that's okay. And I want to know what shaped you to become the Craig that we see today.
Chapter 4: What shaped Craig Newmark's values and moral compass?
I've recently reflected on my background and how things started, and I realized it has to do with Sunday school at the Jewish Community Center in Mars 10, New Jersey. Mr. and Mrs. Levin made sure that I had a pretty good grounding leading to a good moral compass. They taught me to treat people like I want to be treated. They taught me to know when enough is enough.
And they taught me that now and then I should be my brother's keeper. my sister's keeper, and that defined my initial moral compass. It was reinforced at different points of my life. For example, in high school, I took a really good U.S. history and civics class.
Mr. Shulsky made sure I understood the role of the Bill of Rights in the Constitution and how you have to both simultaneously fight crime while respecting due process and those rights in the Bill of Rights. There's been other influences. Most recently, very importantly, there's this guy named Leonard Cohen, who is effectively my rabbi, and his music also serves to reinforce my moral compass.
I just love that. And I love that you reflected on what shaped you. I want to take you back in time to your childhood. Again, like you said, small Jewish boy, New Jersey. If that's okay to take you there, Craig, and tell me if not, at age 13, you lost your father. I personally, when I lost my mom, I literally wrote how losing my mom changed my life.
How did that heartbreaking experience impact you?
I'm not sure. I've been thinking that I went numb on the event, on the whole situation, and I think I was already having some socialization problems. So as a way of retreating from people, maybe, That pushed me pretty hard in the direction of poor socialization, inability to read social cues. Some of that's the essence of being a nerd in the original sense.
It helped and didn't help that I was smart in the academic sense, good at science, technology, math, but I grew to be pretty poor at reading people, working with people in high school. And that nerd quality, that lack of social skills, that's still a problem for me even now. I mean, I've learned a lot of things the hard way, and I can simulate or fake social skills for a while, but not very long.
I love how you laugh about yourself, about being a nerd. You even write about it on LinkedIn. And you still were able to change the world with your nerdiness. So we'll talk and you continue to do that, which to me is mind blowing. But also, how amazing is that? But I do want to take you like you with that. You started working as a computer programmer, right? And like IBM and Charles Schwab. Wow.
How do you think did that help you get out of your shell? Like tell us a little bit of how that shaped you.
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Chapter 5: How did Craig Newmark transition from CEO to customer service?
The biggest shaping experience in my professional career was being very serious about providing good customer service at Craigslist, or the best customer service that I could.
You may know that around the beginning of 2000, having realized that as a manager, I suck, well, the deal is simply, I realized that I should become a full-time customer service rep, and I am a really good customer service rep.
If you believe that you don't have enough emotional, you know, intelligence, how can you be so good at customer facing? Like you would think they're connected or no?
Well, for me, it was because while I was doing it, I had to treat people like I want to be treated. I guess in a way, I am my customer's keeper. And I followed through with that, and that developed far greater empathy in me. I'm still working on it. I will always be working on it.
But I'm in a much less bad shape than I was in the past, even if frequently when it comes to social skills, I'm faking it.
Well, you're faking it great. And I love that conversation. But let me take you even back in time. I don't want to jump to 2000 yet. We'll get there. I actually want to take you to kind of like, I don't know, around 95, 1995. And you started basically an email distribution for your friends, as far as I know, in San Francisco, focusing on local events. Talk to me about that period.
What started this?
Well, I had moved to San Francisco and I was starting to rediscover the internet. I went around Charles Schwab saying, hey, here's what the internet looks like. We're going to be doing business some way, eventually this way. So people helped me get into the internet pretty quickly and understand what was happening.
And a lot of people help me with everyday stuff, kind of boring stuff, like neighborhoods, restaurants, stuff going on that I might like. And then I decided early 95, I should reciprocate. I should give back to the community. So I started a very simple events-related mailing list. It just grew much faster than I thought.
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Chapter 6: What were the challenges Craigslist faced while scaling?
So before that, before that, so you have an email list. I'm still stuck there. You have just an email list. Like how does that become so big? I know in 1996, you say, okay, maybe I need to create a web-based platform, but how do you move from one to the other?
Basically, we provided a really useful service that was simple and fast, kept plugging away, maintained our values, and because of the unique time and place, the site just kept growing and growing. Jim, having taken over, expanded it into different cities, and that's worked out great. And we just kept our momentum, kept a connection to what our fundamental values were,
And in my case, I just stuck with my moral compass. That worked. We did at one point way back then, maybe in 99 or 2000, we took a couple ads out in HR magazines for job ads that felt wrong and didn't work. And so we just didn't do that. And I've never done it since.
So your moral compass was there all along. And I do want to touch that as well, because I think for a lot of leaders, yes, that can get wonky pretty quick, you know, with business. So a few things. So first of all, you have an email list. You run into a 250 address limitation or whatever.
You realize that you have to create a web-based platform for classified, you know, if you really want to do better. You decide to... leave the name Craigslist, right? Why? I mean, it basically catches, but I want to hear that.
I need to rewind. In the middle of 95, that's when the address list problem occurred. I had to start using a listserv. And there was a guy, Eric Theissa, who offered to let me use his server with a major domo on it. Now, I'm a nerd, very literal, so I wanted to call it San Francisco Events, because it was still pretty much events then.
And people around me told me they already called the thing Craigslist. They told me I had inadvertently created a brand. They explained to me what a brand is. I realized pretty quickly they were right. So we adopted that name. The only tricky part of it is that I insisted it be spelled as one word, all lowercase, to de-emphasize the Craig in Craigslist.
And you literally created a movement. And I think this movement is still alive, which is pretty mind-blowing. But in 1996, and by the way, congratulations, Craigslist is 30.
That's correct. Surreal and a little horrifying.
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Chapter 7: How does Craigslist operate without significant funding?
We're the tortoise, and I'm the tortoise, and that's what works for me.
Well, I will correct this a little bit, Craig, because a million page views was very rare at the time. And I was in Intel. So we, you know, knew how to measure these things. And that was very rare. So you created something that was catching on really fast for that era. How did that feel? And what does it feel like to scale something like this? I mean, I'm sure it comes with challenges.
The whole thing feels, again, very surreal, in some respects, fascinating, and in some respects, horrifying. But the commitment was in place. And even though I've retired, the commitment remains in place.
But you did have some scaling challenges, right? There's fraud when you scale, there's monetization issues, right? So let's talk a little bit about this thing is growing and you're probably starting to see fraud or things that you don't like on the site. What was it like and how did that make you feel and what did you do about it?
Well, first, context. There have been problems along those lines. We found that they were artificially exaggerated by bad actors. We've tracked down some cases of people who were paid to greatly amplify the perception of a crime. However, it really was an actual thing. So we started working with the cops like 20 years ago, maybe 25 years ago.
They brought me to the Secret Service-based Electronic Crimes Task Force meeting when I talked to a lot of cops, and they were unhappy that dot-coms would not treat their subpoenas or search warrants seriously. I've remembered what I learned in U.S. history and civics. You know, you got to fight crime, but you also have to respect due process and the Bill of Rights and the Constitution.
And at that point, I said to the company, hey, we got to do the right thing here. And we proceeded to do that, sometimes running pretty comprehensive meetings. operations with law enforcement, which was pretty expensive, but that was the right thing. What we didn't anticipate was one other related effect of scaling, that people would attempt dirty tricks operations.
We were completely unprepared for that. And even now, personally speaking, I'm not good at that because I'm basically honest, and an honest person is never a match for someone who's a dirty tricks operator.
Oh, I agree. And we actually had a full episode with somebody called Don Ariely about hate in the digital world. But let's talk about this then. I mean, you're talking about all these things that you needed to spend money on. But on the other hand, you're very, very lean in Craigslist and you decide not to raise capital. How do you have enough capital for a team or to run this thing?
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