Thirty Minute Mentors Podcast Transcript: Interview with Craigslist Founder Craig Newmark

I recently interviewed Craig Newmark on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is the founder of one of the most disruptive companies of our time. Craig Newmark is the founder of Craigslist. Craig is also the founder of Craig Newmark philanthropies. Craig, thank you for joining us.

Craig: Hey, it's my pleasure. I'm glad to be here.

Adam: Craig, do you still use Craigslist? And what are some of the most interesting things that you've bought or sold? 

Craig: Over the years through the site, my wife and I use Craigslist somewhat. Probably Mrs. Newmark more than I do. For example, we've given away a lot of stuff. We've sold very little. But also, we look for deals or things that we need or people in our family needs. A recurring theme seems to be that our families in the New York area need new dinner tables with chairs.

Adam: Interesting. Well, full disclosure, I'm an avid Craigslist user. If anyone listening is looking for a parking spot in Westwood, feel free to contact me if you don't contact me through my Craigslist ad. Can you share with listeners how Craigslist came together from idea to business and what are your best lessons from the early days of Craigslist?

Craig: Well, the way things happened is that early ‘95 I was thinking that a lot of people that helped me out on the net, particularly as I moved to San Francisco, you know, like a couple years before that. And it's time for me to give back somehow. I thought I could tell people about the technology and arts events that I was hearing about. And I built a simple cc list, like a dozen people that I know and started sending announcements to them. People started sending me stuff to post events, but eventually jobs, stuff they wanted to sell. I said, they have apartments, because that's when the apartment shortage started. It just kept growing from there, word of mouth. And I listened to what people wanted and did something about that. After a while, I realized that oh, I could. While I was getting emails of the ads that I was sending out, I could write some code which changed emails into web pages. And I had instant web publishing. Around the same time, people realized that I had something real going. And I had to turn what was a cc list into a listserv. I was going to call it SF Events Sites. You know, San Francisco Events. But people around me who were smarter than me, told me that they already called it Craigslist. I had inadvertently created a brand. They explained to me what our brand is, and then I stuck with it. I mean, there's more going on from there. Like, when I needed to make my hobby into a company to make it real. You know, a lot of bankers and VCs were telling me they’d throw billions of dollars on the table. And, you know, that's the normal way of doing things in Silicon Valley. But I remember my Sunday school teachers, Mrs. Levin, who told me that, you know, told me to know when enough is enough, I'm thinking, no one really needs a billion dollars. That's why the site is monetized very minimally. So I made a mistake for a while using volunteers. When I had to really you make the hobby into a real company, so that you could pay people. I was neglectful of communications and PR, because if you're not attentive to that, there will be bad actors trying to make a buck or worse, defining your image, contrary to what's really going on. So you do have to decide your monetization model early. And you do have to pay attention to how your entity is perceived.

Adam: Can you talk a little bit more about your strategy to in your words, monetize as little as possible, and what advice you have for other entrepreneurs and leaders thinking through how to monetize their business models, you took a very unconventional path. And what advice would you give to listeners?

Craig: Well, for a few years, it was only me. And you know, when something took cash, well, that was very little money. 35 bucks a month, hosting costs back then. And when I needed new code, I just wrote it myself. But this was in the earliest days of the internet, when something that small scale would actually get the job done. That's not true anymore. But I did remember the lessons of my Sunday school teachers thinking that you got to know when enough is enough. And I'm also thinking like a nerd. Like once I make enough to live comfortably, to help out friends and family. It feels a lot better to make a difference. So I figured we would charge people who would otherwise have to pay more or less effective ads. We've kept that philosophy, or I should say Craigslist has, I'm retired, Craigslist has and just charging people who would otherwise be charged a lot more.

Adam: Craig, you previously told me that one of the best decisions you ever made was walking away from Craigslist relatively early on, and turning over managerial responsibilities to Jim Buckmaster. You felt that Jim was better suited to take Craigslist to the next level and it allowed you to focus on philanthropy. What advice do you have for entrepreneurs on when to walk away? And more broadly, how can listeners understand how they're best suited to spend their time and channel their focus?

Craig: There's a bunch of questions and one there, so 2,000 people helped me understand that as a manager, I suck. I turned away from all management, all decision making responsibilities and powers. So 21 years ago, I stepped out of Craigslist management and basically have had nothing to do with Craigslist decision making for 21 years. But I put myself into customer service, because I really believe passionately that you should treat people like you want to be treated, which means good customer service. That's another lesson from my Sunday school teachers. Treat people like you want to be treated. And in business, that translates in part to treat people like you want to be treated. About five, six years ago or so, I started going very heavily into philanthropy. And I’ve gotten to the point where I've retired from the company. I haven't done company customer service for a long time, because they don't need me. But I decided to go full time and more into philanthropy, figuring that I have a fair amount of discretionary cash. And I could see since 2016, a major crisis, an existential crisis arising in the USA. So I figured I should help out.

Adam: What advice do you have for listeners on how to figure out like you did, it sounds like you were very self aware. And you were able to understand when your team came to you and said, Craig, you're not the best person to run this company. You're better off doing something else. Instead, you took that feedback. What advice do you have for listeners on how to understand how to spend their time and how to focus their energy and efforts?

Craig: When people start telling you that maybe you're not the right manager, and that was people outside the company, plus some on my own thinking, and everyone, I think needs to be evaluating themselves in their roles in a company or anything else. And be aware that it might be time for them to move on. Sometimes that's really difficult for folks. You know, like there's people who just are assured that they're right all the time, that and they're never going to listen to anyone, they're never going to get out of the way. And they do a lot of damage. Few people are ready to hear that. I moved out of the way, but it's very, very individual. I just hope that if you're responsible for, say, running a country, that you know when the time is to get out.

Adam: Craig, I'm with you on that. You created a company that disrupted the way we buy, the way we sell, the way we hire, the way we find housing, and do so many other things that are essential to our personal and professional lives. How can others create companies or cultures within companies that fuel and foster disruption and innovation?

Craig: Well, I think the most disruptive thing that can be done in a company these days, is to get serious about customer service. Remember the lesson; you want to treat people like you want to be treated. And if you think that through, that means you provide good customer service. And that's something that was part of Craigslist from the beginning, you know, to the extent possible, and that's what I do even with my philanthropies. I'm pretty much constantly online, responding to questions, and either approving or rejecting grant requests. Treat people like you want to be treated.

Adam: Craig, I love that. And I would love to go a little bit deeper given that this is a topic that I'm extremely passionate about. I have started a few different businesses, none of them anywhere nearly as successful as Craigslist. And a core theme of what I write about and speak about as well is the importance of building a customer centric business. So customer centricity; treating customers in the way that they would want to be treated, you would want to be treated. I'm with you. 110%. Can you give some examples of things that have taken place over the years whether it was with Craigslist or with your philanthropy that would illustrate to leaders listening, how to approach customer service and customer centricity?

Craig: Well, the biggest unexpected thing that I did, maybe more than one, was keep the site as simple and obvious as possible. At the very beginning, I had the advantage of knowing that I knew nothing about fancy design. So I just made things as straightforward and simple as possible. And GM maintains that philosophy. Then beyond that, you should have mechanisms and customer service, such that management decisions are made based on what's good customer service. I had cast that into the company's DNA in my year as a CEO, and before that, the ideals that you listened to people, listened to your customers and did something in response to that. Listen to your own employees, regarding what's good for customers, and frankly, what works for the employees because Craigslist has a set of internal tools that need to be good software for the employees again, a pervasive lesson is the golden rule. And we all know that we should follow the golden rule. But it's so easy to forget as you grow up. It's so easy to take for granted, such that if you follow it, that's one of the most disruptive things you can do.

Adam: What was your daily routine during the years you're building Craigslist? And what is your daily routine now?

Craig: Basically, when I was building it up in its first four or five years, it was simply, I get up in the morning, I see what needs to be done and do it until I'm ready to get ready for the day. For example, I'll get emails that I have to respond to. We're off to do things like getting things posted that were waiting to be posted. For that matter, way in the earliest days, I would have to manually get rid of the items that were no longer there and had expired because in the first years, I didn't use a database, I just used the pine email tool, which made it very easy for me to post things. It made it very easy for me to delete the oldest items. In my last year doing things actively coding, I had to write code which automatically deleted all the items. But the idea is that I get up and I get up in the morning and immediately I do everything that needs to be done. And only then can I take a break. And then I just get back to work. I have time off. I can see friends or my wife. I can do some reading or even watch TV. But I'm checking pretty much all the time, if there's something that needs to be done. And that describes not only early Craigslist, but it describes my work today.

Adam: Craig, what are the skills that you developed early on in your career that were most instrumental to your success? And what advice do you have for the listeners? Some of our listeners are in college. Some of our listeners are CEOs and leaders of large organizations. What advice do you have to listeners on the kinds of skills that they should be thinking about developing?

Craig: Well, there's always listening and patience. I mentioned those first because I'm not very patient and I'm still working on it. Listening is a big deal. And I was lucky that I read a book 25 plus years ago by Deborah Tannen called, You Just Don't Understand, and it's about the ways people don't listen to others and what you can do about that. The book is much better than I'm implying, but that's the gist. And so listening and being patient with people is really big. And those are hard skills to develop, in part because one of my skills is going the other way. I can get to the point really fast. And getting to the point really fast is a rare skill, and hard. And when you're good at it, that creates impatience. But the deal is that you want to develop the skill to get to the point and fast but you also have to be patient and listen to people which is counterintuitive and awkward. And when you're urging someone to guess, at a point, sometimes it's hard to be as nice as you'd like it to be. Nevertheless, I will be as diplomatic as I can, but that requires social skills. And I'm a 1950’s style nerd. I can show skills, but they're only a simulation.

Adam: Craig, what are your thoughts on what makes a great leader? You recognized early on that Jim was perhaps better suited to be the leader of Craigslist, but you've been seeding and funding all kinds of organizations run by different leaders and led Craigslist in its early days. What advice do you have for listeners on the topic of leadership?

Craig: I know a lot about leadership. Part of that involves the ability to inspire people. I understand that in the abstract- and rarely had I been inspired, or at least I've known when I was, the only thing I know how to do is to lead by example, and to practice what I preach. That is, for example, I like to preach the golden rule. And then I like to practice its practical application, like good customer service. I guess I also realize along with that is that perfection. The perfect is the enemy of the good. So I know that I'll always be flawed and give myself a little bit of a break, but only a little bit.

Adam: Craig, your foundation is involved in a number of different efforts to help make the world a better place. From fighting misinformation to protecting the right to vote to empowering women in tech and military families. How can anyone listening regardless of Where they are on their journey, whether they're a college student or CEO, play their part in helping make the world a better place?

Craig: In this narrow scope, this time and place in the U.S., the important thing is to register to vote and to vote in such a way that you make sure your vote is counted. It can help when you see people seriously addressing the issue in social media, you can, say, retweet or share good information as far as you can. You can always contribute cash to those organizations fighting the good fight like the lawyers committee for civil rights the Brennan Center for Law, the Leadership Conference for Civil Rights, Voto, Latino. There's kind of a boundless need for resources, and people can choose paths, similar minded people can choose paths. Oh, kind of like what I do. But the idea is to act in good conscience and help the people who are already doing a good job or something, and maybe join up with them to do a good job or something.

Adam: Can you talk about your decision making process on the philanthropy side and your decision making process in general? How do you make good decisions and what advice do you have for listeners on how to make effective decisions?

Craig: Well, I make the best decisions that I can given a limited knowledge and given the notion that most everything in our lives now are moving targets partially because of the pandemic, partially the political environment, and it's just that the future is accelerating. So I decide what are those areas which I feel are most important, like protecting the country, whether it comes to the election, or cyber security defenses, anything like that. So I've decided what I think is most important by my own criteria. And then I find groups who I can tell are doing a good job in a specific area. I help them with resources, including dollars, and influence, and communications help. And I work with them then to give my good advice in subsequent areas for subsequent decisions.

Adam: What advice do you have for listeners on how they can make good decisions?

Craig: Basically, on a given subject, it's important to learn what you can do. Don't go crazy learning everything you can find people who've already made the decisions and talk with them, except that you will make mistakes, sometimes expensive mistakes. But for my part, I'm happy if I have a whole bunch of successes and a few failures because the world comes out way ahead with a bunch of successes. And the failures were valuable in the sense they were experiments with negative results. But that's what's involved with science experiments. You succeed and you fail. And you learn from both.

Adam: Can you talk about a notable failure in the course of your career and how you were able to overcome it? I have to be

Carig: I have to be vague in some ways, because sometimes there's confidentiality agreements. A failure on my part, was not learning how to talk well, about things that were going on with Craigslist or whatever. I should have instituted that in the DNA of things, because when you're not telling the story and telling it right, that gives an opportunity for bad actors to run scams based on misinforming people. And once you've let them go first, you've pretty much ceded victory to them. And sometimes people get hurt. That's why about six years ago, I decided that if I blundered badly in communications, I would have to get pretty smart about it, subject to my limitations as a nerd. So I've learned as much as I can about communications, I would get help. And I would forever get help and learn how I can do better. And that continues to this very moment.

Adam: Craig, I think that that's great advice for listeners on a number of different levels. Number one, acknowledging shortcomings and recognizing areas in which you don't have deep knowledge or that don't come natural to you and when it's something outside of your comfort zone, seeking out subject matter experts who can really help you in those areas. Correct. How can anyone develop a winning mindset?

Craig: In my very narrow experience, you don't develop a winning mindset. You figure out what needs to be done. And then you go ahead and do it. Again, do it in good conscience, keeping in mind the golden rule. And as far as I'm concerned, he'll be winning. But my take on winning may not be the same as anyone else's. What is your definition of success? As long as the world is a little better than it was before and that you're happy about it.

Adam: I think that's a great definition. Craig, can you give any last tips on how anyone tuning in can become more successful, personally, professionally, just live a happier life?

Craig: I'm thinking again of those lessons I got from my Sunday school teachers. Aside from the golden rule. You want to know when enough is enough because sometimes you actually achieve enough, you get enough. And that's the time to take it a little easier. You don't have to keep getting more and more because sometimes you don't need as much as you think you need.

Adam: Yeah, Craig, I think that's great advice. And something that you've mentioned a couple times in this conversation is the impact that your Sunday school teachers had on you and 30 Minute Mentors is about the impact that our guests can have on all kinds of listeners. So clearly, mentorship has played a big role in your life and the Sunday school teachers that you had sounds like a mentor to you. Is that fair to say? Can you maybe share a few words on the topic of mentorship and what it's meant to you and any advice you might have on the topic?

Craig: Well, I don't know if they qualify as mentors, but in school teachers, Mrs. Livan certainly taught me a lot of stuff that sent me on my course. Something I didn't realize until recent years. Also my high school, U.S. History and Civics teacher, a guy named Anton Solski. He had a big influence on me, because he taught me the importance of the Bill of Rights as amended the declaration in the Constitution, and from him, I learned that a trustworthy press is the immune system of democracy. There have been others that helped. One guy at IBM taught me one lesson that when you're doing something, if you're acting emotionally, he told me I should ask myself what I wanted to accomplish. Another kind of mentor at IBM told me that sometimes my only saving grace was my sense of humor. Beyond that, there's a whole bunch of lessons from my Rabbi Leonard Cohen.

Adam: What is your best lesson from Rabbi Leonard Cohen? I didn't have him as a rabbi in the Jewish schools that I went to, and maybe I would have liked Jewish school more if I had him as one of my rabbis.

Craig: Well, one of his songs says he’s stubborn as those garbage bags, which time cannot take as junk, but he's still holding up this wild little book, a democracy is coming to the USA. And I guess I take that as a directive for the hearing now.

Adam: Craig, that's great advice. And I hope that everyone tuning in internalizes that. Thanks so much for joining us, and thank you for all the great advice that you shared throughout the conversation.

Craig: Well, thanks, I appreciate it.