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- [00:00]
A
When you got an offer for $11 billion, what did that feel like?
- [00:06]
B
Turning it down? I had a little twinge. But, you know, then my values, my moral compass asserted itself. Thinking, having this much money is bullshit.
- [00:18]
A
Was there a point at any time in that deal, mechanic, that you thought, $11 billion is a lot and I could actually give away even more?
- [00:27]
B
It just didn't feel right from the beginning. And I thought about what I could do with that. Like, I could buy a yacht, but what's the point? I could buy a fancy car. What's the point? And I just didn't get it.
- [00:42]
C
Craig Newmark started Craigslist in 1995 off a mailing list. He turned down what he says was an $11 billion offer. And since then, he's given away $570 million. And he wants to give away a billion dollars before he dies. He funds cybersecurity, work with the FBI, gear for the nypd, bomb, military families, journalism, a whole bunch of stuff. And even does AI research projects, trying to catch heart problems early. Craig is such an interesting dude. And by the way, this conversation started the way most Money Wise episodes do. Inside Hampton, a private network for founders and CEOs. Hampton is where founders who do 3 million or more in revenue or who have exited for 10 million or more talk about all the details of their lives, their business, the money they have to spend, where their burn and all their revenue comes from, if they're raising or not. These episodes tackle the same problems that Hampton founders do. If that's the kind of room you want to be in, go to joinhampton.com in this episode, we'll go through the actual math. What $11 billion turned down looks like and $570 million given away actually breaks down to. And whether or not giving away that much money actually makes him happy.
- [01:56]
B
Happy.
- [01:57]
C
And why he even gives it away at all. And while you're here, please subscribe to the Money Wise channel. That means more to me than you might think. Now, let's get into the episode. This is Money Wise. I'm Daniel Burke. Here's Craig Newmark from Craigslist.
- [02:11]
A
I would love for you to tell me a little bit about the way that you were raised and grow. You grew up around, you know, a very specific lifestyle without the Craigslist story. And so let's start there. Tell me about who Craig is before Craigslist.
- [02:29]
B
Raised in New Jersey. Dad died early, but they did send me to good Sunday school. And this was at the Jewish Community center in Morristown, New Jersey. Anyway, I Got lucky. I got a real good pair of teachers at first. Married couple from Europe. I only learned their story a couple years ago, but I was paying attention. They set my moral compass, helping me understand I should treat people like I want to be treated. I should know when enough is enough. And I should think about being my brother's keeper, my sister's keeper, whatever that means. How literally do I take it? Not long ago I learned maybe that I should do things like selling possessions and feed the poor, which from my point of view is the same lesson. And I just have to avoid taking it too literally because growing up then, I was really good at science and technology and grew into the nerd stereotype. However, as far as I could tell, doing a lot of reading, I may have invented the nerd stereotype. Not only limited social skills, but thick black glasses, taped together, plastic pocket protector. And again, I just was completely oblivious to social cues. Okay. And nowadays I'm still largely oblivious to social clues. I can fake it for about 90 minutes, after which point I will show signs of wear and possibly get cranky.
- [04:24]
A
Yeah. And when you started Craigslist in 99, my understanding is part of the reason why you hired a CEO was due to some of those social cues and management styles. Tell me more about that. What was your thinking?
- [04:37]
B
I started in 95. Well, you're almost right. Started the thing in 95. Mailing list. And then about a year after I realized I am a programmer and email has a fixed format so I can write code which would turn emails into web pages. I had instant web publishing basically for free. I mean, the most I paid in that period was 35 bucks a month for hosting services. And I basically ran it by myself for three years. Ran it with volunteers for one year. That didn't work out. People need to be committed and paid. And so in early 99, Craigslist became a real company and I had to make a tough decision at that point. Bankers VCs back in San Francisco wanted to throw what turns out to be billions at me to do things the usual way. But thinking back to Mr. And Mrs. Levin, I'm thinking I know when enough is enough. If I live a really good life and help my family do that, the rest is discretionary and might become a burden. And so I decided to minimally monetize Craigslist. Mostly just charge some people for ads that they already had to pay for elsewhere. The ads weren't as effective, so that was pretty good. That's been expanded over the years, particularly in New York where apartment brokers went out of control about 15 years ago, posting the same ad multiple times a day. Everyone hated that. Brokers and apartment seekers. So I spoke to a lot of brokers, asking them what was a fair price per ad. The successful brokers had 20 bucks. The ones who were just started say said 10 bucks. Because normally a new broker would only make 20k a year. And even 15 years ago in New York, not enough.
- [06:54]
C
Sure.
- [06:55]
B
You know, you had to work three jobs or more. Yeah. So in a sense that's the gist of Craigslist. I mean you were right. In 2000 I realized as a manager I suck.
- [07:12]
A
When you say that, what do you mean? Because I've seen that online and you've said that before.
- [07:16]
B
I had no talent or taste for making tough decisions and being a manager. Hiring, firing, where do you put resources? Those are difficult decisions and I hated doing them and I wasn't all that good at them. But I just hired Jim to lead technology and he was good at them. So I stepped down completely. I became full time customer service because if you want to treat people like you want to be treated, you do good customer service. And I gave up all management influence and responsibilities. I mean I stayed on the board and I'm on the board now. But board powers are intense but very limited. So Jim has been running things. He maintained the monetization philosophy and to my surprise, Craigslist has done really well financially. That puts me in a, let's say in a moral dilemma of making lots more than I need. What do I do with that? And in some, sometimes, in some respects, I've even literally helped feed the not so much poor as food insecure. That's the term of our now and I focused during the pandemic on military families.
- [08:42]
A
When you think of the shift from this website that was primarily a one to one messaging social forum in many respects in 1995 to what it became, what did that feel like when you started to see 7 and 8 and 9 and 10 figures on a balance sheet or VC offer? How did that feel?
- [09:07]
B
It felt good and surreal. I some ways didn't believe it was happening. I'm pleased, but I'm again challenged. I'm perplexed. What will I do about this? And at first the company accumulated money because that's financially responsible. But at some point people with equity got some and I'm thinking that I would keep some for myself and my family. Mrs. Newmark has the largest vote there. Seriously. But I should do something like putting all my Craigslist equity into Charity. And I did that officially a few years ago. I created what they call a 501c4 foundation. I'd made that decision shortly before turning 70, because I'm very, very old.
- [10:04]
A
You do not look a day over 60.
- [10:07]
B
Thank you. But in December, it'll be 74. And so I called the thing the Septuagenarian fund, because I have limited imagination, but I do have a sense of humor, which I have a hard time stopping. Except nowadays, sometimes I can tell when I'm not being funny. And so I put it all in there. And now I'm embarked in a process of spending it all down during my lifetime.
- [10:41]
A
And when that shift happened, when Craigslist started to make real money, before you put all of it into a substitutionary fund, where was that money going? Early days, there was no real overhead, very few employees.
- [10:55]
B
That's right. The company. Well, Jim runs it pretty lean, frankly. Not much in the way of bullshit. There is a customer service and billing department. There's technology, and then there's Jim. Yeah, one point. In 2000, we experimented putting a couple ads in HR magazines decided wasn't useful and so never marketing. For the most part, word of mouth helped the sites succeed. We relied on that too much in some ways when bad actors. Oh. Tried to hurt us and we should have fought back, but we didn't.
- [11:43]
A
Yeah, putting that amount of equity into a 501C4, a lot of people would say that's a really interesting decision. And the moral dilemma, I think is, I would just love to know more. What is the moral dilemma you felt about amassing wealth for yourself versus socially giving back to these nonprofits and 501c4?
- [12:06]
B
I don't want to overdramatize my thinking back then. I do recall thinking that, gosh, it's nice to have all that money. Not feeling insecure. My family grew up not poor, but not middle class either. But I figured at some point for sure, I had more than enough, and people were already approaching me about good things I could do with nonprofits. Most of the first requests were just for help, consulting about what's it take to build community? Because back then, Craigslist, even though classified, built community, to my surprise. And so I'm thinking that I'm making all this money. I feel comfortable now. I could start giving it away to people who might need it. I'm beginning to see the need for nonprofit work, for funding in areas that didn't seem to get enough, like experiments in journalism, like support for military veterans. Now and then I would do Something miscellaneous, I think started small, got organized in 2015, 2016, and I've just been getting my act better and better together. I take some pains to remain a amateur because I'm finding that foundations, which don't. Well, if you do the formal things, the best practices that foundations are supposed to be, sometimes those are paralyzing. So I'm getting more professional. But frankly, what I do is when I need help, I gather my networks, ask for help, make a decision that works.
- [14:07]
A
Sure. When you think of the philanthropic division of your wealth and what you want to leave and how you want to spend some of that money, what's your thought process behind where the money goes and even how much you give away and in what cadence?
- [14:26]
B
I guess maybe I'm a little bit of a contrarian. I. I'll find areas which need help and which people may say they're even. Lots of people are helping, and they're not. So I would fill in. That includes military families and vets. They were getting some real support in the decade after 9, 11, but that is tapered off. I just read a newer report about that this morning from Bob Woodrow foundation, and I. Well, I was right. Remember, raised in Marston, New Jersey, which is also the capital of the revolution. Washington spent a couple of really hard winters there with the Continental Army. And so growing up, all around me are reminders of what the revolutionaries had to work with, how much they suffered because they didn't have adequate anything. And I figured, well, I can't help them out, but military families and vets are hurting, and I've helped.
- [15:36]
A
You told me you want to give away how much money by the time you pass away.
- [15:42]
B
By the time I pass away, in aggregate of a billion. I am not a real good investor, but I've done a good enough job that I can see the money and the foundations growing to that extent in between 10 and 20 years. That's my horizon, because I'm guessing at 73, I'll live another 10 to 20 years.
- [16:10]
A
Yeah, I think so.
- [16:12]
B
That's my hope. The cardiologist next week. So far, he's told me he's been extending my warranty.
- [16:20]
A
Okay, well, we have fingers crossed for the cardiologist appointment.
- [16:23]
B
That's a cardiologist joke, and I may. I may use it preemptively. Yeah.
- [16:32]
A
That's great. Yeah. I have some cardiology stuff running in my family, so I relate to a lot of that.
- [16:40]
B
Yeah.
- [16:40]
A
When you so a billion, by the time you die, 10 to 20 years. I mean, maybe longer. We don't know, how much have you given away already to philanthropy?
- [16:49]
B
Depending on how you want to measure, right now, it's around, I'm guessing, a little bit, 530 million. When I consider commitments like dollars that I've promised I would provide, given milestones, that goes up to about 570.
- [17:09]
A
Okay. So when I think of philanthropy, I'm in a very different situation. But I give to causes I care about and I give to people I want to see succeed or who need particular money for something. And I'm talking $1,000 here, $5,000 there. $570 million is a lot of money. Early on, did you think you would give away that much money?
- [17:38]
B
I don't think it's a lot of money. In philanthropy, there are people giving away billions like Mackenzie Bezos. What matters is, oh, let's say the percentage of your net worth. I guess what matters is how committed you are. And people do what they can. There's a lot of, well, first, getting through the day sometimes is just too much of a challenge. Making ends meet, too much of a challenge. And it's not fair to expect people who are working two jobs to feed their family. They're not going to contribute to anything, and I don't want them to. They should be recipients.
- [18:20]
A
Yeah.
- [18:23]
B
Me, I figure I'm doing what I can, what makes sense, subject to negotiations with Mrs. Newmark.
- [18:31]
A
I like that answer. And when you think of the delta from 570 to a billion, do you have some places or causes in mind beyond the ones you've shared already that you really foresee giving to?
- [18:44]
B
Right now? There's two big buckets that I contribute to military families and vets, and then fighting scams and fighting cyber attacks. Both big buckets are about protecting the country and helping regular people, well, fight bad guys. So those are areas where I've stood up. I'm also helping journalism, but not as much as I used to. Like. I'm providing substantial support for Wikipedia, for the City University Journalism School, for the Columbia Journalism School, and some other things like the Ford, which is a historical New York based Jewish newspaper. Beyond that, sometimes I'll support some things on a whim, like, well, I love birds. I have a sense of humor. I really do support pigeon rescue, which
- [19:48]
A
I wanted to ask. Pigeon rescue, especially in New York, sounds like a bit. Because people initially think, why rescue pigeons? They're a nuisance.
- [19:59]
C
But walk me through your thought here.
- [20:01]
A
I mean, how did you come up with that idea even originally?
- [20:05]
B
Well, the pigeons made it known to me and they're birds can love birds, and they're graceful and smart. And I figure they may be our replacement species if we're not careful. Although, frankly, rats have hands and conceivably opposable thumbs. Someday.
- [20:29]
A
How much have you given to birds or to.
- [20:32]
B
To pigeon rescue and birds? Yeah, I'm guessing about 150k. Particularly for the Wild Bird Fund, Upper west side. Because they're opening up a place in Brooklyn.
- [20:44]
A
Yeah.
- [20:45]
B
And this is God's work, I guess. Even if it is secondary to feeding people in New York. Aside from military families. I really like God's love we deliver.
- [20:58]
A
And yeah, philanthropy seems to be. And I would love for you to correct me if I'm wrong here, but from what I'm hearing, it seems to be the way that you're solving the way you feel about having amassed, let's say, hundreds of millions of dollars. Is that why you're giving money away?
- [21:17]
B
That's not it. It's just that I really. I guess I internalize brother's keeper, sister's keeper, selling what I have and feeding the poor. I guess I internalized that long ago. But when people ask me that question, which people have been asking for 10 years or more, I realize that's my motivation. I'm not trying to prove anything. I know really rich people think how much money they have is keeping score. And if you give away a billion, that affects your place in the leaderboard. I don't think that way. I'm amused to have more money than I need and see no point in having it. My wife and I live far below our means.
- [22:09]
C
Sure.
- [22:10]
B
My idea of luxury is having a walk in shower with grab bars. That also reflects the fact that. That I now understand why really old people want to be able to walk into their shower.
- [22:24]
C
Sure.
- [22:25]
B
And then have a bar to grab onto. And that's not a joke.
- [22:28]
A
Yeah, no, I know. I would say. I like that too. And I'm not quite there yet. So that's nice. So beyond philanthropy, when you think of living below your means and what you're spending personally on, I mean, what are some of those things that you value beyond the walk in shower? I mean, where is personal spending today?
- [22:45]
D
All right, money wise listeners, quick reality check. It's that time of year when you catch yourself thinking, why didn't I start earlier? We knew summer was coming.
- [22:54]
A
It always does.
- [22:55]
D
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- [24:14]
B
Well, basically, whenever I feel like indulging myself in more expensive food, like I like sushi, I'll do that. Although no matter where you go, what you eat in New York, in Manhattan, you're. You're spending it expensively.
- [24:30]
A
Yeah, it's like $100 sushi roll wherever you look.
- [24:33]
B
I don't think I'm capable of doing that. But we moved here five years ago from San Francisco. We still have family ties there and friends, so we kept a place there. So I don't need two homes, but I have them. Just two or. Just two. But people, I guess you'd say, in my position, often have a half dozen homes. No point in that. We don't have a car and I haven't driven in 10 years.
- [25:03]
A
Great. So beyond the obvious spending of groceries and eating, are you spending much money any given month?
- [25:14]
B
It's hard to say because my wife tracks all that, which I really appreciate. I can buy whatever luxuries I want. I get all the books I want. I'm on all the streaming services I want. I do love books and tv. And then now and then I'll buy, let's say, a new charger or cable to make my desktop neater because I do like things tidy. And I'm not exaggerating. I will make things neater. Sometimes I'll get this new stand and my setup will look even cooler. And then I'll usually the no matter what? It is even a chromebook. We have 24 nephews and nieces, so someone will want it.
- [26:02]
A
Yeah. So you know you're buying something for you, but eventually it's something for someone else, too.
- [26:06]
B
Yeah.
- [26:07]
A
Yeah.
- [26:07]
B
Well, kids in school use Chromebooks these days. When I move on to something better, they get something better than they previously had.
- [26:18]
A
Yeah. That's great. So give me one practical example. If, you know, a few months go by, there's something you really want that's, let's call it expensive, relatively one example of something you've bought that's crazy expensive.
- [26:33]
B
From my point of view, this jacket is far more expensive than anything I got. But my wife told me that I needed something that genuinely fit me.
- [26:44]
A
How much did the jacket cost?
- [26:45]
B
I think it was well over a thousand. And it does fit, right? And my friends like it. And it reminds me that I did lose weight using a GLP1 drug, and it works. So it was a wise purchase. I'm wearing new shoes because I had been wearing $50 Skechers and now I'm wearing $80 Sketchers.
- [27:18]
A
That's a huge upgrade. Yes. Craig turned down an $11 billion offer,
- [27:23]
C
and his big purchase this year was upgrading from $50 Sketchers to $80 Sketchers. That is not a bit.
- [27:30]
A
That's his literal answer.
- [27:32]
C
This is why I love Hampton, the
- [27:35]
A
private network for founders.
- [27:36]
C
Half of what gets talked about in Hampton isn't the number. It's what you do once the number
- [27:41]
A
stops changing your Tuesday.
- [27:43]
C
Craig's answer is basically nothing. He gets whatever he wants. And what he wants is a new pair of shoes. Check out joinhampton.com if you want to discuss your money, businesses and lifestyles with other founders who actually get it.
- [27:56]
A
Yeah. Okay. I love that. Yeah. And the jacket looks great. I want to circle back to the Craigslist offer that you turned down.
- [28:06]
D
Okay.
- [28:06]
A
When you got an offer for $11 billion, what did that feel like? And how you told me about a moral dilemma earlier, how did that kind of wrap into that?
- [28:17]
B
The way that story has been retold got it wrong. The deal. And I think the guy at first got it right. When I decided to not to sell it, what the VCs and bankers are offering me amounted to 11 billion. That's our analysis. In retrospect, both this other guy and that's kind of what I guess, too. And that's all guesswork and turning it down. I had a little twinge, but then my values, my moral compass asserted itself. Thinking, having this much money is bullshit.
- [29:01]
D
Wow.
- [29:02]
B
And since Then at one point, we were shop. Well, see, someone I gave equity to wanted to sell it, and we. We worked together to shop it around. Google wanted to buy. Well, not just that equity, but the whole company. And we decided we didn't want to do that. But now, in odd coincidence, I work with some of the same Google people when it comes to scam fighting and better cybersecurity.
- [29:39]
A
So there was a point when you twinged and the moral compass kind of took over. Was there a point at any time in that deal, mechanic, that you thought, $11 billion is a lot and I could actually give away even more?
- [29:56]
B
I wasn't thinking that far ahead. It just didn't feel right from the beginning. And I thought about what I could do with that. Like, I could buy a yacht, but what's the point? I could buy a fancy car. What's the point? And I just didn't get it. And that may tie into my dysfunction as a nerd because I didn't understand the social cues associated with prestige items, so I just didn't bother with that kind of stuff. Now I do get some stuff, which is kind of prestige in a way, I guess. Although, if you look at my watch, it may look cool, but it's far cheaper than you're thinking.
- [30:45]
A
So is mine. $300. It's a.
- [30:47]
B
Actually, that's pretty much the price. Although the band. Well, that was an indulgence. Yeah. And again, kind of, what's the point? I can buy the gadgets I want. I can tell my wife to buy what she wants, but she feels like I do, so she doesn't do enough of it. And life is strange. Yeah. But that is my life. And fortunately, I have a sense of humor, which just doesn't stop. I restrain it. Because something I've learned in multiple contexts is knowing when to stop. When it comes to pizza or talking or comedy.
- [31:32]
A
That's good. I have a problem stopping with pizza as well. I was talking to a friend of mine and I mentioned. I tweeted, I'm. Hey, I'm talking to the founder of Craigslist, and are there any questions you'd like to ask him? Okay. And one of my friends said, all I want to say is, thank you. I met. This is what she said. I met my husband of 17 years on Craigslist. And the question I have is, when you originally built Craigslist, was there any world that you could think of where that type of connection would happen? From the website?
- [32:09]
B
No clue. It's great to hear because I've heard It a lot, including through misconnections and. Yeah, it just feels real good. Oh, to hear that. It reminds me that when the site was very young, maybe five, six, seven years old, going to a dot com party in San Francisco, I talked to some women, and they were telling me they looked at the roommate ads because they figured a guy posting a roommate ad is less likely to lie than for a personal ad.
- [32:47]
A
That's interesting.
- [32:49]
B
And that makes sense to me because a roommate is a intense relationship from the first moment. And you can't. They're not selling your. Your place to them. You're. Yeah, well, you are kind of at the beginning of a relationship where if you have unsav you or your roommate have unsavory habits, you're kind of screwed. Yeah.
- [33:20]
A
That's interesting. Yeah. I mean, when I think of Craigslist, it looks more or less exactly the same as it did 20 years ago. Is that intentional? Did you just always say, hey, don't make it look any more modern than it is right now?
- [33:35]
B
Well, the history is simple. When I made the first site, I'm thinking that I don't know how to do real design, not fancy design, but I know to put something up there that will be fast and simple because I wanted people to look at it and it would be obvious what they do. Yeah. And that's what I did and expanded on that. Jim took it over and kept it simple and fast. And then when we talk with pretty much everyone who uses the site who's not a designer, they say, yes, simple, fast, helps them get through the day, because what they want to do is get a job or a place to live or buy or sell a table. They don't want fancy stuff getting in the way, slowing things down, making it hard to use. So the only people who seem to want it fancier are designers or bcs, probably. Well, maybe, but. And I'm oversimplifying, but the deal is fast and simple and obvious. Those are great design skills. As long as I guess, as well as I guess those reflect my personality. Fast, simple and obvious. That's new material. I need to remember. I wrote it down. I will be doing that.
- [35:03]
A
Great. Have you ever used Facebook Marketplace?
- [35:07]
B
I've looked at it, and it did have such potential when Facebook was much more serious about trust and safety. And the problem, I thought at first, Facebook, LinkedIn, you have to create a profile there. And doing so, can you build a bit of a history and so people can see, oh, that person looks real. But then I've spoken of a Lot of cops and people in the intelligence community and people build what they call legends, backstories in social media so they seem real. The professionals will put years into it. And oh, the deal is we need better mechanisms for identification online without creating ID mechanisms that could be used by bad government to hurt people.
- [36:09]
A
And when you think of security, privacy, some of what you just mentioned, how do you view AI and the way that it will either make a Craigslist site better or change it or evolve. And how are you personally thinking of technology now?
- [36:26]
B
AI is a mixed blessing. It can be used in a number of areas for real great advantage, like for medicine, biochemistry, like protein folding. I'm funding a doctor who arguably saved my life at NYU Langone with a heart ablation. And what he's working on is now training LLMs to detect problems like afib or low ejection fraction from ECGs, which you get. And they're pretty easy to get because they're just putting electrodes on you. They can look at those for problems and catch them early without expensive tests. He's working on stuff that allows somebody to measure the results. Well, to analyze the results of a echo test, a ultrasound test. The LM can look at that and look for problems. And they're in the process of deploying that right now. And I much prefer a nonprofit to control that technology than a. Well, an intensely for profit organization who would milk it. Yeah, so I'm funding that and I'm almost.
- [37:49]
A
Is that through your 501c4 you're funding it or personally?
- [37:53]
B
Well, it's all the same in a way. Well, I fund things either through the C4, a C3 or a donor advice fund. So I take dollars, put them in there. I've locked them up, I can't use them for myself. And that's how I fund all that. The rules are different depending on the mechanism you use. And so far though I haven't done anything special. I've had no special needs for controlling all the funding. Like a C4 allows you to spend money on advocacy. And I don't really do that, not like professional organizations do. The closest I've ever come is like telling a congressman that hey, we really should feed our military families better because they're going hungry. And that's why through Blue Star families I funded a food pantry at I think it's Fort Wadsworth in Staten island which used to be a Coast Guard base. I think they still have stuff there. But things change.
- [39:09]
A
I would love. So moneywise audience is typically founders, CEOs or ultra high net worth individuals. And so people who listen to the show love to hear how people like yourself think about money, where they put their money and then the thoughts they have on what other people should do with it. So if you had a chance to talk to 10, 15, 20 high net worth individuals right now, what would your advice be for them for what they should do with their money?
- [39:39]
B
I guess I'm biased towards the things that I believe in, so I would talk about the stuff I believe in and what I'm doing to help them out. And I guess what I have suggested to people is they find causes that they believe in and then figure out what's reasonable to contribute to them. I do try to remind them of some of the things I've learned, sometimes the hard way, like you don't want to give people a big check all at once. You may want to spread it across a few years contingent on milestones.
- [40:17]
A
And is that for philanthropy or for investing in businesses?
- [40:21]
B
Well, I don't invest in businesses. I guess I would kind of use that attitude for businesses. But this is what I explicitly do now for the nonprofits that I support.
- [40:33]
A
And is that just to help manage their own spend of the giving?
- [40:38]
B
Yes. And also mean it's basically I'm telling them they got to do due diligence on this stuff because there are non profits which are running very plausible sounding scams.
- [40:51]
A
Yes.
- [40:52]
B
And some of them are people hire to do bad things. And there I've. I haven't gotten scammed in that manner, but I've enjoyed the attentions of someone running that kind of a scam. It started off as an attack and then became a fundraising scam. And maybe I'll blow the whistle someday. I mean, I do a lot of things that I wind up believing in. Like recently and we've announced this, but now loudly, I figure, well, the city, New York City, is having budget problems. I live near the New York City police bomb squad. They don't have the funding to get current generation, protective gear, radios. So I'm funding that. Wow. Now I talk to the FBI and others about fighting scams and protecting the country against cyber attacks because our enemies have already infiltrated what they call critical infrastructure like our water supplies and for that matter, electrical supplies and transportation networks. I don't know about you, but if the Chinese army shuts off our water, that would be bad.
- [42:16]
A
Yeah, that would be bad.
- [42:18]
B
Yes. So I'm funding efforts to recover from that.
- [42:22]
A
Okay.
- [42:23]
B
Wow.
- [42:24]
A
And are these all just kind of happenstance? You serendipitously fall into, I care about this. Let me see if someone's doing something about it, and if they are, let me give them money. Or what's the due diligence process that
- [42:35]
B
kind of is it that somehow, I guess I do a lot of reading, I do a lot of listening, and I hear things where no one's paying attention.
- [42:47]
A
Yeah. That's so interesting. I want to ask you about what community looks like moving forward. Craigslist was started really to make connections, a community connection. But now, 25, let's say 30 years really later, people, I think, are using the Internet to actually isolate. And while connections still do happen, people feel more isolated than they ever have.
- [43:15]
B
I used to think I might know, but AI has changed everything. And so I don't really predict much of that. I do know that I crave, oh, community. I have more of a social appetite. I need people more than I thought. Despite being a nerd, I'm still figuring that out. I mean, I. And I'm bad at it because I can't read social cues. And so I just have to guess things and frequently commit a faux pas. I mean, I'll just embarrass myself. No fun. But though people are willing to give me a break, like I'm somewhat face blind, I find it difficult to recognize people until I've met them like 10 times. And people are willing to put up with that, particularly since I talk about it and I see the comedy in there.
- [44:15]
A
Yeah. What you're doing now more than when you were building Craigslist,
- [44:21]
B
it's mixed. And the amount of work. Well, the work I do now is more intense because I'm making tough decisions frequently.
- [44:29]
A
And you're influencing very specific and emotional, in many cases, causes.
- [44:35]
B
Yes. And so the rewards are, I guess, louder and more immediate, which is nice. It is gratifying. But then after hearing that, then it's back to work. I do need to explain to people better that I am a nerd. And we don't take flattery well, because in some circles, some institutional bureaucratic circles, flattery is routine. And I need to find a nice way, a diplomatic way to let them know. Flattery has the opposite effect sometimes in.
- [45:14]
A
In what way? Tell me more.
- [45:15]
B
It's just that flattery may. Flattery may increase skepticism.
- [45:24]
A
Like they're flattering me to get something. There's an ulterior motive.
- [45:28]
B
Yes. Or they'll be using flattery as a substitute for saying something substantive and working on the problem.
- [45:36]
A
Yeah, that makes sense.
- [45:38]
B
Yeah.
- [45:39]
A
You also mentioned your father Passed away when you were young, did he have similar values to the ones that you had growing up in Sunday school?
- [45:48]
B
I have no idea. He died and we never were close. We never spoke much. And all I recall is that he lived long enough to see me get bar mitzvahed and to start dating. And that my intuition tells me that meant a lot to him.
- [46:09]
A
Yeah. Have you ever thought about what he might think about Craigslist and the life that you live now?
- [46:17]
B
I think he would enjoy my hit, my success, my mom did. And I would be sharing it and indulging them. And I did indulge my mom in the last years of her life.
- [46:31]
A
In what ways?
- [46:32]
B
Well, the biggest way she wanted to be to get assisted living. So we got the nicest possible assisted living in her area. And she was happier there than she had been for decades because she would hang out in the common areas and make new friends. And she was good in that. In a way. In the. In a way that I'm not. So that was pretty good. And I arranged also. Well, we found the best one not far from where my brother lives. Lived. And his wife was very good at showing up.
- [47:14]
A
Yeah. You had mentioned before our conversation something about building an LLM that really continues to be your philanthropic arm when you're gone. Can you tell me more about that?
- [47:29]
B
The deal is I could train a system to know how I would respond in a lot of circumstances. One reason for doing this is because I could make sure it was giving accurate information. Again, as a nerd, I harp on that. The other thing is I may not last long enough to perform due diligence on my contributions. Well, a really, really well trained LLM could help make those decisions. It might help the people I've already engaged. And my problem is that a smart enough system could think that my continued existence was a distraction, an annoyance, and interference in its decision making. So maybe it would just decide that it should dispose of me.
- [48:30]
A
So, like Skynet type stuff.
- [48:32]
B
Exactly. Skynet or Matrix. And my problem is I read too much science fiction.
- [48:39]
A
Matrix is one of my favorite shows or trilogies of all time.
- [48:42]
B
Yeah, the deal is, yeah, a smartphone may just put. Put me into a battery nodule and that might suffice.
- [48:53]
A
Yeah, that's funny. I think what you've built is so fascinating. And it was accidental, kind of. Obviously Craigslist wasn't accidental, but it became something you were never really planning for
- [49:07]
B
it to become Craigslist from my point of view, during my time was a happy accident. I did something simple, listened to People committed, followed through, and then I was repeating that cycle continuously. Jim did the same thing when he took over, so the Jim part is much more methodical and organized. My part, I listened to people and reacted. And I didn't have that many original ideas except just to start and then to realize that I could automate a lot of things. Like during the first years, when I found a task that was taking me too much time, I would figure out how to automate it. The whole thing or maybe apart. And what might take an hour a day would take five to ten minutes.
- [50:02]
A
Yeah, I think that's incredible. Happy accidents that give you the ability to give away hundreds of millions of dollars is incredible, especially for causes you care deeply about.
- [50:12]
C
In this episode, Craig keeps calling Craigslist an accident, but what he did with the money after wasn't. He's been intentionally generous and philanthropic for decades because of his own core values and moral compass. Craigslist just made all that possible. Every conversation on the show echoes similar conversations that happen inside Hampton. Those are private and these, luckily, are public. If you're building something that's doing $3 million or more in revenue or you've exited for $10 million or more, you need to be in Hampton.
- [50:41]
A
Go learn more@joinhampton.com yeah, my situation and
- [50:47]
B
the decisions I made, I'm guessing, are unique in American business. Other people have done great stuff along those lines. Jimmy Wales Wikipedia, that's bigger. And we want to give credit there to Isaac Asimov, who wrote the foundation novels and the Encyclopedia Britannica. So he was a co founder even though he didn't ever know it, and that was a big thing. And Linus Tovalds was the father of Linux, which runs a big chunk of OR technology, and he deserves a lot of credit publicly that he hasn't gotten. And I should do something about that someday, something loud to give him that credit. And I guess I'll. Maybe sometime when I'm in the mood, I'll figure that out.
- [51:46]
A
Are those some of your inspirations?
- [51:49]
B
Yes. Well, what Jimmy and Linus have done is genuinely heroic, and I know enough about the history of these things that that's an accurate characterization. I'm just including Isaac Asimov. Well, since I've been reading his stuff for over 60 years and he greatly influenced me, for example, regarding AI and thinking of his science fiction in the great sweep of history.
- [52:22]
A
He was way before his time. I'm a huge Isaac Asimov fan. Irobot is just an insane, like almost peek into the not so distant future now but when it was written as a book before the movie, I mean, it's really like, can't believe this.
- [52:36]
B
I'm looking forward to William Gibson's Neuromancer to be made into tv.
- [52:42]
A
Yeah, me too. Well, great, Craig, I appreciate you coming on Money Watch today. This has been a fascinating episode, and I think what I'm taking away from it is to really think more deeply about causes I care about and where money can go a really long way if given properly.
- [52:59]
B
Well, I'll continue doing what I do, sticking my neck out now and then, but I'll be very cognizant of my limitations. You've seen recently that I've outsourced my social skills to Sesame Street's countervon count. And that way I can focus on my core expertise, which is social awkwardness. And the deal is, the count has charisma and personality far superior to mine.
- [53:30]
A
Is there anything you want the listeners to know about you that you haven't shared yet?
- [53:38]
B
People should realize that, like, the Batman would say, I'm not the nerd you want, I don't think, but I'm the nerd you got.
- [53:50]
A
I love it. You call yourself a nerd so much. Is there something specific about you that says I'm a nerd, or is that just kind of your brand?
- [53:57]
B
It's marginal social skills. And really, back then, I wore a plastic pocket protector, thick black glasses taped together, and Dr. Seuss, I like to feel, in 1950, reinvented the term nerd in one of his books to describe me. At the very end of stock photos of myself on my site, I've inserted a picture of the nerd from if I Ran the Zoo.
- [54:31]
A
That's awesome. I think nerd is almost like a term of endearment. Now, I know at one point it wasn't, but I love, you know, you walk into a room, hey, hey, bunch of nerds. You know, it's like term of endearment in some cases, but I love that. Love that for you.
- [54:45]
B
I have very mixed feelings about that, so I've earned it the most difficult way possible.
- [54:52]
A
Yeah, you are. You are certifiable nerd. Everyone else doesn't get to have that title, right?
- [54:57]
B
I'm certifiable.
- [54:58]
A
All right, Craig, this has been awesome. Thank you so much for agreeing to come on the show. I appreciate you.
- [55:05]
B
My pleasure. Thanks.
- [55:06]
A
Thank you.