#52 - Erik Torenberg: Future of Media, Institutions, and Risk

We had this thought that, hey, maybe people would only pay for stuff that they see as valuable, but it turns out people like subscribing to something that says that the other side is evil. They get value from the validation that they're a good person too. I don't know if there is an ideal business model for media that keeps things honest, but it just turns out that reality is messy. Life is messy. Making sense of things is messy. But if you allow for that mess, You're able to have sort of the evolutionary process at work. Consensus can emerge among all the different sort of versions of reality, and the ideas that are most fit will win out.

That is Erik Torenberg. Previously, he was founder and chairman of On Deck, which started as a dinner series and became a Stanford for the internet, raising $70 million from the likes of Tiger Global and Founders Fund and creating countless outstanding companies along the way. He was also on the founding team at Product Hunt. Erik started angel investing in 2014 and later formalized those efforts by starting Village Global, a venture fund built like a network with $500 million under management and whose portfolio has gone on to raise $5 billion in follow-on capital. Beyond how thoughtful he is, what I've always admired about Erik is his innate ability as a dual-threat CEO. He's someone who can invest and operate at the highest levels and even at the same time, which makes him difficult to put in a box.

In the East Coast, if you're covering something and you have an investment in it, there's a conflict of interest. But on the West Coast, if you don't have an investment in it, you don't have skin in the game. And so it's this idea that in order to fully appreciate something, you have to be a player or else you're just talking from the cheap seats.

In recent years, we've seen a renaissance in media with user-generated content networks like Twitter, Instagram, and TikTok. But today we're seeing another transformation driven by AI as the barrier for creation drops even lower. But as things get more democratized, the world's about to get a lot noisier.

Tech was sustaining and then it was disruptive. Every time there's a new disruptive communication technology, chaos ensues. You give everyone a voice, you know, don't be surprised if some people use the voice to say, fuck you. It's become much easier to build things and get things off the ground and a lot harder to get distribution. In the way that I had a technical co-founder to build it, maybe I'll have an audience co-founder to, to get all the customers.

Today, as a result, Erik's charting a very specific path in media with a new company, Turpentine.

The unique insight here is that in a world where content itself is commoditized, what matters isn't so much how much is being said and how many people are listening, but Who is saying it and who is listening? Turpentine is a media network of experts that serve niche, high-value audiences and critically get knowledge out of those experts' heads and into the world.

People have always wanted to hear from individuals. They just didn't have the ability to, because after all, institutions are just collections of people. And what you get when you hear from the people, as opposed to this faceless institution, is you get accountability. You get transparency. It's meant to take a lot of the conversations that happen— turpentine talks— that happen among practitioners and bring them to a wider audience. And we're aiming to take information that's in people's heads around company products and people and bring them to a wider audience that can make better decisions at their job as a result of it.

Erik's path is also one of tripling down on strengths. Early on, he discovered his superpower in community building, and be it in company building, investing, or fundraising, It's something he's leaned into in some way every step of his career, including over 1,000 interviews of his own.

I think more people should be asking what is easy for them to do that looks hard to other people. Great communities are about value and values. One thing that impressed me about Bill Gates in particular is how obsessed he is, how curious he is, even at his age. And he knew about different industries like agtech, longevity, certain areas of healthcare almost better than the founders did. And he's just insatiable. He just looks at every interaction, how can I learn more?

We spoke about the future of media, creating more startups, how to build community, probabilistic versus deterministic mindsets, the hypocrisy of elites, and our relationship with risk.

It seems like on an individual level and on a macro level, We're pretty bad at understanding risk. Marc Andreessen started Ning. It was like a social network for dogs or something. It was this kind of crazy idea. He ran it for a number of years. Reid Hoffman started a dating site. You're known for your biggest win. You're not known for your losses.

This is the Levasseur Podcast.

We choose to go to the moon. We deliver right to the desktop.

We're going to reinvent the phone.

Well, thanks and again, bye.

I want to start with a quote from Picasso that's been kind of a slogan for Turpentine, your media company. It goes, when art critics get together, they talk about form and structure and meaning. When artists get together, they talk about where you can buy cheap turpentine. To sort of stretch an analogy here and liken artists to entrepreneurs and art critics to investors, what do you think is the secret to being able to play in both worlds, that of the artist, that of the art critic, of people who You sort of, you know, sit at the intersection. You're one of kind of a handful who can do really well at both at scale. And the narrative is very different personality types tend to be better at founding versus investing. You've kind of been able to do both. Why do you think that is?

Yeah, it's interesting. I was speaking to Balaji about this a few years ago, and he gave me this sort of framing that I think is interesting. He says, in the East Coast, if you're covering something, and you have an investment in it, there's a conflict of interest. But on the West Coast, he's meaning this more metaphorically.

Yeah.

If you don't have an investment in it and you're talking about why something's great in it, great, you don't have skin in the game. And so it's this idea that in order to fully appreciate something, to be fully able to describe something, you have to be a player, you have to be involved, you have to be a stakeholder, or else you're just talking from the cheap seats. And so I think that's something people appreciate in tech is this sort of craftsman-like approach. And one of the reasons why we call the company Turpentine Media Company is because most other media companies have had this separation. They're by design not players, and they take pride in that. They're players in a different way. They take pride in sort of this detachment so that they feel that they can adequately cover without any bias. And I appreciate there's a certain sentiment to that, but there's a new kind of media, almost like a trade media, that people like Lenny Rachitsky, people like Packy McCormick, people like Harry Stebbings are engaging in, which is helping people get better at their job. And in order to help people get better at their job, you have to have done the job or do the job yourself. And so to play both, you have to care enough to want to be a player, to want to be good, and care enough to want to explain to other people how also to be good, how also the world works, how also to rise up. And so that's how I think about the intersection.

For the last number of years, and it's funny you mentioned some of these creators, there's been a much more apparent effort on the part of a lot of people in tech, and now much more outside of that, to sort of fight back, quote unquote, against legacy media institutions by going direct, right? By building out distribution solo. This is kind of what you're doing at Turpentine, which we'll get into, is sort of an example of this. But as a premise, it seems like people want to hear from individuals more than they want to hear from institutions. Gallup— this is something I think you shared— has been running polls on trust across a wide variety of American institutions since the 1970s. So federal and city governments, churches, public schools, the military, the press, lots of other stuff. They found that institutional trust peaked in the '60s, then declined rapidly in the following decades. And on a national level, almost every major US institution followed this pattern over the last 50 years. It seems like we take it for granted, right? It's only recently that we've really had the means to circumvent legacy media in favor of going direct, you know, sort of at scale and seeing individuals like wield audiences the size of massive institutions. But the deeper question of trust still remains. What do you think happened? Where did we go wrong?

Well, first off, I think people have always wanted to hear from individuals. They just didn't have the ability. There wasn't Twitter back in the day. Because after all, institutions are just collections of people. And what you get when you hear from the people, as opposed to this faceless institution, is you get accountability, you get transparency, you know who made the decision. And then you could ask them, how did you make that decision? Why did you make that decision? Do I agree with it, with that decision? And one of the reasons why we've had institutional distrust is because there's been a lack of accountability. There's been this sort of ongoing bureaucracy, bureaucratization of a lot of these organizations where you don't know who's making the decisions. You don't know how the decisions are being made. You don't know— you are able to see that they don't represent what the people want, depending on the institution, depending on the people. And one of the reasons why there's distrust is because the institutions across the board are performing less well. And that's for a bunch of reasons. When institutions don't have market incentives, i.e., they can't fail, they don't have competition, there's no need for them to innovate, there's no need for them to perform. They don't get the best people anymore, because the best people want to work in environments where they can rise up, where they can make a lot of money, where they can sort of be rewarded by the market. So these institutions become sclerotic and stale over time. But also because what the internet and social media has done is it's made the world a lot more transparent by force. They used to be able to hide behind sort of 3 cable channels or whatever, but now we get an insight into exactly what's going on, or closer than we had. And we see, hey, these people, they're incompetent. And so the combination of the shining a light on what's happening, And the combination of these institutions just becoming curdled, sclerotic over time, because they don't have to innovate, they don't have to reform, they don't competition, has led to declining trust.

The Economist a while back, this is a nice segue, coined this term called the techlash, right? That's supposed to describe this rising hostility towards tech. And you mentioned that this is, you write about this, that it's always kind of been an odd phenomenon, because the average American really likes tech, actually. They use Airbnb or DoorDash or Uber or Facebook or Amazon. It's all just really improving their life across the board. Of course, most media sentiment on tech does not necessarily follow that, right? It's gone pretty sour over the last decade. But you argue, like I said, most people aren't really worried about the latest battle between taxis and Uber or whatever else. They're just too busy enjoying how tech is improving their lives. And it's actually supported by the Gallup poll, right? Tech ranks highly among industries with net positive sentiment scores. So what actually happened here? Like, why did media go sour on tech?

Yeah. And just to amplify your point, nowhere did we see the sort of dissonance between what the critics thought and what the public thought than during COVID where the services that you mentioned, DoorDash, Amazon, others, saved us. They were what we relied on to function. So people by and away, by and large, love tech, certainly more than these other institutions that we were sort of alluding to previously, certain government institutions, certain media institutions, certain education institutions have a much lower score. And what happened is a few things. Basically, tech used to be an enabler of these institutions, it used to make them stronger. If you look at the early 2000s, what happened with the Arab Spring, Right? Twitter was a force for democracy in sort of the Middle East. Actually, it's unclear if that was a good thing, or maybe it's clear that it actually wasn't a great thing for stability in the Middle East. But at the time, that was widely celebrated. Barack Obama was the social media president. So social media really helped uplift the establishment at the time. It made them stronger. But what giveth can taketh away.

Yeah.

And it just so happened that Trump also could use social media And so that's kind of the TLDR is Trump. But there's actually a lot more, which is tech first was a sustaining technology for certain, and a certain elite class of institutions and people made them stronger. But then it started to disrupt them in a bunch of different ways. A lot of top people at some of these institutions went to work for Facebook and Google and, you know, and sort of Silicon Valley institutions. And then Facebook and Google started to compete with the New York Times, for example, for ad dollars? How can— and these other institutions, how can these institutions cover Facebook or Google in a neutral way if they are taking away business from them? If they are competing, they have direct business relationships, Facebook will pay them a lot of money. And so what happened is these institutions, the tech was sustaining, and then it was disruptive. And anytime there's a you know, some disruptive technology, it reorients sort of the status hierarchy. And some people rise in status and some people fall in status. And the people who fell in status got really mad. And that was a lot of the media class. And what happened in 2016, post-2016, is tech kind of just took it. They apologized. They thought that they'd done something wrong. This Cambridge Analytica scandal got blown up to be this massive thing that maybe swayed the election. It turned out— It's not as bad. It was overblown, not as bad as people thought. But there was a real apologetic tone in Silicon Valley, which at the time was 99% Democrat, basically, and still remains far and away a Democrat-affiliated political class. But what happened then is this media class went on to fire some critical founders, right? Uber, Away, there were just all these hit pieces, the media became negative. Some people say it's because of a sort of a bias where maybe they were competing, or maybe they just didn't like what was happening. But maybe there was an audience that really liked it. So an audience outside of tech that ate up this sort of anti-tech sentiment. I don't think it was a huge audience, which is why they didn't crush it. Numbers-wise, the white numbers continue to fall, but there seems to be some audience for anti-tech sentiment. But at the same time, it never really captured the nation. The polls are always, you know, people like Amazon, people like Facebook, people like Google. What I find really interesting is that in the last few years, tech has regained a sort of political consciousness or consciousness as an industry that, hey, we are good for the world. Actually, we shouldn't be beholden to what the media says. You saw Brian Armstrong fight back against the New York Times. You see OpenAI most recently say, hey, the New York Times is wrong. New York Times is suing OpenAI. And you're just seeing this sort of go direct saying, hey, you don't have more moral authority than me. You don't get to hold me accountable. Who are you to hold me accountable? Who holds you accountable? You have your own warped incentives just like us. A journalist is a person that posts on Twitter. If they're more accurate, they're more accurate. But just because they call themselves a journalist doesn't make them more accurate. They're not a priest class. A lot of journalists are more accurate, and that's great. Not all of them are.

Yeah.

We should Just reward people on their level of accuracy, not on the sort of the label that they claim for themselves. And so this is what is behind some of the excitement of EAAC, right? It's sort of a philosophy or a tribe that says, hey, tech is good. And that seems to some people like substanceless because it's like so obvious. But for the last 10 years, tech did not have the moral sort of confidence to say, We are good. And just because you say we caused this bad thing, or the thing that you think is bad, we don't have to agree with you. And that's why you see Zuck sort of getting— Elon obviously is the most extreme version of someone who's willing to stand up for himself, fight right back. But Zuck, the other tech CEOs, tech as a class has just gained a lot more confidence and willing to stand up for itself.

Yeah. So with that as a backdrop, And this kind of all brings us to your latest venture. I'll use a quote from the announcement, which is, Turpentine is a network of podcasts, newsletters, and more covering tech, business, and culture from the perspective of industry insiders and experts. But actually, that's like super one-dimensional, and there's a lot more to it. So let's set the stage for a moment. What is Turpentine?

Turpentine is a tech media company that is trying to get information that's in people's heads that is really valuable about company building, about certain products, certain companies, certain markets, trends, and bring it to the internet, bring it to the world. It's meant to take a lot of the conversations that happen, Turpentine Talks, that happen among practitioners, and bring them to a wider audience to help people do better at their job. And we've started with just podcasts. I think podcasts are underrated for a lot of reasons. We've talked about some, and we could talk about more, but we're aiming to expand to all platforms. And we're aiming to take information that's in people's heads around company, products, and people that would help guide investment decisions, purchasing decisions, and hiring or joining decisions, and bring them to a wider audience that can make better decisions at their job as a result of it.

All right, let's go back like a number of years. As a kid, you grew up listening to tons of interview shows. Charlie Rose, Terry Gross, Howard Stern, Marc Maron, You're obsessed, right? And to such a degree that at 19 years old, you wrote a review of your own talk show that you hadn't even started yet.

Yes.

You write, Erik Torenberg has the most interesting intellectual and personal interview show on the air right now. For almost 30 years, Erik's show has been a salon for extended, thoughtful, and honest conversation about culture, business, technology, politics, literature, entertainment, lifestyle, education, and any other topic that Erik wishes to explore. He's interviewed everyone from Bill Gates to David Brooks to Lil Dicky. He sometimes even gets random people to freestyle, including Margaret Thatcher, Malcolm Gladwell, and the Asian kid from School of Rock. But here we are, like, a decade later, and you're not even that far off, right? Like, you've done what, maybe 1,000? How many interviews do you think you've done?

Yeah, about 1,000.

1,000 interviews with some really heavy hitters, right? Not to mention. The sort of larger question here is, having spoken to so many really brilliant people, what have you found to be the most surprising thing or things that are common across many of them?

Well, we did have Bill Gates on the Village Global Podcast, but I've not yet reached the Asian kid from School of Rock.

School of Rock.

So at some point, you know, he's a man now. I should get in touch with him. It's interesting. One thing that impressed me about Bill Gates in particular is how obsessed he is, how curious he is, even at his age. We sat him down with a few portfolio companies, And he knew about different industries, like agtech, longevity, you know, certain areas of healthcare, almost better than the founders did. And he's just insatiable. He was asking a lot of questions. He just looks at every interaction, how can I learn more? And I find it really interesting when the people I bring on for an interview, I'm asking them questions, but then they ask me questions.

Yeah.

So they're looking at every interaction as, what can I learn? And so they're just relentless, insatiable learners. And they're often pretty modest too. They're modest about what they do know, what they don't know. And just that, that just gives them an edge, 'cause every interaction, they're just compounding their knowledge transfer.

All right, let's take it back even further. The year's 1440. The printing press is invented. Suddenly there's a new era of information distribution. Thoughts and ideas can spread faster than word of mouth for the first time in history, right? very first form of broadcast media, even though it's sort of weird to think of it in that way. And eventually you get newspapers, you get TV, you get radio, which still sort of act as, like, centralized media aggregators, right? Like, everyone reads the same papers, everyone watches the same shows, everyone listens to the same stations. There's basically a single source of truth. And then the internet makes everything peer-to-peer, and we're not even sure we're seeing the same stuff anymore. People are sort of living in their own personalized worlds. You have this interesting, like, sort of cut, that reality is up for grabs, because, great quote here, while people have always disagreed, at least we had the same coordinates by which we could disagree. Now we're looking at different maps entirely. The question is basically this: where does media go from here? Like, do we get more and more isolated? What do you think?

Yeah, when the printing press comes out and people can start writing and reading sort of at scale, people start writing things like, hey, the church is a bunch of bullshit. And similarly, when the, when, you know, you give everyone a voice, you know, don't be surprised if some people use the voice to say, fuck you.

Yeah.

To say, hey, this doesn't work. We now have visibility into some things that are kind of messed up. And so the— and like we said, you know, COVID, like imagine sort of World War I or World War II with Twitter. Like imagine, you know, historical events with Twitter in terms of how lit it would be or how chaotic it would be.

Yeah.

And The reality entrepreneur idea is this idea that instead of 3 cable channels, you now have this entire ecosystem of people competing to try to give you a version of reality that makes sense to you. And it's all these niche versions of it, from tapping into where you're from, to your race, to your gender, to the way that your brain works, to your set of cultural references. And so there's been an explosion across everything. And what typically happens, of course, with everything on the internet, there's a barbell, which there are some, you know, the hits are bigger than ever, the Taylor Swifts for everything. And then there's just this long tail of people who are able to have their voice, who are able to create sort of like a self-sustaining economy around their value set. And so you ask me, what is the future? I don't see why that trend would stop. I see the sort of big winners continuing to get big in whatever, like, field or industry that it is. And that's just kind of how the internet reorients economies from whether it's music, whether it's video games, whether it's religion, whether it's whatever it is. The big— the hits get bigger because they become more accessible to everybody, a more common denominator. And the long tail just gets longer, because there are people who are going to be constantly seeking out this thing that is customized exactly for them. And so, what is that? And I wouldn't be surprised if countries go that way too, like, China gets bigger and bigger, US gets bigger and bigger. But then we have the long tail, just all these new network states in the future. So, there's just way more countries. And so, I think what that leads us to a lot more tribalism, a lot more, you know, people finding their group and self-segmenting, right? Because even in the US, we have people who can't agree on basic things, basic facts anymore. People say it's more polarized than ever. And sometimes polarization is good, right? Like, North Korea could use a little bit more polarization.

Yeah.

Polarization is, you know, shows that different worldviews can be compatible with each other, they can coexist even if it's challenging. And maybe that's why filter bubbles are good, because for people who have incompatible worldviews, they should stick to each other. Why would they spend time with people who have incompatible worldviews? And the internet and sort of modern society today enables people to reorient among people who share their value set. And so I see that only increasingly happen.

Gotcha. All right. I mean, before any of this, we were just talking about the sort of tech versus media kind of clash. We were talking about sort of this changing role of what actually constitutes a journalist. When we still had, you know, capital J journalists all over the place, they had a more reliable source of revenue, right? In many ways, they could do deeper, more thorough journalistic work. And the business model shift to advertising meant they needed to produce things that, like, kept you watching, not necessarily things that were straightforwardly true or deeply investigated. So I think begs the question, was journalism better, like pre-internet, do you think?

Yeah, it's hard to run the counterfactual because there wasn't the same scrutiny. There wasn't the same visibility into, you know, who holds journalism accountable. Actually, Twitter holds journalism accountable, where everyone can be a journalist, or everyone can look at the same data that maybe they're looking at or can respond, and you can see the the response before maybe was the letters to the editor, and maybe there were tons of people critiquing, but the world wouldn't see that. And so if you were sending a letter to the editor, you were like, hey, maybe I'm alone in having this concern. But if you see thousands of people also being like, this is bullshit, you're empowered to be like, hey, let's organize here and really make something happen.

Yeah.

And so I think it's unclear. I don't see a reason why it would've been more accurate back then, because You mentioned advertising leading to people trying to appeal to the most common denominator. And I see why that's bad in some ways that you see like the BuzzFeed cat stuff and other stuff that just kind of dumb or lowest common denominator. That said, at least you had to appeal to a wide set.

Yeah.

Whereas with subscription, you know, we talk about people's biases just being confirmed. That's all you need to do, right? We had this thought that, hey, maybe people would only pay for stuff that they see as valuable. But it turns out people like subscribing to something that says that the other side is evil. Like, they get value from the validation that they're a good person too. And so that's why you see the New York Times subscription site crushing it. But that's also why you see The Daily Wire, or, you know, and not to equate the two necessarily, but the left and the right—

Yeah.

Both have subscription sites that say that the other side is is bad.

Yeah.

And people, guess what? People like to pay for that. So I don't know if there is an ideal business model for media that keeps things honest. I think social media keeps things honest, and it also keeps itself honest, because people are lying on each other, or, you know, fighting with each other. But it just turns out that reality is messy. Life is messy. Making sense of things is messy. But if you Allow for that mess, you're able to have sort of the evolutionary process at work, which is the, you know, consensus can emerge among all the different sort of versions of reality, and people can pick and choose, and the best ideas win out, or at least the most popular ideas certainly win out, and sometimes they're the best, sometimes they're not. But if they're not, they won't— or at least the ideas that are most fit will win out.

Mm-hmm.

And so I think we're likely to have a world that's more accurate today, even if it's more messy, than a world where all the noise is hidden. But I think there's likely to be much less signal or accuracy too.

Makes sense. To start thinking about the future in this context, I'm curious your thoughts on the future of creator monetization, right? Currently, it's sort of a question of whether you can get people onto like Patreon or some other platform. Where does monetization go from here, right? Like, what can you build on top of a creator or a network's audience? I'm sure you've a lot of really great perspective here 'cause it's literally what you're doing at Herpentine.

Yeah, I think what hasn't been figured out yet is price discrimination in the creator side. So if you think about your favorite artist or your favorite writer, think about someone who's really changed your life, and then think about a favorite musician, think about how much you've paid them. My guess is it's like $10, $100. But how much should we pay them? We should probably pay them thousands of dollars, maybe more. And so what the internet does is it tends to align value creation and value capture. And right now we're still at the earliest innings of that. What we've done is we've created mechanisms by which creators can monetize directly from their fans. without middlemen. So instead of having to go work at the New York Times, you can go work, you can have a Substack. You know, Matt Yglesias was working at Vox, and he was making some sort of salary, and now he works at Substack and gets a multiple on that salary because that's what he was worth before, but the economics just weren't totally efficient.

Yeah.

Now he's made them much more efficient. In that, because people were subscribing for Vox in this case, for Matt Yglesias, for at least some of them. And now they can subscribe directly to him and he can get a greater fraction of that value, a more accurate fraction of that value. But would they— what we still— and we've done that in different industries too. But we haven't done it in many, like music still, you know, record labels host a majority. We were talking about athletes still, you know, the NBA itself makes almost as much money as the athletes. It's my belief that whoever generates the demand will capture the value. And so whoever is the star, whether it's the athlete, the musician, the entrepreneur, the creator, there's usually some producer or some middleman. But the internet erodes sort of the monopoly that the middleman has, or it serves as its own middleman from this creator and this audience, this person who makes a thing and a person who buys a thing. And the internet, and then there's all these different layers in between, but the internet helps get the creator and the customer closer together. So the creator can create, can derive a bigger percentage of that dollar, or what the customer's paying. But then also, I think the next opportunity is for creators to price discriminate accordingly, where let's say I sort of like this artist, you live for this artist, we're paying the same amount. But they can offer new products, new experiences. And we saw this with NFTs, we see this with different sort of iterations on this model, where you as a fan can show, can align what the artist is worth to you with the artist and maybe get a richer experience because of it. And then there's this other experience that is going to be enabled at some point too, which is because you love this artist, you want to get upside in this artist. You want to be not just a fan, but also a participant in their growth. You discover them early and you're like, wow, this person's going to be really big.

Yeah.

I want to support them, but I also want to benefit from them. And so that will enable even more money going from your wallet to the creator. And so when we talk about the future of creator monetization, I think about new ways of price discrimination.

Yeah.

And ways of audience to get economic upside in the creator. And I'll give one more example, which is TEGIS. It's a really interesting business. And it's what Turpentine is trying to do too. It's trying to use media as a sort of almost a freemium model or a way to generate all of this data that then we can price discriminate accordingly. So if you look at TEGIS, TEGIS is an expert network, like a GLG, or one of these other alpha sites, etc., that records the calls. So right now, they have, I think, something like 70,000 transcripts of calls that they've recorded, that if you want to go, if you're an investor, and you want to diligence a company or trend or get deeper, or do customer reference, you can do a call yourself, or you can read the transcripts. And reading the transcripts is a lot more efficient. But if the transcripts, and it costs like $25K per seat or something very high, if they were released to the public, it's not like they would have, they would go viral. No one would listen, watch them basically. They would have very few views, fewer views than your and I podcast. But the people who do watch them really get a lot of value out of them.

Mm-hmm.

And so they're price discriminating amazingly. And I was, I had this insight while I was reading a Forbes article. It was a piece on Stability AI. And the journalist, I think, spoke to like 30 sources for this interview. And then I looked at TIGAS and I was like, hey, how many interviews do they have on Stability AI? And they had very few. So I was like, journalist has the best qualitative dataset on Stability AI in the world. That's just maybe ex-employees, investors, they really understand the company. But the way that they're monetizing is in a flat way, just on ad dollars on the article. Where they should be monetizing, they should be charging a lot of money for these investors who want to determine whether or not to put tens or hundreds of millions of dollars into Stability AI. And I'm not picking on Stability AI, just a random example of a company. So the journalists are collecting this data, but they're not price discriminating if they were optimizing for money. Now, because journalists are journalists, they have values other than profit maximization. And that's great. They should continue to go do that. But from a purely creator monetization standpoint, that's just another example of either selling to the wrong customer or selling at the wrong price point. And that's what we're excited to do.

Fascinating. Okay, this next one's a little funky, so bear with me. You wrote this piece last year called Does Evolution Have a Direction? comparing the arguments of Richard Dawkins and Robert Wright, these 2 pretty prominent academics in their own right. Dawkins argued that evolution reveals a universe without design, right? He says that natural selection is the only mechanism of evolution with no, like, particular direction. direction or anything beyond fitness to one's environment. Robert Wright, on the other hand, disagrees. He argues that evolution does have a purpose or direction, which is increasing non-zero-sumness, which is basically to say growing interdependence of organisms and societies where cooperation dominates rather than competition. This kind of got me thinking, does media have a direction? Like, if we take it to the furthest extreme, whether or not this is societally optimal, it's probably complete and total personalization. What do you think?

That's a really interesting question. While I think about it, say more about what you think. Is that where you think it's going?

I think probably, and I think it brings up this really interesting point of, like, what is good in technology? Because, like, I had this conversation with, or like a similar question with Anthony Pompliano not too long ago, and the point was basically that, like, the quote-unquote best product you could be building from the point of point of perspective of TikTok is, like, not necessarily what is societally optimal, right? Like, anybody is going to pick the sort of, like, terrible, like, wireheading thing that, like, just puts out as much dopamine as possible over the thing that's teaching you about, like, science experiments or whatever.

Yeah.

So there's, like, an interesting dynamic there where, like, what is good, quote unquote, is not necessarily aligned across, like, a product versus the person using it.

Yeah.

Anyway.

It inspires a few points. So first, Robert Wright is just a fascinating person and thinker. He's inspired me in a number of ways. One is that he started a podcast network, Big Think, like a decade, maybe 15 years ago, that I've been an avid listener of and inspired me to create one. Originally, I created it as a passion project, and then I figured out, oh, there's actually a really big business behind it, or there could be. But Also, because he wrote this book called Nonzero, which is sort of an intellectual historical explanation for why non-zero-sum thinking or positive-sum thinking has emerged. He has a biological explanation for it and a cultural explanation for it. And one of these LDRs is basically, are the fates of people become, as technology advances, become increasingly interdependent and intertwined. And so many years ago, you just lived in your tribe, all you cared about is your tribe. And so what was happening on the other side of the world literally did not affect you, didn't matter. And so you didn't, you didn't have a relationship with them. And also, if you were exposed to the neighboring tribe, and this is like, let's say, pre-technology, the world is actually a little bit zero-sum. Right? Because if they get food, that means, you know, that's your food. Like, there's a world of limited resources.

Yeah.

In a world of constant productivity, where the, you know, world is economically interlinked, where we have nuclear bombs, where, you know, we have impact to the environment, what happens in the other world, other side of the world, actually does impact us. And so we create these technologies to reflect that. And so Twitter, in some ways, is this global village. It's taking sort of the— what's happened in the tribe and expanding it globally. And that's why you see positive things that emerge from that. You also see sort of the negative tribal things that emerge from that too. But one thing he says, and one thing Martin Gurri writes about in his book, Revolt in the Public, is that every time there's a new disruptive communication technology, Whether it's the printing press, whether it's social media, there is chaos ensues, right? We had the Thirty Years' War after, like, there, people cannot handle the sort of the change. And so we have, it takes a generation to develop immunity. And so, to give a different example, cigarettes. Yeah, it's like, okay, it's a great business model, get people hooked. But we developed immunity to some degree. And we, you know, tax them, We stigmatize them. And maybe me in the 1950s would've been smoking cigarettes. Today, I would never touch a cigarette. And so right now, people are making a big commotion over Instagram.

Hmm.

It's TikTok. It's addicting. Well, I think we should ban TikTok for geopolitical reasons. I don't think we should ban Instagram. I think we should develop cultural immunity to it. And that's gonna take some time, and it's messy. But I think to the point that you were talking about with Pomp and sort of trying to take advantage of human weakness or addiction, there's a school of thought around it. You know, Reid Hoffman's had it for a long time and others sort of build consumer social around the 7 deadly sins. 7 deadly sins, yeah. Don't— like all these mental health things or these habit things or these, you know, these things that you say you want to do, but you don't actually want to do. aren't going to— don't work to sort of— it's like news, but good. Yeah, good luck with that. Good luck getting an audience there. Although God bless the effort. And so you have to understand human nature. But if you prey on that too much, how durable will it be? Because people will develop immunity to it at some point. And so is everything personalized? I think so. But people, people, I think it's personalized less to individuals and more to tribes. Like, because people still want to be in community, right? Like, people still want to be in groups. We'll see with AI if they're able to simulate this idea, AI VR, like, maybe you're just all alone, but you feel like you're part of a part of movement. But that's the reason why these reality entrepreneurs are so exciting to people, or these movements are so exciting, whether it's Black Lives Matter, whether it's QAnon, whether it's sports, whether it's whatever, politics, people want to be part of something. And we used to have traditional religion, and science put an ice pick in that, or, you know, reduced the moral credibility of that. That's not cool anymore. It's hard for super high IQ people to reconcile with that. But humans are spiritual creatures. Humans are spiritual creatures in that they need to be part of something. They need to be part of a movement, part of a tribe. And so there's all these People on the internet trying to offer, trying to create the most compelling sort of tribe. So I think people are gonna still keep trying to do it. It's not gonna be called religion, it's gonna be called QAnon, it's gonna be called BLM, it's gonna be called new sort of moral movements that people can get behind.

All right, so I wanna start talking a little bit more about the business side of things for a moment and what you're doing at Turpentine. You sort of, this is a quote, you've said, Media companies are tremendously underrated because they're not just distribution machines, they're also data aggregators and reputation generators. And you spoke a little bit earlier about that, but in sort of pulling off this like media to data rather than data to media kind of reverse Bloomberg style approach to building a media business, I'm curious how you think about what actually gets built out peripherally, right? Because sort of have said this to you before, at the surface it looks like you're building lots of disparate things and media talent and reputation and other things, but you look closer.

Yeah.

And they really do stack into something much greater. So if you could break it down, what complementary components are you building out? And what does this whole thing look like at scale?

Yeah. First, let me just say kind of the high-level trends that make Turpentine more interesting to build now than, you know, a few years ago. So one is, it's become much easier to build things and get things off the ground, and a lot harder to get distribution. And I sort of took advantage of that with with Product Hunt. It's like people really need access to customers. And that's even become even more true today, especially with AI. It's just easier to get things off the ground. It used to be much harder. It used to be you needed more money or you needed more technological tech competence. But now with no-code and AWS and now AI, it's easier to build things, harder to get eyeballs. So distribution is really what matters. And as such, we've talked about sort of the rise of creators on the consumer side. You have people like MrBeast who are not just, you know, getting— I don't know if he has a billion subscribers, followers at this point, but like hundreds of millions of people, you know, watch MrBeast regularly. And what creators have realized is that they can also be entrepreneurs.

Mm-hmm.

If, you know, MrBeast doesn't have to advertise for other products, he can just incubate his own products. And use his reach to sell his candy bar or his hamburger. And this happens across verticals in consumer, and it's starting to happen in business too, where it's even our narrow niche of tech, people like Harry Stebbings, you know, he's got this VC podcast that he started when he was 18. And he then used it to raise a massive fund. But maybe in the future, the next Harry Stebbings, not just will raise a massive fund, maybe he'll compete and try to incubate the next Carta or the next AngelList, or something that sells to his audience, where some engineer on the side is saying, hey, I can build the next Carta or AngelList. But what's really hard, or what's harder, is to get all the VCs to use it, to get the trust with them. And so I'm going to, in the way that I had a technical co-founder to build it, maybe I'll have an audience co-founder to get all the customers. And Harry doesn't even have to be full-time on it, because what he's full-time on is talking to VCs all day. So it kind of overlaps. With what he's doing already. And then you see Lenny Rachitsky doing the same thing with product managers, right? It's this independent voice. And there should be a Lenny for everything, for every position, for every sector. There is a trusted person who would make more money, like Lenny's making more money doing what he does now than being a product manager, way more money. And so there's someone who would, who is a practitioner of the craft. They're great at the craft. They would love to teach the craft, and they'd make more money being the Lenny of X than doing it, and they'd have more fun doing it. And it's interesting, people, you know, VCs hate media businesses. I never invested in media businesses as a VC because you saw all the money in 2010s go down the drain. You saw Vox and BuzzFeed and Upworthy and, you know, great people. Some of these are my friends, But the money wasn't well spent. But VCs ignored B2B media. There's this company Industry Dive that is a collection of 25 or so publications, like HR Dive, Pharma Dive, CFO Dive, niche media. And they sold for $500 million. And if they were independent, they'd be, you know, much more today. And they were just publications. And so this company Workweek that has inspired me a bit, they're trying to do the same model of this niche media, that's worth so much more than the general media because people are trying to sell to heads of HR. People are trying to sell to finance people, and it's hard to reach them. It's hard to access them in organic, trusted ways. And so there's these niche creators forming up, and Workweek, and what we're trying to do is create a collection of them to build a trusted voice to sell to these enterprise buyers. And so if you own relationships with these enterprise buyers, one, you could build a really strong business just like Industry Dive did. Mm-hmm. Just selling to them. But 2, you can, you know, be of value to a portfolio company that's trying to sell to them. You can incubate your own company that is trying to sell to them. So we're trying to create a portfolio of like the Lennys or the Harry Stebbings or the Packys. And so podcast was an interesting way for us to start. But when you ask us what upcoming products we have, we want to get into the sort of TechCrunch game, basically. If we want to cover fundraise announcements, we want to cover new— not exactly all the news that, like, The Information would cover, like, we'll let them do what they do best. But we want to cover information that helps people understand companies better, like the business performance of how companies are doing. And we see fundraise announcements as a really interesting wedge to, one, help out a lot of founders who want positive coverage, and thus build a trusted voice with a lot of founders at scale, but to get a lot of data from them during that process to help us better understand and explain how these companies work. So I could see us— so we're going to do fundraise announcements. Using that and others, we're going to build our own version of— I'm really inspired by Contrary Research, CB Insights. These are 2 websites that break down companies, break down markets. We're going to have our own research team. We're going to get in the list game. I think lists are cringe and corny when done well— sorry, when done poorly. But when they're done well, they, one, educate the market about who's really good, and they also uplift the people who get on them. And so you have to do them well. And whether that's, you know, best companies in a certain sector, best investors in a certain sector, or best sort of people at a certain position, what those lists also enable you to do is get a lot of information on these companies, on these people. And so it's like media is a way to get paid to build a data asset, if that makes sense. So we look at every media property as, hey, we're going to produce this podcast, or this article, or this list, or this fundraising announcement, we're gonna get paid to do that by the advertiser, or some other party. And we're going to, through that process, we're gonna get a bunch of data that helps us get a proprietary understanding, combining everything about the company, about the market, about the trend, about the person, and then potentially invest on that information, or sell that information in some sort of data product, something like a TIGAS. So there are other things that I've started that are like that, like these different review sites, like a company review site, like a VC review site, like a SaaS tool review site. And I have thoughts on how to make review sites positive. I'm not trying to make a hate fest here, but things that help people use better tools, join the right company, work with the right partner. And then we also have a social network that we've been building for founders to start, but it'll be for other players as well at certain tiers. And so I think of these products as an ecosystem that all feed each other. and help us build this compounding data asset of information that helps people make better investment decisions, purchasing decisions, and hiring decisions.

Amazing. All right, let's take a step back and talk about startups more generally here. The premise that I hope we can agree on is that disproportionately they contribute to economic growth, right? They're really engines of innovation for society, and we should be promoting their creation. Your first blog post ever is, at least I think ever, is titled Starting a Company Is Less Risky Than You Think. You write, in my opinion, starting a company is usually a better way to build your network and your brand relative to joining a company, in addition to having disproportionate financial upside. Even if this is true, how do we increase the number of startups? Is the bottleneck idea discovery? Is it finding co-founders? Is it fundraising? Is it a cultural problem? What do you think?

There's a number of factors. I first want to focus on the attitude Or understanding of risk that you mentioned. It seems like on an individual level and on a macro level, we're pretty bad at understanding risk. You know, there's this idea of the invisible graveyard of something like the FDA, for example, where they will, you know, be very strict in what they let in because they're worried it might, you know, there might be some casualties. But the invisible graveyard is you don't see all the lives that were saved because of some new drug. that could, you know, solve some sort of disease or cure some sort of disease. Similarly, self-driving cars is another example where it's like, oh, it might cause more— you know, people think, oh, it might cause some deaths, but they don't see all the lives that it would save. So we have this blind spot in not understanding risk in a macro way and in a micro way too. One of my close friends is a guy named Ryan Hudson. He's the co-founder of Honey. And I always love linking to his LinkedIn profile because what you see there is someone who after college started a number of companies that were all failures. Like, decade-plus of just starting company, fail, starting company, fail, starting company, fail. When he started Honey, he was working, he had to, he started it, and then he had to work another job while still working on it. So that's how much it wasn't working and how hard it was. And the reason I say that is because if your eventual goal is to start a company, the biggest risk is not that you fail on a company, The biggest risk is that you don't take enough shots on goal to get your honey. Because it's going to take a few shots. You're most likely not going to hit it on the first shot. And if Ryan had spent that decade instead of failing, working at Goldman Sachs or Bain or going to Harvard Business School— he actually did go to business school, but I don't think he would say it helped him— Then he would have not done the 5th company, or whatever amount of company that Honey was. He might have just had a few, a couple failures, And so I think that is something that people don't appreciate. If their goal is to be a founder, they'll say, oh, I should work at Bain, I should work at Goldman Sachs, I should work at Facebook, and I'll learn how to be a founder. The best way to learn to be a founder is to be a founder. And I think one problem people have, the reason why they don't do it, is because in the same way that people— we talked about price discrimination earlier, there's also this idea of reputation discrimination. In the sense that they care what their parents think. They care what their people from back home think. They care from you know what the wide population thinks, and what what Silicon Valley values, what the entrepreneurship ecosystem values, is very different. Actually, they would rather you start a company and fail than go work at McKinsey or go to go to business school. But most people care about McKinsey or the business school. And so if your goal is to be a founder, you know, sometimes people say, don't care what people think, just do it. But you actually wanna care about what the right people think, the people who you wanna be more like. And so the, what the people who you, the right people know is that starting a company actually gives you more optionality than working at Facebook to start a company. Just as an example, at Facebook, you know, the argument is you'll have more money, You'll have, you know, some sort of Facebook network. These are all positive things. But if you start a company, people will respect, oh, he or she's got some founding experience. You get a network talking to investors. You learn, you get an education on how to do that. I started my first company, Wrapped FM. It was a music tech company. It didn't go anywhere. I worked 3 years on it. It's, you know, critical part of my career. And yet I built a really strong network. It's how I met Ryan Hoover, the CEO of Product Hunt, and then joined him. It put me on the map, it helped me move to Silicon Valley, and people don't see that you're known for your wins, not your losses. You know, Marc Andreessen started Ning. It was like a social network for dogs or something. It was this kind of crazy idea. He ran it for a number of years. Reid Hoffman started a dating site, SocialNet. You never hear about it. You're known for your biggest win, you're not known for your losses.

There's this really interesting meta question here that I think comes from Elad Gil. I was talking to him about this, which is whether entrepreneurship is fundamentally founder or market limited, which is basically to say, if we throw more people at the same problem, would we actually have that much more success, or is it the case that there only really exists a finite number of opportunities and you need to be able to capitalize on them at the right time? You worked on, I think tangentially here, a lot of this at On Deck, so you might have kind of an interesting perspective. Yeah.

I think there's no way that we are at the optimal allocation of the, you know, of all the ideas that have been picked. There's a lot of startup ideas that exist out there that have not been solved yet. And that's why if we thought that we were at optimal, then there would be no VCs, there would be nothing to invest in. And so I think to me, it's a little bit of the why not both meme.

Mm-hmm.

I think There are—

what founders do is they experiment in different markets. They're the way that we test the markets. They're the shots on goal as a meta ecosystem. And so more founders means more shots on goal. Now, if it's the wrong shots on goal, that's not helpful. So I would love for there to be much better coordination, collaboration across the startup ecosystem on, hey, What are the market opportunities? What are the customer problems? And how do we get— how do people get in touch with these customers? It's a shame that when someone does a deep dive, let's say, you know, they just leave a company, they're like, I want to do something in healthcare.

Mm-hmm.

They kind of start from scratch. They don't get to learn from all the thousands of people who did that same deep dive. There's no shared knowledge across the ecosystem. I'm gonna— one of the podcasts we're about to start is called Requests for Startups. And another one, or maybe it'll be the same feed, is called Navigating the Idea Maze. And it's just meant to get the knowledge that's in people's heads of people who've traversed healthcare or fintech or whatever industry, know where all the bodies are buried, and then share it with the rest of the world. So I think it's both. And going back to your original question, what's constraining founders? I think there's a number of things. One is, that sometimes the economic calculus for a founder is not as compelling as the economic calculus as a VC, for example. That's why a lot of people want to be VCs. They don't want to brag, or they don't want to say it publicly, because it's kind of like cringe or something. But deep down, a lot of founders actually want to be VCs. Why? Because it's an easier life, and it's a better calculus. Basically, you don't work as hard, you have this broader purview, and you You make more money in salary, like way more money, or like multiples more. And you have a diversified portfolio. A founder is all in on one thing, they are likely to fail. And they have a low salary. For what, right? For the joy of creating something epic. And, you know, I'm a founder and all this stuff. But if we want to have more founders, we should let founders have a diversified portfolio. You could do that via equity pooling, You could do that via scout funds. You could do that via giving some founders some percentage of the VC's portfolio. And so some VCs would snicker at that and say, hey, no, because the founder is all in, they're giving it their all. But I think it's a little selfish. There might be some truth to it, but I still think you could diversify just a little bit, and you might get more founders. I think we have this calculus in tech where You either get all the equity and no financial security by being a founder, or you get all salary and very little equity. And there's nothing in the middle. How about, like, people who are like, hey, I want $150K salary and 15% of a company. And this is why I think there's opportunity for incubators and studios to just appeal to someone with a different risk-reward perspective. Maybe they have kids, but they want upside. And so they can't take a huge financial guarantee, but they also don't want to raise venture, because that puts them down a clear path. And so there are these, all these kind of warped incentives that I would like to expand the opportunities of incentives. And there are all these players, like VCs, who have incentives for there to just only be one model, which is every company that could, you know, considers venture capital first. And so that's one thing is making it more economically attractive for founders to start companies. Another thing is things like healthcare, things like immigration, things like having better ideas, you know, finding co-founders. This is what On Deck was focused on, and I'm still very passionate about and want to do more in.

To that point, I want to touch on community for a moment. You're one of the best of the best when it comes to building communities and having done this at On Deck with such, like, success at scale. The question here is actually very straightforward. What do most people get wrong about community building?

I think great communities are about value and values. And by that, what I mean is they offer utility to the person to— there's a reason for the person to join. It solves some problem that they have in their life, but it also is about values in the sense that the community represents something they care about. So it both solves a need for them, but it also— like a practical need, but it also solves this almost like identity or spiritual need, which is, I like who I am, I like what this community says about me to be a part of it. And when communities get wrong, they only focus on one thing. They're like, hey, everyone cares about this cause, Thus, they should want to join this community. But there's often unhidden— hidden reasons why people do certain things or don't do certain things. And if, yes, they might care about this cause, but if it makes them seem uncool or doesn't introduce them to people who they want, or it doesn't solve some more practical need, some need that usually relates to their career in some way, something that where they get paid more if they do it. You know, people say often, you know, social— great social apps either get you paid or they get you laid. I think communities, to some degree, there's some truth in— I don't know if it's not necessarily only those 2 in particular, but it's got to solve some core thing for them because the opportunity cost is massive. And so I feel like people either focus too much on sort of this fluffy stuff and think that everyone will just vibe on that level when realize that, hey, people have needs too. Or they focus too much on the transactional component without trying to get in touch with something deeper that will encourage them to, you know, put their name behind it. Like, you know, Forbes 30 Under 30, as an example, not to pick on Forbes, I think their other lists are fantastic. But that list has become a bit tainted where people don't like what it says about them, even though it, you know, offers a very practical utility, which is it It, um, that same thing that it offers has also become tainted because of sort of this more values component.

Gotcha. I want to take a moment to talk about mindset. You've spoken about this otherwise unassuming quote from Giannis, whose name I can't, can't pronounce ever, who plays for the Bucks in the NBA. And after a loss, some guy at the presser asked him if he feels like the season was a failure, and he goes, You know, it's the wrong question to be asking. There's no failure in sports. There's the good days, there's the bad days. Some days you're able to be successful, some days you're not. Some days it's your turn, some days it's not your turn. And this really struck you somehow, right? Because I think because it speaks to being like deterministic when you're in the thick of things and probabilistic when you're out. Can you speak to that at all?

Yeah. What's so fascinating to me about that quote is because if you would have asked Giannis before the playoff series if a loss would have been a failure, he would have said, Yes, absolutely. He would say, we have to win.

Yeah.

There's no question. He would have been deterministic. And it speaks to this idea that we can pick and choose sort of perspectives when they suit us. And when you're in the game, or when you're, like, you know, when you're competing, you want to have everything on the line. You want to say, hey, there's no plan B, because in the back of your head, you might think, okay, there's a plan B in case I fail. But, like, If you're already thinking about Plan B, you're already hedging, and you're competing against somebody who's like, no, no, this is it, it's absolutely everything. But then if you lose or when you lose, being able to shift on a dime and into the more reactive, hey, everything's a lesson, you know, it's all random, etc., that allows you to both compete at the top level, put your all into everything, while also softening the fall when it doesn't work out. So you're able to have a chance at win— it's asymmetric upside. If you go all in, you win. And if you lose, hey, it didn't really matter in the first place. But if you don't hold that juxtaposition, and most people don't, what happens is if you go all in, you lose, you beat yourself up. Or you kind of are wishy-washy, you know, a little bit kind of detached, you don't go all in.

Mm-hmm.

And a lot of life is like this, where you have to, have like faith that the thing will work out. Because if you don't like take a leap of faith, you'll just sort of logic yourself out of taking that commitment. You'll reason it away. And so you have to be impervious to reason. You have to be impervious to sort of talking yourself out of it. And so you have to— I'm all in with everything that I got. But then when it doesn't go your way, when you fall flat on your face, You have to be able to pick back up. And so that sort of productive hypocrisy is all about, I think, what world-class performance is about, because it takes iterated, it takes a lot of tries to start a company, to do whatever. And you have to both take the leap of faith while also being able to change your mindset and bounce back when it doesn't work out.

This kind of speaks to this idea of decision-making through faith over logic. Sometimes it's really easy to see life as this optimization problem, but it turns out that being, like, super hyper, hyper-rational all the time isn't, A, isn't necessarily the most meaningful thing you can be doing, but B, also, like, kind of impossible sometimes too.

Yeah.

Antonio García Martínez, who you do a podcast with, has this really great quote. He goes, tell us what Bayes' theorem says about Israel versus Palestine. Tell us what Bayes' theorem says about how to be a good father. Tell us what Bayes' theorem says about the meaning of life. So in sort of a two-pronged way here, I'm curious, how can faith over logic help in prioritizing commitments in life's biggest decisions? And then when is logic necessary?

Yeah, so it's certainly necessary when things don't work out, as I explained in that previous situation. But what Antonio was speaking to, this broader idea that sort of utilitarianism, or sort of the expected value view of the world in terms of, you think about what's the EV here? It's, um, while it can be a very helpful tool, if it's the entire toolkit, it will prevent you from, uh, really committing to things long-term. Because, um, if you, you know, why would you ever commit to marriage, for example, till death do us part, if actually what you believe is, hey, as soon as this doesn't make sense for me, I'm gonna leave? But if, if you communicate that commitment to somebody then how are they gonna commit to you? And it's sort of, you sort of, you know, back into, actually, we'll just be together until it, you know, until it doesn't make sense. And then as soon as it doesn't make sense, you back out. And if you both know that in advance, you might think, well, you're just not as— there's something about the commitment that makes it more powerful.

Yeah.

And so it's a little bit the right mindset at the right time, or speaking to the deterministic, like, We talk to people all the time who want to start companies, who have ideas. But if they think about all the reasons why it won't work, and there's a ton of reasons why it won't work, there's no foolproof plan just to start a company that you have 100% certainty about. And so you can't, if you over-index on this utilitarian or this EV way of thinking, on this sort of logical way of thinking, you'll find reasons not to do it. not to start a company, not to pick one person for life, not to have these greater commitments that supersede sort of, or overpower any sort of, you know, changing of the mind. And people want to be associated or affiliated with people who are loyal to them, who even when things are hard, even when things don't make sense, that's what allows me to trust you, is that you'll get my back. even when it's not in your— because I won't trust you if you'll just change your mind as soon as you want. And so when making commitments, one has to take a leap of faith. Now, you could use logic about determining which leap of faith makes the most sense. And then when you've taken it, how to best go about making it successful. But that's one challenge with people who take the— who over—

Overcommitment.

overly EV everything, overly cost-benefit analysis everything, is that everything's always got costs. And if you make those costs front and center, you won't make decisions. And that's why so many people become paralyzed. So many smart, brilliant people, in some ways, are too smart for their own good. So Nat Friedman had this tweet once, we start companies not because they're easy, but because we thought they would be easy. Which is to say, If you knew how hard it would have been—

You wouldn't have done it.

Exactly.

Yeah. So without getting like too woo-woo here, it does seem like optimizing for meaning is actually what makes up— ends up making you happier than optimizing for happiness itself, because you're prioritizing things outside yourself. Which brings me to this next point. You write about the emergence of modern liberalism as the idea of being free from society itself, right? Including religion and culture and customs and norms and relationships that get in the way of individual desires. And Catherine Boyle has this great piece on how a lot of these societal commitments, like patriotism and religion and attitudes toward having children or marriage or community involvement, are kind of on a downswing. The long-winded, very long-winded question is this: with this incredible explosion of media that we were talking about earlier, that we've seen for every niche imaginable, do you think it's easier than it used to be to fill the space those commitments took up?

Yes, exactly. That's exactly what's happened. You needed— used to need to get married in order to survive, right? You needed— women depended on men economically. Men depended on women, or men and women depended on each other for a whole— this bundle, right? It was sort of economics, it was support. And what we've done with the modern economy is we've unbundled all of those needs, right? You don't need a person to do XYZ for you because you could just pay to get it done. And sort of the dystopian version of that is, you know, men don't need women anymore for sex. You have porn and sex robots and all this stuff. And women don't need men anymore to have kids. You have artificial wombs and all this stuff and AI boyfriends and— You know, and so that's one example of how modern technology has unbundled the bundle and thus made the bundle less attractive, while also making the opportunity cost so much higher, right? This is why people are having less kids. It's just more fun to do other things.

Yeah.

Like have a really fulfilling career, like have an amazing social life, like date someone with a press of a button. You could date people every day for the rest of your life, whereas back then it used to be you needed, you know, just whoever's in your village or whatever. So you get married. And so the— so yeah, that is both, you know, one amazing thing about modern technology is all this choice and all this option and all this freedom, but it does require— one challenge is it's harder to make commitments in general. And so it does require sort of a consciousness or education about the importance of how these commitments might have long-term benefits.

Okay, homestretch here. I want to take a minute to talk about another really interesting concept you've written a lot about called the hypocrisy of elites. The idea here is that elites in society today will recommend harmful behaviors and counterproductive policies for quote-unquote non-elites while being the ones most insulated from the consequences. Can you break this down?

Yeah. So there's this trend where people will recommend something for other people about, you know, how society should be, should be run or how people should operate. So they'll say, you know, defund the police was a very popular one during, during COVID And defund the police while also living in heavily policed, you know, areas or gated cities or, you know, communities or whatever. But there's other more insidious ones like trying to destigmatize. And destigmatize is another word for Lower this, you know, for celebrate. Basically, you can't destigmatize something without celebrating it. So you're lowering the status of hurting something, but you're raising the status of being it. And so they tried to say, "Hey, you don't have to get married. You don't have to be fit. You don't have to work hard. You don't have to do well in school. You don't have to." They what they identified or believed. is that these stigmas were hurting people because they were making them feel bad when they weren't meeting those standards. But what these stigmas did is they actually— they did hurt some people who didn't meet them, but they helped a lot of people follow those norms. They helped a lot of people be fit, get married, have kids, you know, when they do get married instead of out of wedlock. And so when you take away the stigma, You also, you have what we've had, which is a drop in family formation, to example, or a drop in, increase in obesity, or there's a whole number of things. But the hypocrisy of the elites is that instead of setting the norms, holding everyone else to a high bar, they drop the bar for everybody else, but they don't for themselves. They get married at higher rates. They are more fit than everybody else. They are adopting a set of norms. They don't have kids out of wedlock that are productive for themselves while recommending that other people don't do those things. Or if they're not actively recommending it, they're sort of being blasé about it.

Yeah.

That's on the micro level. On the macro level, things like defund the police, things like no charter schools, not letting sort of privatization of charter schools, when they themselves send their kids to private schools. So it's this just sort of lack of skin in the game of what they're recommending.

All right, a couple more. I wanna start to close out by asking questions you ask people you interview a lot. The first one is, when you look back on the arc of your career, what's the thread that ties everything together, and what threads have you kept pulling?

I write about personal moats a lot, or this idea of what What advantages can someone accumulate in their career? And the one that I've sort of stumbled into is community building for founders, from Product Hunt to On Deck to Village, or community building for the startup ecosystem, basically enabling entrepreneurship, and even more broadly, helping people find their people, whether it's their co-founder, whether it's a teammate, whether it's the right investor, That has given, or whether it's a close friend or in the future, working on this dating thing, whether they're a partner. Like, helping people find their people is one of the best gifts you can give to someone. And it's something that I've found myself good at. And building products, communities, services that help people do that, make sort of the market more efficient in a bunch of different ways, gives me a lot of joy. And I'm gonna keep doing that. And then also just following my curiosity and doing it with other people, doing it publicly, helping other people do it, helping people learn, helping people advance in their career. These are, these are some common trends.

The second and last classic Erik question I'm gonna ask you is, when you look forward to what you aim to achieve in the decades to come, what do you want your eventual Wikipedia page to say?

I think what's far more important than a Wikipedia page is your funeral. And so I hope at my funeral, people, people close to me, say I was a good person and that I was there for them and that I supported them and that I helped enable them in their flourishing. Wikipedia page, I hope I contribute to some institutions that really touch people's lives, that are transformational, whether it helps them find their people, helps them find their path, helps them grow. It helps the broader economy or broader ecosystem. I hope I created or contributed to some institutions that had a massive impact on people's lives.

One more question for you. It's the same one I ask at the end of every interview, which is inside or outside the scope of anything we spoke about today, what do you think more people should be thinking about?

I think more people should be asking what is easy for them to do that looks hard to other people. And I think more people should ask for feedback. They should— on that exact question, they should ask 20 people in their life who know them pretty well, maybe worked with them, or they're their family, or they're their best friends, or they're their partner, and say, hey, what do you think flourishing looks like for me? Like, when you think about my unique set of skills, my unique set of interests, the opportunities that exist in the world, where do you think I can do something that is the most me, the most sort of that I can have the most impact in the most unique you know, something that's true to who I am, what I can do, what I care about, and what's holding me back from that? Am I not in the right opportunity? Have I not developed the right skill? Do I have personality traits that are holding me back? I think more people should be more observant of their patterns. I wish for a world— I had a friend who was working on this product that would record everything you're doing. You could turn it off and on and give it to a coach. And that coach could give you feedback, observe. It's almost like game tape, you know, athletes on game tape, but for everyday life. And people fall into all these patterns. And if they can get more awareness of activities that they're doing that are contributing to people distancing from them or not being trustworthy or just making their life worse and be able to change that, I think that would be transformational. So I think both feedback on the macro level. What are they doing from people they care about? Not the people they don't care about, or sorry, people who they trust their opinion. Like, they might care about their family, but if the family wants to work at McKinsey or something—

Yeah, yeah, yeah.

You don't have to listen. Don't listen to them, right? But they might know when you're, you know, your breaking points, you know, emotionally or whatever. So more feedback on the macro perspective, but also more, you know, feedback on the micro perspective when you do XYZ, it makes me feel, you know, like, et cetera, so that they can, you know, be better. 'Cause I think what's really interesting is that there's like things you could start doing and things you could stop doing. And I feel that would make your life better.

Yeah.

And if you, it's like addition by subtraction. If you can make life better for yourself and for other people you care about by doing less, and if you just knew what those things were and could be more mindful of that, that's transformational. 'Cause you don't have to do anything new, you just do less. But better. And that's a lesson that I've struggled to learn. I've been working on learning and will continue working on learning.

Erik, that's all I got for you, man. Thanks so much for doing this.

Thank you.

I'm a big fan of what you're doing.

Appreciate it.