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Invested by Aleph

21 Oct 2026 · 1h 4m · 32 chapters

Episode artwork

Josh Kopelman, Founder of First Round Capital and Half.com, on Why Buying Anthropic, OpenAI, and SpaceX Is a Cyclical Trade, Catching the Last Chair in the Dot-Com Game, and Earning Tens of Millions in Free Media with Viral Marketing

In short

Josh Kopelman (First Round Capital; Half.com) discusses dot-com timing, “cyclical” venture trades, and how to win attention and distribution with low-budget, high-creativity marketing. He argues fund size is a tactic, not a strategy, and that venture is a “hits” business where most bets fail but a few create outsized value.

Guests

No other guest is named in the provided transcript; the episode is a conversation between the host and Josh Kopelman.

Guest background

Kopelman founded Half.com (launched Feb 2000; sold to eBay in June 2000) and earlier co-founded Infonautix (student-era “Homework Helper” sold on AOL/CompuServe/Prodigy; later went public and merged with Two Cows). He later founded First Round Capital, starting with under $150M and growing to a ~$500M last fund.

Key claims

“Fund size is not a strategy.” Founders are “cartographers”; investors “raise navigators.” Late-stage “trillion-dollar” buying can be a risk-on cyclical trade; private-market washouts are societally preferable to public-market ones.

Notable examples

Half.com’s town-name stunt (Halfway Oregon → Half.com Oregon) generating Today Show/WSJ/60 Minutes coverage; urinal guards (“don’t piss away half your money”); fortune-cookie coupon channel; dot-com conference “last chair” timing; Infonautix scanning newspapers for searchable education; AI as a tool that increases founder agency.

Written by AI. May contain mistakes.

Chapters

0:00

Introduction to the Podcast

The hosts introduce the episode and the guest, Josh Kopelman.

“If you want to get on the map, just convince a damn town to change its name to half.com.”
0:49

Early Memories and Fast Talking

Hosts reminisce and joke about their age and speaking pace.

“Welcome back to another episode of Invested.”
1:24

The Birth of Half.com

Josh shares the inception story of Half.com during the dot-com era.

“And very few people know that you were actually a key part of the early internet, having sold one of the first kind of, I think, successful companies in the early internet era.”
1:56

Innovative Business Model at Half.com

Discussion on Half.com’s business model and early challenges.

“that most people buy a book, buy a DVD, buy a CD.”
2:58

Strategic Naming and PR Stunts

Josh describes the strategic naming process and the media stunt with Halfway, Oregon.

“We were able to coordinate a stunt and launched on the Today Show.”
4:09

The One-Year Town Name Deal

Details about the agreement with Halfway, Oregon and the impact on marketing.

“Now, can you tell everyone about the stunt, which wasn't just the Today Show, but there was a stunt about a naming?”
6:01

Viral Marketing Through Unconventional Ads

Josh explains unique marketing tactics like urinal ads and fortune cookies.

“We were willing to pay them more, but they only wanted a one-year deal.”
8:01

Lessons for Entrepreneurs

Discussion on creative marketing and avoiding traditional ad spending.

“And our hunch was that no one's job was to pull them out.”
10:40

Reflections on the Dot-Com Era

A look back at the companies and conferences of the dot-com boom and their relevance today.

“It's like Lemonade doing graffiti on ads today.”
11:39

Comparing Cycles: Then and Now

Josh compares the current market to the dot-com era, discussing valuation trends.

“And so if you weren't at PC Forum, right, Chris Shipley at the time and Esther Dyson at PC Forum.”
Show all 32 chapters
14:00

Investment Insights: The Cyclical Nature of Capital

Explore the cyclical nature of investments in technology and how market conditions influence valuations.

“And you can just go down the dot-com list and look at the dozens and dozens of companies that got funded, got public, that no longer operate and, you know, ceased operations.”
21:43

The Role of Founders in a Volatile Market

Discusses how founders navigate market volatility and the importance of timing for exits.

“If I go back to your half.com story and to the kind of early internet stories, the timing there was critical, right?”
28:00

Valuation and the Trade Mentality

Learn how founders view investments as trades versus partnerships in venture capital.

“The company is now north of 12x the revenue and is probably just now growing into that valuation.”
29:54

The Role of Experience in Venture Capital

Explore how experience shapes the support venture capitalists provide to founders.

“Are you able to still partner with these younger founders?”
31:28

Conviction and Risk in Investments

Understand the importance of conviction in investment decisions and the associated risks.

“from the prospects that don't convert to customers, from the press, from their shareholders, from the VCs that don't convert into shareholders.”
34:56

The Rise of Infonautix and the Internet Era

Learn about the founding of Infonautix and its significance in the early internet age.

“and you're excited to partner with the founder on that swing.”
38:49

Innovations and Challenges Faced by Infonautix

Discover the challenges and innovative strategies of Infonautix in the pre-search engine era.

“So Infonautix built, so back in the day, there was no, this was pre-search engine.”
41:20

The Legacy of Infonautix and Early Investment Banking

Reflect on the legacy of Infonautix and its journey through the investment banking landscape.

“We said, we want to sell to consumers for this price, and we'll set aside that amount of money.”
42:00

The Echoes of the Past: Lessons from the Four Horsemen

Learn about the historical significance of early tech firms and their impact on today’s market.

“And Cowan, I believe, is still around, actually.”
43:00

Generational Insights: AI and Learning Styles

Explore how different age groups engage with technology and education.

“He said that my high school class is divided between people who spend their time on AI and learning on YouTube versus those that are on TikTok and Instagram.”
44:10

Navigating the Conveyor Belt of Education

Understand the structured educational system and its effects on creativity.

“But I also think it's an incredible time in that the ability to use AI to learn and to create is unlike anything I've ever experienced before.”
45:50

The Role of AI in Empowering Founders

Discover how AI tools can enhance innovation and entrepreneurship.

“Like, the students don't need to guess what to read.”
47:30

The Evolution of Software Creation

Learn about the shift in software creation from code to language-based interaction.

“that's already so powerful and bringing it into your areas of interest, your areas, like the areas of focus.”
49:20

Investing in Founders: The Seed Funding Perspective

Examine the nuances of investing in startups and the importance of people.

“than it is to take someone who spent 20 years in business and teach them how to code.”
51:10

The Challenges of Competition in Startups

Analyze how competition affects startups despite technological advancements.

“We invest so early that by the time we as a firm are smart enough to come up with a thesis, it's too late.”
52:50

Branding and Value in Venture Capital

Discuss the significance of branding in venture capital and how it influences funding.

“The deviation of those businesses is massive.”
54:00

Embracing Imagination in Entrepreneurship

Explore the concept of 'Imagine If' and its role in fostering innovation.

“What does the Josh Koppelman and First Round Capital brand stand for?”
55:40

The Philadelphia Inquirer: A Nonprofit Model

Learn about the significance of the Philadelphia Inquirer as a nonprofit newspaper.

“you know, for me, I still like imagine I get very excited about the, the, the phase that we play, right.”
56:00

The Transition of the Philadelphia Inquirer

Learn about the challenges and strategies involved in transforming a traditional newspaper into a digital-first organization.

“So you got involved with the Philadelphia Inquirer.”
59:03

Taking a Stand After October 7th

Explore the motivations behind the decision to confront controversial figures in light of recent events.

“And I think hopefully we're sharing some of those lessons through our partners at the Lenfest Institute, which Jerry set up with other local news organizations to help them evolve as well.”
59:53

The Impact of Public Discourse

Discuss how public opinion and social media influence business relationships and public perception.

“We were just all traumatized by what happened on October 7th.”
1:02:20

The Search for Founders in Israel

Understand what venture capitalists look for in Israeli startups and the potential for U.S. market entry.

“I know the answer to that question is yes.”
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Transcript

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0:00Michael Eisenberg: If you want to get on the map, just convince a damn town to change its name to half.com. You ever go to the urinals and you see those little urinal guards? We went and got them printed up to say, don't piss away half your money, shop at half.com.

0:14Josh Kopelman: It was the ultimate form of streaming media.

0:16Michael Eisenberg: I believe that your fund size is not a strategy. Your fund size is a tactic to achieve a strategy. Back in 2004, when we started, it was a little under 150. Our last fund was about half a billion. Founders are cartographers, and we raise navigators. Patty started tweeting about Israel as a genocidal actor. I just started screenshotting his tweets because I figured he would at some point want to take them down. And then I started tweeting about it.

0:42Josh Kopelman: What's the price you paid?

0:49Josh Kopelman: Welcome back to another episode of Invested. I'm thrilled to be here with my old friend, not that either of us are old, although we are the same age, Josh Koppelman. Welcome, Josh.

0:57Michael Eisenberg: Thanks. Great to be here.

0:58Josh Kopelman: Everyone introduces you as the founder of First Round Capital. I still remember you as the founder of Half.com and Infonautix. Wow. Does that make us both old? It really does. We're going to tell those stories in a second. But you cannot listen to this podcast on 2X because otherwise you'll never be able to keep up with Josh.

1:17Michael Eisenberg: Well, you speak pretty fast yourself.

1:20Josh Kopelman: Josh, I actually want to start with Half.com, can we? Sure. Okay, so we both lived through the internet bubble or the takeoff of the internet. And very few people know that you were actually a key part of the early internet, having sold one of the first kind of, I think, successful companies in the early internet era. I just want you to tell us the story of Half.com because I think it's really insightful for this era.

1:46Michael Eisenberg: Sure. So I started Half.com in 98, 99. So right in the insanity of the dot-com era. And the basic premise was the following, that most people buy a book, buy a DVD, buy a CD. That's how you bought media at the time. And watched it once, read it once. And they had hundreds of dollars, if not thousands of dollars of value trapped on their bookshelves. So what if there was a way for you to buy a book or a movie or a disc for half price and then turn around and sell it for half price? And originally, we were actually going to be called eBazon because we thought it was the best of eBay combined with the best of Amazon, right?

2:39Michael Eisenberg: It was like person-to-person like eBay, but structured commerce with a shopping cart, credit cards like Amazon. And our lawyers told us that eBay and Amazon were ruthless competitors, but the one thing they would both agree on was suing us. So we changed our name to half.com, launched in February of 2000. We were able to coordinate a stunt and launched on the Today Show. And then eBay came knocking a few months later, and I feel like we were one of the last chairs, if not the last chair in the game of Internet musical chairs because the music stopped and we caught a chair.

3:18Josh Kopelman: I mean, my memory may be fuzzy. But my recollection was is that NASDAQ had already peaked, but this was considered a very successful outcome at the time, meaning that NASDAQ wasn't really crashing at the time. And I think there were a lot of public companies at the time that looked at Half.com as a harbinger of, hey, the music is still going on. It was a successful exit.

3:40Michael Eisenberg: It was a very successful exit in a very short period of time. You know, our investors, like their biggest challenge was it might not have been long enough for long term capital gains. Yeah, we were pretty fortunate in the timing, the exit, the scale of the exit, given that the Nasdaq peaked in March of 2000 and we sold in, we closed, eBay called us in February 2000 and we closed in June of 2000.

4:09Josh Kopelman: Amazing. Yeah. Amazing. Now, can you tell everyone about the stunt, which wasn't just the Today Show, but there was a stunt about a naming?

4:17Michael Eisenberg: Yeah, so everybody—

4:19Josh Kopelman: I'm old, but I still remember a few things. You have a good memory.

4:21Michael Eisenberg: I'm really impressed. There's nowhere to hide here. Look, this was back when Pets.com was spending tens of millions of dollars buying media with their sock puppet. Trying to create awareness and recognition was really expensive. We didn't have a lot of money. We raised venture, but we didn't have Pets.com money. So we kept saying we wanted to do something at launch to really put us on the map. And we kept brainstorming in a room and like, no, that's not audacious enough. It has to really put us on the map. And then finally, after like four hours of fruitless conversation, Mark Hughes, who I give full credit to on this, our head of marketing, basically said, well, if you want to get on the map, just convince a damn town to change its name to half.com.

5:05Michael Eisenberg: And there was this like laughter slash, huh like you know and it was a little odd like you didn't know is this a good idea because I just want to get out of this room or is this a good idea so we went and we searched all towns like Half Moon Bay well that's probably expensive and the smallest town with the word half in it was halfway Oregon population 350 something and it was a gold rush town that got left behind Needless to say, the next day, Mark Hughes was on a plane to meet with the mayor of Halfway Oregon, and they agreed to change their name from Halfway Oregon to Half.com Oregon. And that got us tens of millions of dollars of free media.

5:49Michael Eisenberg: A four-minute segment on the Today Show, Wall Street Journal, 60 minutes. It just put us on the map.

5:56Josh Kopelman: It literally put you on the map.

5:57Michael Eisenberg: It literally put us on the map. It was a one-year deal. We wanted it to be permanent. It was only a one-year deal? We wanted it to be permanent. We were willing to pay them more, but they only wanted a one-year deal. So it was like a licensing deal for the name of the town. They changed their name for a year. We got them 20 computers for the school. We hired four people, so over 1 % of the town, to work in customer service. For half.com. For half.com. Yeah. And the big thing was the snowplow. They needed a snowplow, and that's what closed the deal. You bought a snowplow with venture capital dollars?

6:29Michael Eisenberg: Yes. we bought a snowplow and donated it to half.com or again i didn't know that part of the story

6:35Josh Kopelman: yeah that was what closed the deal i thought that buying endless amount of nvidia chips with venture capital dollars was a big one but buying a snowplow that's a new one yeah at shopping.com at the same time we were dressing people up in jumpsuits with uh bags helping people carry their christmas shopping from fifth avenue and i thought that was odd everyone had to do stuff i mean we

6:56Michael Eisenberg: wanted to advertise at Internet World, which was the big trade show at the time. Again, the ads were so crazy expensive. We went and got a bunch of interns. Meanwhile, it's not so much today, but Internet World was all mail. It was all mail. You ever go to the urinals and you see those little urinal guards to prevent cigarettes from getting flicked down there? they all say like they all have something like 1-800-URINAL-GUARD or something like that. So we went and got them printed up to say, don't piss away half your money, shop at half.com. And we said, who the hell's going to go put them in? So we hired interns.

7:37Michael Eisenberg: We hired like five interns to do hands-on viral marketing. But we gave them gloves so they didn't catch a virus. And, you know, it was the ultimate form of streaming media. And we went and just went to the Javits Center in the morning and to Penn Station and just said, go put these in the urinals. And our hunch was that no one's job was to pull them out. They sat there for a year and a half. They sat there for a year and a half. But it got us a ton of attention as well. Like, yeah, so just stupid things like that. We had like, why not?

8:17Josh Kopelman: What's the takeaway for entrepreneurs from all this?

8:21Michael Eisenberg: I don't know. Don't buy rate card. Don't buy rate card. Like, you know, you could buy, like for half.com, a one page, a full page ad in the book section for one week was like$50 ,000. The urinals were like$2 ,000. Like the town was less, you know, like, and so like, I think people tend to be really creative in building a product. and then get really traditional on marketing. Oh, there's a way that it should be done. And at least for consumer products, we saw that you could be just as creative, if not more creative, in figuring out distribution and go-to-market. And rate card is for suckers.

9:03Josh Kopelman: Was there anything else other than naming a town in the urinal?

9:07Michael Eisenberg: So my VP, say Mark Hughes, we were out to dinner at Chinese Food and we were talking about the New York Times book review. And like, it made sense. It's where everyone went to find out books at the time, but it was 50 ,000 and no one reads it. So we finished the meal and they give you the fortune cookies with, you know, you crack it open and there's a little fortune in it. One side is a fortune and the other side of your lucky number. And he's like, everybody reads these. So the next day he went to Wonton Foods in Brooklyn, New York, and apparently Wonton Foods manufactures and sells 2 million fortune cookies a week to every Chinese restaurant on the East Coast.

9:49Michael Eisenberg: And he walked in and he realized no one spoke a lick of English. So the next day he brought a Chinese translator and just asked them, how lucky are your lucky numbers? How much money do you make on them? And they're like, nothing.

10:06Michael Eisenberg: So he's like, well, what if I put a coupon code on the back of them and I'll give you 10 bucks every time one of these is redeemed. And it said, save a fortune at have.com. And we were on the back of 2 million fortune cookies like a week later. And it was for years, one of our biggest channels of customer acquisition because everybody reads it and it is outside of like the media noise. Just getting attention was part of it. So just countless examples of things like that.

10:40Josh Kopelman: It's like Lemonade doing graffiti on ads today. instead of buying the ad space itself. That's amazing. So in the course of the last 10 minutes of conversation, you've mentioned eBay and Amazon on the one hand. You mentioned Internet World, which doesn't exist anymore. I think we met the first time at Demo, it could be.

10:56Michael Eisenberg: Yes.

10:56Josh Kopelman: Which is another now extinct, either Demo or PC Forum. I can't remember which. Both of them. Both of them.

11:03Michael Eisenberg: What does that say about us?

11:05Josh Kopelman: I guess we're endangered species. We are endangered species. I think you mentioned Pets.com. And before we sat down here, we talked about Globe.com, and we talked about JDS Uniphase. And these are all companies that were worth lots of money, at least on paper, in the stock market, in many cases, that went to zero. And a lot of conferences, by the way, which were the place to be, you had to be on stage at Demo to launch your company. Yes. You know, if you weren't at PC Forum.

11:37Michael Eisenberg: We launched Half.com at Demo.

11:38Josh Kopelman: You launched Half.com at Demo. And so if you weren't at PC Forum, right, Chris Shipley at the time and Esther Dyson at PC Forum. If you weren't at PC Forum, you weren't part of like the Digerati. And then there was Stuart Alsop's conference in Scottsdale. Agenda. Those were like the – none of this exists anymore.

11:55Michael Eisenberg: Nothing.

11:55Josh Kopelman: We're still around, but none of this exists anymore. Yes. What does that tell you about the current moment we're in where, again, it feels like things are taking off to the moon? There's a lot of companies. By the way, today, big difference between now and then was revenue run, right? Although JDS Uniface had a real revenue run rate at the time, but Lowell.com did it.

12:13Michael Eisenberg: JDS Uniface was probably worth over$20 billion with less than$30 million in trailing 12 months revenue. Was it that little? Yeah. Sycamore Networks. There were a bunch in the fiber space.

12:22Josh Kopelman: Yeah, I think that— What was the other one with the C? It was called—that was sold to Cisco. It was the Chromatis, which was the Israeli one, and that was the U.S. one called also with a C. Because every time seven rows and backed the company, it had to be called C. With a C.

12:35Michael Eisenberg: Yeah. I don't remember. Yeah, I think, look, we've seen this in every cycle. Companies, rightly so, during speculative times, get valued based on their high potential rather than their high revenue or their high, like, actual financial numbers. Like, VCs do this all the time. In every cycle, it's happened. So what happened, I think, back in the dot-com era is those companies went public. I took one public, Infonautix, trailing 12-month revenue,$600 ,000. What year was that? That was in 95. You had companies that were valued based on their potential. And what ended up happening is not a lot of them lived up to that potential.

13:25Michael Eisenberg: Right now, I'd say that's not happening truly in the public markets, but that is happening in the private markets. probably the$1 to$10 billion range in the private markets are the companies that tend to be valued most on potential, like potential energy rather than latent energy, you know, in terms of, you know, potential business, they're being valued into the future. And guess what? Several of them will be worth that and more. We're funding, you know, we're in those companies and we're hoping that that potential gets actualized. But probably, like most cycles, the majority of them will not.

14:03Michael Eisenberg: And you can just go down the dot-com list and look at the dozens and dozens of companies that got funded, got public, that no longer operate and, you know, ceased operations. And, but that's the business we're in. We, you and I, we recognize potential in people, potential in markets, and we invest in that. And we overpay for it. And the industries get overcapitalized. A lot fail, but some succeed.

14:37Josh Kopelman: And does this moment rhyme to you with the previous one? Or do you think it's different?

14:41Michael Eisenberg: It's familiar in that, like, if you ask me, again, you're seeing speed to revenue, which is very different than the last. So it's not a direct pattern match, but there's enough here where you say in moments of excess, in moments of exuberance, in moments of risk on, which I'd say the industry has been in over the last several years, you're going to see a number of companies get funded at valuations that won't end up being long-term durable. But that's fine because enough will get funded and will exceed all of their expectations that, you know, that I just think that's the business we're in. That's the business that founders are in and funders are in.

15:28Michael Eisenberg: It's a hits business. It's a hits business. And, and in, in the moments like this, more capital gets spread to try to create as many hits as possible. And, you know, I, I, I have no ability right now to assess, is this 97 where we have three more years of boomtown? Or is this 99 where we have three more quarters? I don't know.

15:54Josh Kopelman: Or is it February 2000 where you want to sell your company? Do you think there's a difference? You made the point, you alluded to the point that back then this played out in the public markets. Everyone went public. Today's playing out in the private markets.

16:07Michael Eisenberg: Private markets are a better product for founders right now.

16:10Josh Kopelman: But is there a difference when ultimately a lot of these companies get washed out? Does it matter if it happens in the public markets and private markets?

16:20Michael Eisenberg: You're talking about the washout in particular? I'd argue that if I had to sort of look societally, I think it's probably better it's in the private markets than the public markets. Because what tends to have happened, if you look at what happened to the dot-com boom, is VCs foisted these stocks and these prices, inflated prices, on the public markets, on individuals who were speculating. And when you sit down and say who took the gains and who took the losses, you had sort of VC and their ecosystem taking the gains and the public market and Joe Public Investor taking the losses. Whereas if it's playing out in the private markets right now, the gains and losses are kind of owned by the same people.

17:10Josh Kopelman: Mm-hmm. Although the pension funds, one could argue, although it's not at that level of scale, they're in the private market. It's pretty hard right now.

17:17Michael Eisenberg: They're very, yes.

17:18Josh Kopelman: You started first round capital, you'll correct me if I'm wrong, with about$150 million first fund. That's right. Okay. And you ran the$150 million fund strategy for how many funds?

17:28Michael Eisenberg: That fund strategy, it grew almost every year. What we built, I believe that your fund size is not a strategy. Your fund size is a tactic to achieve a strategy. So for us, our strategy might be we want to have 70 companies per fund to give us diversity. We want to own 12, 15 % of a company going in to have ownership. We want to have some time diversity. So we want it to be at least two years, ideally two and a half. So if that's our strategy, then we sit down and say, okay, based on the market today, we want to own 12 and a half percent of a company. And we want to have 70 of them. What would we need to deploy?

18:07Michael Eisenberg: And so back in 2004, when we started, it was a little under 150 million. Today, our last fund was about half a billion. Why? Same exact strategy. It's just that if you plot a chart from 2004 to 2026 of seed round sizes or seed round valuations, you'll see from 2004 to 2026, it went up about 4x. And so our fund just moves up. Like, I don't believe that you build a fund, a strategy around a number. I think that the best thing is to understand what your strategy is and say, what does it take to execute that strategy in the market? Recognizing you're a player in the market. You know, as much as I'd love to get 2004 valuations, not happening.

18:55Josh Kopelman: And exit size is up enough to cover for that? Yes. And then some.

18:59Michael Eisenberg: And then some. For the winners. From 2004 to 2014, so in our first 10 years, U.S. public and M &A exits was about a trillion dollars. And so the first decade, there was about a trillion dollars of value created. From 2014 to 2024, the next decade was$2 trillion. So it doubled.

19:25Josh Kopelman: And the concentration, though, I believe is bigger between 2014 and today.

19:28Michael Eisenberg: Yes. Yeah. And now today, one could argue that SpaceX, Anthropic, and OpenAI, there's like, if you add them up, SpaceX, what, where is it now? About a trillion and a half? Anthropic, you know, probably the same. Maybe more, maybe less.

19:48Josh Kopelman: As Gavin Baker has been on this podcast, he thinks we're at the three trillion, I think.

19:52Michael Eisenberg: But like, even if you say that the three of them all average a trillion and a half, I'll just say that's$4.5 trillion. Those three companies are double, more than double, the entire amount of exits during the last 10 years of every company. Put another way, those three companies will have created more value than every exit in the last 20 years and more so. And so I think what we're seeing now is, yes, I would argue that the size and scale of exits is more than enough to cover the valuation increase. At the seed stage, at the early stage, yes. The seed stage is an evergreen business. And what do I mean by that?

20:45Michael Eisenberg: If we invest at a 20 post or 30 post, if it's a great company, we'll do well. Yep. And if the company's not great, we're going to lose it all. But late stage, the folks that are coming in now at the$10 billion,$20 billion,$50 billion prices, like historically, that's been a cyclical play, not an evergreen play. It worked really well for Tiger Global until it didn't. It really worked. It worked really well for SoftBank until it didn't. And so, but by the way, you could make, they made all money hand over fist while it was working. And so I think, you know, I'm not smart enough to be able to time the cycles.

21:27Michael Eisenberg: So I just sort of, I'd much rather play in the kiddie pool, like play in the shallow section and play in a business where we could make money, whether it's a risk on environment, risk off environment, and not have to play into a cycle.

21:43Josh Kopelman: If I go back to your half.com story and to the kind of early internet stories, the timing there was critical, right? If you got out and got cash out before the bloom came off the rose or the market tipped or whatever you want to call it, the bubble burst, you were fine. And actually, people thought you were a genius. And if you didn't, had you missed that half.com window by another 30 or 45 days, you could have had a very different outcome. And so when you look today, for example, at OpenAI or Anthropic, at that end, and other companies, I'm sure you're investing in. How do you think about the timing of the exit from those?

22:21Josh Kopelman: How do you think about the lasting or staying power of what you now refer to as the trillion-dollar companies, Anthropik and OpenAI, which will account for a large percent of venture returns?

22:30Michael Eisenberg: I'm not sure I spend a ton of time thinking about it just because it's not my day job. My day job is helping founders at the earliest possible stages, the hunt for product market fit. I'd much rather spend time on that than trying to guess the durability of trillion-dollar valuations. But I'd also say there's another key difference, which is, you know, over the last 20 years, their capital markets, as I said earlier, public markets versus private markets. Private markets is a better product for most founders. It's regulatory, less complex. They don't have the stock trades on appointment rather than day in or day out.

23:11Michael Eisenberg: and the private markets have basically solved a lot of the challenges of you want liquidity sure we have a vibrant secondary market now that didn't exist when you were at shopping.com and

23:22Josh Kopelman: what i was it's not like the public market still though it's it's by appointment yes it's got complexities you have to coordinate with the founders the board you can block it there's a

23:31Michael Eisenberg: lot of things to yes it's not the same level of liquidity not the same but in in at least in today's market, you know, we're seeing founders take advantage of that. And I think that's not a bad thing because we want a founder to be motivated to go long. We want a founder to, you know, VCs are diversified. VCs have a, you have a portfolio of a couple dozen, you know, two dozen, three dozen companies. I have a bigger portfolio. Why shouldn't a founder be diversified a little bit? Because it's his. It should be his or her decision. It should be their decision. And like, I don't like, is that a signal for you?

24:09Josh Kopelman: If a founder decides to sell?

24:10Michael Eisenberg: No. In some cases it enables the founder to go long. I've had plenty of companies or, you know, in the last few, in the last few years, we've had some companies sell right under a billion dollars. And that was, those were companies that I think my partners and I thought had the opportunity to, to go on, to be worth multiples of that. But I don't begrudge the founder of that, that's what they wanted to do. Had they actually taken, in those cases, those founders had not taken secondary. And I've had plenty of founders who have taken some secondary off the table and it motivated them to turn down some of the offers.

24:43Michael Eisenberg: And again, it should be their call, not the investor's call. Like we're in service of the founder. And so I feel like it's been a healthy development.

24:52Josh Kopelman: This has always been a home run business or hits businesses, as they say, it seems to be getting more so. One of the things you hear from LPs is, hey, we're in Anthropic, OpenAI, or SpaceX, because those are the big three.

25:04Michael Eisenberg: Today, that's cyclical. That's cyclical. That's a cyclical trade.

25:09Josh Kopelman: Explain what you mean by cyclical trade.

25:10Michael Eisenberg: What I mean by cyclical is that you see these businesses, you have LPs that were able to get, I bought into Anthropic at$200 billion, and now they're looking like geniuses. And that's because you're in the back end of a boom cycle where things compound and asymptote very quickly. That's a new phenomenon. But by the way, you saw similar types of trades in the dot-com boom where things, JDS, as we were talking about, Sycamore, tens of billions of dollars.

25:44Josh Kopelman: That didn't asymptote.

25:47Michael Eisenberg: Well, it went up and then it cratered, right? 99 % drop or liquidations or bankruptcies. So I think what I'm arguing is that, But sure, that trade, that's a good trade for LPs while you can do it. And while it works. You know, the question, though, is there always, like, there has to be an ultimate buyer after you. And who's that marginal buyer today? In the private markets, yeah. I think the private markets ultimately expects the ultimate buyer to be the public market.

26:20Josh Kopelman: Right, and if that doesn't happen because the better product is in the private markets and the value accretion happens in the private markets. Yeah. You're handing the public a bag that is asymptotically.

26:29Michael Eisenberg: And I'm not sitting here saying, like, last thing I want to do is be shitting on OpenAI or Anthropik. I think they've built amazing businesses. And I think there's a very legitimate strategy on buying in the private markets, expecting these to be, you know, again, there's not just one way to make money in this business. I just think an evergreen strategy is, like, Like, you know that businesses go through cycles. We go through risk on and risk off. Yep. We go from FOMO to fear. And so the trade that you're talking about is a risk on trade. And it works well in risk on environments. It doesn't work well in risk off environments.

27:09Michael Eisenberg: You get stuck holding assets where, you know, the challenge of the private markets is it trades by appointment or it doesn't trade. Right. And we saw during the set, like that, if you look at the number of unicorns minted from 2017 to 2021, you know, more than half of them today. So you're talking about hundreds and hundreds of them haven't raised money in four to five years. More than half of them are either shrinking or growing up to less than 20%. And they're, you know, and, and, and. They're zombies. Yeah.

27:42Josh Kopelman: From a financial perspective.

27:44Michael Eisenberg: I still respect the hell out of the founders that show up every day to try to grow back into that valuation. And we've seen some of them do it, right? Like we've seen companies. It's happened to us. We saw companies that they raised$8 million in revenue and raised money at a crazy multiple in 2021. That money gave them the runway. The company is now north of 12x the revenue and is probably just now growing into that valuation. And I have a ton of respect for those founders. They're doing it the hard way. They're eating glass for years to grow it to that price. But just know that's part of what happens in this business.

28:24So, you know, as an industry, we price ahead.

28:29Michael Eisenberg: That's what we do. We don't price behind. We price ahead. And the more you're risk on, the further ahead you price.

28:41Josh Kopelman: You've used the term trade a bunch here. Yes. You think the founders think about this as a trade?

28:47Michael Eisenberg: Differentiating between the people buying into these trillion-dollar companies, the founder doesn't know who they are. You're a pension fund putting a billion dollars into a$30 billion. You're not investing to partner with a company. You're not partnering with the founder. You are trading. Previously, that would happen in the public markets. you would go at a Robinhood or your broker and you'd trade the stock. Today, you trade the stock in the private markets. I would differentiate that as a trade versus partnering with founders

29:25Josh Kopelman: in the C to A or B phase stage where that isn't a trade. That's partnership. Historically, the venture capital business has been what I would call a young man's game. Yes. Bill Gurley and I used to joke about this a fair amount. When was the point that we became old guys in the game? So you and I are the same age. You've been doing this for a fairly long time. You had a startup career before doing this. I had no career before doing this. And, you know, we're both doing this a long time at this point.

29:54Michael Eisenberg: Yes.

29:55Josh Kopelman: Are you able to still partner with these younger founders? Are you still as relevant? Do they think you're as old? Like, why do they want to partner with you?

30:03Michael Eisenberg: I think every founder is different. But in general, I've been fortunate that I've seen a lot of movies. hundreds and hundreds of founders, both the ones we backed and the ones we said no to where we should have invested. Venture is a humbling business. I look back now at the tables I pounded inside my partner meeting to either invest or not invest over the last several decades and realize that my level of confidence, yeah, it's okay to be wrong, but the level of confidence I had in those decisions is the thing I regret. So I feel right now the benefit that I offer founders and the reason founders choose to partner with me is because I feel like I owe them two things.

30:51Michael Eisenberg: I owe them my unvarnished opinion, whether I agree with them or not. They have a lot of choices as to who to choose. It's a founder's market. They have a lot of choices as to whose capital to choose. So if they're going to choose mine, they should at least get what they're paying for, which is the benefit of the movies I've seen, where I can tell them most of the time when the movie starts like this, it finishes like that. But after I offer them my unvarnished opinion, I also recognize now that I owe them my unwavering support. I am one data point. Every day founders are just like besieged by data from their employees, from their customers, from the prospects that don't convert to customers, from the press, from their shareholders, from the VCs that don't convert into shareholders.

31:36Michael Eisenberg: And they have 10 times the context and the data. So I feel like, look, if I offer them my unvarnished opinion, then they're driving the bus as they should. And a large part of what we do is incredibly relevant, right? Going from zero to one, the hunt for product market fit, your pricing, positioning, distribution, go to market. All of those challenges are real challenges that every business faces, whether you're building hardware or software, whether you're AI or SaaS, whether you're putting rockets in space or doorbells on doors. These are the business, these are the challenges that every founder has in the beginning.

32:18Michael Eisenberg: The first 24 months of a company's life are just a magical time. You are hiring the 10, 20 people that are going to hire everyone else. You're not just writing what the culture is, but you're actually instantiating it through your actions. And sort of having been privileged enough to partner with so many founders at this stage, I just consider myself really fortunate to have learned an incredible amount from the people I invest in.

32:45Josh Kopelman: I want to push back on something you said about your own humility, which is You said, if I regret one thing, it's the conviction, the level of conviction I had. I think one of the interesting things about the venture business is you actually need to have that conviction to invest the money, even when you're wrong. Because, A, the founders are looking for that conviction from the partner they're going to partner with. Because it's a hard journey for the founders, and you need to have that conviction. So even though you're going to be wrong about your level of conviction six times out of seven, it's for the one that you happen to be right about.

33:20Josh Kopelman: And being along with the founder of that journey, you need that level of conviction.

33:23Michael Eisenberg: I hear that. And there's a lot of truth to that. Where I'd push is that I think situational awareness is really important.

33:34Josh Kopelman: That's a hot phrase these days.

33:37Michael Eisenberg: I'll change the phrase. It's okay. It's good. He's back in the game now. I think the honeymoon's over.

33:43Josh Kopelman: He's back in the game. Good for him. Good for him.

33:45Michael Eisenberg: And he learned a lesson. Good for him.

33:47Josh Kopelman: Listen, I think he's directionally, my own view is he's directionally righteous over levered.

33:51Michael Eisenberg: He won't be that. He won't be going forward. Yeah. And so I think it's fair to acknowledge that when you start a company, there are more unknowns than notes. There are. and so actually when I say sort of talk about the conviction I mean that I would sort of just focus on the few data points that were known and I wouldn't sort of acknowledge look VCs in general we have to be risk seeking like that's where we are we get paid to seek risk not avoid risk period like we work on behalf of our limited partners to seek risk out but I also feel it's important to be able to identify the risks you are taking.

34:36Michael Eisenberg: And so I feel that it's fine to have conviction in a company and to believe that, but you should at least do so knowing the full sets of risks that you and the founder are signing up to on this journey. And you could have conviction that you will overcome those risks. You could have belief that the bet is worth, it's a big enough, bold enough bet, and that you should swing. and you're excited to partner with the founder on that swing. But you shouldn't delude yourself, I think, into sort of ignoring the areas that are against you. I think because if you actually know those things, you could structure a strategy and build a plan around them rather than hiding it.

35:21Josh Kopelman: Did you know all the risks at Birchbox, at Uber, at Roblox? at, what was the first investment of

35:30Michael Eisenberg: first-round capital? I couldn't even tell you.

35:34Josh Kopelman: Did you know the full set? There's no way to know this.

35:39Michael Eisenberg: No, nor do I think you could know all of them, but you could know some of them.

35:42Josh Kopelman: Some, yeah.

35:43Michael Eisenberg: I keep finding I'm undone

35:44Josh Kopelman: by risks that I didn't know existed. And in many cases were unknowable. Yeah, that's fair.

35:50Michael Eisenberg: But there are knowable ones.

35:51Josh Kopelman: There are some knowable ones. Rumsfeld's unknown unknowns though. The upside and the downside tend to attend to informers. So at 16, you started in Fanautix. I want to go back to that one second.

36:02Michael Eisenberg: 16? Were you 6L or you were 6L? No, I was in Fanautix. I was 20. 20.

36:08Josh Kopelman: You were still a student though, right? Mm-hmm. And what did you see that caused you to start in Fanautix?

36:16Michael Eisenberg: So I co-founded Fanautix. Look, I think we grew up at a magical time. Went to college, got there in 1989. The web browser didn't exist. um ncsa mosaic the first web browser came out 90 you won and you know i graduated barely because i started i co-founded a company in 91 but i graduated barely in 93 so we went from a world with no internet to a world where the internet existed we went from college with no email address to they still didn't give them out to everyone by the time we graduated but you could go get one so I had one of the first UPenn email addresses because I went to get it and so I think it was my sophomore year the web browser came out and I just got hooked I just went down that rabbit hole what's really interesting is I think when new technologies come out there's a very interesting phenomenon and it's happened multiple times over the last few decades, it's a leveling thing.

37:27Michael Eisenberg: For a short period of time, when a new technology comes out, the gap between the expert, who's been in the business for 20 years, and the rookie, who's a sophomore in college, levels. And that's kind of what happened, you know, in 91, 92, 93. I spent all my time pretty much on the internet, building an internet company, going deep in what's happening. And I think by the time I graduated, there weren't many people, if any people who were in the traditional package software way of selling and building software that had more internet experience than I did. By the way, you saw the same thing happen when Bitcoin came out.

38:13Michael Eisenberg: Yep. When Bitcoin came out, there were people in dorm rooms at universities who had far better understanding and trading strategies around Bitcoin than the derivatives or special desks at Goldman Sachs, J.P. Morgan, or Morgan Stanley. Now, over time, it catches up. But there is a moment in time where it really favors the rookie over the incumbent. And I just feel very fortunate that the internet wave was one of those times. And, you know, and I was that rookie.

38:49Josh Kopelman: What did Infonautix do?

38:50Michael Eisenberg: So Infonautix built, so back in the day, there was no, this was pre-search engine.

38:58Josh Kopelman: Nobody's going to believe this story. So it's just important to get it out for the modern audience.

39:00Michael Eisenberg: There was no, like, newspapers weren't online. Magazines weren't online. Wikipedia didn't exist. So if you were a kid in school and you did research, you went to your library and physically found things. Maybe the library was advanced and had a CD-ROM. So we said, well, why don't we build, I think LexisNexis was around at the time, and Westlaw. And there was a dial-up service called Dialog, which had like newswires for business. And we said, why don't we build something. And CompuServe. CompuServe, AOL, and Prodigy with the three big online channels. And we said, why don't we build something for students?

39:37Michael Eisenberg: So we built a product called Homework Helper that we sold on America Online. And we sold on Prodigy and CompuServe. And it was the first educational-focused sort of reference. So we went and got newspapers. What's crazy is newspapers didn't have digital archives. They didn't even have digital formats. They went straight to printing press. So we were scanning newspapers in. We were shipping. We cut deals with 50 magazines from Newsweek to Time to newspapers to Cliff Notes to encyclopedias. And we were shipping it all overseas to be scanned and keyed in. And we made it searchable. And we sold it to families, schools, libraries.

40:27Michael Eisenberg: We were ahead of our time in so many places. But we were wrong in that we bet that information will be protected and closed. We bet on closed rather than open. And what ended up happening is like, you know, everyone ended up hosting their own information on their own web servers. Newspapers went open. Magazines went open rather than closed.

40:52Josh Kopelman: You know what's stunning to me as I think about this? There's this whole conversation going on now about Anthropic, you know, cutting the bindings off of books and scanning them to teach the LM. And it's like back to the future.

41:03Michael Eisenberg: And then Google, there was a period of time where Google was doing it. They had a massive class action lawsuit in that area. You were way ahead of your time. Now, we had permission from every single source that we put in there. You know, the other thing, you know, I learned so much. The other screw up was we went to the publishers with a business model. We said, we want to sell to consumers for this price, and we'll set aside that amount of money. It was only like 18 months later that we realized if we need to change our price or our strategy, we had to go back and renegotiate with every single one of these publishers to have the flexibility to be agile.

41:40Michael Eisenberg: And so, yeah. And what happened to Infonautix in the end? Infonautix went public, went public, and ultimately ended up merging with a company called Two Cows that I believe was still around now. Is it really two cows? I think so. Who took you public? Infonautics outlasted its bankers. It was Hamburg and Quist, Cowan, and Oppenheimer.

42:03Josh Kopelman: But Oppenheimer is still around. Yep. And Cowan, I believe, is still around, actually. And Hamburg and Quist became part of J.P. Morgan. This was the old days of the Four Horsemen.

42:11Michael Eisenberg: Yep.

42:12Josh Kopelman: Hamburg and Quist, Robertson Stevens, Montgomery Securities. Look at you.

42:16Michael Eisenberg: Good memory.

42:16Josh Kopelman: I'm doing a lot of work on this these days. I think that time may be coming back. I'm hoping he's going to come back on the Tel Aviv Stock Exchange as the place where these infinitics companies go public, maybe with a little more revenue, even adjusted for inflation. So at 20, the university I went to where I edited the college paper was one of the first places to get desktop publishing, which no one knows what that is anymore. But PageMaker, Aldous PageMaker, and Quark. and quark in the days where the real newspapers, like the ones you did business with, wouldn't let desktop publishing, because that's not the way you lay out a newspaper.

42:50Josh Kopelman: That's right. The Harvard Crimson wouldn't have it. And so I'm thinking today about 16 to 20-year-olds, and I had sitting in that seat not long ago a young man named Amir Fisher, who's 16. He made a fascinating observation. He said that my high school class is divided between people who spend their time on AI and learning on YouTube versus those that are on TikTok and Instagram. And the brain can compound a lot faster taking in content from YouTube. He's talking about educational content from YouTube and AI, whereas it decompounds, so to speak, when it's on TikTok and Instagram, which I thought was a profound comment for a 16-year-old, for anyone.

43:32Michael Eisenberg: It's a profound comment. It's a profound comment.

43:33Josh Kopelman: But the point about the 16-year-old, the teenage brain compounding at that rate, is stunning. So here you are at a ripe old age, but you started compounding when you were in college. What are you telling kids today who are teenagers to do to compound their brains or to compound, you know, the learnings, for example, that you got out in phonotics at that time that you then parlayed into after common adventure career?

43:59Michael Eisenberg: I think it's an incredible like it's a scary time because there's so much uncertainty. The aperture of possible scenarios is so broad. But I also think it's an incredible time in that the ability to use AI to learn and to create is unlike anything I've ever experienced before. And so if you are 16 years old and you're into fantasy football, great. You can do fantasy football. Just cloud code a tool to help you win the draft. and it's not hard to do. It's pretty forgiving and it gets better with every release. If you're into research, great. I just believe that you have the ability to create things.

44:48Michael Eisenberg: Look, by and large, most of our societies have created a culture of conformity. And what does that mean? It means that they figured out that in order to educate the widest number of people to achieve the widest possible outcome to get as many of them up to middle class, they have a pipeline. And it's this conveyor belt that we put kids on. We put them on this conveyor belt and we say, all right, in high school, you're going to take these classes and a teacher is going to stand up and teach you this thing from this curriculum. And then towards the end of high school, you need to have the right summer internships or summer activities to get into the right recommendations to get into the right college, where, again, you need to have the right major, right advisors, right summer jobs in order to land.

45:34Michael Eisenberg: And, like, these kids are on this conveyor belt of conformity. You know, like, there's an overused term, but I think it's true, which is, like, we've taken the agency away from these kids. Even in college, they show up their first day. The teacher hands them, here's the syllabus for the class. Like, the students don't need to guess what to read. The teacher tells them what and when. The students don't need to guess what's going to be on the test. The teachers actually give them test prep. The teachers give them the cheat codes to the class and say, your final is 50%, the midterm is 30%, class participant, whatever it is.

46:16Michael Eisenberg: They know what winning looks like. And yet in life, no one, when you're starting a company, no one tells you what to read and when to read it. No one tells you what winning looks like. And so, so much of what, like we've seen with founders is they have to, they can't follow a map. They have to, they have to build their own map. Founders are cartographers and we raise navigators. And I think AI is reducing the friction to be a cartographer, to have agency, to build and to create. You know, like for most of our careers, software engineers were the folks that created value.

47:02Josh Kopelman: Yes.

47:02Michael Eisenberg: They sat down and listened. They were the ones, they were like the scribes who could like hear what you want to build and write in, instantiate it in their language, which was code. And they were the limited commodity. We're rapidly approaching a point where English is going to be the language of creating software or creating something. And that's going to be massively freeing. So that, you know, for me, I'm like, I think that at least for the next five to 10 years, not just like being AI native, but AI fluent and taking the tooling that's already so powerful and bringing it into your areas of interest, your areas, like the areas of focus.

47:49Josh Kopelman: I want to ask a nitpicky question. Is AI a language or a tool? Is English the language and AI the tool or is AI a different language?

47:58Michael Eisenberg: I don't know. I would argue that the way it's being built today is English is the language. I found myself up to three in the morning because I have so many cloud coding. And I'm not a strong engineer. And I'm speaking English to it. What are you running? So I'm building MCP servers for things that don't have MCP servers because I'm hooked on like the ability to query things. So, you know, whether it's like, oh, you have ring cameras, there's no MCP, no problem, I'll build one. And, you know, and so that's pretty much what I'm doing. And my basic setup is just a cloud code setup. Like it's a tool, like you could be a collector of baseball cards and you want a tool to manage that.

48:38Michael Eisenberg: You could be in fantasy sports. You could be doing medical. You could be like, you think you want to be a doctor. You're great. Like, just build something. Is your wife building? She is building with different tooling. So she's using a program called Town, which is a first-round company. But it's basically like a managed Claudebot type of thing, and she's using that to help her manage her life.

49:02Josh Kopelman: My wife decided this summer to teach herself Claudecode. And? I'm waiting to see the results still. No, no, she just started a few weeks ago. And I think it's inspiring. It is. It's inspiring. And I think it's giving.

49:16Michael Eisenberg: And I think five years from now, you won't even view it as code. Five years from now, like there's so many things that YC got right that I didn't give them credit for in the beginning. I was skeptical. But one of the things that I think they realized early on was that it's far easier to take a 23 year old engineer and teach him or her business, teach him or her how to sell, teach them what word revenue and margin means and the hunt for product market fit. than it is to take someone who spent 20 years in business and teach them how to code. And sort of that whole generation of, you know, sub-26-year-old technical founders just got put in business because of that.

49:58Michael Eisenberg: And they were right, and it created a ton of value for the ecosystem. It'd be interesting to see five years from now if that is still the case. I think that's profound.

50:09Josh Kopelman: I agree with that.

50:10Michael Eisenberg: because I would argue that they previously recognized the value that these scribes have. And these scribes captured so much of the value. Why should they be translating someone else's program? We'll just like a business idea. We'll just give them the business. And it was so much easier to teach them business than teach everyone else to code. Not today, but maybe 2030, around 2030, where if you just like extrapolate the data points, I wonder what it means for the... And again, I don't want to speak in absolutes. Of course, there's going to be massive opportunities for technical founders. But I think there will also be a ton of value unlocked, created for non-technical founders who previously didn't even know where to start.

50:53Josh Kopelman: If that was YC 12 or 13 years ago, and today the world is headed to what you described.

50:58Michael Eisenberg: It's one scenario.

50:59Josh Kopelman: One scenario. What are you investing in today?

51:05Josh Kopelman: What do you want to invest in today?

51:07Michael Eisenberg: I mean, at the seed stage, we pick people and problems. We want to... No theses.

51:12Josh Kopelman: What?

51:13Michael Eisenberg: No theses. We are not thematic. Okay, so no theses. But what do you want to invest in? People and... I mean, like, by the time... We invest so early that by the time we as a firm are smart enough to come up with a thesis, it's too late. So, you know, we're hearing from founders about problems that we didn't know about. we love founders who have gone unreasonably deep with customers it could be a technical founder it could be a non-technical founder and we love problems that are urgent, large and pervasive and we've done a lot of application layer in AI but we've also done some info we've done tooling and dev tools we've done military and defense tech We've done life sciences in some cases.

52:06Josh Kopelman: There's a thesis that AI breaks the seed model. You clearly disagree with that. So give me a case as to why AI does not break the seed model.

52:14Michael Eisenberg: And you're saying it breaks the seed model because companies don't need seed capital to get started?

52:17Josh Kopelman: Yeah, they get much farther along. I don't know.

52:21Michael Eisenberg: I think that at least what we've seen is that to date, even – let me give you an example. You could have five, you could have 10 different companies using today's tools to create a company in the same space. We see that all the time. There are 10 companies chasing the same market. They all don't build the same thing. Like, it's not like they say, oh, we all have access to the great tools. It's not like all 10 of them build exceptional businesses. The deviation of those businesses is massive. Why? It comes down to the people. It comes down to who do they have around the table. And today, it all costs money.

53:06Whether we're funding, like, now, could things change?

53:10Michael Eisenberg: Of course. Like, if you look, you and I, historically, we've been in the money business. That's it. Like, we sell money. We sell money for stock. Like, you're a money salesman and I'm a money salesman. Now, we give advice and other things around that, but, like, we're money salesmen. And what did people who bought our product? The founders, they bought our money. What do they do with it? Historically, they probably spent 60 % to 70 % of that on people. Maybe now they're spending it on tokens. But they're still going to need the money and they're still going to spend it. And in a competitive environment where things are moving really fast, where the barriers to entry compress, the need to actually accelerate that spending actually increases.

53:51Before I switch gears for a couple of last questions, you said we sell money.

53:57Josh Kopelman: which I agree with. I mean, like... And when you sell a commodity product like money, brand matters. Yes. What does the Josh Koppelman and First Round Capital brand stand for?

54:06Michael Eisenberg: Well, I'll talk about First Round. I think if we do one thing, we want to be known for backing founders at that... First Round. Well, at the Imagine If stage, right? Like last year, we saw about over 10 ,000 businesses, all different. But all those founders used some variation of those two words. Probably the most powerful words in history, imagine if. Imagine if all children are created equal. Imagine if there was no taxation without representation. Everything unreasonable got started by someone seeing the world differently. And every founder walks in because it all is imagination at the stage we see it, walks in with their version of an imagine if.

54:55Michael Eisenberg: And we believe that through trial and error, through partnering with founders in good times and bad, in the hunt to sort of turn their imagine if to reality, we've learned a lot of lessons about that process. And we believe that we could be incredibly valuable, and we've proven to be valuable to founders who want to turn their imagine if into a, an obvious, like no longer, it doesn't no longer requires imagination to sort of something real and enduring and durable.

55:32Josh Kopelman: What's your imagine if, um, for first round for you, um,

55:39Michael Eisenberg: I think like, you know, for me, I still like imagine I get very excited about the, the, the phase that we play, right. I just get very excited about partnering with founders from day one. And so imagine if there was a partner who's been there, done that, seen that, who could be an ally in your corner. And that's like what I tend to aspire to be.

56:02Josh Kopelman: So you got involved with the Philadelphia Inquirer. I'm going to switch gears a little bit. The local newspaper.

56:10Michael Eisenberg: Yes.

56:11Josh Kopelman: By the way, did you scan that for Infonautix or no?

56:14Michael Eisenberg: No, we didn't go deal with that.

56:15Josh Kopelman: Why did you go for as chairman of the Philadelphia Inquirer? Am I correct?

56:18Michael Eisenberg: Yeah. So the Philadelphia Inquirer is the largest U.S. local newspaper that got that. Jerry Lenfest was a Philadelphia philanthropist. He started Gerald Cable and Lenfest Cable and sold it to Comcast and did very well. And he saw the Philadelphia Inquirer and he bought it and donated it to a nonprofit. So Philadelphia was, and I still believe is, the largest nonprofit-owned newspaper in the United States. And he asked me to join the board, and I said no. And he asked me a few other times. And then finally, there was an incredible investigative reporting series that they did in Philadelphia where they sent people to school playgrounds, reporters, to sample the soil and around the schools and detected a ton of asbestos.

57:09Michael Eisenberg: And it caused massive change, both at the state level, but even the EPA coming in. And, you know, our kids were playing in that. And when Jerry Glenfest showed that to me, he's like, who else is going to do this? Who else is going to be present in your community doing a public service? And the Inquirer, like all newspapers, is under massive assault, a disruptive business model. And I know the disruptors playbook. I could sing that A to Z. You know, being on the other side, you have to sing Z, Y, X. It's going the other way. And that's really hard trying to figure out how to help an organization adjust and adapt.

57:52Michael Eisenberg: And what did you do? So we've done a ton of things. I mean, when we started off, there were three separate newsrooms. You had a Philadelphia Daily News, Philadelphia Inquirer, and Philly.com. So mayor held a press conference, three reporters went, you know, baseball game, three reporters. We went down to one newsroom. We went to a digital first format where historically you would write an article for the paper and then figure out like right now we were, you know, digital is our product. We've embraced podcasting. We've sold, we sold our printing press, right? Like we had a printing press at a plant and we sold it.

58:28Michael Eisenberg: It's a little bit like the giving tree where, you know, you keep cutting off branches. I hope it's still there. I hope you end up with more than a stump. But our digital product now, we went from having no mobile app to a full mobile app. Digital represents the entire future of that business. Does it make money? With philanthropy, we are finally breakeven.

58:50Josh Kopelman: With philanthropy.

58:51Michael Eisenberg: Each year. And philanthropy is going to be a part of it. Philanthropy has to be a part of it. But I think basically the newspaper went from default dead over the last 10 years to default alive.

59:03Josh Kopelman: That's amazing.

59:04Michael Eisenberg: Yeah, and look, it's not as large of a newsroom, but it still packs a pretty important punch to our community, both in terms of health and wellness and local reporting, but also just a quality of life of living in a town. And I think hopefully we're sharing some of those lessons through our partners at the Lenfest Institute, which Jerry set up with other local news organizations to help them evolve as well.

59:32Josh Kopelman: So speaking of taking on hard problems and impossible problems, post-October 7th, you took on Web Summit and Patty Cosgrave. Maybe some other people had some hands in that too.

59:43Michael Eisenberg: Yep.

59:44Josh Kopelman: You paid a price for that, I think.

59:46Michael Eisenberg: I did.

59:47Josh Kopelman: Take us through your thinking, the price you paid, why you decided to do it. I consider you, by the way, among not just venture capitalists, but people generally fearless.

59:57Michael Eisenberg: I appreciate that. Look, I think we're in the States. We were just all traumatized by what happened on October 7th. And I live in Philadelphia on October 8th. October 8th, Rittenhouse Square is the main square. It's like Central Park in New York in Philadelphia. And on October 8th, there was a massive anti-Israel protest, screaming of genocide. Like the buildings were still burning. We didn't know what happened, and it was the day after. And I think maybe the day after that, Patty started tweeting about Israel as a genocidal actor. And so I just felt like, I don't know, it kind of triggered me, which was I just started screenshotting his tweets because I figured he would at some point want to take them down.

1:00:51Michael Eisenberg: And then I started tweeting about it. Because just a few months earlier, he invited me to, I think, was it Doha? I forget where Web Summit was going to be that year.

1:01:00Josh Kopelman: He was in Portugal or Doha. I was also invited before.

1:01:03Michael Eisenberg: Yeah. I don't know. I feel it was a fraction of the commitment you've shown. And I appreciate everything you've done.

1:01:14Josh Kopelman: What's the price you've paid?

1:01:18Michael Eisenberg: Look, there are people out there who won't do business with me. there are people out there who are tweeting about me supporting genocidal actors and you know like i'm here in television you're okay i'm okay you're okay you and rena your wife also had the jewish encyclopedia oh boy you really converted to digital we have a crack team here well yeah so

1:01:39Josh Kopelman: when i was don't mess with delete well look when we uh at a phonetics we understood how to take

1:01:45Michael Eisenberg: content and get it available online. And I found this, this encyclopedia, it was the first Jewish encyclopedia ever created. Um, it was published by Funk and Wagnall, so I ended up publishing an encyclopedia and it was out of copyright. So the copyright lapsed. So I said, all right, I'm doing all this stuff for work, scanning all this stuff in and making it searchable. Why don't I make that searchable? And so we put that online. It's now, we ended up giving it to Safaria and they, it's part of their, they're doing incredible work at Safaria.

1:02:13Josh Kopelman: They really are.

1:02:14Michael Eisenberg: It's part of their collection. That was a random piece of trivia.

1:02:18Josh Kopelman: Have you invested in Israel from Fresno Capital? I know the answer to that question is yes. Now you're here in Tel Aviv. What are you looking for?

1:02:25Michael Eisenberg: Looking for founders picking incredible problems. I think for us and probably looking for companies here where the U.S. is their first market just because that's where we could be the most helpful and impactful.

1:02:39Josh Kopelman: I want to go back to a question I asked before to wrap up.

1:02:41Michael Eisenberg: Yes. If you had a Josh Koppelman, imagine if for the world or for Israel, what is it? Right now, I think narrative gets lost. I think facts are supposed to set you free. The truth is supposed to set you free. It's really hard for people to discern the truth. So, you know, my broad imagine if would be sort of imagine if the truth was knowable.

1:03:10Josh Kopelman: what would you do to make that happen

1:03:13Michael Eisenberg: I don't know I think a lot of it comes down to storytelling I think a lot of it comes down to advocacy and sharing facts

1:03:20Josh Kopelman: we need a demo for sharing facts bring Chris Shipley back for demo to sharing facts you should become a storyteller for this you're the best at it I know thanks Josh for joining me on short notice also we'll do another one

1:03:38Michael Eisenberg: Take care.

1:03:38Josh Kopelman: If you enjoyed this episode with Josh Koppelman, please rate us five stars on Apple Podcasts, Spotify, subscribe to the YouTube channel. If you want to get the content early, subscribe to the Aleph newsletter on our website, aleph, A-L-E-P-H dot V-C. And if you wanted to learn more about Josh Koppelman, you can follow him on X at J-O-S-H-K, Josh K. I got that right?

1:03:59Michael Eisenberg: You got that right.

1:04:00Josh Kopelman: Thanks, Josh. Appreciate it.

From the publisher

Josh Kopelman, founding partner of First Round Capital and Half.com founder, on OpenAI and Anthropic's valuations and whether AI breaks seed investing.

On this episode of Invested, Michael Eisenberg talks with Josh Kopelman about building Half.com at the height of the dot-com era, when the company convinced Halfway, Oregon to rename itself Half.com, put coupon codes on 2 million fortune cookies, and sold to eBay in 2000. Josh compares that bubble to today's AI boom and explains why First Round's fund grew from a little under $150 million in 2004 to about half a billion without changing its strategy. He also argues that late-stage bets on SpaceX, Anthropic and OpenAI are a cyclical trade, while seed is a business that can make money in both risk-on and risk-off markets.

Josh goes back to Infonautics, the company he co-founded as a Wharton student, which scanned newspapers and magazines into Homework Helper for AOL, CompuServe and Prodigy before search engines existed. He explains why founders are cartographers, why he stays up until 3 a.m. building MCP servers with Claude Code even though he is not a strong engineer, why he doesn't think AI breaks the seed model, and how The Philadelphia Inquirer, where he served as chairman, went from "default dead" to "default alive."

Josh also describes publicly calling out Web Summit founder Paddy Cosgrave's tweets after October 7th, what it cost him, and what First Round looks for in Israeli founders.

Josh is a founding Partner at First Round Capital, a seed-stage technology venture fund.  Josh has been an active entrepreneur and investor in the Internet industry since its commercialization.

In 1992, while he was a student at the Wharton School of the University of Pennsylvania, Josh co-founded Infonautics Corporation – and took it public on the NASDAQ stock exchange in 1996. Josh founded Half.com in July of 1999, and led it to become one of the largest sellers of used books, movies and music in the world. Half.com was acquired by eBay in July 2000 -- and Josh remained with eBay for three years, running the Half.com business unit and growing eBay’s Media marketplace to almost half a billion dollars in annual gross merchandise sales. In late 2003 Josh helped to found TurnTide, an anti-spam company that created the world's first anti-spam router.

Josh founded First Round Capital in 2004 to reinvent seed-stage investing. And since that time the firm has invested in over 350 emerging technology startups – becoming one of the most active venture capital firms in the country. Josh was ranked 3rd on the 2018 New York Times list of Top Venture Capitalists and consistently ranks in the top 20 of the Forbes Midas List of the top 100 tech investors. Josh has been named as one of the top ten ‘angel investors’ in the United States by Newsweek magazine, one of "Tech's New Kingmakers" by Business 2.0 magazine and a "Rising VC Star" by Fortune magazine. Josh also is the proud winner of a second place ribbon in the 2011 Nantucket Watermelon Eating competition.

Josh is an inventor on sixteen U.S. Patents for his work in Internet technology. In June 2000, he was awarded Ernst and Young’s prestigious “Entrepreneur of the Year” award for the Greater Philadelphia region.

Josh earned a Bachelor of Science degree cum laude in Entrepreneurial Management and Marketing from The Wharton School of the University of Pennsylvania.

KEY TOPICS

00:00 - Intro

01:46 - Half.com's Origin: eBay Meets Amazon

04:22 - Renaming Halfway, Oregon to Half.com

06:53 - Half.com Ads in Internet World Urinals

08:21 - Why Rate Card Is for Suckers

09:07 - Coupons on 2 Million Fortune Cookies

11:58 - Dot-Com Bubble vs. Today's AI Boom

16:20 - Why the Washout Belongs in Private Markets

17:29 - First Round's Fund Size From $150M to Half a Billion

19:28 - SpaceX, Anthropic and OpenAI vs. 20 Years of Exits

25:05 - Why Late-Stage AI Bets Are a Cyclical Trade

30:03 - Unvarnished Opinion, Unwavering Support

33:24 - Venture Conviction and Knowing the Risks

36:16 - Co-Founding Infonautics as a Wharton Student

40:27 - Infonautics' Bet on Closed Information

43:59 - Why Founders Are Cartographers

47:58 - Building MCP Servers With Claude Code

49:19 - What Y Combinator Got Right

52:07 - Does AI Break the Seed Model?

54:06 - First Round's "Imagine If" Brand

56:02 - Saving The Philadelphia Inquirer

59:32 - Calling Out Web Summit After October 7th

1:01:30 - Digitizing the Jewish Encyclopedia for Sefaria

1:02:18 - Investing in Israeli Founders

1:02:42 - Imagine If the Truth Was Knowable

RESOURCES

Follow Josh on LinkedIn: https://www.linkedin.com/in/jkopelman/

Follow Josh on X: https://x.com/joshk

Learn more about First Round Capital: https://firstround.com/

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Follow Michael on Twitter: https://twitter.com/mikeeisenberg

Follow Michael on LinkedIn: https://www.linkedin.com/in/mieisenberg/

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CREDITS

Executive Producer: Erica Marom

Producer: Sofi Levak, Dalit Merenfeld

Video and Editing: Nadav Elovic

Music and Creative Direction: Uri Ar

Content and Editorial: Jackie Goldberg

Design: Nimrod Sapir

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