Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia

8 Jan 2026 · 1 h 28 min · 39 chapters

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In short

Kevin Hartz (Astar, Eventbrite, Zoom, Sauron) discusses how tech and venture changed since the late 1990s, why he calls AI “the mother of all bubbles” while arguing we’re still early, and what AI startups can learn from dot-com survivors like the PayPal “mafia.” He also covers his teen-founder investing thesis, his PayPal-to-Palantir fraud-model connection, and personal details about having two babies five months apart via genome editing and surrogates. He explains Astar’s pre-seed/seed focus on founders and highlights several Astar-backed companies and incubations.

Guest backgrounds

Kevin Hartz is a 30+ year tech builder/investor and co-founder of Astar, Eventbrite, Zoom, and Sauron. He invested in PayPal’s seed round (reportedly ~100% of proceeds from his first startup) after reconnecting with Peter Thiel.

Key claims

AI is in a boom phase but still early at the “application layer.” Venture terms are fairer now due to more capital sources. The best early signals come from extraordinary founders and “end-of-one” opportunities (being the only team doing something weird).

Notable examples

PayPal seed investment; Palantir’s fraud-model inspiration from PayPal; Zoom built on PayPal’s API; Eventbrite’s PLG ticketing built from a PayPal-app prototype; Astar-backed Decagon and incubated Multiply (AI mortgages), 15th (AI tax/accounting), and Sauron (home security using the self-driving stack).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Kevin Hartz's Background

0:45 to 1:34

Discussion about Kevin's extensive experience in technology and investing.

“the PayPal mafia from Peter Thiel, and what makes Founders Fund so special.”

Investing in Young Founders

1:34 to 2:30

Kevin shares his philosophy on backing young founders and his fund's investments.

“This episode is brought to you by Numeral.”

Lessons from the PayPal Mafia

2:30 to 3:38

Insights from Kevin's experience with PayPal and its influence on his approach.

“It's the AI native private bank for business owners.”

AI Bubble Discussion

5:20 to 7:30

Kevin discusses the current state of the AI industry and the concept of a bubble.

“They just had these incredibly sort of aggressive term sheets and terms and could really get away with that.”

Early Stages of AI Innovation

7:30 to 9:30

Exploration of the early stages of AI and its foundational technologies.

“Then there is the sort of oligarchy of venture firms, you know, the like Sequoias and Excel and Mayfields and so on.”

Investment Strategies at Astar

9:30 to 14:00

Kevin explains Astar's focus on talent and their investment strategy for early-stage startups.

“And when that happened the last time, do you think, are we in an AI bubble?”

Evaluating Investment Opportunities

14:00 to 15:00

Learn how to distinguish between smart and risky investments in today's market.

“We still got at least 80 % of the game yet to play, maybe 70 % of the game yet to play.”

The Importance of Talent in Startups

15:00 to 16:40

Understand why investing in the right people is crucial at the pre-seed stage.

“And so we hope we can continue to deploy capital, you know, towards that.”

Lessons from the PayPal Experience

16:40 to 18:20

Discover key insights from the PayPal founding team and their journey.

“with Peter Thiel when he came back to the Valley.”

Taking Risks in Early Investments

18:20 to 20:00

Explore the mindset behind investing everything into a single opportunity.

“Were you not thinking like, oh, I should, you know, create a portfolio of angel investments?”
Show all 39 chapters

Comparing Market Conditions: Past and Present

20:00 to 21:40

Reflect on how historical market conditions relate to today's investment landscape.

“better to take, you know, those shots, you know, in my case back then, you know, I guess I went for it all at once and it just worked out.”

Navigating Startup Success in Competitive Markets

21:40 to 23:20

Learn how to identify potential leaders in crowded sectors.

“um paypal or its predecessor started in i think it was 97 and they launched the paypal product i think at the end of 98 they pivoted a few times and then you know really took off and in 99 and beyond.”

The Role of Team Dynamics in Success

23:20 to 25:00

Understand why the right team can determine the fate of a startup.

“The parallels are very strong that these patterns kind of emerge.”

Recognizing Unique Startup Opportunities

25:00 to 26:40

Discover how to find startups that stand out in their approach.

“is there were a number of search engines during the 90s.”

Reflections on Missed Investment Opportunities

26:40 to 28:00

Learn from past investment mistakes and misjudgments in the VC space.

“You know, how extraordinary, you know, grit, resilience, all these things.”

Analyzing Investment Strategies and Market Size

28:00 to 29:20

Learn about the importance of capital models and identifying market size in venture investments.

“No, I had spent some time with Lyft and kept looking at the numbers.”

Founders Fund: Culture and Decision-Making

29:20 to 30:50

Discover how investment decisions were made at Founders Fund and the cultural nuances of the team.

“And one thing you mentioned was, you mentioned Founders Fund.”

The Role of Conviction in Venture Capital

30:50 to 32:50

Understand the significance of high conviction in investment decisions at Founders Fund.

“So how did, how were like investment decisions made?”

Contrarian Companies: Palantir and Anduril

32:50 to 34:30

Explore the contrarian business models of Palantir and Anduril and their market evolution.

“The fund will return itself multiple times over.”

Palantir's Genesis and PayPal's Influence

34:30 to 37:10

Learn how the fraud detection models from PayPal inspired the creation of Palantir.

“Historically, it's like, you know, the government moves slow.”

Launching Zoom: Building on PayPal's API

37:10 to 42:00

Hear the story behind the founding of Zoom and the journey of building a business on PayPal's API.

“amongst, you know, say devices or IPs or otherwise, and then, you know, identify and find this kind of networked fraud.”

Lessons from Early Startups

42:00 to 45:00

Explore the challenges and learnings from Kevin's early ventures, including Zoom.

“and became the very first developers on that API.”

Transitioning Roles in Business

45:00 to 49:30

Discuss the importance of knowing when to step back in a company leadership role.

“So then obviously you didn't do that with Zoom right away.”

Creation of Eventbrite

49:30 to 53:10

Learn about the origins and development process behind Eventbrite's ticketing platform.

“And so we kind of worked like almost two years on just kind of iterating and optimizing that.”

Eventbrite's Acquisition News

53:10 to 55:00

Kevin shares insights on Eventbrite's recent acquisition by Bending Spoons.

“And, you know, this is just the general notion that you don't go and you don't do what your parents did, like which is go to one company and work your whole career and get a W-2.”

Investing in Young Founders

55:00 to 56:00

Discussion on the trend of investing in teenage founders and early-stage entrepreneurs.

“and it's like a sensationalist headline.”

The Rise of Teen Founders and Z Fellows

56:00 to 58:20

Explore the trend of young entrepreneurs and the impact of Z Fellows on their success.

“He's got a program called Z Fellows and he backs dropouts.”

Investing in Diverse Sectors: A-Star Insights

58:20 to 1:00:20

Learn about the various sectors A-Star is investing in and the innovative companies involved.

“So you think it makes the most sense when it's something that's like, they have an insight or an industry is like, obviously going to look radically different.”

Innovating Home Security: The Sauron Approach

1:00:20 to 1:02:30

Discover how Sauron is revolutionizing home security with innovative technology.

“with a number of companies that didn't make it.”

Challenges in the Home Security Market

1:02:30 to 1:05:30

Understand the limitations and challenges faced by traditional home security providers.

“And then my kind of like little darling incubation has been Sauron, which is home security.”

Family Life and Parenting Challenges

1:05:30 to 1:10:03

Listen to a discussion about parenting challenges and the dynamics of children's food preferences.

“settled into is a number of the assets you mentioned settled into private equity or again into the like big oligarch, tech oligarchs.”

Navigating Children's Eating Habits

1:10:03 to 1:12:05

Discussing the challenges and strategies in introducing diverse foods to children.

“And I mean, huge credit to my wife of like being super patient and like, you know, strategically introducing different foods.”

Cost of Dining Out: A Modern Dilemma

1:12:06 to 1:13:18

Exploring the increasing costs of family meals compared to fine dining options.

“You could pay 20 bucks and get a really nice dinner.”

Making Choices in Family Planning

1:13:19 to 1:14:57

Reflecting on the decision to have more children and the impact of technology on family planning.

“I don't remember his name, but he's got the book.”

Understanding the IVF Process

1:14:58 to 1:16:55

Describing the steps involved in IVF and the role of genetics in embryo selection.

“resolution of, of all the embryos that we chose from.”

Ethics and Concerns in Genetic Selection

1:16:56 to 1:19:56

Discussing the ethical implications of selecting embryos based on genetic traits.

“So you mentioned you, you get to see the embryos and does it, does it like simulate kind of what might happen to the baby in terms of like, I don't know how they like grow health things.”

The Art of Collecting: Insights and Strategies

1:19:57 to 1:23:32

Exploring art collecting as an investment and its emotional significance.

“It's just like, your kid is hit with something that like, is uncontrollable.”

Getting Started in the Art Market

1:23:33 to 1:24:00

Providing guidance on how to enter the art market and build connections.

“kind of hit rock bottom relative prices.”

Navigating the Art World: Tips for Beginners

1:24:00 to 1:26:45

Learn how to start investing in art and the importance of relationships in the art market.

“happening in the auction houses and elsewhere.”
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Transcript

Automatic transcript. May contain errors.

0:02Turner Novak:Welcome to The Peel. I'm your host, Turner Novak, founder of Banana Capital. Today's guest is Kevin Hartz, co-founder of Astar, Eventbrite, Zoom, and Sauron. Kevin has been building and investing in technology companies for over 30 years, and we talked about how the industry has evolved, why he calls AI the mother of all bubbles, why we're still early, and lessons today's breakout AI companies can learn from those that survived the dot-com crash. Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at Astar is invested in teenagers, and he shares how he identifies that wire talent so early from seed investments in Airbnb, PayPal, and Pinterest to many of today's hottest AI companies.

0:39Turner Novak:He also shares the insane story of investing 100 % of the proceeds from his first startup into PayPal's seed round, how PayPal's early fraud systems inspired Palantir, what he learned from the PayPal mafia from Peter Thiel, and what makes Founders Fund so special. We also talk about how he and his wife recently had two babies, five months apart, using genome editing and surrogates. I also want to call it the obvious that Kevin is a co-founder of Eventbrite. If you've been following the company, they're in the middle of closing an acquisition, selling to Bending Spoons. For legal purposes, we had to cut most of our conversation related to that, but hopefully Kevin can join the show again sometime and we can run it back.

1:14Turner Novak:A quick thank you to Ramtin Naimi, Navia Goodimetla, and Bennett Siegel for helping brainstorm topics for Kevin. A reminder that I publish two episodes of The Peel every week, exploring the world's greatest startup stories, just like this one. Check out the back dialogue of over 100 episodes and tune in next week for conversation with Marcelo Lebre, co-founder of GlobalHR Platform Remote.com. Now, let's talk to Kevin after a quick word from Numeral and Flex. This episode is brought to you by Numeral. Numeral is the fastest, easiest way to stay compliant with US sales tax and global VAT. It's easy to set up and they automatically handle all registrations, ongoing filings, and their API provides sales tax rates wherever you need them with all the integrations you need.

1:55Turner Novak:Numeral supports over 2 ,000 customers in both the US and globally, and they pride themselves on white glove, high touch customer service. Plus, they guarantee their work, and they'll cover the difference if they mess anything up. They're fresh off a fundraise, closing a$35 million Series B from Mayfield, which they're going to reinvest into building an even better product. If you want to put your sales tax on autopilot, check out Numeral at their new domain, numeral.com. That's N-U-M-E-R-A-L.com for the end-to-end platform for sales tax and BAT compliance.

2:30Turner Novak:This episode is brought to you by Flex. It's the AI native private bank for business owners. I use Flex personally, and I love it because I use AI to underwrite the cashflow of your business, giving you a real credit line. The best part is 60 days afloat, double the industry standard. Flex has all the features you'd expect from a modern financial platform like unlimited cards, expense management, bill pay that syncs with your credit line, and their new consumer card, Flex Elite. Flex Elite is a brand new ramp-like experience for your personal life. A credit card with points, premium perks, concierge services, personal banking, cards and expense management for your family, net worth tracking across public and private assets, and a whole lot more fully integrated with your business spend.

3:13Turner Novak:One card for your businesses, one card for your personal life, one card for everything. To skip the waitlist, head to flex.one and use my code Turner to get an additional 100 ,000 points worth$1 ,000 after spending your first$10 ,000 with Flex Leap. That's flex.one and code Turner for$1 ,000 on your first$10 ,000 of spend. Thank you, Flex. And now let's jump in. Kevin, welcome to the show. Thanks. So excited to be here. Thank you, Turner. Yeah, I'm excited to have you. You've been investing in and building technology companies for the past 30 years. A lot of stuff we can talk about. I think probably the most interesting thing to me is just like how things changed, in your opinion, over the past couple of decades.

3:58Well, Turner, I have been mostly building companies over that period of time since the mid-late 90s. And then it's kind of like, I don't know, when you're not as effective building anymore, you invest maybe? No, I'm kidding. But how has it changed over time? Like the thing that I will certainly say is that everything like in the structure of how we do things today is almost like identical to long ago. You know, the difference is that there was just it was such a smaller industry. Like I can't believe how much of a cottage industry it is. And, you know, in hindsight, I've now seen like the just sheer breadth and growth of this market.

4:54you know, the tech industry was this niche-y, small little area, and now all of a sudden, you know, it just covers so many different things. Then when you go to the, when you think about venture and investing, without a doubt, the, you know, the power or the authority or so on was in the hands of the venture capitalists. They just had these incredibly sort of aggressive term sheets and terms and could really get away with that. And that's changed dramatically as well.

5:37Turner Novak:What do you think caused the change? Is it just there's more fun? So like if you give me a bad deal, I just go to someone else? Exactly. It's a supply and demand thing. There is, you know, much more capital, much more capital sources and somebody's, as you said, will do things, you know, to the terms that are much more fair. So, you know, you see valuations rise, but also you don't see these ratcheted terms of, you know, 3x liquidation preferences or things that used to be fairly common in the past. So even in a down the fairway seed round, companies raising$5 million, it's like a good product in business, they would still get like a 3X liquidation preference from a good fund?

6:33I guess I'm like giving an example of like a ratcheted term. It really depends from deal to deal. You know, it was much more bespoke. You know, here in this day and age, we just do these like quick safe notes and they're all fairly standard. But everything was kind of cooked up individually to its own situation. And that situation was usually very well controlled by the investor. And it was probably that it was a lot harder.

7:06Turner Novak:Like you couldn't just go on the Internet and type in best seed investors and get a list of like a thousand people. And you're probably connected with some of them. Some of them probably take cold pitches and you get 100 meetings today. I don't want to say it's easy, but probably way easier to meet 100 investors today than back in the 90s. Yeah, I don't even know if you could find a list that long back in that time period. Then there is the sort of oligarchy of venture firms, you know, the like Sequoias and Excel and Mayfields and so on. Is there any other ways you feel like the broader venture industry has changed?

7:53Turner Novak:Like, do you feel like people behave any different or like, are we smarter, maybe dumber than we were, you know, in the past? I don't know. You just see different behavior primarily motivated by the amount of competition, you know, which by the way is good. And I'm not, you know, I'm actually an advocate for an environment such as this because it's great for founders. You know, I guess if I put on my A-star hat, it would be nice to have not as much competition out there. But, you know, this is where innovation comes is when you have relative plentiful capital available for these businesses to experiment in a lot of ways that in previous eras and periods and so on, the money just wasn't there.

8:51And now you see financings in all these different countries of the world and all these different segments of, you know, innovation and technology. And so that's really, really great.

9:07Turner Novak:Yeah. One thing you mentioned, you kind of hinted the current environment. And I guess, you know, some people would say like today, are we in the AI bubble? I saw a tweet from my friend Finn Murphy saying he saw his first 1 ,000x ARR round close, which is, I think we're round tripping back to 2022, the very beginning of 2022. And when that happened the last time, do you think, are we in an AI bubble? Or how do you feel about the AI bubble if we are in one? well we are in an ai bubble and i would call it the mother of all bubbles it'll be a bubble that you know makes every other bubble look like a tiny tiny you know little bubble you know we can call it a super cycle is is a good description of it however you know two things one is we're still in the very very very early stages whereas like the wall street journal and new york times and everyone else is saying oh it's going to pop any minute and core weaves down 50 and it's already starting to happen and uh you know two i think it's it's really good and i'm you know when i say bubble like i always see capitalism as like a pendulum.

10:36It never just kind of stays right in the middle. It's either swinging, you know, too far towards, you know, like the bust side or too far towards the boom side. And we're on the boom side, you know, right now. But to the point earlier, we're in the early stages. And the reason I say that is that we're still at the very low layers of the innovation revolution here in AI. And that is, if you go all the way down deep into a system, it's the chip and NVIDIA is still cranking along and selling chips. And that just kind of lays the groundwork for all the great things to happen on top of it. Of course, you're building data centers around that.

11:27But then the foundational models, you know, Anthropic and OpenAI, not to mention all the existing players, you know, have these, are building these foundational model platforms. But what I'm most excited about in what we've been, you know, investing in as aggressively as we can is the application layer. And we're just in the early innings. And so, you know, if you can kind of picture things coming up and up and up, we're now starting to see, you know, companies like Cursor and Cognition and the Codeco pilots really ramping off as like the ramping up as these like kind of first enterprise segment.

12:16And you're also seeing, you know, Decagon and Sierra and the customer service world ramping up, but there's still so much more to be done. And, you know, there's still so many categories to happen that, you know, again, I think this is going to, or I know this is going to continue for some time.

12:39Turner Novak:So those are like famous last words, though. It's like, you know, we're still early, like this has more room to run. What makes you so confident? Is it just that like, not enough people are using it and it's a useful technology and it's clear that like this is you know this is what the future of all software is going to look like where it's you know quote unquote applying ai to like do work for you and we're only like 0.1 penetration and it's going to get up to 100 software so there's just like a thousand extra room to run or something like is that basically the argument or is there something more than that right i mean you know, like what are these chips producing?

13:17What are these foundational model companies producing? You know, it's the application layer. And you look out at all the companies throughout the country and the world that can lower their OPEX and dramatically decrease things through, you know, kind of BPO replacement or, yeah, just all the other areas of automation. you know, it's like, it's almost embarrassing how far along we are. Like we're just, you know, just in the like first inning or maybe we'll say second inning, not to be too bullish.

14:01Turner Novak:Yeah, fair. We still got at least 80 % of the game yet to play, maybe 70 % of the game yet to play. So then when you're investing today, like you run A-Star, we can talk a little bit more or maybe about the kind of theses you guys have, where you fit into the market. But how do you kind of separate what is maybe smart to be deploying capital into today versus not deploying capital? So ASTAR is a pre-seed and seed fund primarily. And we're the$300 million fund. We're just wrapping up our second fund. And, you know, for us, it's really a focus around talent and people. Because, you know, at those stages, what else do you really have?

14:52You don't have working products and things of that nature. So we're really making bet on the right people. And so we hope we can continue to deploy capital, you know, towards that. We backed Decagon, for example. We seeded Decagon, which is this customer service, AI customer service rep. And it's Ashwin and Jesse, the two co-founders are extraordinary people. And that's really what's lifted and drives the business.

15:28Turner Novak:Is the people, the founders and the team? Yes. And, you know, they set the cadence. they you know find that right talent you know in like kind of in the the notion that they expect to you know hire towards you know like their vp of engineering or their new vp of sales like all in incredibly driven like fast builders so i think if i was talking to pretty much anyone else and they told me this, that it was all about the people and the talent, I'd be like, every VC says that, you're full of shit. But when I look at your track record, it's like, you did this with Pinterest, Airbnb, PayPal. There's probably a bunch more that I'm forgetting that they're in my notes.

16:22Turner Novak:You've done it so many times. So how do you do it? How do you find really good founders super early like that? Well, I think like I was lucky that fairly early on in my career, Peter, like I invested in the seed round of PayPal, you know, reconnected with Peter Thiel when he came back to the Valley. I had known Peter from student politics at Stanford. And, you know, he was an extraordinary person. Like at Stanford, people are smart. And then there was like Peter who was, you know, like head and shoulders above that. Am I remembering that you guys were kind of like opposite sides in the political spectrum?

17:05Turner Novak:Am I remembering this right? I was chair of the Stanford Democrats. And, you know. Okay. And he was, he like added the Stanford Review, right? Yeah. Yeah. I mean, you know, like it was at a time where some of these issues were boiling that people actually, you know, could listen and respect other opinions, which is makes me sad today. But that's an aside. But Peter's was just extraordinary at bringing, you know, his team together. And so I got this amazing lesson. And, you know, I'd come off a very modest sale of a company. We were providing high-speed internet access to hotels in the mid-late 90s.

17:53And a public company called LodgeNet acquired us. And I had no large portion but, you know, some cash and put as much as I could into, you know, into PayPal.

18:12Turner Novak:What percentage of the exit proceeds, you know, post-tax and everything, do you think you invested in PayPal? I think it was like 100%. What else would I do with it? Yeah, fair. Were you not thinking like, oh, I should, you know, create a portfolio of angel investments? Or was it just like, this is an incredible team and insight and market and time, and I'm just going to give them all my capital because they're going to build something amazing? It was the latter. And, you know, I was at an age where I could, you know, take these shots on on goal. And the status quo at the time was like, oh, you should always put aside, you know, most of your earned income and maybe put some into mutual funds or something.

19:01There were all these stock gurus and money managers that would tell you how to save up and that in 50 years, you could have enough to retire. And that just wasn't of interest. And maybe that's where my early VC self was showing. Yeah.

19:26Turner Novak:I mean, if you're thinking about, if you look at the data on the asset classes as a whole, venture typically outperforms on average. And then there's a massive skew too with inside venture. It's like the highest performing, widest variance. So you either make a lot of money or you lose it all. So it's, I mean, if you're really thinking about, I'm trying to make a lot of money here, Like it's probably the smartest bet if you know what you're doing. Yes. I mean, you know, the venture side, you get a number of shots on goal and it's almost better to take, you know, those shots, you know, in my case back then, you know, I guess I went for it all at once and it just worked out.

20:18But to the point, I think it was like more of seeing this team together and seeing what an incredibly functional and the ingenuity of that team and the things they did to win, like, were just above and beyond. They just outsmarted everyone on every plane when they were expected to not be able to do that. And you see why now today, when you look at the caliber of all those people, they're all extraordinary in their own right. And what a special period to have them all together.

21:02Turner Novak:Yeah, so I think I was probably six or seven when PayPal was founded. So I do not remember what it was like at that time. So were they, was like the PayPal team kind of today, it's the PayPal mafia. Most people listening to us have probably heard of that. Were they not kind of as highly regarded back in the 90s? Like was it just kind of a bunch of random guys and nobody knew what they were going to become? Yeah, I mean, completely disregarded. in fact you know what happened is that you had the dot-com boom in the late 90s you know they um paypal or its predecessor started in i think it was 97 and they launched the paypal product i think at the end of 98 they pivoted a few times and then you know really took off and in 99 and beyond.

22:00And then, so when they were really cranking, you know, it was 2000, 99, 2000, and the internet economy was like over in overdrive and everything looked like it was incredibly great. And nobody could do, you could do no wrong in the internet side. And then the bubble burst. And, you know, they, then they were almost seen as anonymous or they, They weren't considered, it was just considered like they would go out of business or that they wouldn't make it or they would kind of count it out when in fact, you know, it was a substantial business and it was growing so fast and doing so well.

22:42Turner Novak:And so, like, are there any parallels between now and today? Like when you look back in the same time periods, like I have a friend who there's a certain category of AI company. And he's just like, every single startup in this category is working. Like everyone is ripping and all my friends are invested and they're like, oh, you know, blank, you missed out by not investing in this specific category or you got to put some capital to work. And his thing is like, that is bad. Like, I'm scared that everything in a category is working. So I don't know. It's kind of like that story really resonated with me.

23:19Turner Novak:I was like, man, But there's definitely something to that of like, you know, is it does like the success of certain categories today kind of mask or hide certain under radar founders or like, are there any do you feel like there's any parallels between now and today? The parallels are very strong that these patterns kind of emerge. Maybe the difference is that there were a couple different PayPal competitors, copycats, and when the dot-com crash occurred, they mostly went out of business, or they all went out of business. but the businesses in that time period you know if you recall you needed I guess you wouldn't because you were six or seven years old but like they needed like the infrastructure like you buy your own servers and you fill up like your server cage you'd go down to like stop the market and go into your cage and like you know rack your your servers up and so things were expensive to manage and maintain and there is like high complexity.

24:27And so now we can see this hyper growth happen, like, you know, say on the, you know, coding co-pilots, you can see this rapid growth happen. And then the markets today are so much larger, like you have such a larger TAM of who you can reach. The number of developers, you know, for example, that you just see a group of players up and to the right. However, if I were to draw back another analogy that's maybe more appropriate is there were a number of search engines during the 90s. There was like two dozen search engines and a few different that had been public or so on. And in the end, it was really just Google, like the almost last to market became the market leader.

25:21And the kind of lesson there is that, you know, on the coding co-pilot space, like, you know, there's going to be an enormous number one and then, you know, significantly smaller number two. Then who knows what happens after that. But, you know, that's about it. And so, like, the important thing is to be the market leader. Hmm.

25:46Turner Novak:And so are you thinking about that one when you're investing your building today? It's just like, can this be the number one in the category? All the time. That's so relevant. I mean, you know, in the next generation, it was MySpace and Friendster. I was an angel in Jonathan Abrams, Friendster. MySpace, had won the market. And then Facebook, the last entrant came along and took everything away. So really ensuring that you're in that and you don't want to be the one that's not going to be positioned to win the market. Yeah. How do you figure out if they're positioned to win? Is there anything you'd be dissecting or does it come back to team again?

26:39You've got to invest in the next Peter Thiel. Really comes down to team. You know, how extraordinary, you know, grit, resilience, all these things. But the other side is, you know, what you do want to find is like what we call this end of one effect or end of one factor is, you know, you meet a company where you're the only one doing something that seems pretty far. afield and really weird. I always felt like Founders Fund was so good at finding companies like that, you know, that if Sequoia, when they make an investment, you would say like, oh, that's so smart. You know, wow, I get it. You know, like how cool if, you know, Founders Fund would make an investment and you'd be like, what are they doing?

27:28That's so weird. I don't get it. And then, you know, three years later, you'd be like, wow, you know, And that's kind of the mindset. I think like Cyan Bannister, I worked with her at Founders Fund. I felt she had that great sense of finding these kind of weird things, but could see where it goes. She was a seed investor in Uber, for example. I didn't get in there until Series A. Or no, sorry, Series B.

28:04Turner Novak:Did you try before that? No, I had spent some time with Lyft and kept looking at the numbers.

28:15And, you know, I was with Logan and I like secretly felt sorry for them. I was like, oh, man, this is going to be a tough business.

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28:23Turner Novak:And I was very wrong on that one. Yeah. What do you think you got wrong? I should have thought through the capital light model more appropriately. And then certainly the size of market. But I wouldn't say Series B is later, but it was$300 million versus I think the market caps, what,$170 billion? Yeah, that's usually my threshold is like 100x, you know, post dilution, etc, like changing share price. If you get 100x increase in share price, that's, that's a venture investment. Like that's, that's kind of the target. And you can, you get all nuanced, maybe 95x counts. But like, if you get into something and it's up 300x, like, that's pretty good.

29:15Turner Novak:Like, that's hard to do. that most people, 99.9 % of investors will never get that. And one thing you mentioned was, you mentioned Founders Fund. They're really good at finding these kind of weird, wonky things. I think you kind of joined early on for, it was maybe like a fund cycle. I think you were there for like two-ish, three-ish years. Yes. What was it like back then? Was it pretty much the same? or has it changed much? I mean, it's such an extraordinary group of investors. It is weird. It's like I grew up in the East Bay near Berkeley and we used to call it Berserkly and Founders Fund was this weird place that was so kind of, it was like counterculture.

30:12and, you know, the anti-VC. And so it had this, and that just like gave it this like coolness around it. And then, you know, like process and all these things that anal retentive people, neurotic people like myself, like hate. Like there was, you know, no partner meetings and, you know, like no organizing your list of deals. And it was, you know, like very much each individual would go out and, you know, kind of find, you know, that next great company.

30:50Turner Novak:So how did, how were like investment decisions made? Because usually you think your classic venture fund is like a Monday morning partner meeting. Maybe there's a Thursday. Everyone talks, kind of pitch. The founders come in and present. And then, you know, you vote. or sometimes it's just like a dictatorship. How did it work at Founders Fund? There was voting and it was based on number of, or, you know, check size. Like, so the larger the check, the more number of partners needed to get something through. So there was, you know, so there's always some aspect that reels it back in. But the most important part and what Brian Stingerman would always say, you know is like he would always kind of like come up to you and sort of berate you like are you sure you have absolute conviction you know and you would lie down on the train tracks and this is going to be bigger than google you know and and um i didn't maybe appreciate the berating as much at the time as i do now like that's you know you like if a individual partner at Founders Fund has like that high, high, high conviction, then, you know, like votes, all that is almost irrelevant to, you know, just saying, okay, like, we'll do it.

32:20Turner Novak:And I feel like that's kind of the point of venture. Like the point of it is, we are putting some capital into this pretty early, like business or product or team, go up or down the list of how early or late this thing is, and it will become one of the most consequential companies of all time. It's going to become a generational business. And we don't actually know. The statistics say that it probably won't. But if it does, we're going to make a lot of money. The fund will return itself multiple times over. And that's kind of the point. I feel like a lot of people maybe lose that. It's more of like, oh, people are blogging about this certain thing.

33:02Turner Novak:And like, we know that all these other funds are looking at this, like if we can just get in before them, then they'll mark us up and we'll be able to raise the next fund. And by the way, the product doesn't even work or like they have no customers, but you know, we got markups, but who cares? No one needs to talk about that. Yeah. I, you know, while I was there, Trey Stephens and Palmer got together and started at Andrual and, you know, inside of Founders Fund. And that was extraordinary. I mean, it was exciting. But I, and, you know, watching them go through the process and seeing, you know, the company get off the ground was exciting.

33:46But now it's extraordinary in light of, like, you know, how far that business has gone in just these few short years.

33:56Turner Novak:And it's interesting, like when you just look back at the time they started the company, like you had, you know, Google was signing a deal to basically provide cloud services for the military and employees were protesting it. Like we will not serve the like the U.S. military because it's unethical or whatever. And just like it was like the most contrarian possible position you could have is like we're going to. And also selling to the government is like on paper, you'll talk about VC blog posts. Historically, it's like, you know, the government moves slow. Don't sell to the government. They never make decisions.

34:36Turner Novak:It's like all corrupt, et cetera, whatever. But then you flip it and you look at today, Palantir has like, I don't know, I'm sure they have some nine figure customer deals with certain governments around the world, like enterprise software, like the beauty of just these massive contracts. So I mean, same thing with Anderil. It's like, I'm sure they have some customers where they're making nine figures. They have nine figure contracts or probably will eventually. And just like contrast it today and back when they started, it's like so different. Yeah. What's interesting is like, yeah, both Palantir and Enduro were these like, you know, contrarian beliefs rolled into companies, you know, with Peter very much.

35:21you know involved in in both and i mean and now the value i mean the value of what's of palantir is just extraordinary like of you know how far it's come then you know in the case of palantir it took you know 20 years to then like really inflect because like palantir kept like moving along at like a good-sized business um and it was almost like kind of lying in wait of of transformers and you know this awareness of this being needed and it had found the perfect audience of you know government and so on to to spend those first 20 years and then exploded is as you know this ai boom has happened

36:09Turner Novak:yeah i remember there's even maybe like as recent as like six or seven eight years ago maybe it was like 2018 you'd you know someone do a presentation of like these are the most overvalued private startups and Palantir was like always on those lists like it was always pretty close to the top of like this is like an example of like you know bubbles in the private markets and these companies are zero for deployed engineers we're called consultants and we're a negative thing and you know it's just a company that does consulting and shouldn't get any kind of high you know marks so yeah like the you know and seeing that from like its creation it was really based on your one of the kind of currents that like pushed it forward was the fraud models at paypal which could you know in a networked way you know kind of find find similarities like amongst, you know, say devices or IPs or otherwise, and then, you know, identify and find this kind of networked fraud.

37:23And that was like the inspiration, you know, with Palantir as well.

37:29Turner Novak:Interesting. So like using just data of, you know, broader internet usage, like pick up potential threats to a nation or to a democracy or to like civilians or the military, et cetera. Correct. You know, like Max Lepshin and the team would see that, you know, a whole set of IPs had somewhat similar attributes or some tie and then, you know, transfer that over to discovering, okay, there's a terrorist cell and they used a phone over here and computer in a different country and tie those all together and find gain insights was like the original premise. Interesting. So you think that the premise of Palantir started at PayPal?

38:28I think so, yeah. And in fact, the day that the day that uh that paypal announced the acquisition i i'd been i had lunch with peter and he said that you know he said like i'm going to start this company and it's going to be based on like similar to how paypal models are used um to you know like find to find fraudsters we can use them to catch the bad guys interesting i've never heard that before that's crazy

39:04Turner Novak:I guess, well, you also sort of started a company off of insights from PayPal. Yes. Was it the very first company built on kind of like the PayPal platform or API? I guess I don't know the inside full story. But what's kind of the story with kind of getting that one started? It was called Zoom, right? Is that how you pronounce it? XOM. Not to be confused with the video conferencing. Yes. XOM is a money transfer business, much like a remitly or wise or so on. And, you know, the business is really about helping immigrants send money back to their family overseas. But, you know, how it began, my business partner and I, Alan, who went to UIUC.

39:55and so he was in school with folks like Max Levchin and, you know, Libor and all these other, there's this like whole mafia of UIUC folks.

40:12And like I had had a conversation with Michael Moritz and he said like, you know, the most successful companies are not just companies, they create industries. You know, enormous industries sprout out from it. And, you know, certainly you look at Apple and the iPhone and, you know, the App Store. Like, there's just an enormous sort of, like, universe created of value, which, you know, Uber and Airbnb benefited massively from, despite Apple's hefty tax on everything. And, you know, and so when I saw the world melting down, you know, in 2000, March of starting March of 2000, 2001 and so on, you know, everything was kind of collapsing except for Google and PayPal.

41:12And like PayPal was like rocketing up. And so, you know, the thesis was like, well, let's build apps on top of PayPal. And there was like a kind of mutual desire to do this by the PayPal team because at the time they were like 99 % relying on the eBay auction markets, marketplace. and they were concerned that Meg Whitman, the CEO at the time, would shut them off one day. And they wanted to drive non-Ebay GMV. So Alan and I, we talked to David Sachs and convinced him to open up an API and became the very first developers on that API.

42:05Turner Novak:What was that process like? Like, was this like 2001, I'm assuming? Yeah, it was towards the fall of 2001. And in fact, like, I think we launched Zoom not long after 9-11, which, you know, it's like.com plus 9-11, you know. It was like a crazy, but, you know, like, I guess I've always found that a time to be very sort of counterintuitively greedy is during these really terrible times because, you know, one is like you kind of can't fall off the floor. And, you know, it's like this time where you really learn how to be scrappy and build like great bones to a company. And, you know, and it's the warm up and the run up to, you know, the next kind of accelerated period.

43:06So, you know, no doubt there were a lot of great companies that were started or came out of that, like, kind of downturn period, as the same as with 2008, 2009, as the same as with, you know, that 22, 23 period. Yeah.

43:25Turner Novak:So was there anything that you did differently between Zoom and the first company? I think it was called Connect Group, the one that you sold to the hotel internet. Okay. So what was your approach second time? Or maybe there's multiple companies in between here that I'm missing, but what was the difference between the first time and with Zoom? Well, the first time with Connect Group, there were five founders. we had you know we had hardly got off the ground you know we hardly really built we didn't really build a business you know we had one installation and you know then a suitor came calling and we went with them so I don't know I honestly didn't learn that much you know from it why did you sell the company then if it was still so early i think we maybe felt there were greener pastures and you know they they came calling and it seemed like a good option that would but i don't know i i don't at that time you didn't have like all these great podcasts or you know material sub stacks to read up on like when you should exit your company and when you shouldn't.

44:50Turner Novak:So it's basically just like you thought it seemed like a good deal to take. Just risk-reward seemed good, make some cash. Good enough, yeah. So then obviously you didn't do that with Zoom right away. I think you guys sold it like 13 years in. Yeah, well, Zoom was yeah, we were founded in like 2001-ish into 2001 we went public in 2013 and were acquired by PayPal in 2015. However, in 2005-ish, I moved on to the board out of the CEO role. You've done that like a couple of times. I know we're going to talk a little bit about Eventbrite. I think you did a similar thing. How did you know it was the right time?

45:38Turner Novak:How do you think about when you kind of shift away into more of like a chairman role? Yeah, I think in general, the best practice for it is really spending time with those that mentors, people you respect, to hear through, is this a net positive or net negative for the business?

46:06What are the trade-offs one is doing?

46:10Turner Novak:so it's kind of like is there somebody else who could actually do this better than i can and let's plug them in there's certainly that yes but you know do always be aware that you know it's it's if you have somebody an outsider come in it's rare that they'll have that founder quality they may have great skills and leadership and building but that you know kind of founder variable would be absent but we kind of got the best of both worlds with Eventbrite because it was my co-founder Julia who took the seat. So then with did you start Eventbrite around the time that you stepped down from Zoom? I'm just I'm trying to remember the timelines.

46:58Yes in fact in in fact we back to that period with Alan when we were becoming the first to build on PayPal's new API, we built a whole range, like over, you know, a number of weeks or months, we built a number of different payment related applications. And one of them was like a very rudimentary ticket, ticketing application that, you know, when I've done myself with more time on my hands was like this, you know, took a look at the like admin and there was like volume and people were publishing events and nobody was touching the thing. It was just like running on its own.

47:47Turner Novak:Oh, so this was just like a little mock-up that you had built? More than a mock-up. I mean, it was a functional application. Did you just like take it and say like, this is Eventbrite, let's go? Or are you like, let's like rebuild this from scratch? Uh, well, I, with the two new founders, the founders of Eventbrite, Renovasage and Julia Hartz and myself, we, um, kind of took a close look at it and also would kind of debate, maybe there's other things to work on or what do we do, but let's start working on, on this. And we just started to kind of iterate like the product. I mean, it seems like obvious or no big deal, but, you know, it was a PLG product like at a time that there really wasn't much.

48:47Maybe Netflix or something and Gmail, you know, out there. and we would have this 24-hour dev cycle because Renaud was over in, and he was based in France for most of the year, hit a flat over there. And so we would, you know, like I'd kind of work on product mocks and specs and things and file bugs and throw them over the fence and he would go after it.

49:17Turner Novak:You'd wake up and he'd have it fixed? Yeah. And we did that for a fairly long amount of time. You know, I had felt like, oh, we raised too much money for Zoom. And so the reaction to that is to like be in a very like go the other direction. And so we kind of worked like almost two years on just kind of iterating and optimizing that. and what what like was or is event right for people who are not familiar i've done like some research over the years followed it but i'm sure i don't even know exactly what like the core product and like customer base is got it it's it's really kind of ticketing for the rest of us not for Madison Square Gardens or the large, you know, football stadium, it's ticketing for everyone else.

50:17And it's, you know, simplicity, ease of use allows you to really kind of get the word out about one's, you know, event, but also around, you know, we like benefited greatly on lowering the cost of acquisition because you would see, you would get these Eventbrite invites and you would see these pages, Eventbrite registration pages. And that really helped spread the word.

50:53Turner Novak:and i think you like there there's a a significant chunk of people that like that run businesses on eventbrite if i'm remembering right like there are people who they just host a lot of events as sort of like how they make money and make a living and and i think you guys essentially just like take a cut and then there's maybe some advertising revenue too once you hit scale that that's right it was it was kind of this religion for us to you know one take very low fees as opposed to, you know, what you would see from, you know, the incumbents in the space.

51:30But, you know, also just this notion that we only take a fee if you actually make a sale, you know, was kind of like this religion at the time that was, like, substantially different than most of these or most of the services or so on out there. Yeah.

51:51Turner Novak:And I think I remembered you've, you've said before in the past that when you did decide to raise money, it was kind of tricky because this wasn't like a well-known market. Like you couldn't Google, you know, what's the TAM of this thing. How did you kind of size this and figure out how big of a company it could be? Yeah. I hated this part because coming from Zoom, like you know you could just get the the bank the like the the central bank figures for remittances in the philippines in india and mexico and you had this like very clear enormous tam and take your percentage of it but in in this case you know it was it was like a kind of smb audience You know, I would call them creator.

52:40Like it is a, it was an early creator audience. And those that, you know, made their living with this type of craft. And there's, you know, and this is now just multiplied. I'm on the board and we're investors in a company called WAP, which is general creator tools. think of it as like Shopify for services. And, you know, their volumes are now in the, GMV is now in the billions. And, you know, this is just the general notion that you don't go and you don't do what your parents did, like which is go to one company and work your whole career and get a W-2. Now you get a 1099, you know, and you're like your own boss, but you need the infrastructure to do that.

53:37But that was like, Eventbrite was very much a kind of early version of that. There is.

53:46Turner Novak:And I know people listening to this are like, Turner, you got to ask me this. I know you guys recently, there's some news that came out. You had, I forget like what the phrasing around this was, but you're under an LOI or closing an acquisition, you're getting acquired. Not sure what you're allowed to say, but what exactly is going on right now with Eventbrite? Yeah, so Eventbrite announced that it is being acquired by Bending Spoons, a Milan-based.

54:19I kind of describe Bending Spoons as kind of like a new age IAC. so it's sort of like a holding company. It's a number of different companies that are assembled together

54:33and Luca has just done an extraordinary job of building that business. We just announced this happened and because of all the SEC regulation and so on, it can't go into grand detail until it closes.

54:54Turner Novak:Well, I did want to ask you a little bit more about... We kind of hit on it a little bit, but we didn't get too deep into it. So there's a headline, if you look at TechCrunch, and it's like a sensationalist headline. Like, oh, this fund invested 20 % of their fund in teenage founders. I think that's the headline, if I'm remembering it right. We hit on it a little bit more. So that's a pretty big thesis for you at A-Star right now, is just finding people very, very early in their professional journey and their building journey and just helping them out, giving them some capital, seeing what happens?

55:28Well, it's funny because we didn't really seek it out. It's happening. If you're in the pre-seed market around universities or the Twittersphere or so on, And, you know, you're seeing like the age has been dropping precipitously, whether it's through YC or whether it's through. Like I do a lot of work with Corey Levy. You know, known him for years. And he is. He's got a program called Z Fellows and he backs dropouts. and it was always drop out from college. But, you know, in the last like 18 months, like drop out from high school, it's like extraordinarily high. Then running into and meeting founders that, you know, one of the Z fellows was the creator of the Cal, you know, the calorie counting app guy.

56:40And, you know, I think at the time when I met with him, he had something like$30 million in net revenue.

56:47Turner Novak:That's wild. He's like a bootstrap company. He's not raised any capital. Correct. He hadn't raised a dime. And, you know, and he was like, you know, and had this great, you know, business he had assembled. Yeah. It's interesting because there's like two sides of the coin of this. When you look at Facebook was started, I think Zuck was like 1920-ish, something like that, when he started it. Now one of the most consequential companies of all time. On the other side, there's like a lot of cases you could say, you're giving this 17-year-old or 18-year-old like, you know,$10 million. This could end in absolute disaster.

57:29Turner Novak:Like they have no idea what they're doing. Like in some cases, you know, like a Facebook or an Apple computer, you know it's almost like you need that style of you need that new manner of thinking you know describe it as kind of seen around corners like like that age segment just knows what the world is going to look like in five and ten years whereas you know we all like don't see the world that way anymore, if that makes sense. But it doesn't, but there are certain businesses, like if they were going into like, you know, enterprise resource planning, the ERP systems for the enterprise, it's probably not the best place for a teenager to try to mess around.

58:20Turner Novak:So you think it makes the most sense when it's something that's like, they have an insight or an industry is like, obviously going to look radically different. and you're like, holy shit, this is like the craziest thing I've ever heard. And like, it could work. Like this could be, you could be the kid to do this. And then, you know, look, like there's the reason why Marines are 18 years old is like they charged into battle. And, you know, that energy is, you know, and like fearlessness is pretty amazing to see. Yeah. Like I think when you, when you think about like Facebook, like we were talking about earlier, like there was 15 other social media companies.

59:06Turner Novak:It's like any rational person might say, I should find a different market with fewer competitors, I guess. But, and so aside from just investing in people dropping out of high school, any other areas you're really interested in right now at A-Star? Well, we're generalists, so we try not to take sides to say. We're just looking for those extraordinary people. And that has brought us to everything from all the AI application layer companies. You know, Decagon is exemplary of that to, I mentioned, WAP on crater services that isn't AI oriented to general biological, which is where Avi is a graduate from Yale at age 21.

1:00:01And he's a chemist that is really building this industrial biotech company. So instead of using petroleum to make chemicals, he does this with sugars. And there was like a kind of wipeout in the market about five years ago, 10 years ago, with a number of companies that didn't make it. And how the market has changed and how things have evolved. We think this is the right time and he's the right person. So he's got a, he's got a, he just bought out of, you know, quasi bankruptcy, a factory in Louisiana to make his product, which is interesting. And then we're on the defense side. We're in companies like Mach Industries, which is, you know, like propulsion-based drones.

1:01:00That was started by an 18-year-old dropout of MIT for NEROS, which is a military drone business.

1:01:12Turner Novak:And I think you also have incubated some companies too, maybe more than I know of. Is that also kind of a part of the strategy or is that more of like a one-off thing? Yes, we've incubated three companies. in the five years that we've been around. And we try to be very thoughtful and deliberate about the incubations. So we're not like churning them out every week. There's some people that do. I guess, you know, like, what is it? Like, I guess you have more chances of success with higher numbers, perhaps. But, you know, our first is a company called Multiply, which is AI mortgages.

1:02:05And that's backed by Mamoon and Kleiner. The second is a company called 15th. And that is a kind of AI-powered tax accountant. So you get your tax return done.

1:02:23Turner Novak:On the 15th of the month? Is that what it is? That is, yes. Okay, nice. That's a nice name. And then my kind of like little darling incubation has been Sauron, which is home security. Yeah, I wanted to ask you about that. So what's the thesis there? Because that sounds, some people might say that sounds super boring. Market might not be that big. Like, I don't know. What makes it interesting? Well, like the notion behind Sauron and the home security market is just we haven't seen innovation there. And, you know, maybe it was maybe Ring 10 years ago. There's just not a lot of change. Like the companies that were in the space, they've been like gobbled up by the, you know, big players there.

1:03:16And there is a, in the big players, the oligarchs have this, you know, kind of third rail of privacy where they can't do aggressive things like face recognition and so on. And, you know, and of course we can and we are. But we're really, you know, what we saw was that over the last like two decades, you have had, you know, 100 billion plus dollars put into self-driving. So all the different sensors have come down dramatically in price, all the different, like the perception stack, a lot of innovation has happened there. And so I take the self-driving stack and move it over to home security. And, you know, we think that's that's pretty exciting.

1:04:09Turner Novak:Yeah, because I guess I kind of think about I did have a home security system for about two years. We lived in a not the not greatest neighborhood and we had a baby. So we were like, we should probably get a system. I think we use a company called SimpliSafe. I don't know if they're still around. I think it was like most affordable slash seems like the best option. And then it seemed like I think Comcast had like a home security, but it was basically like a bundle with your cable bill. And I don't know, product never seemed that great to me. I think like AT &T maybe had one. ADT maybe was a big player.

1:04:47Turner Novak:They're really expensive and didn't seem that great. Kind of your classic big conglomerate price increases, etc. etc. So and it was all like no tech. Like it was like, you'd have like a box on the wall right next to the door. And then there would be like a motion sensor on the door. And like if the door opened, you had 30 seconds to like press a button and then and then the alarm wouldn't go off or would. I think maybe there was an app if I'm remembering right, like, yeah, you can maybe control it remotely from an app. But it's just like, you know, didn't seem like people were doing that much with it to your point.

1:05:22Yeah, it's interesting. In some cases, maybe the innovation failed as it settled into is a number of the assets you mentioned settled into private equity or again into the like big oligarch, tech oligarchs. But all of them, like what they don't share is like the kind of real-time nature is that who's really, like, is somebody going to come if there's truly an emergency? And you described the sensors at ADT. Well, that alerts their help center, but it doesn't mean the police are going to be dispatched because, you know, 90 % of the time it's a false positive. of somebody set the alarm off by accident and they call to confirm and go through this.

1:06:15So what we're trying to do is have that situational awareness, be able to see what is happening in real time and have high resolution sensors to know if there's an urgent situation. Wow.

1:06:34Turner Novak:So depending on what you sense, you might just call the fire department. And so it doesn't even go to the Sauron help center and just go straight to calling 911 and say, there's a fire. We need someone in the house. Will it always be, you know, kind of confirmed by people, the help center? You know, it's kind of like self-driving where you had humans in the loop. So we have humans in the loop and ours are very well trained. I think all of them are military veterans, and a lot of them had exec protection and so on. And that you're not paying 20 grand a month to have a security person on site. You have this virtual security.

1:07:24And over time, you know, as we train the system, the computer vision will allow us to kind of scale many more homes, you know, and not have 10 ,000 virtual guards.

1:07:40Turner Novak:I know we were talking about this before we started recording, but it's kind of like, it's like a way to get into someone's home, right? Like, it's like, almost like land and expand. Like, people spend, the average person, their biggest line item on their monthly budget is their home. and it might be like rent mortgage if your home is paid off you're just like buying shit for it basically like you're making your upgrade and stuff so it's like an interesting way to just kind of like get into that kind of budget of a high percentage of someone's income honestly yeah we like to even think you know as we wouldn't trust like what would it look like to have store on sensors in the home, you know, and it'd be something like, you know, where did I leave my keys or where's my blue sweater?

1:08:27Turner Novak:That'd actually, that'd be amazing. I run into that problem daily. Yes. Or catch your, your child's first steps, your baby's first steps. Yeah. That'd be awesome. The thing I w I like can't wait for is so like I make my kids breakfast every morning and there's so many mornings where we're like out of peanut butter or out of oatmeal or yogurt and you know it just like turns into like a disaster in the morning because like they don't get the yogurt they thought they're going to get and you're like trying to figure out what to make them for breakfast it'd be awesome if it's just like hey we placed an instacart or amazon order and just there's going to be peanut butter that shows up tomorrow like that'd be amazing what's your go-to breakfast in the morning for me personally or for the kids for the kids for the kids i have one that likes oatmeal and i have one that likes yogurt and specifically vanilla yogurt and i so the the the oatmeal one will she'll have like strawberry yogurt she'll have oatmeal whatever but like the one that only likes yogurt she will only have vanilla yogurt so if you give her anything any other flavor she completely loses it What can you put fruit in the yogurt or like nuts or anything?

1:09:43Turner Novak:Yeah, you can, but it has to be vanilla flavored. So like if it's vanilla yogurt with like cut up blueberries and strawberries, she's fine. But if it's strawberry flavored yogurt that has whatever else in it, she just doesn't, she like won't eat it. Is that the nine-year-old or the five-year-old? It's a five-year-old, you know, she's, she's gotten so much better over the past year, like trying different foods. And I mean, huge credit to my wife of like being super patient and like, you know, strategically introducing different foods. And we always encourage her, like we make it a big deal of like, oh, you tried, you know, beef or, you know, you tried green beans or something.

1:10:20Turner Novak:And, you know, we make it a big event and celebrate it. And, you know, we make it because I don't know, some kids, she like she used to be really good at eating. And then suddenly she just decided she doesn't like anything that's green, which is basically no vegetables, which is, you know, not good. Is it an age thing? It's just like all of a sudden, yeah, there's, you know, what they say is that there's, I think they say like at a certain age, you become very picky about food because you don't want, you know, the four or five year old to like walk out in the woods and just pick a mushroom and eat it and drop dead.

1:10:55And so it's actually a like Darwinistic thing because our 16 and 11 month old daughters, like we were feeding them, you know, broccoli and salmon and like just best food. We're eating everything, you know, like they're just taking like down stuff. And now I'm like thinking forward like, oh, God, yeah.

1:11:18Turner Novak:Probably the funniest thing was both my kids really loved sushi when they were babies. And it got really expensive. They wanted sushi every night. And still, when I'm like, hey, let's go out for dinner. And they always want to go to the most expensive sushi restaurant. I'm like, we can't go out to get sushi every night. That's like a six-figure run rate on the dinner meal for the family. We can't do that. It's like a conundrum. You want to get the high-end sushi too. You want to get the nicest fish for the kids, but you can't go every night. And we've evolved. So when we used to do date night, when we were first married, you're scrapping every penny and we'd go to a place where we could split a meal.

1:12:06Turner Novak:You could pay 20 bucks and get a really nice dinner. But it's super fascinating. The past couple of years, I think it's like we make a little bit more money, but also the price of everything has gone up. So like there's almost this like relative difference of like before, you know, family meal was like 50 bucks and like a really nice meal was 100. And like the difference in price was like 2x. And now the family meal low quality is like 100 bucks. And the really nice meal is like 150. And like on a relative basis, just getting the better food, it like actually seems cheaper. so what we've been doing is we've just been like you know what if we're gonna go out to eat we're just gonna go to like a nice place and we're gonna enjoy it because it's actually not that much more expensive than going to the you know like we'll go to steak shake shack and it's like a hundred bucks for the family and i'm like what this is insane like let's just go to like the fancy you know fine dining and pay 150 for the family and it's like way better and the the kids like it a little bit more.

1:13:06That makes perfect sense. Like Shake Shack probably has like 17 MBAs figuring out like how to keep pushing the price up.

1:13:14Turner Novak:And Shake Shack is good. I love Shake Shack. It's like a family favorite. Yeah, yeah. It's who's the famous chef that's behind it? I don't remember his name, but he's got the book. It's like tabletop manners or something, or it's like how to treat your employees really well. And like that leads to a good business, I think. But I actually wanted to ask you, So you have two older daughters, but you mentioned you have two younger daughters. So how did that come about? I think you described it as like your second cohort of children. Yeah, a second cohort. Nice antiseptic term for like our child rearing.

1:13:53Turner Novak:Cohort analysis. You're running like spaghetti charts and analyzing. Cohort one, cohort two. Keep up on their growth curves. so we have four daughters 17 years old 13 years old and then 16 months and 11 months which is like the most confusing thing to most people yeah five months difference you're like what's how did that happen yeah julie and i just decided like we weren't done and and you know we were kind of exposed to all this different tech. And so we decided to kind of like have two more babies, or should I say like, like cook up or, you know, like grow two more babies. They create with science, two more babies.

1:14:40I'm an angel in a company called Orchid. Nor is an amazing founder and that's like a full genomic test for babies, something, sorry, for embryos, something that just hadn't existed before. So we were able to see like this, like fine grain resolution of, of all the embryos that we chose from. So I don't know. I think it's, it's, you know, it's a little bit costly. And but, you know, I would imagine in 10 years time, that as the prices of all this cost of all these go down, that you'll have a lot of different families having kind of later in life children.

1:15:30Turner Novak:Hmm. So how does this work? Kind of practically, like, if I was going to go through this process, do i like so what was it like kind of from the like beginning then can you just kind of explain how it works for somebody because i'm i'm curious but i've never done it so i just yeah yeah well we you know first like one would create like the you know the embryos like you know you need sperm and egg put them combine them in like a lab environment of some kind in And yeah, like IVF style, combine them and then like freeze them and keep them on ice. And then you have, you know, kind of optionality. And that was relatively inexpensive versus some of the other areas.

1:16:22The next component there is that you do need a surrogate to, you know, carry the baby to term. And that seems to be growing in popularity. In the U.S., the Wall Street Journal reported that, I guess, there was some foreign national who was trying to have something like 100 babies with circuits. And so...

1:16:47Turner Novak:Yeah, I saw the headline. Yeah, I foresee regulation coming in the area. And it's probably a good idea because, you know, there's kind of scary things that can happen on both sides. um and you know and and once that happens then you know it's the surrogate that is going through the different checkups and making sure everything is healthy and and so i mean i described a relatively simple process but it just ours took quite a quite a long time to get everything together properly. So you mentioned you, you get to see the embryos and does it, does it like simulate kind of what might happen to the baby in terms of like, I don't know how they like grow health things.

1:17:39Turner Novak:Like what all do you get to see when you're kind of getting like all the data around it? Um, you know, it's, it's like, it's like just it's really describing traits and you know i should probably like pull the report back but you know there's this dystopian you know sort of like concern that you'll choose babies based on iq and you know and honestly that can be done to a certain extent or these like traits can you know, now be like, you know, you could pick embryos that have, you know, certain traits versus the other, but, you know, you're looking for a healthy, healthy embryo that there's not some significant disease or the like.

1:18:33Turner Novak:So the main thing that you get from this is it says like, there's a percentage chance of like this thing, this thing, this thing, and you're kind of looking for like the lowest percentage of there being some kind of like life-threatening or very debilitating issue that will come up throughout the course of the baby or the child's life? Correct. And, you know, like one, you know, thing like a embryo, if the embryo has like a BRCA2 gene, you know, there's that very high likelihood of breast cancer then occurrence. So then you would say like, okay, let's try to select one of the embryos that just has less of a, less lowest likelihood of probably like as many things as possible.

1:19:20Exactly. Yeah.

1:19:23Turner Novak:Cause I think, I mean, if you don't have kids and you're listening to this, me and my wife were just talking about this the other day, like literally our worst fear is something happens to the kids, like something that we can't control. And so, So, I mean, it's like, I feel like it's most parents. It's just like, you really just want a healthy kid. Like, it's not even like, I want my kid to be the smartest in the world. It's just like, I want them to have all the opportunities of everyone. And like, the worst thing you want to do is like, you have a child who struggles with something that's kind of like outside of their control.

1:19:54Turner Novak:So, I don't know. We've thought about that a lot. It's like our worst fear. It's just like, your kid is hit with something that like, is uncontrollable. So, I don't know. Yeah, I recommend any couple just also freeze a bunch of embryos and then be able to have some degree of preventing these bad things from happening by being able to have this higher fidelity look at the embryo. our mutual friend, Navia, who works for you at the moment, mentioned you've been getting really into art lately. I was like, what's something I got to talk to him about that he's probably, you know, might be interesting to get into.

1:20:43Turner Novak:So tell me what's your favorite art piece of everything that you own? Well, I mean, first I have a mentor, Michael Ovitz, who is like just this incredible collector he's collected since the like late 70s he was the he was the founder of CAA and so I have him and he's very shrewd and in how he collects and how he conducts business and so on and so it's been great to have him you know help me or provide insights and then I also collect alongside with rompton naemi from abstract whose fund is just a block away and so we get this like kind of fun little competitive element to you know like collecting although i don't know i i have to admit i think he's like has an incredible eye and he's like done a great job um but you know my i would say like i i'm into this there's this this group of artists that have come out of like they came out of yale in like the mid 80s like john curran and lisa yuskovich and and others and they've been they've been out of vogue in some regards like from you know like art goes through this in and out um you know sort of thing and you know i just love their work and, um, you know, see it as an opportunity to, to, you know, build the collection more.

1:22:27Turner Novak:So do you, when you're investing in art or do you see it as investing, like you're trying to buy things that the value will appreciate, or is it like, this just kind of looks cool. I want to put this in my house. I think it would look nice, like on the vase on the table or picture on the wall? Like, how do you think about it? It has to be both. So, you know, I have to love it. And, and I want to believe that, you know, the, the artist, him or herself is, is something very, very special. You know, that kind of, you know, like those very few entrepreneurs that in this case, is producing something that's going to stand the test of time.

1:23:15And that's represented by the appreciation over time. Interestingly, over the last five years, we've had this terrible market where art has been overlooked, kind of hit rock bottom relative prices. And so, I don't know, Ramshan and I think it's a great time to like... Scooping up, scooping up new pieces. But it looks like, you know, just as expected, you know, with the super cycle that we've entered, the art market's starting to pick up. And just in the last like couple quarters, you're seeing like pretty astounding records happening in the auction houses and elsewhere.

1:24:03Turner Novak:So how do you get into art? Do you have to have like a broker? or do you like, you know, like email the contact email on like one of the auction houses? Like, how do you get started? It's a very particular space. So you, you know, the best thing to do is to go to the major art fairs. Art Basel in Switzerland is like sort of the major one over the summer. And there all the galleries gather together and bring works from their represented artists. And, you know, like, then there's Basel, Miami just happened. And they tend to be a scene and a lot of parties and things of that nature. And then you build relationships with the galleries.

1:24:56So, like, Gagosian is like a very well-known gallery. Larry Gagosian has been, you know, running his gallery for, you know, what, three or four decades. And he is probably, they probably sell like a couple billion dollars worth of art a year, which he takes a nice cut of that.

1:25:18Turner Novak:A nice cut. Yeah. It's going to be a good business. Yeah, but I have got a representative over at Gagosian that will help me. Or if something comes into the gallery, they'll share a PDF of a particular artist. They represent John Curran, for example. and there's a and then the other piece is Christie's and Phillips and you know on the auction house side so that's interesting to see where prices are happening and it's great to have you know friends at the auction house that that also can give you insights, you know, at the same time. Yeah, I'm probably not quite there yet where I can start acquiring art, but I want to, hopefully soon.

1:26:22Turner Novak:Need some liquidity on the venture portfolio first. But you can start, like, you know, local artists or, you know, some of the, like, you know, you try to get somebody coming out of art school. Yeah, that's true. Maybe, plus, it's like pre-seed investing in art. like, you know, buy something for a hundred bucks versus 10 ,000. It's like investing early. Exactly. Well, this has been a lot of fun. Thanks for, thanks for doing it. Where can, where can people find, kind of find you? Do you tweet LinkedIn? You don't have a podcast where, where, how can people follow you? Twitter and LinkedIn are, you know, are, are fantastic and DM me, but love doing this and thank you so much turner yeah this is a lot of fun and i hope you had fun thanks again to numeral and flex for supporting this episode if you missed it make sure to check out last week's with jason calcanus going inside the all-in podcast and everything he's learned from elon oprah and travis kalanick tune in next week for remote.com co-founder marcello libre on building one of the largest companies in europe if you like this conversation please like, comment, subscribe, and name your next child after me.

1:27:34Turner Novak:If you don't want to miss a future episode, subscribe to my newsletter, The Split, linked in the description to get each episode plus the transcripts emailed directly to your inbox every week. Thanks again for listening. See you next time.

From the publisher

Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron.


Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash.


Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies.


He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special.


We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates.


Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation.


Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠


Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz



Timestamps:

(4:25) Power shift from VC’s to founders since the 90’s

(9:08) AI is the mother of all bubbles

(12:40) Why AI is still underhyped

(14:10) What Kevin and A* are investing in today

(16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round

(21:21) What made the PayPal Mafia special

(23:37) Parallels between the 90’s and today

(26:40) What makes Founders Fund special

(35:07) How Palantir evolved from PayPal’s fraud models

(39:06) Building Xoom on the PayPal API

(43:38) Lessons between Kevin’s 1st and 2nd startups

(46:52) Starting Eventbrite off early PayPal API app

(51:51) Eventbrite’s hidden TAM challenge

(53:49) Selling Eventbrite to Bending Spoons

(54:59) Investing 20% of A* in teenage founders

(1:02:33) Incubating Sauron, the home security company

(1:08:44) Making breakfast for our kids

(1:13:33) Having kids with genome screening and surrogates

(1:20:31) Collecting art, how to get started



Referenced

https://www.a-star.co/

https://www.eventbrite.com/

https://www.xoom.com/

https://www.sauron.systems/

https://www.orchidhealth.com/

Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763

20% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/

https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/



Follow Kevin

Twitter: https://x.com/kevinhartz

LinkedIn: https://www.linkedin.com/in/hartz


Follow Turner

Twitter: https://twitter.com/TurnerNovak

LinkedIn: https://www.linkedin.com/in/turnernovak


Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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