The Investor Who Bet on SpaceX, OpenAI and Anthropic Before You Could | Term Sheet

11 Jun 2026 · 54 min · 27 chapters

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In short

Episode topic: The rise of venture secondaries (buying private-company shares from existing holders) amid “hot IPO summer,” focusing on pricing risk, SPV opacity, and what happens when lockups end for SpaceX, OpenAI, and Anthropic.

Guest backgrounds

Larry Ashbrook, founder of G Squared (started 2011). He began investing via secondaries after early Silicon Valley “doors slammed shut,” including trying to invest in Twitter when he couldn’t access primary deals. G Squared now manages about $8B+ and invests largely in secondary direct stakes.

Key claims

Secondaries shifted from taboo (cease-and-desist letters) to mainstream as companies stayed private longer due to regulation and structural liquidity constraints. SPVs can create “daisy-chain” ownership confusion and layered fees, so investors may not truly know what they own. When lockups end, share supply can overwhelm demand (Facebook example), potentially causing price drops. Litigation risk may rise if SPV paperwork misleads investors. The biggest risk isn’t fraud alone, but overpaying based on “smoke and mirrors” pricing/momentum.

Notable examples

Twitter first secondary deal; Uber/Lyft outcomes; Facebook lockup “falls like a brick”; SpaceX S-1 described as science fiction; Anthropic valuation surpassing OpenAI (~$900B).

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

Chapters

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Introduction to Venture Secondaries

0:00 to 0:21

Discussion of the venture secondaries market and its evolution.

“With Red Bull Summer All Day Play, you choose a playlist that fits your summer vibe the best.”

Introduction to Venture Secondaries

0:54 to 1:52

Discussion of the venture secondaries market and its evolution.

“For years, no one in Silicon Valley talked about secondaries.”

Setting the Stage: IPO Summer

1:52 to 2:39

Overview of the current IPO landscape featuring SpaceX.

“There is only one piece of news, and it's that hot IPO summer is underway.”

Interview with Larry from G Squared

2:39 to 3:37

Interview with Larry about his experience and insights in venture secondaries.

“Larry, welcome to the Term Shoot podcast.”

The Evolution of Secondaries

3:37 to 4:14

Larry discusses how the perception of secondaries has changed over the years.

“Pinterest, Airbnb, all these businesses that changed our lives through the smart device.”

The First Deal in Secondaries

4:14 to 4:37

Larry recounts his first secondary deal involving Twitter stock.

“Tell me about the first deal you ever did.”

Mosaic Theory and Data Gathering

4:37 to 5:36

Exploration of how Larry used mosaic theory to gather data for investments.

“We didn't have any data then I had a research team in India that would do the work I would pay them for their memos so you had a research team and in this is 2000 yes 2011 2011 you have a research in India Find Twitter.”

Understanding Secondaries

5:36 to 7:40

Larry explains what venture secondaries entail and how they differ from primaries.

“I mean, that early generation was like, this is pretty cool.”

The Role of SPVs in Investing

7:40 to 9:21

Discussion on Special Purpose Vehicles and their implications in investments.

“So secondaries has a lot of meanings, come to find out.”

Market Dynamics of AI Investments

9:21 to 10:29

Larry shares insights on the cyclical nature of the investment market, especially in AI.

“How many layers of an SPV have you seen?”
Show all 27 chapters

The Shadow Market of Secondaries

10:29 to 14:00

Discussion on the challenges of accessing data and the risks in the secondary market.

“That's just SpaceX which is as we're recording this SpaceX is probably a few weeks out of going public.”

Investing in High-Profile Private Companies

14:01 to 17:22

Explore the dynamics of investing in private companies like SpaceX and OpenAI.

“but they've been out there, not just one.”

Understanding the Risks of Public Market Trends

17:22 to 18:49

Learn about the volatility in public markets and its implications for private investments.

“One of them is this dynamic around not knowing what you're buying.”

The Evolution of Secondary Markets

18:49 to 23:08

Discuss the changes and challenges in secondary markets for private equity.

“You have to operate in our industry at a high level of productive paranoia, especially on the secondary direct market.”

Concerns About Share Dilution and Market Dynamics

23:08 to 26:13

Examine the potential issues surrounding share dilution and how it affects investors.

“Anyway, Facebook goes public, trades okay.”

Regulatory Challenges and SPV Management

26:13 to 28:00

Understand the regulatory landscape and best practices for managing SPVs effectively.

“With that said, there are plenty of bad actors.”

The Evolution of SPVs and Secondary Markets

28:00 to 29:30

Explore the development and implications of Special Purpose Vehicles in investment.

“And by the way, there are plenty of great SPV shops that are out there.”

Current Trends in Venture Capital

29:30 to 31:10

Discuss the trends and challenges faced by the venture capital industry today.

“of assets, it's remarkable to see the journey of this industry.”

Understanding Investment Risks in Private Companies

31:10 to 33:00

Learn about the risks of investing in private companies and the complexities involved.

“They're really, truly, remarkably, you know, differentiated assets.”

Valuation Challenges in Emerging Tech Companies

33:00 to 36:00

Insight into how emerging technology companies are valued and the difficulties therein.

“assets in the world, but also our peers.”

The Importance of Data in Investment Decisions

36:00 to 40:30

Discuss the role of data and tools in making informed investment choices.

“So our LPs come to us and say, well, you know, I can buy this business over here through this broker.”

Future of Secondary Markets and Investment Strategies

40:30 to 42:04

Speculate on the future of secondary markets and evolving investment strategies.

“trying to sell you that piece of paper to actually give you proof that they own the shares.”

Counterintuitive Investment Strategies

42:04 to 44:38

Learn about unconventional investment strategies and the evolving landscape of private market financing.

“Be counterintuitive a bit and take a perspective that's different, which is, by the way, in our industry, not popular.”

The Rise of Anthropic

44:39 to 46:06

Discover the valuation surge of Anthropic and its implications in the AI startup space.

“And the SPV market, in my opinion, provides a major proof point that the appetite is there for the masses to get access to this asset class, which is now we can say it's an asset class.”

Comparing Approaches: Anthropic vs. OpenAI

46:06 to 49:09

Explore the different fundraising approaches of Anthropic and OpenAI and their market impact.

“There was so much chaos that I was hearing about in the market for Anthropic shares in the lead up to this round that I was just sort of like, yeah, that makes sense.”

Conflicts and Collaboration in Investments

49:10 to 51:11

Understand the dynamics of investor conflicts and the collaborative nature of supporting multiple companies.

“Got here in a SpaceX shuttle and Elon's going to walk through the door and we're going to fly around with R2D2 on the front.”

The Capital Landscape and Future Predictions

51:11 to 53:00

Analyze the current capital trends in private markets and the potential future for high-growth companies.

“And we're a part of that value creation.”
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Transcript

Automatic transcript. May contain errors.

0:01Allie Garfinkle:Ready to soundtrack your summer? With Red Bull Summer All Day Play, you choose a playlist that fits your summer vibe the best. Are you a festival fanatic, a deep end DJ, a road dog, or a trail mixer? Just add a song to your chosen playlist and put your summer on track. Red Bull Summer All Day Play. Red Bull gives you wings. Visit redbull.com slash bright summer ahead to learn more. See you this summer. so good so good so good new markdowns up to 70 off are at nordstrom rack stores now stock up and stay big on shoes tops dresses accessories and more must-haves for summer join the nordy club to unlock exclusive discounts shop new arrivals first and more plus buy online and pick up at your favorite rack store for free great brands great prices that's why you rack How taboo was it?

0:55Everyone hated it.

0:56Allie Garfinkle:For years, no one in Silicon Valley talked about secondaries. The time that it's went from, you know, you're a bottom feeder to we need your help is remarkably fast. A shadow financial market where investors buy and sell shares of companies before they go public. Early days, I received a lot of cease and desist letters. But that's all changed. The U.S. venture secondaries market has grown to an estimated$112 billion. But that's ultimately a guess. Most transactions are happening under the table. There's no traditional IPO anymore. They all look different. Larry Ashbrook saw the opportunity back in 2011 and investors seeking liquidity are now calling him.

1:35Allie Garfinkle:As SpaceX, OpenAI and Anthropic prepare to go public, investors who've poured in billions of pre-IPO dollars may not know what they actually own. In some cases, people are not going to have anything. They're not going to own anything. And that's the scary part of it. Welcome to Term Sheet. I'm Ali Garfinkel. And now for this week's news. There is only one piece of news, and it's that hot IPO summer is underway. SpaceX is set to go public this week. It will be the largest IPO of all time. Last week, the company set a price of$135 per share and is preparing for a swell of retail investor interest.

2:13Allie Garfinkle:How SpaceX fares will likely determine the fate of IPOs from OpenAI and Anthropic. And if all three do in fact go public over the next few months, we could be looking at up to$4 trillion in market value. If all three do go out, who do you think is going to be the long term winner in the public markets? Drop a comment and let me know below. And now who better to talk to than somebody who already owns shares in all three? Here's Larry from G Squared. Larry, welcome to the Term Shoot podcast. Secondaries has been a topic our audience is very interested in, and it's something you've been interested in for quite a while.

2:47Allie Garfinkle:You founded G Squared in 2011. Yep. You're like, yep, yeah. What were you seeing back then that made you say, oh, companies are going to stay private longer, and these private shares of companies are going to matter? Well, first of all, thanks for having me. You're welcome. I've been a big fan of your work and enjoyed being a contributor, some of which is printed and some not, but it's okay. We won't hold that against you. For me, the journey here today is a bit different. I didn't start a business in 2011 thinking I'm going to create this multi-billion dollar firm and do a bunch of secondaries.

3:23It was really trying to invest in the businesses that were changing our life at that period of time. This is early Twitter and Spotify and Palantir and SpaceX, early generation. Pinterest, Airbnb, all these businesses that changed our lives through the smart device. And I was really just trying to give money to the companies, but they wouldn't return my call. So I found ways to invest through secondary. Now, fast forward 15 years, multiple vintages and a lot of capital. It's our strategy and we've embraced it. So first it was kind of taboo and nobody wanted to talk about secondaries. And traditional Silicon Valley firms hated them because they thought it was like misalignment.

4:07Now everyone's embracing them and feeling like it provides alignment. So like anything in life, it's cyclical. It comes and goes.

4:14Allie Garfinkle:Tell me about the first deal you ever did. The first deal I ever did in secondaries was Twitter stock. Twitter stock. What year? How did it happen? Trying to give$3 million to Twitter in the form of a primary and they wouldn't return my call. So we found some former employees and figured out how to buy their shares. That's really how it happened. Mosaic theory of research. We didn't have any data then I had a research team in India that would do the work I would pay them for their memos so you had a research team and in this is 2000 yes 2011 2011 you have a research in India Find Twitter. No, no, no.

4:57We found it. They just through mosaic theory. I'd have to put together memos Yeah, and I didn't have a team and I wasn't equipped because I didn't have a background What's mosaic theory? Just like all the publicly available data and like pulling it together and trying to build a thesis around what's available publicly. Because now, and we use it still today, but we get direct company information. But to fill in the gaps, if you scour the internet and now Twitter and all kinds of different mediums, you can pull a lot of data that isn't normally provided just by the way people are having conversations.

5:36Allie Garfinkle:And how did you decide on Twitter? I liked using it as a product. I mean, that early generation was like, this is pretty cool. I think I can make some money on it. I think I can make some money. Here's$3 million. You won't return my call. I see another way. Basically, it was doors are slammed shut. I needed to make a living. I had a little bit of capital, a few people that supported me with money, and I needed to deploy it to make money. and so I had to hustle to figure it out and that kind of snowballed into an actual business when I realized there was some value creation that could happen just on the value of the discount immediately be in a positive mark because there's illiquidity and these people didn't have a method a method of getting cash they had paper shares tender offers weren't common no there was I mean the first actual venture back tender offer in its form today with the new laws didn't happen for many years after that.

6:38This is like early, early industry kind of wild west type of secondaries that started to take place. And it wasn't Facebook and LinkedIn and Twitter, Spotify, those were all kind of the early movement that's now become widely accepted. And a lot of dominoes fell in place to make it an industry including companies now staying private much longer that's

7:06Allie Garfinkle:really helped us when we're talking about secondaries what are we talking about simplest possible terms secondaries are buying shares from others not directly from the company at a time of an issuance where the company would normally use the money for growth capital or whatever other use of proceeds where they would sell you a new share secondaries are buying shares from people who already own the shares, either existing employees, former employees, existing fund managers, and providing them with capital and them giving you the shares. It's important to say we're being, we're talking about venture direct secondaries here.

7:40So secondaries has a lot of meanings, come to find out. Primaries have different meanings, depending upon where you're at in like the investment chain. For us, secondaries are direct shares that we're buying from others who have already been either awarded shares through their employment or advisory services or investors who provided primary capital and received shares for their capital. And then secondaries for us means we're buying those shares from others where the use of proceeds is in their pocket versus a primary investment which is providing the company capital for growth we do both but 70 percent of our capital is used on the secondary direct market well and tell me

8:27Allie Garfinkle:a little bit about where spvs special purpose vehicles yeah fit into this you're like yeah yeah yeah look i think they serve a purpose um uh many firms get their start with spvs It is cyclical in nature when SPVs are more prevalent than other periods of time. And we've went through a few cycles over the past 15 years. And SPVs, the interesting part about them is they provide access to the great logos that everybody wants to invest in. The negatives are often those SPVs are layered on top of other SPVs. And oftentimes, it's difficult to understand what you own. Real talk. How many layers of an SPV have you seen?

9:25In more recent days? Yeah. It's interesting. Today, and if you rewind the clock back to when the companies we just mentioned were hot, similar types of things happening where there is three four layered SPVs with

9:42Allie Garfinkle:fees in each layer and these fees are 30 % 20 % so they range that you see I mean we don't do any of this stuff but I've seen the paper where it's if you add up all the layers and all the fees probably 20 % upfront and carry somewhere in the similar range. Well, and the reason we're talking about this rate is these special purpose vehicles are often the vessel by which lots of people are investing in, say, Anthropics or OpenAI right now. Yeah, and this was the issue, though. When I say it's cyclical, it happened in, let's say, 2012 through 14. It happened again in 2020, and now it's happening again with the more recent kind of AI revolution businesses and some businesses have transcended that entire time and have had an SPV market in their stock such as SpaceX.

10:37Allie Garfinkle:That's just SpaceX which is as we're recording this SpaceX is probably a few weeks out of going public. We'll see. It's a behemoth and reading the S1 is like reading a science fiction novel. Well and it actually has it actually has a glossary of terms that does read like a science fiction novel but one of the things that I find really interesting too. And I think part of the reason our audience was so interested in this is because how do you price something in a market that exists in a lot of ways in the dark? For example, anybody who's rushing to buy anthropic shares right now knows what a lot of the reports say, but they don't actually have financials.

11:13Yeah. And I think that's the darker scary side of secondaries and the shadow transactions that take place. And I can totally appreciate because we get to see the data and touch and feel the companies directly. I understand why people are enamored with these logos and they're in many cases recently companies like N of One and they're they're generational businesses and it's exciting to try to own them. I think the ability to actually get the data is very narrowed and companies are narrowing it even further and it's...

11:53Allie Garfinkle:What do you mean by companies are narrowing it even further? The industry is becoming a group of people who can get the access directly, and then there's the rest. And it's becoming a smaller and smaller group. And the companies are looking for partners to solve different problems. We happen to start a business at the right time and have all these macro benefits of companies staying private longer, the legislation and new laws and Dodd-Frank and all these structural issues that were created by our regulations that have forced companies really to stay private longer. And the benefit of that to us is there's more secondary direct shares to buy because there's no liquidity.

12:37And now even as the macro environment looks like it's going to provide potentially some big liquidity, the scale of it's not large enough to solve all of the private problems so when I say groups can get access it's what's kind of one of two it's you're either really providing a service to the companies in the form of operational expertise in the primary focused investors and there's a number of logos out there that do great work and we partner with them in their portfolio from the Lightspeeds to the Thrives to the Green Oaks and the DSTs of the world and firms like that to the crossovers and the altimeters and the Black Rocks.

13:16And there's many, many awesome firms that have a seat at the table, insight as well. And then there's very few that companies let get in and do the work on the cap table of consolidating it and pushing the secondaries to few. And in order to do that and build very large conviction positions, because we run a concentrated equity portfolio, really large stakes in these businesses, mostly through secondary direct, you have to have the data. And what today's day and age with the secondary transactions, the way they're happening, and mostly off the books, the companies don't like it. They're trying to stop it.

13:57We've seen a lot of blog posts over the past few years from a number of companies. We'll leave the names out, but they've been out there, not just one. There's many who are saying this.

14:04Allie Garfinkle:I can say name the most recent cases in Anthropic. But there's also SpaceX. There's also OpenAI. Andruil has been very vocal. Andruil has been very vocal and we appreciate why that is the case. The biggest issue for people trying to access these logos today and chasing through the SPV market in my opinion is it's going to be very similar to when the dominoes kind of fell in the previous crazes. And in some cases people are not going to have anything. They're not going to own anything. And that's the scary part of it. and I always tell our LPs all the time who like to come to us and tell us well I can get access to these names today fine you should if you if you if you want to just know what you what you own and I tell all of our LPs anyone who asked me the same question follow the daisy chain get to the underlying do real due diligence even if you can't get the company information understand that there's actually physically a share at the end of the, at the train.

15:09Allie Garfinkle:Well, and you and I are both laughing because it seems on the surface of it, you think, how is that possible? But actually it's very possible. Walk me through who some of the folks are who are investing in these businesses, but don't necessarily have visibility. Like, are we talking about doctors? Like, why does somebody do this? It's the ultra high net work. They do it because I think people are frustrated with the public markets. Oh, why? Where do you get that sense? I get the sense of, you know, there's 10 companies in the public markets that gather most of the attention. In our opinion, it's become kind of the safety of the world versus the U.S.

15:47Treasuries. They just go to seven companies in the S &P, and it's fully liquid, and you still get some beta, and in rare cases maybe some alpha, but you're going to get some appreciation and full liquidity. So I think the capital has flown to them. It's very difficult to understand how companies are going to behave in 90-day increments. Some are rewarded for investment in R &D, and others are destroyed in the same earnings period. In one earning period, they were rewarded. The next earning period, they're harmed.

16:23Allie Garfinkle:And then maybe the SaaSpocalypse comes, and everything is down. Some 20-something-year-old writes a white paper using AI, and everybody wants to believe there's such thing as Sasspocalypse. So I think the public markets and the inability for people to really get outsized alpha, beta, is easy. I think sophisticated, high-net-worth individuals want to be a part of the real value creation, which has now transpired to almost all being private businesses. and touching and feeling them and using them people want to be a part of that and I appreciate I do too I mean that's what we do that's why we do what we do yeah that's that's why we do what we do you look at Twitter and you're like I want to give them money but they won't take my money it just it's kind of started and then it became a business and then when I realized there was an actual business getting institutionalized was a completely different journey you're getting at a lot of things I find very interesting.

17:24Allie Garfinkle:One of them is this dynamic around not knowing what you're buying. One of the metaphors I've sort of been playing with is it's sort of like saying, I want to buy a piece of this Picasso because I love Picasso and have exceptional taste, but I don't know the person who owns this Picasso. I think you can do that with like an NFT now, right? I think you actually probably can, honestly. Or there's... Like actual pair of sneakers that Jordan wore or something? Yeah, and you can get your tiny piece of like the soul of the sneaker. But it's the sort of thing, like you say, I really want the Picasso, but I don't know the person who owns the Picasso.

17:56Allie Garfinkle:But I know a gallery who says they know the person who owns the Picasso. And I have a PDF that says the Picasso is real. And that's, I guess, a two-layer SPV, give or take? Yeah, I mean, art appreciates. It's a great investment. Well, you know, I think that the theory that some of these folks have, at least in my conception of it, is it's kind of like, well, I didn't get into NVIDIA, but maybe I can get into Grok, for example. Yeah, or maybe think about similarly but different if I could have invested in NVIDIA when it was private what would my stock be worth today which is insane in that particular yeah but yes and there's many cases where the public valuations don't meet the private expectations as you chase and the worry I have just in general I'm a Peter Theo wrote a great book that I found really like it was speaking to me productive paranoia.

18:50You have to operate in our industry at a high level of productive paranoia, especially on the secondary direct market. Because in the early days, people wanted to sell you the stuff that was their garbage. Like line up a Silicon Valley brand name firm. They tried and in some cases succeeded and we lost money.

19:12Allie Garfinkle:So you bought some of that. Oh yeah. Yeah, well, they want to be my friend. Is there one? Yeah, is there one? Is there any? Are you going to name names? Can you name names? No, well, not name names. Can I guess? But it's, you know, you go up and down Sand Hill Road, and there are firms that early days of this craze tried to take advantage of new entrants. But I would say today there's a new group. There's, like, the new sheriffs in town are the GPs who were formed all about the same time. All are being run by their founders. all are creating real value in a much faster-paced way, and a lot of it has to do with the acceptance and the widening of the secondary market, which was once taboo.

19:56Allie Garfinkle:How taboo was it? Oh, everyone hated it. Is there an anecdote that takes you back to the moment of just how taboo it was? Early days, I received a lot of cease and desist letters. Don't talk to my employees. They can't sell their shares. Stop. You know, to me, that was primary focused investors who were still living in a period in where they believed that it was harmful to their value creation. The idea of a founder or an employee selling a percentage of their stock before it was like, they're not all in. It's easy to say that if you're managing a large fund, making a lot of money, and you're living in Silicon Valley and you can afford to buy a house.

20:40But as this craze started to happen in real ingenuity with companies, these businesses we talk about today, like we take them for granted. Remember the first time you took an Uber? It was like blew your mind. Like this is, and then you're like, well, why didn't I think of that? Right. That's like the Uber experience.

20:57Allie Garfinkle:I remember my parents taking an Uber for the first time. Actually, I actually believe you said you lost money on Uber and made money. How did that come to pass? I did. You know, just public market investors not seeing what we saw in uber i guess how did it go down it's just this you know and the price we paid was wasn't low enough and it would uber chose to go public during a tough time in the public market lyft was the little little brother so to speak and it just was a more of a value play and we had access to both of them directly and the data was was good for both but But yeah, sometimes in our space, all the things can line up.

21:36It can be a great process going in. You can feel like you have real good value. And ultimately, two, three, four years later, public markets see it differently. And that's today some of the worries that just in our own portfolio that I look at and say these companies are appreciating at such a rapid pace in value. How long will that continue and will it hold? Because we have a job to do. We're hired to return capital and make money without taking outsized risk. And that's part of the benefit of being a secondary direct investor is you should be able to get some value for the paper you're buying better than others because you're providing liquidity in an otherwise illiquid market.

22:18as momentum takes over and and we've seen this in different periods where every doctors and dentists in the world already gets access to the name the doctors and the dentists it is wherever you all are the doctor good for them and some of the worries you know spacex is a great business we've been an investor for a long time um and it's just the perpetual tenders and the SPV market around it, I get a little worried about what it looks like post lockup.

22:50Allie Garfinkle:Walk me through that fear. Well, we've lived it before. Look at the Facebook. What happened with Facebook? Tell our audience, please. Tell me a story. So if you don't remember Facebook. The artist formerly known as Facebook. So for me, I keep the old names. I still call it Twitter. I'm going to call it Facebook. You know, it's just like to me, it's like it helped build my business. And I'm very emotional about it. I'm passionate about the early days. Anyway, Facebook goes public, trades okay. The lockup comes off. It falls like a brick. Why? Because everybody who already wanted to own it, owned it.

23:31Not everyone. That's a broad statement. But a lot of people owned it around the world. And as that lockup comes off and there's a big push of available shares, If you think about the scale and size of these businesses today, the amount that they're raising, even the mega cap privates that they raise as a public market entrant, is not a lot compared to their overall private valuation. But then all of that valuation that's pent up and behind it, when that lockup comes off, a massive amount, an abyss of shares are available. and then it's just plain old economics, the supply and demand. If there's a ton of shares, the price goes down.

24:18And if there's not a ton of demand to buy, that regardless if it's picked up by every indices, think about the size of this business. The S1 is, I mean, it's a fantastic read.

24:30Allie Garfinkle:I mean, we think you said science fiction novel, and I completely agree. I learned that there was... According to that, we're going to do this show on Mars in a couple of years. Yeah, I mean, maybe next year for all we know. But I learned that there are civilizations that are powered entirely by their own stars in that S1. And now that we're in SpaceX territory, I think it is time that I kind of come out and say the thing that I have been wondering about. Okay. What is your worry? Because I can tell in your voice you've got to worry. Yeah, I am worried. I actually am deeply worried. So I think SpaceX could force an inflection point, a reckoning for secondaries.

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25:08How so?

25:09Allie Garfinkle:Lockup period ends. Yeah. Scary place. Scary place. Already scary just in terms of the possible glut of shares that hit the public markets. Yeah, yeah. Massive amount. Unless they do some type of, by the way, there's no traditional IPO anymore. They all look different. They all have different bells and whistles to try to hold back this flood of shares. So let's see what that looks like. So we'll see actually how they handle it. But one thing that I do think is going to happen, and you alluded to this earlier, and I want to bring it back. is there are going to be a lot of people who invested through SPVs who realize they don't own shares at all, or they own a lot less than they thought, or they didn't read the paperwork and the return is not what they thought it was going to be.

25:53Allie Garfinkle:And it is going to create a wave of litigation. Matt Levine rules apply. Everything is securities fraud at a certain point. And it is going to be an entirely different era in the market. And there's going to be a lot of people tied up in it. Yeah. Yeah. I don't think you're far off from probably what reality is. My belief in general is that people are inherently good and they want to do good work and people who are trying to run a business, regardless if it's a business like ours or another traditional manager or an SPV shop, they're trying to hustle and make money and provide a good outcome. With that said, there are plenty of bad actors.

26:33and we have a regulatory environment in which some of them probably should be regulated and they're not. They probably fall below the radar. A firm like ours, fully regulated, SEC regulated, we opted into the regulation from day one. We've lived that life the whole time and you have to have the custody of shares. I mean, you have to follow it down and every once in a while we'll do some SPV investing with other quality managers and that due diligence is in some cases harder than when we're doing the due diligence with the companies because it's it's one thing to tie out the share ownership that's just that's a piece that's a moment in time but constantly tracking to see if there's been any changes in the SPV is another thing because it's

27:31Allie Garfinkle:not just that first time that's right over time it could change it's not static it's a living it has a life of its own so there's a world of people too who may be originally yeah they felt they did good work they checked all the boxes they followed the custody they read the paperwork they everything tied it out and then um someone sold the spv brought people in and out who knows and a lot of those those layers of the onion that I like to tell our own limited partners if they choose to do these things outside you got to peel the onion back and then but you got to constantly grab the new onion and keep peeling it back you can't you can't ever stop unless you're doing it with a very high quality third party that is regulated and provides audited annual statements and all these things that exist.

28:27And by the way, there are plenty of great SPV shops that are out there. They exist. And they're hustlers.

28:32Allie Garfinkle:To be clear, SPVs definitionally aren't bad. Yeah, yeah, yeah, yeah. They're not like any other. Like any instrument. But as the access continues to get tightened, you'll see more and more of these layering effect. And in fact, now, just full transparency, one of our portfolio companies, Polymarket, is trying to figure out a way with a partnership with NASDAQ private markets, who is one of our partners, to figure out how to do this in a way that actually provides real data to understand what you're buying and not suggest that you're owning an underlying share. Playing more of the prediction of the value in the future and that's super interesting to me and that's all all of this still comes from the genesis of the secondary market.

29:24And for me, 15 years into running the business, and now we're closing in on north of$8 billion of assets, it's remarkable to see the journey of this industry. From taboo and don't talk to me, we don't want anything to do with you, to we need your help. When you think about financial services and history, the time that it's went from you're bottom feeder to we need your help, in my mind, is remarkably fast. And I don't think it goes back. I think that the need of help for companies staying private longer, we're just at the beginning. You could have 20 massive IPOs this year, and it's not going to come close to solving the problem of pent-up liquidity.

30:09Allie Garfinkle:I was going to say, why is that? The average age just in our portfolio of companies is 14 years old. The venture community builds their funds based upon a 10-year fund life. And that's the average age. That's the average age. So if you think about the GPLP relationship just in preferred shares, 70 % of the stock we buy are from other funds. It's not from employees. Wow. Well, it's also one of those things, too. One of the key narratives about the secondaries market that I think is, as far as I can tell, true. Yeah. is that a lot of volume does concentrate around the biggest companies. But it sounds like what you're saying...

30:46In times of today, yes. So as the momentum's carrying and chasing, few names are relevant.

30:53Allie Garfinkle:Who's relevant right now? Well, the ones that are all written about. So it's SpaceX, it's Andril, it's Anthropic, it's OpenAI, it's Databricks. It's the ones that people... Stripe. It's the ones that people are drawn to because of the scale. They're really, truly, remarkably, you know, differentiated assets. And what they're achieving at scale, it's insane, this size. And it's accelerating at scale. And private companies, it's important to say like this, didn't exist in that form 25 years ago. No, even 15 years ago, the average age was three years from inception to exit. Five years. Then the middle part of our thesis, it was like eight years.

31:36And now with what I was mentioning before, with the GP-LP relationship being a bit frayed, meaning if you invest your money in most GPs, there's a staff that's followed in our industry, which is contribution-to-distribution ratio. It's at all-time lows, meaning for every dollar you give a traditional GP, what you receive back in actual cash return is much lower today than it has been in history, like 50 cents on the dollar. so that pent-up demand for liquidity is only getting more as companies stay private longer because you sign up for a 10-year fund life companies now are 14 years old they're not exiting so how do you get your money back as a gp to go raise more funds you have to sell it and so this is existential it's an existential risk to their business model so the companies have a choice to either try to embrace it and stay private longer to solve the problems not just for their employees with change of life scenarios or they don't want to lose them to a public company.

32:36So there's a tender process all the way down to the early and mid-stage managers who invested seven years ago at year four of the company's life cycle. And now they're through two extensions in their fund and they can't get liquidity. So they come back to you to raise more funds and all they have is paper gains. You're looking for actual cash. And so as we've develop our business, now our toolbox we talk about, we have to solve the issues for the best assets in the world, but also our peers. You have to be a trusted partner. So the SPVs fit in that from a standpoint of the massive need of liquidity.

33:11And as monetary policy loosens, and if interest rates come down, there'll be more entrance to the public markets. But with the 10-year yield and the federal funds rate being as elevated as they are, I don't think that there's a robust IPO window around the corner. If it's open, it's open for a few, and even the amount that they raise won't be a lot compared to their private valuations. And I think this SPV movement that you're referring to continues for some time.

33:41Allie Garfinkle:And is that sort of... Assuming that's true, which I think it probably is. I think there's a higher probability that it's true versus not. Like Roger Federer, you just have to be right 54 % of the time. I think the odds of the SPV movement kind of continuing are better than 50 % percent. It's better than a coin point. It's a new industry. It exists. Yeah, and I think it exists regardless. And I think it maybe is worth asking directly. By the way, it has existed for a decade plus. Yeah. Well, and SPVs themselves, as a vehicle, have existed for decades and decades. Yeah, yeah, for sure. I think it is worth asking, though, directly.

34:18Allie Garfinkle:Yeah. How much fraud do you think comes out of the SpaceX IPO? I think it'll be similar to Twitter and Facebook. I think there'll be enough that it will be known, but it's not as much as probably people think. It's not what I stay up at night worrying about. I think there's right to be worried, but maybe for a slightly different reason. Less about will there be economic value in what they bought, but it's what price did they buy it at. That, to me, is the real problem with it. because you can't fundamentally underwrite it to know what you're buying you're just playing momentum you're using third-party validation in these brokerage groups that really are basing their data on what we call smoke and mirrors there's very little transactions actually closing on their platforms and people saying that one of our companies is worth X when we go try to move a half billion dollars worth of paper to someone the value is not x it's x minus something it's much lower than what the the the the the private you know groups are saying it's worth well and i think this is actually a good place to ask because it sounds like you give lps a lot of advice about how they should be thinking about this if they did go about themselves today are the space the company we're focused on investing in the world's fastest growing most dynamic technology companies and helping them stay private longer.

35:44It's inherently filled with the logos we're talking about because that's what we're after intellectually. You know, invest through a primary lens, but using secondary to buy value. That's how we operate. So these companies are going to be in our portfolio. So our LPs come to us and say, well, you know, I can buy this business over here through this broker. And my first question is, that's great. follow through to see who owns the shares, number one. Number two, are they giving you any data? No, fine. And three, you know, do you believe in the price? Because without the data, how do you know what the price should be?

36:29And all these things are based upon trading momentum. It's like when everything's rising and all the boats are lifting with the tide, and there's no alpha being generated it's just all beta in the public markets there's there's no ingenuity in it just stick your money in the s p 500 for the past five years it's hard to beat i tell our lps if i can beat that we've got real alpha and that's very hard to do without the data i i would say it's impossible to do without the data unless you're just blindly lucky which some people are sure i mean if you would have bought sp you know spacex and spv in 2016 you probably feel pretty solid

37:08Allie Garfinkle:right now, assuming. Yeah, even though they've had a bunch of rockets blow up and failed launches and all this, over time, Elon, you've got to get. All those weird mergers. All those weird mergers and Twitter becomes X and you buy Cursor. Why? Because you're just, you're failing the AI race and you read the S1 and it's all about AI spend and people living on Mars. What is the actual business? Well, I actually said at one point, I was like, it's a Frankenstein business at a certain And betting against Elon is not a good way to make money typically. You know, he has a history of creating a lot of shareholder value.

37:43Allie Garfinkle:Well, and any last words of advice for how to think about this question of price? Because I'm going to be real with you. Yeah, yeah. I don't know how I would do it. And I cannot imagine a situation where I have not seen the financials with my own eyes and I'm willing to wire X number of hundreds of thousands or millions of dollars. The difficulty of the companies that we're talking about here with you today is even with the data, they're impossible to model. The companies don't even know how to give you forward forecasts. So it's nearly impossible, other than a snapshot in time to try to understand if you're buying value at the time that they're raising a primary, to know where they're going.

38:24Because they don't ultimately know where they're going. and the the underwriting it now you have financial tools at your fingertips with awesome businesses like mercorn perplexity and all these ai uh tangential businesses it's it's phenomenal what's at people's fingertips today and i built an app on replit in an hour i'm a vibe coder

38:45Allie Garfinkle:i'm a vibe coder my dad also vibe codes it's amazing we had we just had our lp day in london and we had the founder ahmad from replit there and i left the meeting and i'm like i have to try this and so I run a large operating farm I'm like I'm gonna make an app to run my farm and I did it in an hour expecting you to say that I was fully not it's a it's a what's it my point is is at the fingertips of people and enough public data is available now and enough exposure you can use Claude you can use it to come up with relative yes and so just with the amount of data that's publicly available today which is better than ever before people without actual underlying company data if you spend the time my advice would be just regardless of the logo gather as much data as you can do some work with AI to help you like they're your analyst I call my my chat GPT Chuck he never asked for a raise he works 24 7 and now he gets better by himself he iterates on his own it's amazing yeah Chuck he's a little woodchuck with a top hat with glasses and I made them our own internal GPT.

39:55So people can do that themselves and you should and come up with what you think is realistic on pricing versus historical multiples. History doesn't repeat itself, it often rhymes. You can get a sense of what you're paying today and is there real value tomorrow besides just getting to the first tee box and telling your buddies that you own, Anthropic or OpenAI or SpaceX. Actually do the work and ask yourself, is this a fair price with the fees on it in the SPV world? And then go through the pain of trying to get that person, trying to sell you that piece of paper to actually give you proof that they own the shares.

40:37If you feel good after that, give them the money. Why not? It's an amazing environment in which we're working in today. and true value creation happening with these companies that we've never seen before. But if you can't get comfortable there, wait for the next shiny logo. Because what we've learned in 15 years is every three to five years, there's the next N of one. They keep coming. And what's happening tomorrow, we don't know yet, but they'll be the next one. So, anyway.

41:06Allie Garfinkle:So where does all this go over time? Do secondaries ultimately go the way of, say, index funds? and become something that everybody in some capacity is invested in? Do they go the way of SPACs or is it something else? Yeah. So the SPAC thing, I think, you know, SPACs were always a financial instrument that helped the right company become public. I think we all got a little too bored at home during COVID, right? I did too. We developed a SPAC strategy, raised two SPACs in like a week. You're like, yeah, I did it. We did the SPACs. It might as well have just went to my fire pit in the back of my yard and lit all that money on fire.

41:49It probably would have been more enjoyable than the process we went through. Not that we didn't have every right intention. It's just when everybody else is running to do something, don't run and do it is my advice. Be counterintuitive a bit and take a perspective that's different, which is, by the way, in our industry, not popular. right when everybody wants to buy something is when we want to move on from it it's it's like when the house is on fire everyone's running out we're running through the front door and and and but the SPAC thing I don't think it goes by the way of the SPAC that's it's like gone by the way the dodo bird you know I agree with you I think that the the problem that exists will not be solved with the current AUM of the managers that exist today.

42:41And so, and I can just see this in the work that we're doing with the companies. What used to be a mega cap private round was 50 million. It's 60 billion today, and they're done in a week.

42:54Allie Garfinkle:50 million is a nice seed. It's nothing, right? So, the problem to solve for these companies, all those employees and shareholders that have a constraint on time because of the legal documents, there's a massive need for this. So it needs to be solved with more products. Get the doctors and dentists of the world into a product. And by the way, the KOTU brothers, I've been fans of them for a long time, love the fonts. They built a product that I love and I think is the way of the future, a tender product that's available on a lot of different wealth platforms. I'm trying to shouldn't give them you know all the money's gonna flow to them maybe can they listen to your podcast so Thomas and Pierre I think they're doing okay I think they're doing okay but the point is is it's bringing the product to the masses with high quality managers actually get the direct access and fundamentally can underwrite and know what they own and that movement isn't gonna it's like the toothpaste is out of the tube these index funds or ETFs wanting to get access to the tender products or interval funds or quasi liquid evergreen structures.

44:04That's the direction it's going to go. And as a manager in the space, we can either embrace it. Or. It's like the the train tracks, if you if you're on the right track, but you don't move, you're going to get ran over. Right. So you have to evolve in this industry to meet the needs of these companies, because it's not going to go back to being public in three years, four years, five years. There's just systematically structural issues in the public markets that companies aren't interested in it. And they're going to stay private longer. And you have to be able to provide a service to be relevant.

44:41And you need capital to do that. And the SPV market, in my opinion, provides a major proof point that the appetite is there for the masses to get access to this asset class, which is now we can say it's an asset class. For a long time, firms were like, we don't know where to put you. Are you growth? Are you primary? What are you? No, we're a growth secondaries firm. That didn't exist. It does now. And that's a segment of the industry that's getting bigger and broader and more capital. And I think it's really early innings. Ten years from now, just to give you the last ten years, the volumes went from like 30 billion of global secondaries of all types to 300 billion.

45:29And I think it goes from multi-trillion dollars in the next few years. It's just the beginning.

45:36Allie Garfinkle:So secondaries get bigger, probably more regulated over time. I think regulation in this, I'm typically a free market type of person. I do think more regulation in this space, and it's selfish to say it, right? It's going to help me as an established firm in it that embraces the regulation, I think will be helpful. It will be helpful to help the public protect themselves. And I think we need to get there sooner rather than later. As we were sitting here, the news broke that officially Anthropic is the most valuable startup in the world, surpassing open ai with a valuation of 900 billion reaction not surprised not surprised either it's uh not i mean congrats to dario and team i mean we've been a part of the story for um a number of years and when we first got involved i could have never imagined it would get three you know a third of the way to where it is today um it's really remarkable and congrats to them.

46:40I'm not surprised. I'm excited for them.

46:46Allie Garfinkle:I'll tell you why I'm not surprised. There was so much chaos that I was hearing about in the market for Anthropic shares in the lead up to this round that I was just sort of like, yeah, that makes sense. I've seen that number already. Yeah. And by the way, internally, a great team, the CFO, Christian Rowe, we've known for a long time dating back to Airbnb and then to Fanatics and now at Anthropic. Fair but difficult group inside of Anthropic, really trying to build a transformative business. And I think they can probably say they've done that. $900 billion, does that seem high, low, fair? Based upon the financial metrics that they provide today, these businesses change constantly, right?

47:33It's the forecasting that they provided investors a few years ago, they surpassed in the few months after they provide them. And, you know, I think it's one, as I mentioned before, them trying to understand how to model their own growth, inertia kind of took over, right place, right time, solving a need, and a really high quality product, and done in a very different way than OpenAI has achieved their valuation. OpenAI, every time they've raised money, I feel like they've pushed it. They've pushed the price. And they've had all these interesting deals that kind of add it together. Some of it's cash, some of it's compute.

48:16And you get it all together and then you get to$852 billion, I think it was. But there's some interesting components of it that's not straightforward.

48:29And it's been way more frequent than we've thought they would, you know, and I think they would say that too, is the need of capital is clearly more than any of us thought it would be. They kind of just get a deal done quick, maybe leave a little money on the table, and wire the money in a week, you know, versus this long drawn out process. So they've taken two different approaches. But to think that we're a part of both of those stories from the time that we got involved several years ago to now, I would have never believed that if you would have told me we would have this conversation, they would both be valued close to$900 billion.

49:08I would have told you, you know, maybe we are in Mars or on Mars doing this. Got here in a SpaceX shuttle and Elon's going to walk through the door and we're going to fly around with R2D2 on the front. I would have thought that was – An actual real-working R2D2. I thought that would have been more of a possibility than us sitting here.

49:28Allie Garfinkle:This is maybe a dumb question, but do secondaries investors have the same rules around conflicts that traditional venture investors do? Because if you're both at Anthropic and OpenAI, they have beef. I don't know if you've heard. Yeah, yeah, yeah. I think for us, obviously we don't share data with anyone. Even our LPs don't get data on these types of businesses. It's, I think, more of a perceived conflict than an actual one. I mean, our job is to take capital from LPs and invest it into companies and provide them with a return that's outsized to what they could normally get in a liquid market.

50:13That's our job. And if we can outdo that more often than not, we're going to have a business. I think the companies and the boards over time, as long as we're not in the boardroom and we can be active and help them in ways that are beneficial to what their needs are and not show that we have any conflicts, it's pretty common for us. uber lyft turo get around we tend to back multiple winners and one ultimately becomes the outsized winner here we're fortunate enough to be part of two great businesses that are truly individual businesses that are changing our lives every day and different to different people and different to different companies.

51:03And there's enough probably for three more of them. That's what's crazy about it, is they are the clear winners. They will be here for a long time. They are our generations of the Googles and the Microsofts. That's who they are. And we're a part of that value creation. To have one, awesome. To have two, that's got to be a little bit of luck, you know, in the portfolio.

51:27Allie Garfinkle:You say there's room for more, but I wonder if there is enough capital in all the world. That's where the public markets come in. There's still a lot of capital in the public markets, and these companies will access them because they have an unbelievable need for capital. The exciting thing is all the time. It's a sincerely historically unprecedented need for capital. It is, and every time you think that they've exhausted it, they somehow just in a very short period of time are able to put together a massive amount of money. But when you look at the capital flowing into companies today privately, it's a handful of businesses that are getting all the money.

52:06So it's very counterintuitive to traditional macroeconomic trends. When you have high interest rates and low equity risk premium in the public markets, it's actually lower than it was in 2000 today. to have a few companies attract all the capital what's happening with the rest that's that to me is is is is the scary part it's not will they succeed is this price fair they still will go up and up up likely and to the right it's just at some point when do they become wildly profitable and I don't know if anyone knows the answer to that question.

52:55Allie Garfinkle:They definitely don't know. No, they might. They might. I think they don't. That's my hot take. We can ask Chuck. I bet Chuck has an answer. We'll leave it there. Larry, thank you so much. Thank you, Ali. Thanks for having me. This has been fun. And that was Larry. This is going to be a summer and possibly a fall where the usual laws of financial physics do not necessarily apply. That's it for Termsheet. I'm Allie Garfinkel and I'll see you soon.

From the publisher

A hidden market for shares of the world's hottest private companies has quietly grown to an estimated $112 billion, and most of it happens off the books. As SpaceX, OpenAI, and Anthropic edge toward going public, the investors who poured billions into pre-IPO shares may not actually know what they own. Larry Aschebrook founded G Squared in 2011, when trading secondaries made you a "bottom feeder" who got cease-and-desist letters. Today the firm manages north of $8 billion and holds stakes in SpaceX, OpenAI, and Anthropic. Fortune's Allie Garfinkle sits down with Larry to talk about the shadow market behind the biggest names in tech, why layered SPVs could leave investors with nothing, and the reckoning he sees coming when these companies finally go public.

0:00 The $4 Trillion Problem Nobody's Talking About
0:56 Hot IPO Summer Is Here
1:58 They Wouldn't Return His Calls
3:15 His First Trade? Twitter Stock
6:06 What Secondaries Actually Are
7:26 The SPV Trap: Fees Stacked on Fees
14:27 The Doctors and Dentists Problem
18:55 Back When This Was Taboo
21:35 What Facebook's Lockup Should Teach You
23:56 "SpaceX Could Force a Reckoning"
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