Investing Billions - E338: How I Invest $9 Billion into VC & Private Equity

Episode Date: April 1, 2026

Is AI the biggest risk to equity portfolios or the biggest opportunity? In this episode, I talk with Christopher Vogt about how institutional investors think about risk, portfolio construction, and m...anager selection across public and private markets. We discuss AI disruption, why governance and structure matter more than asset labels, and how to evaluate managers using both quantitative and qualitative frameworks. Chris also shares lessons from building an endowment style portfolio from scratch, why patience matters in private markets, and how position sizing can make or break long term outcomes.

Transcript
Discussion (0)
Starting point is 00:00:00 Chris, you run equity strategies at the Margaret A. Cargill Foundation. What part of the equity market keeps you up at night today? Being an investor or an allocator, you have to kind of paranoid in general. So I would say everything, but they'd be more specific. I would say that AI risk is super topical. Obviously, aside from private credit, which I don't manage and is well-publicized in the media, I think software-related private equity could see an adjustment period. You know, the AI risk is real.
Starting point is 00:00:25 I think CEOs of SaaS businesses should be very scared of being disrupted. The critical part here is making sure that if you're invested in private equity, that you have a very good general partner. On the other hand, OpenAI came out in fall of 2022. So it's not new. DeepSeek made their announcement in early 25. So hopefully good GPs are aware of risks to traditional SaaS. And depending on the asset, not all SaaS is going to be disrupted anytime soon.
Starting point is 00:00:52 Think of like system of record, critical software, compliance software, highly sensitive data. The other thing is today there's going to be a lot of opportunities because everybody's aware of the AI risk. So I think there's going to be a lot of stuff that's coming through the pipe right now that could be quite interesting. And lastly, I would say top 10 tech companies in the U.S. today are, I think on average, something like 35 years old. So they've gone through desktop, laptop, mobile, SaaS, cloud. And so not all these companies are going to disappear out of the blue. And on the other hand, it could be an incredible productivity boost. That might help asset prices long term. There's a meta angle to this. Clayton Christensen
Starting point is 00:01:29 famously wrote this book, Innovators Dilemma, which talked about the disruption of cycles, how the next cycle kind of disrupts incumbent. But what happened was that this generation of CEOs, Elon Musk, Mark Zuckerberg, Sergey Brin, they all have this book on their bookshelf. So they're all much more self-aware. Instead of being like the Kodak or the IBM of last generation, they're trying to actively disrupt themselves. I think that's a great point. That's a lot to mention kind of aside from the AI risk, I worry about a lot of what other investors worry about, sovereign bond crisis, higher interest rate spike because of it, you know, we have war going on. And I think probably the bigger one is just structurally higher inflation, which I think is with us for
Starting point is 00:02:11 the rest of my career. That's a big change from the past 40 years. So absent some exogenous shock, I think we're in for structurally higher rates. I'm not saying we're going to vote much higher, but I'm just saying I don't see us going back down below 2% inflation in the next 10 to 15 years. The national debt also keeps me up at night. And thankfully, I have a lot of resources I could call up a lot of people. And it seems to be that the smart consensus view there is that the most likely scenario is not some austerity measure, but it's the increase of inflation over maybe a decade, maybe two decades that's going to be able to allow the government to pay back its debt.
Starting point is 00:02:47 What are your views on us? Yeah, I totally agree. I think David Rubinstein said something to this effect a couple of years back is that he basically made the point of like, you cannot cut entitlements. You cannot raise taxes too much more. They're already very high in many states and federally. So the real way out of this is to slightly inflate. So, you know, 3.2%, 3.2%, 3.5% inflation, which will significantly help over 20-year period. On the other hand, you know, you have a new Fed chairman coming in who, you know, I think generally is considered a hawk. And it'll be very interesting to see if this plays out. If I already
Starting point is 00:03:22 guess, I would say the new Fed chair is not someone who's going to tolerate, you know, three, three plus percentage inflation. Expert calls have always been one of the most powerful ways to build conviction, but today, investors are asked to cover more companies, move faster and do it with leaner teams. With Alpha Sense AI-led expert calls, their TGIS call service team sources experts based on your research criteria and lets the AI interviewer get to work. The magic is in the AI interviewer, purpose-built and knowledgeable-based information to conduct high-quality context-stretched conversations on your behalf, acting as a trusted extension of your
Starting point is 00:03:57 team. Then they take it one step further. Your call transcripts flow natively into your Alpha-Sense experience and become querable, searchable, and comparable, so your primary insights plug directly into earnings prep, digital work streams, and pitchbooks with zero tool switching. And with AlphaSense expert call services, the AI-led expert calls are just one option, because we know the importance of a hybrid expert research approach. AI for coverage and efficiency. Humans for complexity and conviction. It's the institutional edge that scales research without scaling headcount. For hedge funds, that means validating thesis assumptions across dozens of experts before earnings instead of a handful.
Starting point is 00:04:35 For private equity, it means faster pre-IOI scans and deeper commercial diligence. For investment banks and asset managers, it means pulling real operator perspectives straight into models and sector positioning without disconnected tools or manual handoffs. All of it lives inside the Alpha Sense platform. trusted by 75% of the world's top hedge funds alongside filings, broker research, news, and more than 240,000 expert call transcripts, turning raw conversations into comparable, auditable insight. Take advantage of Alpha Sense AI-led expert calls now.
Starting point is 00:05:08 The first to see wins. The rest follow. Learn more at Alpha-sense.com slash how I invest. One of the unique things about AI and this tech revolution is that it's not limited to the technology space in that if you had a biotech revolution, biotech might be transformed, but it's not going to transform SaaS companies. Talk to me about that. How do you look at the AI revolution, how it affects your entire equities portfolio? You mentioned biotech. It's already disrupting biotech. You know, there's numerous examples of AI-led drug research,
Starting point is 00:05:43 which is creating drugs much faster than they have in the past. You know, it affects productivity everywhere. We're using it internally. I'm sure other companies and other foundations, and elements, et cetera, are using it. So that's the kind of crazy impact of this, which is still unknown, right? As I mentioned, it might lead to a massive productivity boost. And similar to software, it's not a vertical. It's across every single thing. It'll eventually be in old school industrials, maybe even utilities and things that are otherwise quite boring. It'll take some time. Again, as I mentioned earlier with the whole critical software type of stuff. I don't know if anyone that runs a nuclear power plant is going to switch
Starting point is 00:06:19 to an AI model anytime soon. But over time, I think it will, it can disrupt just about everything that we know in the economy. It's actually a very difficult question to answer, which is what will AI not disrupt? My first guess is plumbing or electrical work, you know, kind of behind a wall. You need a new light put in your house. I think it's going to be a long time before they have an AI robot that's going to come into your house and do that work.
Starting point is 00:06:41 Although I think at some point, maybe they will. I've seen a lot of very interesting roboticization applications that are coming. but I think that might be, you know, a decade plus off, if not longer. So famous, Moravex paradox, which is AI is going to struggle at things that humans could do and humans will struggle at the things that AI will do. MacP decided to put equities, public and privates under one roof under you. Talk to me about that decision, and how does that play out? But we're a relatively young organization, and one of the benefits, and there were some negatives, too,
Starting point is 00:07:11 but one of the benefits of being young is that we were able to kind of whiteboard on how to organize. Our CIO chose prior to my arrival. I had nothing to do with it, to organize us by risk assets. So equity, credit, and fixed income, and real assets. I was very highly attracted to the structure as it dovetailed well with a piece that I co-authored almost 15 years ago that was entitled, Hedge funds are not an asset class implications for institutional portfolios. This basically was the concept that many hedge funds, among other concepts,
Starting point is 00:07:39 but one of the concepts was many hedge funds have traditional data embedded in their strategy. So they should reside in those. risk assets, if you will. This makes for a much simpler strategic asset allocation as they can be uniform and singular. You don't have to have separate optimizations. For example, you have equity beta in perhaps three or four different asset classes. You have it in private equity. You have it in public equity. You have it in hedge fund equity. And you've been having some credit portfolios, depending on what the strategy is. So running multiple strategic asset allocation optimizations in a vacuum, and each one of those is kind of clearly suboptimal. Moreover, equity is equity. And doing diligence,
Starting point is 00:08:17 on public, private, or hedge equity has significant overlap. There are differences, of course, on the periphery, you know, some short securities, some use leverage, some are illiquid. But in the end, it's all equity risk. I'd also note that I think a lot of other institutions haven't structured this way. And I think about why a lot, at least used to. And I think that, you know, very few institutions had large private equity portfolios in, let's say, the 1970s.
Starting point is 00:08:43 So they added a private equity group when private equity became popular. Likewise in the 90s, hedge fund became popular. So they added a hedge fund team, which totally made sense. And I think today, you'd say, well, why don't they restructure? I just think there's a lot of operational pain there. You'd have to, you know, there's going to be turf warrants amongst people that run those different groups. They're going to have to go to their board and investment committee and see permission to restructure. There could be job losses.
Starting point is 00:09:07 And so outside of a big catalyst internally, let's say a changeover of a CIO or maybe a sustained period of underperformance, I don't see other groups doing a reord to somehow fit our model. And I'm sure they're supposing news to our model. You were the second hire at the foundation after the CIO. How did you go about building your investment strategy from scratch? It's clear from the start that we were going to build an endowment-like model. I say endowment-like because unlike endowments and some foundations, we had a sole donor.
Starting point is 00:09:36 So we don't take in donations. We don't do fundraising, like many peers, in the ENF space. So in terms of risk, we're more conservative. for a couple of reasons. First, we don't have fresh capital. We don't have fresh liquidity to work with or to help cushion the liquidity. Secondly, I think senior leadership here is committed to being a reliable donor to our grantees. So we take less risk in order to meet those commitments in both up and down markets. Aside from these differences, the strategy was to create kind of a lower risk endowment like model. So we have much larger allocations to credit and fixed income and real
Starting point is 00:10:07 assets than other endowment peers for sure and some foundation peers as well. When we last chatted, you mentioned that you used both a quantitative and a qualitative mindset. Talk to me about that. And how do you fit that into the investment process? Until recently with the rise of AI, especially like super AI, the one that does cognitive thinking and has feelings, et cetera, I don't think that there's a model or a quantitative process that can pick the best managers. So I think the best allocators, and this is somewhat self-serving, you know, as I have a liberal arts degree and a MBA from a school that's known for its quantitative analysis. I'll give me an example. In venture capital, data rooms often are
Starting point is 00:10:44 lacking hard data. And the one thing I always mentioned to staff is if we want to select general partners who lie a little bit to us rather than ones that lie a lot to us, I know that's very cynical. But I think it's hard to develop a quantitative model that could detect how accurate or how inaccurate a GP is being with us. If you work with models or if you have an optimizer, it's going to seek a solution. And it might be a corner point solution. The famous example is mean variance optimization. So models love, you know, for example, in this case, a return series that are low-val and persistent excess returns. But the made-off fraud, for instance, was exactly that.
Starting point is 00:11:19 It was persistent returns and a low-ball strategy. So you can't rely on a model just to pick that out because, of course, it's going to go there. That's what the model is designed to do. The other thing I'd say is, like, you know, all models are false by deposition. You know, I say that as a University of Chicago graduate school, business graduate, you know, I'll give another example.
Starting point is 00:11:36 I used to build model airplanes, you know, the plastic model airplanes, like World War II airplanes when I was a child. but nobody would ever assume that you'd fly that over the Atlantic because it's a model. So models are extremely useful. Don't get me wrong. But one should always consider what is the logic of the model, how accurate is the data going into the model? Again, I mean, variance optimization relies on capital market assumptions.
Starting point is 00:11:59 Capital market assumptions are frequently inaccurate. I've got ones in my drawer from 2010, 11, 12. They're all wrong. And so you have to be just highly aware that you're dealing with a model that's useful, but that is not a perfect solution. I'm like you have an MBA from Tuxk School from Dartmouth and a master's psychology from Harvard. And everyone always comments, oh, that should be really useful. But I've actually never met anyone to do both degrees. I think it's just there's no dual program.
Starting point is 00:12:22 It is my simple, my Occam's razor to why more people don't do that. But when it comes to this quantitative and qualitative mindset, if you're to distill the main takeaways from that, when you're diligenting a manager, what exactly are you looking quantitatively? what is in the spreadsheet, and what are you looking that's not in the spreadsheet? The simplest things in the spreadsheet are, you know, are they, are they producing excess returns? And what are those excess returns? You know, there's a lot of talk of alpha and then there's excess returns. I say excess returns because I know that there's alpha in there, hopefully, and there's probably some types of alternative beta or betas that make up that excess return.
Starting point is 00:12:58 It could be timing. It could be sector selection, things that aren't classically considered alpha. That's something we're going to look at on a quantitative side. maybe digging a little bit deeper if it's an active equity manager, we're going to look for idiosyncratic stocks from election. That's the highest, that's the purest form of alpha. So that's got to be high. If it's a hedge fund,
Starting point is 00:13:15 we're going to want to see if they're driving alpha or excess returns out of their shorts. I don't want to just pay to have them short the market if they lose money on their shorts all the time. So that's maybe some of the higher level research that we'll do. On the qualitative research, that's where it gets a lot more gray, a lot more foggy, if you will.
Starting point is 00:13:35 We're looking for consistency and kind of what their strategy is in discussions with them. I'm looking for that consistency through the entire employee staff from partner down to, you know, the first level analyst. It's one of the reasons I like in in person meetings in their offices is that you can kind of get them separated by themselves and ask kind of the same questions. Similar to what a police detective would do in a crime investigation. And so those are kind of the softer things of like hearing consistency across what they're doing. And then on the, you know, away from just the manager meetings themselves, et cetera, is, you know, referencing, particularly off reference sheet references, which you have to do a lot of work there and kind of triangulate and figure out who should I talk to who's not on this list who probably knows this person from the past or maybe other current firm left or, you know, situations such as that. It's funny. You use this analogy of a detective.
Starting point is 00:14:27 Alex Edelson, who's been on the podcast three times. He's arguably the very best person I've ever met in terms of references. and he got his training as a deposition lawyer. So he knows exactly how to frame questions, how to ask questions and references, which are simultaneously probably the most boring part of manager selection and also probably the most alpha is gained in terms of picking managers. That would be a great background.
Starting point is 00:14:51 I'm sure he's superlative at doing that. One of the things I was going to mention is I took a course, it was years ago, by a group of ex-CIA counterintelligence people. and they basically did this whole study on what people say and how they act, meaning like what do they do with their arms and they call them anchor points when they're lying. And they gave many, many examples. And they showed many examples of famous people who were in either depositions or maybe just speaking of the press.
Starting point is 00:15:17 Where they were lying, they clearly lie. And everyone knows now because the stories have come out. And it was really enlightening to see something where you can actually begin. It's not totally foolproof and it's not just that they say one thing that you know they're lying. but you can discern or kind of trace together dots if they're doing a lot of these different behavioral traits when they're speaking to. It's interesting about references,
Starting point is 00:15:37 which I obsess over on the podcast. I just think they're so critical, is that you could have two institutional investors sitting in on the same conversation and they have a completely different qualitative read on the reference from each other, two very experienced people. That's a good point.
Starting point is 00:15:50 I really like the diligence with one of my colleagues. And the reason is, you know, people, you know, I hear things that maybe they hear or they don't hear or maybe I get it backwards. sometimes. So I think it's really helpful to have more than one touch point when you're doing diligence and maybe multiple touch points. I say that multiple touch points being in private equity, I much prefer to meet the general partner prior to a fundraise, you know, a year in advance, two years advance. You meet with them two, three, four times prior to the fund rates. Because
Starting point is 00:16:19 in the fund rate is, you know, there's at least two things that happen. One, the book is marked up in advance of the fundraise, almost always. And secondly, it's a beauty pageant at that point. Everything is framed in the best light. And if you get in there a year or two before, and I always ask what assets are doing well and then give me at least one example of something that's not doing well and what's the learning point from that,
Starting point is 00:16:41 you get much better dialogue prior to the fundraise when they're not in kind of sales pitch mode. You're also measuring the slope. Where were they a year ago? How have they evolved over the last year or ideally two, three years? You mentioned that you like to go to the manager's office
Starting point is 00:16:59 and meet them in their office. Why do you like to do that? First, we want to establish that they have an office. I know that sounds ridiculous, but I think that's important one. Secondly, I want, or that they're even human. Yes. True. Secondly, I want to meet with partners and employees below the partner level.
Starting point is 00:17:18 You know, maybe a famous example of this was during pandemic when they did virtual annual medians. And I was convinced, first of all, it was just the three, maybe four head partners that spoke. Secondly, I was convinced it was the script that the general counsel had reviewed. So it was very sterile and maybe not in lightning at times. It's much easier to meet with maybe the first level analyst when you're in their office. I also start diligence at the front door.
Starting point is 00:17:45 What is the mood of the office when you walk in there? You can sense mood if you look around and kind of see are people having a chat and in a good mood. How are you greeted at the door? I think that's an important one. I think you can get a sense of culture from kind of the minute you walk in. And certainly after you spend a few hours. I also start, I mentioned this earlier, I start with a uniform set of questions
Starting point is 00:18:02 so I can get answers that are hopefully consistent and ensure that I have conversations in isolation. And sorry if that sounds paranoid, but I think many investment managers are, you know, their investment managers, Wall Street, whatever you want to call it, are motivated by most many, not most, many are motivated by fees. And performances can be an afterthought. And so we're trying to figure out, are they high quality and are they really motivated for performance, not just the management.
Starting point is 00:18:30 In many ways, diligence is just the operationalization of paranoia, figuring out whether you're being told is the truth. That's brilliant. I'm going to use that in future. I want to double click on going to the office. So is there one office culture that outproduces others is a happy office better? Or are there like chip on the shoulder offices? What's a predictive office culture that leads to success?
Starting point is 00:18:56 That's a good question. I, you know, I don't know if I know, but I'll say this, in places where we've made mistakes, not always, but many times it's a, it's bad culture. Partners leave or people below the partner level leave. Turnover is always bad. Yeah, exactly. Turnover is bad, especially in a private fund. And so, so I do want a high performing office that maybe has a little bit of edge to it,
Starting point is 00:19:22 but I also want to see a good culture, you know, and I could go into things like this concept of like, radical candor, which is a book by Kim Scott. And it talks about basically this concept that like, I'm going to say what I need to say to you because I care about you and I care about our performance or work as a firm. And I think that's kind of critical. So it's a bit of a balance. It's like I don't want everybody all chummy and like all friends and no focus on making
Starting point is 00:19:46 sure that the hard work is done and that they, you know, that's a high performance up and out culture. I actually quite prefer up and out cultures. But the up and out culture can also be, it can also have a good culture to it where people are. open, honest, communication is good. And so those are the things you're looking for. So it's a little bit of a mix, if you will.
Starting point is 00:20:02 It's kind of like the seven dwarfs. They're working, but they're happy. It's kind of like a jolly, jolly working culture. So as a subset of building out the equity strategy, you had to build out your venture program. What were your first principles when you went about building a venture program? I am going to take it beyond venture. But I would say that, you know, a couple of things.
Starting point is 00:20:20 When we came in, the public side was heavily indexed. So to some extent, we could just start working on private. Plus, private's takes a lot longer to build. It takes longer. You know, funds aren't open all the time. They're closed-end funds by definition. So we spent most of our time in private starting out. You know, if I think back and think, what should I have done differently?
Starting point is 00:20:40 You know, I wished, and we tried, but I wish we had delayed and taken our time, I think for two reasons. First, I think we would have made marginally better picks by doing more comprehensive market mapping, for instance, and just taking our time. Secondly, I think we would have had more flexibility. let's say co-investment, direct investment, specific secondaries. Keep in mind, we were building this portfolio during a very frothy period, you go 2015 through 2019. And my colleague and I were thinking at the time, let's go slow, we're building a portfolio for an entity that will exist in perpetuity.
Starting point is 00:21:12 So why do we want to rush forward in three to five years? And the reason we, I wouldn't say we rushed forward, but we moved with alacrity is that there were some technical items in our reporting related to benchmarking and it was painful from a performance perspective to go slow. These are technical items though. The other thing I'd stress is I don't have a, you know, that's a minor regret. The portfolio is, I think, in great shape, but you know, it's doing well. But when I think about, when I think back, I think this was an area of improvement that we put up,
Starting point is 00:21:45 that may have been improved. A couple of best practices that I found on that. One is, this was originally popularized by Founders Fund. They didn't let any of their GPs make an investment in the first year. So you had to see it's impossible. You come in to venture. You meet a venture capitalist. By definition, they're the 0.1% of person you'll ever meet.
Starting point is 00:22:05 You think, wow, this is awesome. And you invest in the first three funds because they're all 0.1%. You're actually right. What you don't know is that you're actually looking for the 0.01% because everyone's 0.1%. You want to be in the top 10% of that. So there's this principle of you have to see 100, 200, 300, managers before you really make that first investment. and you could operationalize that.
Starting point is 00:22:24 The second, perhaps like a very qualitative approach to it that I've seen some foundations and family offices do is start by investing into secondaries because they get exposure to early vintages, so you get more vintage diversification. You minimize the J-curve, so you get to start to show how venture works. It's very difficult feedback cycle when you invest and you're like, okay, just trust me for 14 years. This is going to work well. So there's a behavioral aspect to that.
Starting point is 00:22:50 And the best way that I found people kind of institutionalize this patience is North Dakota Land Trust, I have the CIO, Frank McHale. And before they invest, they actually find a way to capture the index of that portfolio, whether with an evergreen fund or with some other mechanism. So they're always exposed to, let's say, venture. And then they only invest if they could beat that index. So to allow support for today's episode comes from Square. The all in one way for business owners to take payments, book appointments,
Starting point is 00:23:20 manage staff and keep everything running in one place. Whether you're selling lattes, cutting hair, running a boutique, or managing a service business, Square helps you run your business without running yourself into the ground. It's actually thinking about this the other day when I stopped by a local cafe here. They use Square and everything just works. Check out as fast, receipts are instant, and sometimes I even get loyalty rewards automatically. There's something about businesses that use Square. They just feel more put together. The experience is smoother for them and it's smoother for me as a customer. Square makes it easy to sell wherever your customers are in store, online, on your phone, or even at pop-ups, and everything stays synced in real time. You could track sales, manage inventory,
Starting point is 00:24:00 book appointments, and see reports instantly whether you're in your shop or on the go. And when you make a sell, you don't have to wait days to get paid. There gives you fast access to your earnings through Square checking. They also have built-in tools like loyalty and marketing. Your best customers keep coming back. And right now, you can get up to $200 off Square hardware when you sign up at Square.com. slash go slash how I invest. That's SQU-A-R-E dot com slash go slash how I invest. With Square, you get all the tools to run your business with none of the contracts or complexity. Run your business smarter with Square. Get started today. Support for today's episode comes from Square. The all-in-one way for business owners to take payments, book appointments, man and staff, and keep everything running in one
Starting point is 00:24:42 place. Whether you're selling lattes, cutting hair, running a boutique, or managing a service business, Square helps you run your business without running yourself into the ground. It's actually thinking about this the other day when I stopped by a local cafe here. They use Square and everything just works. Check out as fast, receipts are instant, and sometimes I even get loyalty rewards automatically. There's something about businesses that use Square. They just feel more put together. The experience is smoother for them and it's smoother for me as a customer.
Starting point is 00:25:09 Square makes it easy to sell wherever your customers are in store, online, on your phone, or even at pop-ups, and everything stays safe. synced in real time. You could track sales, manage inventory, book appointments, and see reports instantly whether you're in your shop or on the go. And when you make a sell, you don't have to wait days to get paid. There gives you fast access to your earnings through Square checking. They also have built-in tools like loyalty and marketing. Your best customers keep coming back. And right now, you can get up to $200 off Square hardware when you sign up at square.com slash go slash how I invest. That's SQ-U-A-R-E dot com slash go slash how I invest. With Square, you
Starting point is 00:25:46 You get all the tools to run your business with none of the contracts or complexity. Run your business smarter with Square. Get started today. Support for today's episode comes from Square. The all in one way for business owners to take payments, book appointments, manage staff, and keep everything running in one place. Whether you're selling lattes, cutting hair, running a boutique, or managing a service business, Square helps you run your business without running yourself into the ground.
Starting point is 00:26:10 It's actually thinking about this the other day when I stopped by a local cafe here. They used Square and everything just works. Check out as fast, receipts are instant, and sometimes I even get loyalty rewards automatically. There's something about businesses that use Square. They just feel more put together. The experience is smoother for them, and it's smoother for me as a customer. Square makes it easy to sell wherever your customers are, in store, online, on your phone, or even at pop-ups, and everything stays synced in real-time. You could track sales, manage inventory, book appointments, and see reports instantly whether you're in your shop or on the go.
Starting point is 00:26:43 And when you make a sell, you don't have to wait days to get paid. where it gives you fast access to your earnings through Square checking. They also have built in tools like loyalty and marketing. Your best customers keep coming back. And right now, you can get up to $200 off Square hardware when you sign up at Square.com slash go slash how I invest. That's SQU-A-R-E.com slash go slash how I invest. With Square, you get all the tools to run your business with none of the contracts or complexity.
Starting point is 00:27:10 Run your business smarter with Square. Get started today. It allows their opportunity costs to be exposure to the, to the beta of asset class, which doesn't sound sexy. But behaviorally, I love that because, you know, you're incentivized not to take action unless it's a really good manager. A couple things on that is that we did consider secondaries. And in retrospect, maybe we should have done some.
Starting point is 00:27:30 However, I'll note that like, and the reason I say that is, at least one reason, is that we were building a portfolio. So after we kind of built the portfolio in 2019, our average asset life was like 1.8 years. So we had a portfolio that was, you know, deep in the J curve, nothing mature because we were brand new, if you go. And so that would have helped bring in some kind of older vintage and may have been cash flowing out. On the other side of that is that when you buy a secondary,
Starting point is 00:27:55 let's say it's a, let's say it's 2020 and it was a 2014 vintage secondary you're buying. You're buying a 2014 vintage price in 2020. You're not getting a discount. You're not getting a, you're not getting the initial investment that's now gone up 3x or 2x or whatever the case is. You're buying into the 2x or the 3x. So I caution to say like it's a, it's a,
Starting point is 00:28:14 panacea, some type of magical potion to fix a situation when you're building your portfolio. But I also think, like, maybe we should have stopped and done that. Keep in mind, we were building. So it was very much a startup environment. We were building performance systems. We were building risk systems. So to stop and to do a separate project like secondary, it's as opposed to just continue to fundamentally underwrite direct fund investments,
Starting point is 00:28:37 it would have come at a cost. We could have done secondaries, but then we would have done less fund investments. And maybe that would have been better. But as I mentioned earlier, the portfolio I think is in great shape of significantly outperforming our benchmark. And so, you know, it's ultimately a positive, I guess. When you're investing for a foundation, you want to get vintage diversification, which means you want to get diversification to different years, especially in venture capital because some vintages are way up, some are way down, as we know historically. What do you consider a diversified portfolio from a vintage standpoint? Is this three years, six years?
Starting point is 00:29:12 Is it just, you know, over longer time periods? Give me a sense for how you know that you're adequately diversified. It's a good question. I think three years is too short. Six years might be about right, but 10 years might also be about right. You know, I think what you want to do is because we don't know what the future holds, you know, as I mentioned back to the mean variance optimization, you're lucky to get the sign right in the S&P 500 in any one year, much less whether it's up eight or 12 or 15 or 20 percent.
Starting point is 00:29:39 And so because of that, in privates, it's even harder because you commit, but they call the capital. So you don't know what capital is going to be invested in. So I think you need to be really consistent and have a liquidity that you're putting out kind of, you're equally waiting every year, unless you have a crystal ball and you know that one year is going to be better than another. But we don't have one, and I wouldn't suggest to most investors that they should try to do that. So if you're being consistent and constantly putting out more or less the same amount of capital with respect to your assets each year, I think you can achieve that diversification. The other area that I would mention is, you know, vintage year risk is a bit of a very complicated situation.
Starting point is 00:30:18 I'll give me an example. A fund closes, holds a dry close in September of last year. They call no capital during last year. And we have a current situation like we have with a war and lots of concern over the economy. And so they call 15% of the capital this year. And next year, they call 35% of the capital. capital. And the year after that, they call 15%. What's the vintage year? Is it 27? Because they called 35% of the capital. Is it 26? Because that's when they first started calling capital. And so it
Starting point is 00:30:48 it just creates a complicated measurement as to what the vintage actually is. We have a rules-based approach where it's the year that they first call capital. However, in reality, I know in certain cases, it's actually next year's vintage, not this year's vintage, because they might only call five or 10% this year, and they call the majority of it in the future years. So it's a very tricky question once you actually look into the details of when capital is called. So another way, you might have to be more diversified because it's not, if you invest across 10 years, you're not doing 10, 10, 10, 10, 10, 10, 10. It might be 5, 515. Yes.
Starting point is 00:31:23 I'll give one other example. In October of 21, we committed to a fund that I think is a top tier buyout fund in tech. And they didn't call capital for over a year. So I didn't know that in its 2021 budget that I used. for the private commitment. They didn't call capital, I think, until the end of 22, maybe even early 23.
Starting point is 00:31:43 It's very hard to account. Like, what vintage is that? I would say it's probably 23, 24 vintage, even though we committed it in 21. I've been on a bit of a soapbox about this keeping unfunded liabilities in cash. And everybody says, you have to keep it in cash,
Starting point is 00:31:58 because you don't know if it's going to be called. My perspective is it's better to do it in a diversified public security because you still have 10 days to take it out. Why do you have to keep unfunded? funded liabilities in cash. Well, because you have to meet those capital calls when they come in. I don't think you have to keep it cash.
Starting point is 00:32:15 You know, we basically fund it out of our public equity. If we were an extreme case where equities were selling off super hard or something like this, we might look at maybe we'll tap governments to fund it depending on the size of the call, etc. You know, that's managed by a separate team here. So I would have a, I'd be able to comment on that, but we basically have a mechanism to fund it out of our If it's a private credit fund, it would come out of the liquid side of the credit portfolio. If it's a private equity fund, it would come out of the liquid side of the equity portfolio.
Starting point is 00:32:44 Right now, we have this transformation in venture capital, call it a tail of two cities where Mark Anderson jumps on a Zoom call, one call, raises $15 billion. And you have, by some accounts, 75, maybe even more emerging managers that are on their last fund. What do you see as the future of venture capital? Do you see this consolidation? or do you see a reversion to the mean after kind of some of these emerging managers leave the market? Short answers. I don't know. But if I were to guess, I think I'd note a couple of things. You know, there was a big rise in small seed stage VCs between, I don't know, 2014-15, up until, I think, 2021 or 2022. I think some of those managers will survive and have done well. I think many probably won't raise another thought.
Starting point is 00:33:30 But I also feel like there's definitely a bifurcation going on. You have a very important. small funds, which I would actually categorize between, let's say, 75 million up to maybe 500 million, and then you have the kind of giant multi-stage groups. I think it makes sense to hold both, or to at least have both in your portfolio. I'd say that from kind of a career preservation perspective. But I also find it hard to believe that a multi-billion dollar venture fund, or call it whatever you want, multi-billion dollar fund can have historically venture-like returns, let's say 3x net or higher, 4x, 5x net. It's just a burden of a scale of large numbers.
Starting point is 00:34:07 Turning 10 billion into 40 billion is a big lift. Those funds, I think, frequently are not concentrated. If you have 100 investments like that, you better get a lot of those right if you're going to achieve a 4x return on a $10 billion fund. Where a $100 million fund, it's a lot, I don't say easier, but it's a lot more feasible to achieve a high venture like return.
Starting point is 00:34:33 I could have envelope math, if you have 100 investments of 100 million on average, you have a $10 billion fund. In order for one investment to return the fund, you obviously need 100x, but in order for it to return the fund three times, you need a 300x. And the problem is you're trying to deploy $100 million. So that's not a seed check, although there are some seed companies, some so-called seed around is going on with those kind of capital raises. When we started last year, there was a huge DPI credit.
Starting point is 00:35:02 crisis in the private markets. Has the DPI crisis been solved? Are we still in the midst of it? And if we're in the midst of it, what ending are we? That's a good question. I think it's in the process of being solved. Our portfolio, and I'm talking about private equity, so buyout growth in venture, was very close to our model DPI last year.
Starting point is 00:35:21 For the first time, says 2021. It was well below our model in the years in between. But we need the public market to be able to continue to absorb IPOs. And last year was a much better year than it was. was. You know, there's rumors of some really big IPOs coming here in the venture market soon. You know, part from that, though, I think investors have to realize that companies, and I'm sure many know this already, companies are staying private much, much longer. I think the number of public companies fallen by over 50% since maybe the late 90s or early
Starting point is 00:35:50 2000s for a couple of reasons. There's a very high cost to being public. I'm sure there's other reasons, you know, that the expectations of kind of revenue, you know, years ago, you could go public for a very low level of revenue. and now I think it's probably approaching 500 million or higher. So you have to be much bigger. So we don't have any expectation that venture is going to suddenly cash flow back much faster, et cetera. And in fact, our model, we've extended venture funds to 15, 1, 5 years. And, you know, in most of the limited partnership agreements, it's a, you know,
Starting point is 00:36:21 three to five year investment period, a 10 year term, you know, extensions by the general partner. And I'm like, that probably doesn't fit anymore. It should probably be a 12 to 15 year term and extensions on top of that. because I'd say that some funds might extend out 20 years. Very curious because you have a very unique vantage point in that you do both public and private equity, which includes venture capital. Second order effects, if companies are staying private until they have $500 million in revenue, is the $100 to $500 million venture companies, are they not the small cap of the 2010s? In other words, is there not an argument that you should be invested more into the private markets in order to be,
Starting point is 00:37:01 truly diversify? There's certainly an argument for that. We used to model Russell 2000, small cap index, as like a private equity index. But we may have to go back and think about that. And so far as companies are, you know, have to be or should be much larger now in order to IPO. The CIO of Hurtle Callahan, which has 20 billion under management, he talked about, he explained why value stocks are doing poorly in the cap, in the public markets, because value stocks are not your value stocks of before today. They're broken spec deals. Their companies, fallen angels, companies that used to be mid and larger capital companies
Starting point is 00:37:40 that are now small. But the true kind of high octane value and also small stocks, do you think about that as well on the public side? I guess we do. I was going to make a couple comments. It's like, you know, value for years. Anyway, it's come back a lot here recently. And it's had a couple of, you know, I think a decent run in 2022.
Starting point is 00:37:58 And I was hopeful that once, you know, 2022, when rates went up a lot, The big change was everyone was paying for growth because interest rates were zero. The cost of money was zero. So you'd say, hey, you know what? I'll just take growth. I'll get my dollar in the future because the cost of money is low or zero. Once rates went up, I thought, boy, this is going to be really good for value. Because I want the dollar of earnings today because I'm high interest rate.
Starting point is 00:38:21 And that happened a little bit, and we're continuing to see it. But it's still not. I mean, obviously, like last year, it was growth that kind of finished up at its highs. and value investing, you know, was a great strategy, and it came about, you know, 50, 60, 70 years ago, Graham and God, et cetera. Today, there's something like 7,000 books or more on Amazon at value investing. The cost of computing, obviously, has dropped precipitously.
Starting point is 00:38:46 I'm not talking about AI data centers, but just the cost of a PC, et cetera. And so everybody can run value pricing models at a quite cheap level. I think there's a Cotopia website where there's billions of value models, et cetera. Everybody's focused on values. Value, you know, I want to believe in it in terms of a theoretical, like finance. It supports it. But I also think it's just a heavily crowded, heavily watched area.
Starting point is 00:39:11 And so absent some type of catalyst in these stocks, I don't see what moves the needle, given the immense amount of analysis in that space. What's something central to how you invest today that you've changed your mind on in the last couple of years? Quantitative versus traditional fundamental stock pickings. in the public side. We looked at our portfolio. We have both types of managers in our portfolio. And by and large, over the last several years,
Starting point is 00:39:38 the quants have done incredibly well. They do go through periods of degrossing and de-risking. Trying to think of the time periods of that, maybe 2018, end of the year, et cetera. But in general, quant managers have been able to keep up in this market, which last year was a very narrow market. But if you look at it from a fundamental perspective, let's say if you looked at Palantir,
Starting point is 00:39:58 which was trading last year at one point at, I don't know, 100 or 200 times sales and even higher PE multiples. So any logical, rational, fundamental investor would look at that and say that stock's way overpriced. However, it continued to go up in price. And so a lot of fundamental managers underperformed last year because they couldn't get their heads around an incredibly highly valued tech stock. Quants have somehow found, I think through their momentum models, an ability to keep up in that market. And, you know, you can pitch the concept of like, hey, we'll keep up with an index in up markets, but we're really going to protect on the downside. And that's a great notion. Sounds great. I think you get buy-in from investment committees on that. But that only lasts so long. And so far as they're going to want some excess returns, that's why we're here. And so I've really kind of started to think, is it doesn't make sense to hold any fundamental managers in the portfolio. There are some very good ones that have incredibly good excess returns. But I don't know if we have
Starting point is 00:40:56 lot more data sets to determine if that's a locker scale. And so what I do know is that many good quant managers have persistence in whatever sub-asset class they're in, whether that's Russell 1,000 or MSCI world, et cetera. And so I really think that, you know, well, before I thought we needed a balance in Fundamental versus Quant. I don't know if we want to balance anymore. And that may not even be figuring in fees if you're paying $2.20 to the Fundamental Manager, that's 600 basis points per year. You have to be outperforming by at least 600 basis points because that's a fixed fee. And that's a high bar. Yeah, I totally agree.
Starting point is 00:41:34 I've always looked at a fundamental manager, I'm sorry, any active manager. And if they're outperforming on a five-year basis by 1%, that can be wiped away in any one bad year. So you're right, you need a much larger margin for A to factor in the fees that are constantly a headwind. And B, if they have lumpy performance, which many fundamental managers do, they need to be aware of that. There was a piece written 12, 13, 14 years ago that we actually replicated. It was a Vanguard piece. You can find it online called the bumpy road to our performance. And in that piece, they use just mutual funds.
Starting point is 00:42:04 But the best managers, the ones that performed, you know, over time, you needed sometimes to withstand a seven-year underperformance period. The problem with seven-year underperformance is that people in my seat are not going to go to the investment committee for seven years and defend the manager. They're going to fire them after maybe three. And that leads to, that's a good career preservation move. It's a bad performance move according to this piece and we replicated it last year and found that that piece still holds. But it's just unsupportable if you want to keep your job.
Starting point is 00:42:34 When I sat down with Cliff Hasnes, he used that same anecdote, three years. One year, disappointment, two year, benefit out, three years you're fired. Yeah, exactly. It brings up another guiding principle of mine, which is you can underperform a little bit for a while, but you can't blow up. And if you think about seven years of underperformance would be, I'd put that in the blowup category, and that's a career end and potentially career end. You've had three decades of trial and error. What one timeless piece of advice do you wish you could go back to a younger Chris and whisper in his year
Starting point is 00:43:03 in order to accelerate his career or help him avoid costly mistakes? Again, I'm getting this from another person who I highly respect the industry. But when I think about throughout the career, we're all going to make mistakes. We're all going to get things wrong. So what really matters is sizing the investment. If you get something wrong that's giant-sized, it's a major problem. So the sizing of a trade or the sizing of an investment matters much more than the actual outcome in the investment. Because you're going to get things wrong.
Starting point is 00:43:32 You're going to make mistakes. But if you're thoughtful about sizing any one mistake or even multiple mistakes is not going to create a major problem either in your career or in the portfolio. It's funny because I just watched an interview with Stanley Drunken Miller and he said the one thing he learned from Soros, was that he was undersizing. Yes. I have great respect for him. And I think for a macro manager, especially successful ones, I totally agree with that concept. But I'm talking about managing a institutional portfolio and an endowmentary foundation.
Starting point is 00:44:01 I'm not a macro manager. We're not a macro firm. And so I think that makes sense in that strategy. I don't think it makes sense in a portfolio that we're basically trying to make sure that we can ensure our grantmaking, pay for the organization's costs, and keep up with inflation. I think sizing is such an underrated aspect of investing. There's this whole concept in crypto, which is getting off zero. So many people will spend 10 years debating whether they should put all their money into
Starting point is 00:44:28 Bitcoin or not or 20%, 30%. But there's a strong argument, at least in that asset class, but in any spiky asset to just put a little bit to get access to that asynchronous return so that high upside without having to really put a lot of your portfolio risk. I know there's lots of differences. But in some ways, I would think of it as like an allocation of gold. I think you should have some gold, but you shouldn't have 50% gold. You should have, I don't know, zero to 10, maybe zero to five percent gold.
Starting point is 00:44:54 So I think it makes sense to hold, you know, alternative assets like that, but at the margin of the portfolio. Well, we can have a whole other podcast on gold, but thanks so much for jumping on. It's been an absolute masterclass. I'm looking forward to doing this again soon. Great. Thanks for asking me to do. If you found this conversation valuable, please click follow how I invest so that you Don't miss the next episode with the world's top investors.

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.