How I Invest with David Weisburd - E220: Why Family Offices Quietly 5x’d Their Alt Allocations

Episode Date: October 1, 2025

Why is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices? In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction).

And last time we chatted, you said something that was quite shocking. You said that the number one reason that RIAs don't invest into alternatives, 40% of RIAs is operational complexity. So it's not just one polar survey, you know, in every industry survey, poll after poll, survey after survey, individuals, family offices, RIAs, they overwhelmingly cite operational complexity is the number one reason they don't do more alternatives, or it's the number one. hindrance to them doing more. That's a consistent problem they have. Case and Mercer put out their annual survey, 48%, almost half-sided operational complexes is the number one hindrance they have to their private markets. Said another way, somewhere between 40 to 50% based on the surveys of RAs are not investing in private markets. Why does that matter? Two reasons. One is they're leaving alpha on the table for their investors. The Yale endowment model relies on 40% for zero in privates and

many high net worth investors are roughly at about two to five percent and two perhaps even more importantly specifically for the for the audience is if you're not providing these alternative investments for your clients someone else will so they're going to the cocktail party or the zoom meeting or their kids school and they're learning about these alternatives and they're learning that they're losing alpha in the market they're not going to be very happy complexity in the private markets is has always been a problem it's not new what's different about today versus historically is, you know, historically institutions who made up the LP base in the private markets, they had large staffs. They were very sophisticated. They had a lot of resources. They could also

afford six-figure software platforms to help them manage the complexity problem. Today's investors don't. You know, in the last five years, family offices, by some counts, have quintupled their alt allocations. RAAs just in the last year, and I would argue, like, is a fairly bearish market for private markets, it still has seen double-digit growth in allocations in the RAA space. Prior to starting Unlimited AI, you were at two family offices and asset managers. You were at CAS investments when you joined, when they had $500 million. Now they're at $10 billion. Then you went to Legacy Night.

You helped launch that team, grew to $2 billion. How does that inform how you build unlimited AI? Yeah. So at both of those firms, we were really at the forefront and had a front row seat to the early days of the proliferation of alternative investments with individual investors. And it's important to say, when I say individual investors, I mean both high net worth individuals directly, family offices, and individuals through RAs. So those are the three primary ways they invest. And at both places, I learned about the passion, and I developed

a passion myself for alternative investments. I saw how hungry people were for less volatility, for more diversification. But I also had a front row seat into the pain points people have, the complexity problems they have in the reporting, the management, understanding private investments, understanding J-curves, things of that nature. And that really shaped my passion for helping people in this space. At Legacy Night, we were running a multifamily family office. We worked with ultra high net worth families from, say, 50 to 500 million, largely founders and entrepreneurs who'd had liquidity events. But we also syndicated alternative investments to a much broader audience of family offices. And working with families and managing

their portfolios for the first time, I learned a lot about the problems they have with consolidated balance sheet reporting, understanding how I'm doing, understanding their liquidity profiles, understanding, you know, just where they stood in their investments. And they were very drawn to the returns, but at the same time, they had a lot of problems with understanding the complexity. Additionally, at Legacy Night, we were fortunate. We grew to about a billion of assets organically in the first three years, and we had to adopt tech, to survive, to continue thriving, continue growing. And so we were early customers of a lot of the leading well-tech platforms today. We built a great tech stack there in order to operate at a high level in the

alternative space. We were all the specialists. And that shaped my understanding of what was coming. Through both of those firms, I also was an investor in tech and software companies. And so deployed several hundred million into directly through co-invest, into tech and software companies. And I watched AI. I saw what was coming. I saw how it could revolutionize our industry. But I also saw that a lot of the tech platforms out there today, they really only serve institutional investors at the enterprise level. And so when I was looking around, I was saying, you know, someone's got to solve this problem for individual investors, for family offices, for RIAs. And I thought there was a big gap in the marketplace. And so I left L.K. at the end of last year to come,

try to build something to solve that problem for the investors that I'm very passionate about helping. And last time we chatted, you said something that was quite shocking. You said that the number one reason that RIAs don't invest into alternatives. 40% of RIAs is operational complexity. Double-click on what you meant by that. Sure. So it's not just one polar survey, you know, in every industry survey, poll after poll, survey after survey, individuals, family offices, RAs, they overwhelmingly cite operational complexity is the number one reason they don't do more alternatives, or it's the number one hindrance to them doing more.

That's a consistent problem they have. What's interesting is, earlier this year, I'll give you an example. Case and Mercer put out their annual survey, 48%, almost half cited operational complexity is the number one hindrance they have to their private markets. Interestingly, a third, almost a third, side of due diligence complexity as their biggest challenge. And so, you know, we'll talk about that later on as well. But bottom line is, this is a real problem. It's very widespread. But what's interesting about it is it's more acute and more urgent today. And the reason why is because the audience of the future in the private markets is not the big institutions of yesterday.

it's individuals. And that's where the market's going. That's where the industry is going. And they need better tools. It has to be technology that solves these problems for them, right? They don't have the big resources, the big staffs and things like that to manage them effectively, like big institutions have. And so technology has to be it. But ultimately, this is a widespread problem in the industry.

And again, the unlock here, the opportunity is if you do solve this problem, I think you're unleashing a much broader way of alternatives adoption. said another way somewhere between 40 to 50% based on the surveys of RAs are not investing in private markets. Why does that matter? Two reasons. One is they're leaving alpha on the table for their investors. The Yale endowment model relies on 40% for zero in privates and many high net worth investors are roughly at about 2 to 5%. And two, perhaps even more importantly, specifically for the audience, is if you're not providing these alternative investments for your client, someone else will. So they're going to the cocktail party or the Zoom meeting or their kids' school and they're learning about these alternatives and they're learning that they're losing alpha in the

market. They're not going to be very happy. So obviously, RIAs want to get into alternatives, but they have this problem that we identified as the complexity problem. How do you go about solving the complexity of problem? Sure. You know, as I mentioned, the complexity in the private markets has always been a problem. It's not new. The challenge is, and what's different about today versus historically, is, you know, historically institutions who made up the LP base in the private markets, they had large staffs. They were very sophisticated. They had a lot of resources. They could also afford six-figure software platforms to help them manage the complexity problem. Today's investors don't. So let's talk about what the complexity problem is.

And I'll be super clear. Unlimited.a. Our company, our mission is to solve the complexity problem for individual investors. That's our mission. We intend to do it. So what is the complexity problem? So there are really four buckets to talk about. First, you have access complexity. How do you find these investments? How do you get into them? What are the minimums? You know, finding information publicly available about them is very challenging. You have the marketing rule in the regulatory sense, which makes it challenging to find information, makes it harder for them to find you. And so first you have access complexity. Then you have legal and regulatory complexity. legal. You have lengthy PPAs, or PPMs, you have lengthy LPAs. They're written by some of the most

sophisticated securities law firms on Wall Street, and individual investors lack, you know, an understanding of that. And candidly, cheapishly, most LPs in the individual space admit that they don't even read them. On the regulatory side, you have the marketing rule. You have limitations on how many investors can be in a vehicle, you know, and so those are huge, huge challenges. And then you have reporting complexity. So in the tax sense, you have K-1s. I know everyone here loves K-1s. You know, if you invest in private markets, your tax reporting is late. It's delayed. Quarterly statements. They come maybe 45 days after the quarter, sometimes monthly, you get them two weeks after the quarter. It's a real challenge. It's a real challenge.

Also, valuations aren't standardized. So you get a NAF statement. Well, what made that NAV up? You know, what data points went in that? There's not enough standardization in the industry. And finally, and I think the one that most people think about when they think of complexity is liquidity complexity. You know, when am I? get your money back. Yeah. Well, not only that, David, but when are you going to call capital? When do I have to fund this?

You know, when am I going to get out of this? What's the valuation? What am I going to exit at? All of these are massive challenges that people have in investing in the asset class. But I think what's so encouraging is, even in spite of all this complexity and in spite of all these challenges, private markets are booming. With RAs, with individuals with family offices, you know, in the last five years, family offices by some counts have quintupled their alt allocations.

RIAs just in the last year, and I would argue, like, as a fairly bearish market for private markets, it still has seen double-digit growth in allocations in the RIA space. So people are still very hungry for these investments in spite of that, but we think that solving the complexity problem can unlock an even broader adoption curve in the alt-space, which will be transformative. I interviewed the CEO of I Capital, who he knows all Lawrence Calcano, and he predicts $150 trillion from what's called retail, which is people over $5 million. In the context of billions of dollars, we'll be going into the asset class.

You talk about operational complexity, tax reporting. Another thing that people don't talk about is the asymmetry of information. If you're not a big institutional investor, how do you know as an RIA that you're not being adversely selected? Talk to me about that, and how do you solve for that? So in the private markets, at the end of the day, you have a counterparty transaction, right? You have GP and LP and LP. And I went to law school. I'm not blind to the fact that GPs and LPs should be different and have different levels of information.

That being said, we've never had a greater asymmetry of information between GP and LP in the history of the industry. So let's talk about that. Historically, in the private markets, you had large institutional LPs, insurance companies, pensions, university endowments, things of that nature, very sophisticated parties with lots of resources on the LP side. On the GP side in the early days, you know, you had Blackstone, KKR in the early 80s doing deal. by deal strategies, and largely you had sophisticated, fairly equal counterparties. There was quite a bit of equilibrium. Fast forward to today, you have Blackstone managing $1.2 trillion, KKR, about 700 billion, and your OPs are now about to invest through their 401Ks. We think that that's

in a symmetry that needs to be solved, and it's an urgent need, I think, because again, consumers in this instance need to have better tools to manage them. Because of the lack of human resources at the individual level in the LP space, there's got to be a technology solution. Technology has to solve these problems for the LPs to level the playing field. And we think that AI is really the inflection point that's going to do that. AI, AI is just, you feed in data, you get data back. How could it actually solve the unknown unknowns? How does it solve asymmetry? Sure. So one of the biggest challenges in the private markets is just that. It's always been very private. LPs, and oftentimes, don't even know who the

their OPs are and the fund they're in. They don't share a lot of information. There are no, you know, public sources for, there's no Morning Star in the private markets. And, and so what AI can do is a lot of that data that's so siloed, it's largely unstructured in PDFs. You can now use AI to extract that data, but not just extract it, it's what do you do with it? You integrate that, right? You integrate it in your database. And if you do that, you make it queryable, you make it right at the tip of your fingertips, you know, with a click of a button, you can chat with it, you can interact with it. And also, on the reporting front, you integrate that data, and then you have much more deep, much more integrated performance data. You understand your exposures better. You understand

your obligations better. And so we think AI is really, really truly an inflection point. And look, everyone talks about AI today, how it's going to change the world, and I think it will. But I think there are so few industries that are more ripe for disruption than the private markets with AI. I think it's a tool with a real application case. There's some a use case, right? It's not a novelty. It's not just a fun tool. It really is going to change the way we do things. And I think it's ultimately going to make the industry so much better as a result. There was recently a study. They put the top doctors that evaluate whether someone has cancer against AI, and AI only scored 90%, but the doctors were at 82%. Yeah. So a lot of times

you have, sure, AI is not infallible, but neither are humans. I think that's this kind of false comparison. So let's talk about something that even puts me to sleep, and I'm like the biggest finance nerd, due diligence management. Sounds like the most boring topic. Why are RIA so focused on that and how does AI help with that? Sure. As I mentioned earlier, in the case of Mercer's study this year, you know, almost a third of people said concerns about due diligence was that was the number one reason why they didn't do more alts. While I think there's been a lot of technology advancements in the space, particularly on the access side. That was really the first space to get, you know, disrupted. Due diligence still lags behind. Most individual investors

RAs, I call it their scavenger hunt for documents, you know, maybe the IR person, a firm if you're going directly, you know, has to follow up with you. You're like, oh, where's that document, when's the closing? You know, it's super, super fragmented. Over the past year, as me and my team and going around talking to RAs, talking to family offices, talking to investors about what they were looking for with technology to help them be better private market investors. We were actually really shocked about how much due diligence came up and how often that came up.

And what does that mean? I think people want to be able to make better decisions. Their data is very siloed. They're not making decisions with the complete picture, not only of their portfolios, but with the market and what's out there. Now you can integrate that data. You can extract data out of all the manual documents, your deck, your PPMs, et cetera, and you can integrate that, but also you can track your decision-making.

You can use comparative analytics between funds, between managers. You can use comparative analytics between your own decision-making, you know? Do I make better investments on Thursdays than Mondays, things of that nature? So AI and technology can now integrate that, and we decided to really focus on that, in addition to doing consolidated balance sheet reporting, because at the end of the day, people wanted that. And there's another reality here that people don't talk about, that's really one workflow, Okay? From access to exit, it's really one workflow. And so our mission is coming as to orchestrate

that entire chain for people. Because once again, when you make an investment, you don't just stop there, then you go report on it, right? And then you need to manage it, and then eventually you want to exit it. And you have to handle all of it because if you don't, then you have the same complexity problem. That's right. That's right. Multiple systems. You have to create the full life cycle. You know, and what's interesting is I think a lot of feedback the industry gives to tech today is we have to have orchestrate, or excuse me, we have to have integration. You know, lots of APIs, lots of integration. I think that's true. But I think if you kind of double-click on that and you dig down, what they're really saying is we want a unified platform. We want something that we can stay in one

place and make a lot of decisions and really track investments throughout that life cycle, right? Because, again, you don't just want to look at the investments you made and how they're doing. You want to look at the ones you passed on. So let's level set a little bit. I mentioned this number that Lawrence Calcano, CEO of the capital, he's 150 trillion. That's 150 billion,000. It's an absurd amount of capital. Why is so much capital entering the market? Tell me about some of the variables behind that. What's leading to that kind of capital move from publics to privates? I'll talk specifically about our audience, because that's largely who's here today.

I think that a lot of the old paradigms from public versus private are a bit outdated today. Historically, with institutional investors, largely investing third-party capital, right? It's a fairly scientific, abstract exercise. It's all about performance. You know, do the public markets outperform, do the privates against public benchmarks, et cetera. And I think that that misses the point of today. With individual investors being the future of the private markets, there's a much deeper yearning for the private markets.

Really, I can boil that down and synthesize that into what is often termed the psychology of money. People investing their own capital care a lot more about the volatility of their money. They care a lot more about certainty with their money. And I'm not here to knock the public markets. The public markets are great. But that being said, I think there's been a lot of volatility. And people don't want to watch their net worth whipsaw every day based on news they see.

I think Warren Buffett's also done a really good job of convincing people that investing passively in the public markets is really advantageous. And so therefore, I think that people are looking to the private markets for alpha. I think it's a differentiator. I think through manager selection, through good due diligence, I think people think you can generate alpha in the private markets. And I'm not sure people think they can do that actively today in the public market. Just to put some meat on that, I had Professor Steve Kaplan,

who's the leading researcher, University of Chicago, and he created this Kaplan Shore Index. And they found that anywhere from 350 to 400 basis points of private equity, outperformed S&P 500 over three decades. They also did on venture also outperforms. But 350 to 400 base points doesn't take a math genius to realize how quickly that compounds in the portfolio. What do you think is keeping RIAs really from taking that?

Is it fear? Is it lack of knowledge? Is it tools? Talk to me about the psychology of why RIAs are not pushing alternatives more. I didn't manage this on the last question, David. But I think we wouldn't even be having this conversation if the returns weren't really attractive, okay? So the psychology of money matters, but I also think the returns more often than not do outperform. And you can cherry pick data, right? Of course, there are times when the

public outperforms at the private markets, but that being said, by and large, it's very competitive, right? And so when you combine that with low volatility, some predictability, you know, it becomes very compelling. Now, with RAs and why they're not doing more, I think there are a lot of reasons. I think a lot of RAs struggled to understand the private markets. As someone who got into this space a decade ago, you know, there's a big learning curve. It is complex. There are a lot of platforms doing a really good job to educate people on that. We think education is a critical aspect of this. But I think education's critical. I think also just people understanding that these are, you can predict portfolios better. And I think that RAAs by and large also are going to recognize

over time, they're going to have better tools to do it. And when they do have better tools to do it, they're going to feel a lot more confident. It's that simple. But you're already seeing it. I mean, I think 90% of RAAs in a recent survey said they intend to do alternative investments for their clients over the next year. I mean, it's really astounding because when I got into this space 10 years ago, you know, alts for kind of the Wild West and RAAs viewed them as very, you know, off to the sidelines. I think in this case, they're being pulled by their clients. You need to, in order to survive, you need to offer alternatives. Now, you might decide whether you do Blackstone or whether you do a second or third vintage private equity firm.

That's obviously much more complex. But I think they're coming to realize that privates are necessary to stay in the game. Yeah, I'll tell you, a really interesting phenomenon related to that. So we've obviously always seen a big trend, certainly over the last five years of breakaway RAAs, people going independent, things like that. And therefore, when they do that, they're open architecture. And I was talking to an RIA here yesterday, and it was very interesting. You know, a lot of the old, sure, you have big platforms, you have big distribution. channels through the broker dealers, through the banks, obviously big corporate RAAs.

What's interesting is he was telling me that most of the alts he ends up reporting on come from his clients. And so what a lot of people don't realize is people are doing alternatives. And I think advisors had to realize that. They're saying, my clients are doing these, certainly in the high net worth space, an ultra-in-net worth space. They're asking you to report on them. They're saying, I'm doing real estate deals with my friends. Exactly. Yeah, here's a K-1. What do we do with it? And so people, it's actually coming from their clients, right? And I'll also say that's why we think it's really critical to build a portal for the end user. One GP portal doesn't solve a problem for you because you're going to

have eight of those. And then you're going to have your clients asking you to report on the real estate things or they're doing deals with their buddies, you know, in the locker room. And ultimately, you have to have a platform that is open such that you can report on all of that in one place. So that's one of the reasons why we think consolidated balance you reporting is so important at the LP level. The private market, it's just like any market in the world, is being disrupted by AI. Everyone's talking about it. It's almost tried to say,

but everybody has disagreements on the timeline. What needs to happen specifically for AI to disrupt the private markets? I think it's already coming. I'll say that. It's got to take both sides of the equation to really unlock the potential of the private markets to get to $150 trillion if we ever get there.

What does that mean? We need more standardization. We need more transparent. We live in an era where the private markets still operate largely like they did 10, 20, 30 years ago, but it's a very, very different environment. Blackstone's managing $20 billion in B-Reed with thousands and thousands of investors in that, right? And the GP side can't have their cake and eat it too. They have to understand that if they want to democratize access to their platforms and their investments,

they can't still operate in these siloed shadows. There's got to be more transparency. and ultimately investors just have to feel more empowered in their private market's portfolios. And so I think that it takes there, on the LP side, obviously I think that people need to build better technology for investors to access it. You know, you and I are both very passionate about the LP side of the transaction. And again, I think that by building better tools, and also I think community is important there, what's interesting, because of the siloed nature of the private markets, you don't have

a lot of collaboration on the LP side, right? At the institutional level, you have things like Ilpa. But at the individual level, the family office level, like no one's really getting together and saying, what should we demand of the other side? What should we expect? Highly fragmented. And that's historically been by design.

But ultimately for this next chapter of the private markets, that's got to change. A new standard. So you have an announcement for us today. What's announcement? Well, I couldn't think of a better time to do this, but today on unlimited.a.i. is live. You can visit Unlimited.aii, and our mission as a company is to empower limited partners in their

private markets portfolios, and we intend to do that. So please go take a look, sign up to do a demo, and thanks very much. Yeah. Who does it make, who is it a no-brainer to use Unlimited AI? I'm guessing Calipers here, Calisters aren't going to be your first two clients, but who really needs this and who's really asking for this product? That's right. So our first product, the one that launches today is for family offices and high net worth individuals. We are very passionate about solving the complexity problem for RAs. We've gotten very strong interest in demand from RAs. That tool will be ready in a couple months, and we're very passionate about solving that problem for them, but that's coming soon. Today, individuals, family offices, we feel like it's a very advanced platform

that orchestrates your private markets portfolios in a way that doesn't exist today outside of our platform. So we're really excited about it. And candidly, we're most excited about solving this problem for investors finally. Thank you, David. Thank you. Thanks for listening to my conversation. If you enjoyed this episode, please share with a friend. This helps us grow. Also provides the very best feedback when we review the episode's analytics. Thank you for your support.