E344: How the Top Family Offices are Investing Today

What if the families with the largest fortunes generate the highest returns not by chasing hot sectors, but by pacing capital, managing liquidity, and investing with a multi-decade horizon? In this episode, I sit down with Douglas Evans, Chief Investment Officer & Partner at Callan Family Office, to explore how a $10B family office approaches private markets like an institutional investor. Doug shares how private capital pacing, vintage year diversification, and strategic GP partnerships drive consistent performance, why continuation vehicles and secondary markets are reshaping liquidity, and how focusing on underlying assets rather than labels helps families build repeatable, long-term returns.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  So Doug, you're the CIO of a $10 billion multi-family office. How should large family offices go about investing their wealth?

• 0:09Speaker 01

  It's a good question and tends to be part of the difference making on how we approach investing for the ultra affluent. But it comes down to a pretty simple thesis that the ultra high net worth really can and should invest more like an institution. And what I mean by that is that ultra high net worth families have the scale, the time horizon, ordinarily a tolerance for illiquidity that's more akin to sophisticated institutional investors and less like massive affluent investors. So we had Callan Family Office, we've built a framework around that idea. And we've gathered what we think are the important elements that support the access and portfolio construction to bring those kinds of opportunities to them. And then bring it to bear inside of a taxable environment.

• 0:54David Weisburd?

  It's interesting because I just spoke to Jason Pritzker and his grandfather started the Pritzker family and was the gen one in the family. And at that point, there were 70%, 7-0 capital gains. He was working under that constraint. So he figured out, I want to invest into companies that I'm not going to flip in three years, like traditional private equity today. But what are the companies that could compound for many decades that I wouldn't have to sell that could basically compound tax free? And then he went upstream of that. What are the kind of decisions I would make if I was investing to companies that I want to compound for two, three decades? And essentially it came down to the right sector, the right business model, but also the right team. What kind of partner would you want for 20, 30 years? It seems very simple to think about taxable versus non taxable portfolio,

• 1:38David Weisburd?

  but the downstream consequences of this one difference in the portfolios changes the portfolio dramatically.

• 1:45Speaker 01

  You're exactly right. And for families that have ultra affluent balances in the means and the long-term perspective. It's not uncommon to find them involved in venture, in venture capital. When you look at the preponderance of the seed investors, the angel investors, the pre-seed investors, it's not uncommon that you'll find ultra affluent families like them, among others, especially our clients, that want to participate. And there's a lot of reasons for that. Obviously, there's hockey stick-like growth potentials when you've unlocked something that's critical. But what most people don't quite understand is that the tax code also gives you an opportunity to take those swings and, depending on the nature of the business, can qualify as a small business stock.

• 2:27Speaker 01

  So the category of QSBS, which is a very popular early-stage category for taxable investors, can really create amazing compounding effects for early-stage investors. And so what I mean by that is that if you, and I'm no tax lawyer here, but we have some on staff. But if you look at QSBS, you're able to exclude a great deal of capital gains recognition when you're in early enough. And just last year, with the enhancements that came to the code through the one big beautiful bill, the threshold for how you would recognize the enterprise value of those companies and the amount that you can enjoy in gains without paying taxes, all went up, right? So before, it was $50 million for an enterprise value of a company, now bumped up to 75 million.

• 3:12Speaker 01

  So that just means now the company can be larger and still qualify for that status. And then your ability to exclude a certain amount of your capital gains went up from $10 million up to $15 million.

• 3:22David Weisburd?

  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 AlphaSense AI-led expert calls, their TGS 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-rich conversations on your behalf.

• 3:49David Weisburd?

  Acting as a trusted extension of your team. Then they take it one step further. Your call transcripts flow natively into your AlphaSense experience and become queryable, searchable, and comparable, so your primary insights plug directly into earnings prep, digital work streams, and pitch books 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. For private equity, it means faster pre-IOI scans and deeper commercial diligence.

• 4:33David Weisburd?

  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 AlphaSense 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 AlphaSense AI-led expert calls now. The first to see wins, the rest follow. Learn more at alpha-sense.com/howainvest. Right now, you have an interesting venture environment, to say the least. How should a family office go about starting a venture book from scratch today?

• 5:16Speaker 01

  If you're starting from scratch, you need to have an overall game plan. And that game plan is going to lay out what we call private capital pacing. So you need to think about what's the end state of the portfolio to look like? What are the components? What are the industries? What are the geographies? And you think about how you're going to get from here to there. If it really was somebody starting from scratch and you said, "Boy, we'd like to get going." Typically, that will be accompanied with a desire to get to work right away. A real seasoned book takes a long time to build, takes years to build.

• 5:52Speaker 01

  If you're trying to jump in, then you're probably going to start with some secondary positions and you'll probably start with some broad-based funds and try to get some capital deployed fairly quickly. But then you line up your rifle shots and you really think about where you want to place capital and with whom and how. There's a very important decision to make, which is are you going to lean in and be participatory with these investments or are you just allocating? And there's a, there's a big difference. For people who are serial entrepreneurs, especially former tech founders, they like to lend a hand and be involved with the investments one way or the other if they can make something happen that helps further their, their return or further the portfolio company. Others are saying, no, I actually just want a broad-based basket and I want to participate in the ride and I don't want to be involved.

• 6:36Speaker 01

  You have to answer some bigger questions before putting pen to paper, but ordinarily you have to have that final state and a pacing plan between here and there to really figure out what you're going to pull the trigger on in 26.

• 6:48David Weisburd?

  The private capital pacing is such an underrated point for venture specifically, and there's a couple of reasons for that. One is a lot of people know about the power law and venture capital where you have one out of every 100 startups accounting sometimes for 50, 60, 70% of that basket of 100. But you also have high dispersion between different vintage years. So everybody's aware of the dispersion between top quartile and second and third quartile managers, but there's also dispersion in years where the top quartile sometimes during difficult times is 4, 7, 10% versus in boom times it could be over 40% on the IRR basis. So making sure that you're diversified by vintage year is really critical for venture capital specifically. I've had different people say different numbers on that. It seems like there's a consensus that if you're in six different vintage years, you're doing pretty good from a diversification standpoint.

• 7:33David Weisburd?

  And then the second aspect of capital pacing that's very underrated unless you've been investing in funds is one is of course you have to manage the capital calls. Sometimes you have 10%, 20% being called on the first year and then it could take up to three, four years for other capital to be deployed. If you don't invest into the next fund and the fund's doing well, there's a reputational aspect to that where A, you're not going to get access to that fund again, but also GPs talk to each other and it'll be harder to build a platform. So having this capital pacing model for venture specifically is extremely hard and a lot of people don't even think about their capital pacing model in venture, which is very... Which is not advised.

• 8:09Speaker 01

  If you'd said, how many vintage years, our canned answer would say seven, but it's not much different from six. But there are some people who think that vintage is just between this year and next year. And it's like, that's not the right answer. But you're right. There's a couple of things have been happening. First of all, you do end up with these episodic moments that just hit all capital markets and there's nothing anybody can do about it. When you look at the vintage years of 21 through 23, and you have COVID in the middle of all that, it's a very different experience versus somebody who was fortunate to maybe be allocating between 2012 and 2015. So it's a very different set of experiences. And to your point, you need to stay at the plate. You need to be able to continue to play inning after inning. Because when you walk away, you just never know when you miss the grand slam home run. And you don't, that makes all the difference.

• 8:53David Weisburd?

  And I've looked at the Cambridge data. It's not always the case, but I'd say 80-plus percentage of the time, the best vintages do actually follow the worst vintages. It's even more brutal than the stock market, where if you actually sell at the bottom, you know, you have this V-shaped recovery. But in venture, sometimes it's even more pronounced. And the intuition behind that is pretty simple, which is when you have sharp downturns, a lot of capital leaves the space for the same reasons. They don't want to continue investing in asset class that's on the low. And then the valuations go lower, people invest, and then they re-normalize. And then the opposite happens as well. You have, I think, venture had like a 13-year bull run, or something crazy like that, from 2008 to 2022. And then,

• 9:35David Weisburd?

  of course, so much of what's known derogatorily as VC tourists came in, started putting in so much money into companies like WeWork at the exact wrong time. And then, obviously, they lost that money as well. So there's this momentum trade in venture that's a little bit less prominent, because it's vintage by vintage, but still, still kind of follows those same principles.

• 9:54Speaker 01

  There are definitely Hall of Fame periods, and those come right after the tragic periods. So I remember after the dot com era, you know, everything that started in 99 and 2000, you felt great when you got your money back. But, boy, when you started to lean into the space, call it 2003 through 2006, it just seemed like everything you touched turned into gold. So same thing, post-financial crisis, everyone was limping around. But if you had the fortitude to continue to keep swinging at it, You saw amazing results in the late 2018, 19 into 20. And to your point, that draws in capital that maybe have been misguided. We're living in a time right now when you need the same level of fortitude. And it's difficult because there are some things that have happened that have been discouraging

• 10:39Speaker 01

  to investors, either in the early or even late-stage growth. There's been a combination of effects. Number one, the DPIs that are coming out from the funds have been historically low. And so for a lot of folks, they like to see capital get recycled. Well, when you're not getting the cash flows back, you're not able to recycle as much. You're kind of at a pushed decision. What are you going to do? The second thing that has happened is a number of these companies have been so dramatically successful that they decided not to go public. So it's not the MAG7, it's the magnificent 15, but they're all private. And I think people have really mixed responses to that. Did you need the liquidity or did you want the growth? And so for those who have their piece of Databricks or XAI or maybe SpaceX, I mean,

• 11:22Speaker 01

  there's so many that you can participate and be in the growth. And I think frankly, people probably need to start re-underwriting their thought process regarding continuation products or SPVs that just participate in individual names. And the reason is because if Airbnb is any sign of the times, it achieved most of its value while it was private. When it came public, it went down. It's only just now getting back to where it was, where it had. So the times have changed and I think people have to view the landscape quite differently. Just to pivot and create a match and compare, one of the things that we often help educate for anyone who's new to private equity investing or private company investing. In the early part of my career, I remember when there really was 5,000 stocks in the

• 12:03Speaker 01

  Wilshire 5,000, it hasn't been above 4,500 in three decades. And so it's an ever shrinking resource of public equity. And yet during that same period of time, if you said how many private companies have had some form of transaction, either in equity debt, it's north of 50,000. It's a 10x. So you really do have a much broader swath of opportunity, pre-seeing more talented management teams, more innovation for sure, significantly greater flexibility. And so I think everyone has to rethink how they approach public and private markets. But in that vein, once you come to grips with those facts, then you realize you can't really afford to leave the plate if you want capital to grow over time.

• 12:43David Weisburd?

  I got a stat for you. 50% of funds from 2020 vintage venture capital funds have under a .1x DPI, so have given back less than 10%. This is six years in. So there is a DPI crisis. Taking a step back, I think oftentimes, great ideas start out great. David Swensen came up with this private asset allocation model, but it was in the 80s. And then people, instead of realizing that it was a model for the 80s, 90s, 2000, they just take it at a basis without thinking about it from first principles. And if you stick to the same model while the market is changing, you might have unintended consequences. I'll give you a couple of examples. One is you mentioned small cap value. I had the CIO

• 13:26David Weisburd?

  of Hurdle Callahan, Brad Conger, and one of the things that he believes is that actually small cap value, the companies that are small in the public markets are fundamentally different types of companies than they were several decades ago. They might be SPAC targets that have gone down. They might be fallen angels, large companies that are small companies. And to your point, some of those companies that would before be small companies today are just large private companies, almost to an extreme where you have now SpaceX and maybe Anthropic will be listing immediately into these indexes. So as immediately as a large company. So you have to step back and think, okay, maybe 60, 40, maybe a largely private portfolio. Maybe that still makes sense, but when you double click on it, what assets am I actually buying? When you invest, you should be thinking about what do I own versus what do I allocate? So you really want to think about the underlying assets.

• 14:09David Weisburd?

  What am I buying? Sometimes, public companies today are 100th or 1,000th of the valuation of a private company. So are you really more risk on when you're in the private than the public market and just thinking, rethinking these from first principles? It's not an easy task, but it's something that I encourage everybody to do.

• 14:28Speaker 01

  No, you're correct. And we were pretty big fans of Swensen. He was involved with our group several times in the past. And the first principles of investing do need to be revisited. I think one of the things that's been so disingenuous, to your point, have been all of the labels that I think people like to put on things and calling something an asset class or calling something a strategy. But the truth of the matter is, There's really only two asset classes. There's really only debt and equity. There really isn't a third. And when you realize that you're in one of two camps, you're either in a camp that it has defined cash flows like the ventures and fixed income products. Or you're in an undefined cash flow and you're an owner of or a claim of owner on, you know, future cash flows and earnings.

• 15:12Speaker 01

  And so there's no third door. And I think people mistake different ideas and say, well, this is just an asset class or this is that. The other like, nope, actually you just own equity or you just own debt. They wake up one day and say, oh, this didn't behave according to some historical pattern. And they get disappointed and be like, well, it's because the business didn't do well, or the cash flows were interrupted or something that's pretty foundational and they, they struggle with it. I agree with you. There needs to be a wholesale renewal back to the basics. So that we call things and label things more accurately. And I'll tell you where that that's most, most apparent is the mislabeling of risk.

• 15:52Speaker 01

  Because risk does come in multiple forms and it can, you do have different types of boogeymen that are out there that will come out and destroy return or threaten capital. And I find that when people move away from the basics, those risks have a better chance of creating impact.

• 16:09David Weisburd?

  The worst thing you could do is to, to take equity like risk with debt like returns. That's waiting for the market to turn against you. I don't know how that could possibly work over long term.

• 16:20Speaker 01

  That's a, that's a good quote. And frankly, I think that's what you're seeing or has happened in private credit. I think people thought you have these elevated cash flows. What could possibly go wrong? And then they realize, oh, wait a minute, these companies, they're not guaranteed that, that coupon payment can go down. And so I think the fact that you've seen default rates rising in America and then. Not to go too far afield, but just the rise in LMEs and people don't even know what a liquidity management exercise even means, but it's it's default in another label. And those have been rising as well over the last year or so. So I, I think you're, you're watching this unfold right in front of us with private credit and the knock on effect that came from all the deregulation that happened

• 17:05Speaker 01

  post the financial crisis and it's sort of ushered in this whole new wave. I think we're, you know, encroaching on $2 trillion in private credit and that was all at the, you know, in exchange for middle market lending that used to be done by banks. And so it's a whole different set of rules, a whole different set of outcomes. And I think people have viewed it as, you know, just elevated money market and it's the furthest thing from that. It's truly an equity type position and you're, you're exposed to very material risks. And I think people are waking up to that right now.

• 17:31David Weisburd?

  Just to put a cap on, on the David Swensen discussion. Obviously Swensen was revolutionary at the time, but there's one key difference. The Swensen model was based on one assumption that was true for many decades. Roughly 24% DPI per year. 2024 was 9%, 2025 again was 9%. When your cash going back is two and a half times smaller than your cash going in, the model breaks. That's the fundamental issue. If you don't have cash coming in, the, the private, the private markets cannot function the same way. If that continues, let's just assume that continues for now. What needs to change in the private market? And what, what do you think will be the new normal if a 9% DPI continues?

• 18:08Speaker 01

  One of the big new normals that will come out of this one way or the other is just more free exchange of positions in the private markets. It can't be as difficult or as cumbersome really to exchange private company interests. To today, it's, it's in, uh, it's more accessible than it used to be, but you need to have price discovery in a more fluid way. So that different parties can come to the table and reposition, reallocate, sell and buy private company and private capital interests in a more fluid environment. You've seen multiple online exchanges, you know, crop up. I think you've seen some of the big exchanges try to create secondary markets. That whole effort needs to be supercharged, and I think it will be.

• 18:52Speaker 01

  And I think you'll bring down the barriers of participation and you'll create more price discovery, more liquidity and more free exchanging of positions. And there'll then be some safeguards around that as well, but I do think that that will help. At the same time, I think trying to readdress some of the incentives that have pushed companies towards remaining private and not issuing to a public exchange. I think some of those inhibitors and obstacles will be addressed. I'm hoping that they will be in the near term so that companies do want to come public and make their equity more broadly available and with that come with greater transparency to everybody. So I think of a combination of elements. I think public exchanges may have a breath of new life with policy reform, but I also

• 19:36Speaker 01

  believe that the private markets will self cure themselves and continue to foster these private exchanges.

• 19:42David Weisburd?

  I have a personal theory I'm working on. I want you to poke holes in it. I want you to improve my theory. I believe that continuation vehicles are coming to venture capital and I'll explain why. First of all, continuation vehicles as a whole, they're growing quite fast. They just passed $100 billion. TBG, I had Michael Woolhouse, who has a $1.9 billion fund focusing on continuation vehicles and buyout opportunities. He's so inundated with opportunities that he's literally reaching out to his competitors to co invest with him, which is a sign usually of a lot of supply. But here are the factors why I think continuation vehicles are coming to venture. One is many funds, not the top 10 funds and the large funds, but are having an existential crisis where if they don't bring back DPI to their LPs, they're either on their last fund or they're never going to raise another fund.

• 20:26David Weisburd?

  So continuation vehicles themselves are considered officially a secondary, so they generate DPI. So you do a continuation vehicles, you show DPI and now you could go out and market it. Two, it's around the same issue of DPI. If you're an LP that's back to fund in SpaceX, for example, you might be in there for 15, 20 years and sure, it's great to have a 15, 20 X on paper, but at some point LPs are going to demand that. And because now it's a buyer's market in terms of LPs dictating to GPs what they want, I feel like there is going to be some pressure from LPs to GPs. And then thirdly, of course, I just love continuation vehicles. I'm just going to reveal my bias. I have no economic stake in them, but I just think there's a lot of interesting aspects of it. I think it's maybe an A minus solid for DPI for LPs as well.

• 21:11David Weisburd?

  And then also, a lot of GPs have a lot of asymmetric information, especially if they're on the boards of these companies. So I think it's a very interesting asset class for outside investors. I think what needs to happen, one of the things that really creates this liquidity on the buyout side, is that you have now that this whole system of investment banks are coming in and doing these, raising these funds for them. I think that needs to happen. And I think CVs and venture capital have to get to about 100 million to make that plausible. Scott Voss from Harbor Vest, they're already doing that. So I didn't, I didn't come up with the idea, but that's one of my theories that I think we're going to see much more of that in the coming couple of years.

• 21:43Speaker 01

  Your, your theory is, is a good working theory and there's probably a few modifications that come along the way, but it's, it's true. DPI does create a real challenge and consequently, how does the capital get repositioned? How do investors achieve all the goals that they're trying to achieve? It's not just earning the return, but there may be other things that they're trying to do as well. There could be other budgets, whether it's a gifting budget, a liquidity budget, a distribution budget of their own that they're trying to solve for. So there's a myriad of things that will force the hand of both GP and LP alike to think about these things. For venture in particular, it's such a unique environment

• 22:25Speaker 01

  because the venture land in many ways has become less adventurous. What I mean by that is just look at the very, very long arc when venture meant industrial venture and they were extremely large capex projects that took many decades to bring to fruition. Maybe somebody was building out a seaport or an airport or who knows. And it was capital intensive and there was no way to, to create liquidity. Well, you've gone from that, that's massively capex intensive, lots of uncertainty and different operational risks to now it could be a handful of people working on an AI solution that you're going to know if this works or doesn't work in six months. So things are happening so much faster and you're getting through the curve in a much different way than you were before. And you

• 23:08Speaker 01

  have to think about the incentives for everybody, the incentive for the managers, incentives for the companies, incentive for the investors. You're, you're tripping up through different levels in a much faster, much more rapid ascent than you ever did previously. So consequently, the nature of the holding should evolve as well. I mean, I remember when, you never heard about a D round. I mean, this is early in my career, but you didn't hear it. It was ABC and then it went public.

• 23:33Speaker 01

  But the idea that I remember when we had a D round and my first sell my first E round, I thought, wow, this is crazy.

• 23:38David Weisburd?

  I think Uber was one of the first E rounds.

• 23:41Speaker 01

  Right.

• 23:41David Weisburd?

  The reason the original stock vesting was four years, I had Eric Bond from Hustle Fund tell me this, is that it used to take four years to go from first venture funding to IPO. That's why there was a four-year vesting. So much so that now it doesn't really make sense. If you're four years into an eight-year journey and you have people that are working there, now you have to refresh these stock plans. But that's why it was four years originally. That's how far we've gone. We've gone from four to sometimes 15 to 20 years.

• 24:04Speaker 01

  To your point, do continuation vehicles make sense? They do as part of the evolution recognizing that the system has changed and therefore the tools that we use for people to participate, they need to evolve as well. Because I don't think anyone wants to sit around and keep paying a venture manager and watch it become a $10 trillion company. It's just, it's, it's, uh, doesn't make a lot of sense. So at some point, you're going to, you're going to continue to break down these segments, create greater transparency, create different arrangements, better alignment, better carrying costs as well for the underlying owners. And I think you'll have better aligned incentives for everyone to help make that happen.

• 24:43David Weisburd?

  That's a really interesting point because on the continuation vehicles, you're not getting two and a half and 30. There's much more aligned structure. There's, there's ways to get up to 20% carry but pass certain hurdles. So in that way, it is much more LP from it.

• 24:54Speaker 01

  It is. And I, and I don't think you're just trying to take away from one group to give to another group. I think you're just trying to align skillsets where the value contribution is coming from and, and what the, what the different drivers really are. Because honestly, what you want to do is continue to incentivize those venture managers to continue to find new, great opportunities. Their highest and best use is to continue to scour the landscape the way they do, identify terrific innovation, great innovators, great entrepreneurs, and start backing them. Well, that tends to need new capital. So they want to see capital get recycled as well as anybody else. So if they're constantly locked up, waiting for Databricks to go public, I mean, that's,

• 25:35Speaker 01

  that's a, that's a long wait. So what could they have been doing with that money elsewhere? I mean, maybe it's not magnificent 15, maybe it's magnificent 75. And in that world, you're going to expand GDP, you're going to expand opportunity set, you're going to accelerate innovation, you're going to relieve problems at a much, much faster rate. So capital markets do need to evolve. They need to step up. They need to get to a place where you can pass the baton in a way that's efficient, in a way that makes sense and is rewarding to the entire ecosystem.

• 26:01David Weisburd?

  I'm going to ask you to pick your favorite child, not literally, but figuratively within assets. What is the most under-loved asset class or sub-asset class that you think should get more love and why?

• 26:15Speaker 01

  To me, one of the areas that needs tremendous priority right now are going to be those enterprise solutions that solve for infrastructure and security. Said differently, as you think about where we are in a world of growing automation, growing AI, growing robotics, I don't think you can over-index the security issues enough. So for me, as I look at the sea of opportunities, the area that I hope everyone comes back and

• 26:56Speaker 01

  ushers into first or second place in their CapEx, it will be to improve and elevate those things that impact all levels of security, not just national security or personal security or information security. I mean, all of it. There's a great deal happening. And if we don't continue to reinforce the spinal column of what it means to be safe on how we do what we do, then I think you're wasting your time with everything else.

• 27:27David Weisburd?

  Doug, if you could go back to 1993, I just finished your master's program, and you could go back and tell yourself one timeless piece of advice, what would that be?

• 27:36Speaker 01

  Keep your priorities straight. God, family, others, and then yourself. If you don't keep your priorities straight, it doesn't work out. But when you do, everything else starts to fall into line.

• 27:47David Weisburd?

  Double-click on that. So you said God, family, others, and then yourself. Why is that important? And what's downstream of keeping your priorities straight?

• 27:56Speaker 01

  For everyone, you want to live life well. You come along 30 years later, 30-plus years later, and you realize life's short, and you want to find ways to take care of the people around you. And you realize that that opportunity is a gift, whether you're taking care of your family, whether you're taking care of your colleagues, taking care of your clients. There's a real opportunity to make a difference in other people's lives. And so, living well is pretty important. Of course, the balance sheets and the income statements all flood our minds, but it's how you make a difference in other people's lives that's gonna stay with you longer term. So markets fluctuate, but good relationships, happy family, those are enduring.

• 28:33David Weisburd?

  I'm curious, you're around many billionaires. I've had an opportunity to interview a lot of them. What are some psychological patterns that you see in them? Or are they all just complete snowflakes, one of one, almost no patterns?

• 28:46Speaker 01

  We've had the unique privilege of working with very successful people in the common denominator, at least among our client segment, is that they all built businesses and either sold them or are on their second business. So serial entrepreneurs as well. And what you find is, and I would agree with this, is that they know that you want to surround yourself with good people. They've learned that. We've learned that. And there's a give and take and play well in the sandbox with others. Those who enjoy good team ball and those that do that, well, they tend to develop cultures that are enduring. They come with a value segment that persists, permeates, and it overcomes some challenges that are going to come to the business. So you tend to find people that have a mindset that says, how do I think about the whole? And how

• 29:31Speaker 01

  do I think about the longer term? And these cultural, cultural and value type issues that are more important, it creates a powerful ethos. And for them, that's what wins. It beats everything else. So I found that for the clients that made a difference in the business world also end up as really pretty great people, they were others minded and they didn't have so much concern about themselves. It's a strange humility you find around these folks who are hugely successful. And I think that's very informative for all of us.

• 30:04David Weisburd?

  It's that axiom, leaders eat last. It's that ability to put their organization and their purpose above themselves, which allows them to be more anti-fragile and to stay with it longer than most people could.

• 30:17Speaker 01

  There's a characteristic that we use for our firm and its stewardship. It's the idea that how do I think about? The cause, the purpose, the longer term, the legacy, and less about trying to serve oneself. So I think that mindset, whether you see it in asset management, people building businesses, or people trying to lead their friends, their family, their purposes, those who have that mindset, they're the ones who last, they're the ones who rise above, who persist, who can pass something down. The other versions, it doesn't matter how big the balance sheet is. What we call that is those who take the antithetical approach to that, they're just building a larger and larger Titanic. And it ends up being in this place where no matter how successful

• 31:00Speaker 01

  the enterprise becomes, because the cultural condition was not built in a noble way, if you would, that you find that those folks really suffer more hardship down the road.

• 31:13David Weisburd?

  I've actually thought about this somewhat entertaining dark humor, and that there's some people that spend their entire career kind of screwing people over to accumulate wealth that they never use. And then they use that wealth to buy legacy, buy a public library or something like that, where they could have used that wealth and that to build a living legacy, something that their families and their coworkers could be proud of. So it's ironic that they play this wealth accumulation game, destroy their reputation only to try to recapture it with some library that nobody will really know the origins of.

• 31:41Speaker 01

  And it's because there's some very real statistical data that there's a phrase called shirt sleeves to shirt sleeves in three generations. The efficacy of that statement is near 85%. I mean, the longitudinal studies, the data that exists in the space now, it's overwhelming, it's overwhelming. Either you set up a value system that is going to endure, or you're not. And if you don't, if you fail at that, then you will be in the statistic. And so you sit back, it's no different than thinking about a company. You think about great financial companies, just take JP Morgan. Like, how's that company existed nearly 200 years? How did it do that? Well, it didn't do that because they had smart investors. They did that because they set up a value system, a culture that found a way to endure. And that's not an easy trick.

• 32:26Speaker 01

  You have to be very intentional to go do that.

• 32:29David Weisburd?

  I used to ask this question all the time until I started getting repetitive answers, but it seems like there's, there's two things that successful first gen families that end up raising great second gen, third, third gen kids. One is they, they behave in the way that they want their kids to model. They don't talk about behaving in the way that they want their kids to model. They actually do that on a day to day basis. Kids are very perceptive in terms of all the behaviors that their, their parents are doing. And two is somewhat of a hack is send your kid to investment banking bootcamp for two to three years after college and they will beat out any entitlement from him or her before they ever enter the family business. Those are the kind of the two useful tips of advice I picked up.

• 33:08Speaker 01

  The first part of what you're saying, we refer to as there's more, more is caught than taught. So kids and, and onlookers will see what's important by what is done. So as you role model, you're quote unquote, putting your money where your mouth is. Well, that's the best, that's, that's the wrong euphemism, but it really is. You're putting the table stakes where they need to be.

• 33:31David Weisburd?

  That actually is the right euphemism because what is a value if there's no sacrifice? I could tell you, I want to be a good person, but it's a meaningless platitude to say, if I'm not willing to give something to do that. So it is actually putting your money where your mouth is.

• 33:43Speaker 01

  It's what you prioritize and how you respond to situations and to be in a day in the life and you dissect it and you see how it goes about. There's sort of an old reality that give me 10 minutes with your credit card statement and I'll tell you who the person is. Get a pretty good descriptor. But for, for these families, it looks, it's challenging. They're normal people and they have the same kind of challenges everybody else has. The capital just intensifies those things. So areas around communication, areas around initiative, hard work. If you've ever had teenagers, then you know that those, those don't show up naturally. You, you have to find a way to instill them in the kids. And so it's, it's funny to watch billionaire families and watch their kids go off and work retail. And they do that because they want them to understand what it means to

• 34:27Speaker 01

  put in a hard day's work. So it's a, it's, it's a, it's, it's a trickier situation for them and they need help because it's, it's a bit more pressure cooker than it is for others. But those that are intentional about it and try to live out their values and to help make that difference, be other centric, boy, it really shows up. And, and then you find out whether or not you're dealing with dynastic wealth or if this is going to be a one and done.

• 34:50David Weisburd?

  On that note, Doug, thanks so much for sharing your time and your wisdom and looking forward to getting together soon.

• 34:55Speaker 01

  You bet, David. Thanks so much for having me.

• 34:57David Weisburd?

  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.