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Today’s episode features an exceptional guest, Mike Alexander, 
who brings over two decades of deep expertise in family offices, institutional investing, and alternative assets. Recently joining the Pantheon team as Director of Alternative Investments Portfolio and Capital Markets, Mike Alexander offers a rare, insider’s perspective on how the ultra-wealthy strategically build and protect wealth. Host Dave Wolcott invites listeners to take a behind-the-scenes look at what truly drives effective asset allocation—and how individual investors can leverage these same principles to accelerate their own wealth journey.
Throughout the episode, Mike Alexander shares his origin story in the investment world, from early days at a major insurance company to managing billions for multi-billion-dollar family office clients. He reveals the key differences that set the ultra-wealthy apart, diving into alternative investments like private equity, private credit, and real assets. Listeners will hear how a disciplined investment process and thoughtful due diligence can lead to more resilient, high-performing portfolios that weather any market cycle.
If you’ve ever wondered how top-tier families and institutions invest, or how you can adopt a wealth strategy rooted in long-term thinking, simplicity, and tax efficiency, this episode offers invaluable insights.
In This Episode
- Mike Alexander’s personal journey and lessons learned managing billions in family office assets
- The ultra-wealthy’s approach to diversification, asset allocation, and risk
- The importance of clear investment process and rigorous due diligence
- Strategies for individual investors to adopt an “endowment model” and invest for long-term success
One of the things the ultra-wealthy do is they don’t try and time the market. They invest like they’re the owner. They don’t let the market dictate their investments. So they don’t try and time the markets. Thinking about it over the long term, I think, is really key for them.
Welcome to the Wealth Strategy Secrets of the Ultra Wealthy podcast, where we help entrepreneurs like you exponentially build wealth through passive income to live a life of freedom and prosperity. Are you tired of paying too much in taxes, gambling your future on the stock market, and want to learn about hidden strategies for making your money work for you? And now, your host, Dave Wolcott, serial entrepreneur and author of the bestselling book The Holistic Wealth Strategy.
Hey, everyone. Welcome back to another episode of Wealth Strategy Secrets of the Ultra Wealthy. Today we are sitting down with someone who spent over two decades helping family offices and institutional investors design sophisticated portfolios across private equity, hedge funds, private credit, and real assets.
Mike Alexander recently joined the Pantheon team as our Alternative Investments Portfolio and Capital Markets Director. He brings a rare insider’s view on how the ultra-wealthy actually think about diversification, due diligence, and building resilient portfolios that perform through every market cycle.
In this conversation, we dive deep into the lessons he’s learned managing over billions in family office assets and what truly matters when evaluating funds and sponsors, and how individual investors can apply those same principles to elevate their own wealth strategy. Get ready to rethink everything you know about asset allocation, risk, and simplicity.
Mike, welcome to the show.
Thanks, Dave. Thanks for having me.
You bet, Mike. Welcome to the show, welcome to the Pantheon team, and appreciate your time today. We really wanted to get to know you a little bit more and talk about some of your background and expertise in the private equity and family office space — and how investors can really leverage that into some of their own thinking and strategies to propel their own wealth health.
So with that said, tell us a little bit about your origin story and how you got to where you are today.
Sure. So to start off where life began for me in the corporate world, I started out working for a very large insurance company back in the mid-80s. Before I got started on investing, I started off with the insurance company on the operations side and on the investment operations. I really think that was a great learning lesson for me — to learn teamwork and basic accountability for your work.
So I started off there and worked my way up within the insurance company, finally over to the investing side after a few years. I was able to really cut my teeth on alternative investments at the insurance company, where we were using the insurance general account to make hedge fund investments. I did that for a period of time and had an opportunity to move over from the large institutional world to the family office side, which to me sounded really interesting and entrepreneurial.
So I did. I jumped from the big corporate world over to a multi-family office, where I went from working with 50–60 people down to working with five or six people. If the printer needed paper, I’d stop and put paper in the printer. Basically, if I didn’t have a secretary to type my memos, I had to type my own. It was really roll-up-your-sleeves and do the work yourself.
At the multi-family office, I was tasked with bringing in and formalizing an investment process. I brought in a due diligence process — conducting due diligence on managers, everything from asset allocation procedures to formalizing the investment policy statement for investors, and bringing in a system to capture data.
When I first started at the multi-family office, we had about $50 million in assets under management. Fast forward 10–12 years after that, we had over $1 billion in assets under management.
It was a very successful run at that time. We had clients — family office clients as small as several million dollars to very large behemoth clients that had multiple billions. We really covered the gamut in terms of the type of clients we worked with. Obviously, the multibillion-dollar client required a lot of time and effort, so I focused more on that particular client for their portfolio allocation and investing.
I worked at the multi-family office for approximately 14 years. Near the end of my term there, we had just brought on a very large Japanese family office. They wanted to set up a U.S. corporate entity to make investments out of, and the family office I was working for asked me to move over and essentially run that company for the family.
So before joining you, for the past five years I was working for this Japanese family, essentially running the company. I built them a 70/30 portfolio — 70% hedge funds, 30% private illiquid lockup-type vehicles. No public securities, no public equities or fixed income — strictly alternatives.
It was a great run. I built them a portfolio that’s still in existence today, performing decently, and they’re very happy. I found you not too long ago, and you seemed to have a very interesting process with what you’re doing here at Pantheon. I came over to join you to try and take what I’ve learned over the last couple of decades and move it down to the individual investor level versus the large family office.
An important thing I want to do is take what I’ve learned over the last 20-some years and apply it to more people than just a few — more than just a dozen families. I want to be able to implement these portfolio strategies for the mass amount of single-family or individual investors out there who want this type of exposure.
So I’ll cut off there and let you ask any questions.
Yeah, no, thanks for that, Mike. And yeah, you just really nailed our mission there, where it’s so important to really help people uncover the strategies that a lot of the ultra-wealthy just know because they have access, they have teams, and it’s really, frankly, quite a very opaque world. And it’s very opaque on purpose. You can’t really uncover these types of things, right? And so that’s part of our mission with this show and with our business—to try to help others uncover some of these different strategies that can really be life-changing, frankly, to their wealth, how they live their lives, and in creating legacy.
So with that, what do you think are some of the key lessons from that world of billion-dollar family offices and institutional investments? How are some of those lessons that you’ve learned that you can bring back into the community for Pantheon today?
Well, I think, Dave, one of the most important lessons I learned over the last 20 years is that the typical 60/40 portfolio doesn’t really work through market cycles. It just doesn’t work. What we’ve built and what I’ve been taught from an asset allocation perspective, which is really key, is that you almost have to embrace an endowment model for investing. Instead of a 60/40 portfolio of equities and fixed income, you want 60–80% of your portfolio in alternative investments—things like private equity, private credit, real estate, tax-efficient strategies, and real assets as well, which help protect against inflation.
I think building something like that into an existing traditional portfolio was a key lesson that I learned from the institutional side. The other thing too is due diligence. Conducting proper due diligence on a fund is really critical.
And I think one of the things I govern my due diligence by is what I call the 3 Ps: pedigree, process, and performance. So when I look at a new fund, the first thing I’m looking at is who’s the manager, who’s it run by, what’s their pedigree, what’s their background? The other thing I look at, which is just as important if not more, is process—because the fund manager or the sponsor has to be able to explain their process well enough for me to get comfortable with the investment. Because in turn, I take that information that they tell me and simplify it for the individual investor or the client. So it’s really important that the process is well explained.
And then finally, performance. I’m very curious about how these funds performed over various market cycles. And if they’re newer funds and don’t have that historical performance, then it’s really critical to understand in the short term how that fund has performed over the near term. And can the sponsor or the portfolio manager explain to me, “Why did this fund perform so well when the market was down?” or vice versa?
That needs to be explained because all of that gets translated back to the individual investor. So those are some of the key things I’ve learned over my term as an investor.
Conducting proper due diligence on a fund is really critical… I govern my due diligence by what I call the 3 Ps: pedigree, process, and performance.
Yeah, so let’s unpack due diligence a little bit, right? Because I think this is one of the things that we are constantly refining. I don’t think there’s one silver—
Right.
—and just kind of bringing a whole rigor to that process is one of the things that we like to do for investors because, frankly, it can be a full-time job really trying to know that. And you might not necessarily know what to look for or where to look for certain data points about a fund manager, a particular project, or a particular market. And I know you even co-authored a book on due diligence, Mike. So talk about a few of the key points, in addition to those 3 Ps, that you really look for when diligencing a new investment.
So really, due diligence is broken down into two pieces. One is the quantitative side of due diligence—you’re running metrics on performance or breaking down balance sheets and P&L statements. The other is the qualitative side, which I think I spend a lot more time on, and probably most other allocators do as well.
But really breaking down the qualitative piece of due diligence is key. It’s really a combination of speaking to the sponsor or the portfolio manager, understanding the strategy, going through the legal documents, understanding any special treatments that other investors may get if there are side letters, and reviewing a lot of that.
Also, one thing that’s equally important on the diligence side is the operational due diligence—or as we commonly refer to it, ODD. ODD has just taken on a whole new look these days with things like cybersecurity and AI. There are just so many things now that people on the ODD side have to look at when conducting due diligence on managers.
And all of that really has to get rolled up into a template that is presented to the client at the end of the day, and it has to be simplified. You take—it could be four weeks, it could be six weeks. Some institutions take two months to do due diligence. You take all of that work and information and roll it up into a two-page executive summary and present that to the client.
To me, there’s a lot that goes into that, and it’s really a critical piece to the whole investment process.
Yeah, let’s talk about simplicity for a second. Right? Because I think this world of the financial services industry as a whole—people can basically drown in data. You can turn on CNBC or Bloomberg or pick your choice, and we’re constantly inundated with data. Or if you’re trying to do due diligence on a particular manager, as you said, there are just so many data points and different things to consider.
So when you’re working with clients and really talking about portfolio allocation and just overall strategy or the strategy of an investment policy statement, how do you really try to simplify things for them?
So again, kind of going back to one of those three Ps—the second P, process—it’s critical because I have to be able to take that process that was explained to me and translate that to the client. So it’s really being able to take a complex strategy, say something like investing in secondaries or a multi-strategy fund on the hedge fund side, take something that’s complicated like that, and simplify it to the client and translate it so that they fully understand the strategy.
And you have to also explain to them how that strategy fits into their existing portfolio. That’s also critical so they can understand where it fits. And also being able to explain to them how that strategy should perform over various market cycles, because not one strategy is perfect all the time.
And finally, how do you map that strategy or that asset to where they are currently today? Do they need something that’s tax-efficient? Do they need something for income? Do they need something for growth? How does that all fit into what their needs are? So it’s really that second P that I keep referring to—it’s really taking that process and being able to simplify and explain that to the client and how that fits.
Yeah, couldn’t agree more. I mean, anytime you can really create clarity and certainty in terms of where people are going with their investments and their financial future, that creates confidence. And that’s really what people are paying for—people are looking for that certainty. And there’s certainly not much certainty in the markets right now. It’s constantly in turmoil.
But it’s kind of interesting because when I look back, I mean, I can’t almost remember a year when there hasn’t been uncertainty and turmoil in something—whether it’s geopolitical events, something happening economically, certain sectors, or what the Fed is doing. There’s always something.
And I think it’s also really important for people to take some of that data—number one, with a grain of salt, and number two, from sources that you really trust and that are going to be actionable for you. Because there are a lot of folks out there that are basically into fear-mongering because they have an agenda. They may be trying to push gold or Bitcoin or certain things, right? “You need to sell everything, and we need to put everything into gold,” right? That’s kind of the narrative right now on the debasement trade.
So what are your thoughts around how you really weed through all of this different information to make the best decisions for your strategy?
Anytime you can really create clarity and certainty about where people are goin in terms of their investments and financial future, that creates confidence.
I mean, to your point, there’s a ton of information out there. I tend to rely on a few sources. One is the large investment consultant houses—you know, the Cambridges of the world, the Albournes of the world. I mean, they put out podcasts like what we’re doing right now. They talk about all the different hot topics that are out there in terms of the crypto markets, the private credit markets, things like that. And they just have a ton of resources that they throw at these different strategies. So they’re one data point—an interesting data point to use.
The other thing too is just relying a lot on my own Rolodex of people that I know.
I get invited to certain investment communities where 20 to 30 allocators like myself will go into a room and talk about what the best ideas are, what we’re seeing, what we like, and what we don’t like. We’ll typically bring in someone from a large institution to talk to us about maybe the secondary market, private equity, or what’s going on in hedge funds—things like that. So there’s that big information-sharing aspect as well. That’s another source of information.
And of course, whatever industry publications I can get my hands on, I read. So there’s just a ton of information out there in terms of how best to source ideas. But yeah, at times it feels like you’re trying to drink water from a fire hose, but then you just have to pick your battles in terms of what you read and what you don’t.
Yeah, for sure. I also think that sometimes people ask me the question, “What is the biggest missing link for most investors?” And I would actually pinpoint that as having a lack of strategy. Because if you don’t have a strategy, you’re really just investing deal by deal or getting information from an advisor who’s looking at things one-dimensionally.
But that’s one of the benefits of working inside a family office. The first thing you do is create your investment policy statement, which is a comprehensive strategy—not only your objectives and goals, but what’s important to you, how it ties to your investor DNA, your risk profile, and all these different things. I think you can really protect yourself from yourself and stay in line, not getting caught in emotional cycles as well.
So, Mike, you also talked about an endowment model a little bit, right?
And then you talked about the 60/40 split. So I want to just bring this back up for investors out there. I think part of the biggest systemic issue we have in this country is, frankly, a lack of financial education—in the world, really, but especially in the U.S. Most people think, regardless of what your net worth is, that the things people have been taught are investing in your company 401(k), getting your 2–3% match, so that must be free money, so I must do that, right?
Or yes, this 60/40 type split, or giving all of your capital to a financial advisor or some type of plan in equities markets—but not really understanding all of the things to consider.
First of all, if those are qualified funds, you can’t access them until you’re 59½. No one ever really talks about private markets because it’s a very unique sector. There’s less information on it than public markets.
So I think it leaves people a little confused and trying to figure out a strategy. So talk to us a little bit about what some of the popular endowment models look like in terms of allocation and how you see family offices allocate—just at a high level—to give people more of a sense of investing outside public equities.
The first thing with the family office and the use of the endowment model — you have to remember too that for these families, liquidity is not an issue at this point. Right? They have a time horizon that could be 5, 10, or 15 years before they actually need the money. Versus a typical 401k investor saying, “Well, you know, I’m putting this money aside, I’m going to need it at some point down the road, but I really don’t have many options in terms of how I can allocate it.”
A family has a ton of options. They can, kind of going back to that endowment model, divide that allocation up between growth — which should be more private equity. They’re also looking for income streams, current income streams through private credit or some type of direct lending strategy. They could be looking at some type of a value-add strategy like a real estate investment or real estate fund where they put their money in.
And then they also have that 5 or 10% allocation into venture capital as well. The rest of it — the smaller parts — are spread across more of the typical traditional equities and fixed income. But for them, the key is the time horizon. They could be either building money for their lifestyle over the next five or ten years, or it could be a generational thing. They could be building wealth for their kids, their grandkids, or the kids’ children who aren’t even born yet.
They could be looking out 10, 15, 20 years or greater for some of these investments. So the key with a lot of this investment model — at least on the private equity and private credit side — is the pacing of when these investments start to distribute capital and start to mature.
So, they’ll go into Fund 2 — say Private Equity Fund 2 — and put money into the fund. The capital’s called over a couple of years. As the money starts to come back in years three, four, and five, they’re taking that money and reinvesting it into Fund 3, then eventually Fund 4, and eventually Fund 5. They’re pacing their level of distributions, which is really smart.
What’s happening to a lot of investors today is they have a lot of illiquidity mismatch with their pacing schedule because in the private equity markets today, distributions over the last 12–18 months haven’t come back as fast as people hoped. So a lot of these investors are stuck in investment vehicles, which has created this market for the secondaries.
In the secondary market, funds like Blackstone or Hamilton Lane come in, create funds, and buy out these investors — giving them liquidity. They buy these LPs out at a discount, which is nice, and they’re already buying into an investment that’s in year five, six, or seven. They’ve cut out the J-curve with this type of investing, which is nice as well.
So yeah, for many families using the endowment model, they’re driven around this type of strategy and time horizon, which makes it very unique and beneficial for them. And it’s the same type of institutional investing that you and I can offer Pantheon investors. We can get them thinking along these lines — how to make their next investment using money from previous investments that are now in distribution mode. We should really be steering them toward that type of model to help them continue to generate growth and wealth for themselves and future generations.
Yeah, that’s such a great point and really brings out one of the awesome features in Pantheon Wealth OS, our new software product, where you can actually do tax forecasting and income-level forecasting. It’s so interesting — I think so many people forget about certain things.
Things.
cott [00:27:22]:
You may have a liquidity event from an asset or a certain business and then have a lot of tax liability in a certain year — which isn’t the best year to have the most income. So timing income distributions, like you said, and phasing it in terms of your tax strategy can really optimize your overall velocity and efficiency of capital.
One of the core philosophies is really teaching clients to think like the ultra-wealthy. From your perspective, what are a few key mindset or strategy shifts that separate the ultra-wealthy from everyone else?
I think one of the things the ultra-wealthy do is they don’t try to time the market. They invest and think like owners. They don’t let the market dictate their investments. They think long term — that’s key for them in terms of how they think.
The other thing, too, is being tax-aware — structuring investments to be tax-sensitive. That plays an important role in how they think. We mentioned the pacing of the maturity schedule — all of that is so important and differentiates how they generate wealth for themselves and the next generation.
So what do you think about the economic cycle we’re in — navigating the end of it and positioning into 2026? Again, there’s fear-mongering. On one hand, you can find pundits saying there’s a big correction due, and on the other hand, others say absolutely not — with people of great expertise on both sides. What are your thoughts on where we are in the cycle? What does 2026 look like? Should people be a little bearish or bullish right now?
Yeah, that’s a great question. I wish I had a crystal ball, but I don’t. Politics aside, I think if you look at the current administration, they’re business-friendly. They’re also looking to do additional fiscal spending over the next 12–18 months, along with potential rate cuts.
All of this is good for small businesses, which should be okay over the next 12–18 months. I don’t see any major correction in the markets — there’s too much underlying strength in the fundamentals.
That said, I like private credit. It’s not going away. Every time you open up the Journal, there’s a headline saying it’s a bubble — but why is Blackstone putting in $500 million into a private credit fund? Banks aren’t changing their lending tactics, so small businesses will continue to go toward private markets for capital. That won’t change.
The second thing is the secondary market. There’s an issue with investors not being able to get liquidity out of their private equity investments as quickly as they expected. They want liquidity — so the secondary market is really hot and interesting to get into right now.
And the third thing would be real assets. With inflation not going away, I think the new inflation target is probably 3%, not 2%, anymore. Three percent is here to stay, and to combat that, real assets are a good play for part of your portfolio as inflation protection. That’s what I see over the next 12–18 months — although anything can happen, we’re in very unusual markets right now.
Yeah, for sure. Well, if you could give just one piece of advice to the audience about how they could accelerate their wealth trajectory, what would it be?
I would say, look, don’t try and do it yourself. We offer a virtual family office service. I would say call us on that because that’s an opportunity for an individual investor to not only utilize your service and my service, but we can help them get fractional help in terms of taxes, estate planning, investments — you name it. We can get help in all those different areas.
It’s too hard to try and solve all of these problems by yourself. I think the more people you have working for you and around you, the better off you’re going to be long term.
Yeah. Appreciate that, Mike. What we’ll do for the audience is actually put Mike’s calendar link and contact information into the show notes. So if you want to have a complimentary free call as a portfolio assessment or to connect, we’re going to extend that to our audience today because we appreciate our loyal listeners.
So, Mike, thanks so much for joining us — really appreciate your insights for today and moving forward with the team as well. We’re really grateful to have you on the team. And for the audience out there, thanks again for tuning in, and we’ll see you on the next one.
Thanks, Dave.
Thanks for listening to this episode of Wealth Strategy Secrets. If you’d like to get a free copy of the book, go to holisticwealthstrategy.com — that’s holisticwealthstrategy.com.
If you’d like to learn more about upcoming opportunities at Pantheon, please visit pantheoninvest.com — that’s pantheoninvest.com.