Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights

Portfolio Management Strategies from Leading Investors: What’s Working in 2025

Family Office & Investor Panel

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Discover how top investors are navigating today’s complex markets and what’s driving strong portfolio performance in 2025. In this insightful panel, investors share what's outperforming in their portfolios—from online gaming and digital assets to green infrastructure and AI—and what they're scaling back due to market volatility.

They also discuss:

Rebuilding strategies after climate disasters

Monetizing youth sports and media platforms

The impact of tokenization and digital payment systems

Why art, land, and sports investments remain antifragile

How to position for long-term ROI with resilience in mind

Whether you’re an individual investor, fund manager, or family office advisor, these real-world strategies will give you actionable takeaways to future-proof your investment approach.

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We shift gears a little bit to address an issue that investors need to manage all
the time, which is portfolio management. So I'd like to ask you a question with
several parts, and it's going to take most of our remaining time, and is in your
current portfolio, what is performing the best that you're really excited about,
and in addition that just because you're performing the best, are you looking to
increase it or maybe decrease it because of things that are happening in the market?
So just in general, what's doing great in your portfolios? How are you managing your
portfolios? What do you want to increase and maybe decrease depending on market
conditions? - I guess to start going back to something Jeremiah said, sports is
really big and one of my absolute best personal holdings are in online gaming
stocks. They're doing great. Kids aren't putting their phones down like you had
mentioned and
whether recession happens or it doesn't happen, people are still going to gamble and
they've made it easier and easier. So that, for me, has been one of the best
things that's been performing. And the other thing that I'm heavily invested in is
if you look at the tragedy of what happened in North Carolina and Georgia, there's
There's gonna be a lot of rebuilding that takes place, but the businesses that
thrive within that are gonna be the ones that are involved in building materials
that are resilient, like, for instance, ASAC or Trex materials, that they're not
gonna rebuild these homes with whatever they were built with before. So that's gonna
be something, and also property and casualty stocks. There's a reason why Warren
Buffett, most of his portfolios in that That's what, you know, hurricane happens.
They're not covering for nearly, you know, half those damages because they're
excluded, you know, 'cause most of the folks didn't have flood insurance, but
property and casualty stocks always do well where the economy goes up because they
can charge more of a premium or if they get hit with disaster, they charge more
premium again. So out of my own personal portfolio, those have been my, you know,
best performers outside of my real estate
Chairman? Yeah, absolutely. So for me, again,
it's, there's, the kids aren't going to stop scrolling and so I'm doubling down on
the media platforms that I'm acquiring. And again, as long as they meet my criteria
and I'm able to monetize them efficiently, or sufficiently,
they will keep, I'll keep buying. The second thing is,
again I mentioned earlier, that there are countless hours of content that are left
unsearchable.
That's like, I mean billions of hours of, I mean, if you have kids and they play
a youth sports, you record them. I mean, if there was an environment where you
could load that content in and make it searchable and accessible to an entire team
or an entire club, there's a lot of value Um, and I'm trying to figure out how to
capture that value that like very, very, very focused on that. The other side of,
of the sports world that I think is important, particularly in soccer, given the
World Cup is coming, um, it's really on the human capital side. We've got a lot
more quality coaches. We've got a lot more quality players than we've ever had, and
they lack a lot of education. And it's impacted the culture of soccer. You see it
also in other youth sports, the culture of youth sports from a parent standpoint. I
think we've got a lot of cleaning up to do in terms of educating people on the
way to behave. And I think if we can change the way people behave, I think then
we can start to introduce tools to help them get closer to their goals and then be
supportive experience, et cetera, et cetera. And then the last thing in terms of
what I'm decreasing, so I own part of a professional team and I was going to buy,
I was very close to buying a part of the Houston Dynamo in Major League Soccer. I
have ownership in an MLS Next team, which is a second layer, and all signs pointed
to the fact that the league is going to grow, The valuations of the clubs are
going through the roof, but the problem we have is we have non -business people
running these teams, so they're not monetizing the asset. So for me, I had to make
a decision, do I want to go inside of these organizations and try to use my
companies and the folks that I have working to help teach them how to monetize or
do I just focus on capturing the value that they're not capturing because they're
not set up to do so. So I gotta get the kids to stop scrolling and get them into
more museums too and galleries looking at art. Good luck with it. Portfolio
management is actually hilarious when I think about it in our case because it's like
half the stuff takes up a ton of space and it's like literally like my portfolio's
on my walls. And the other stuff in crypto takes absolutely no space at all, like
it's literally up here. So yeah, it's just, we're gonna keep tripling down and
collecting, like it's just in our blood. It's a problem that we have, we're addicted
to it. It definitely helps a lot of people. We locate artists when they're emerging.
So before the radar mark is even paying attention to them or taking stakes in them
and guiding them. And there's really nowhere but up for their value to go. And a
lot of what you talked about, like getting people involved, it's our thesis for
investing is that price is a fiction and it is born from narrative.
So everything is storytelling. So when we invest, we try to find what's the best
story now and then what's gonna be the best story five, 10, 20 years from now. So
when it comes to crypto, I feel like we're currently living through the greatest
story being told that's ever going to be told. And when we invest in art, we're
investing in people who are going to tell the story. So we're quite comfortable
there.
- Yeah, I think the best ones we've heard have actually been in the sustainability
and the AI side, but I don't want to spoil Linda's thunder, so I'll let her talk
about that. But you sort of stole a bit of mine, so the other big thing we're
focusing on, I think is the greatest upside in the next few years is on the
digital side, all forms of digital, whether it's sort of media, sports content, the
arts. The tokenization and digitization of assets, I think you'll see increasingly
people moving away from traditional financial systems and traditional assets into
tokenization and trading of those as we all look to diversify as individuals,
institutions. So I think what you'll see is payment systems for the global south as
they start shifting away from the dollar into more efficient ways of settling things,
where You're talking hundreds of billions, if not trillions, of transactions going
through payment systems, which you've already seen with Amazon and some of the other
big players going into places like Africa and Latin America having to set up their
own payment systems because there weren't banks. So I think the move to digital,
which also ties in with AI, obviously, and what a lot of the other people in the
panel are doing, will be the big theme of the next five to ten years and where
there'll be massive amounts of money to be made, similar to what happened with the
whole internet .com thing. And similar to that, a lot of money lost as well.
A lot of people ask me in this conference, even, like, what does that mean, impact
investment, right? So what we focus on is that what is in the five,
ten years we're looking forward and when we start to prepare is that what
fundamentally change people's life environmentally and also in terms of the whole
economy so that's what we usually focus on so in terms of how to get the return
like all of us investors so of course you need to sustain your business before you
can you know fit the climate, or fit the charitable, right? So what we believe is
that, is anything you can fundamentally change, a resolutionary change, and there's
plenty of ROI you can make. So that's what we believe on.
So in terms of focus in the next five years or 10 years or next year, we're not
just double down, we're gonna triple down in the areas like reusing the technology
we personally are family invested or we acquire or partner together to be able to
tackle the changes or climate. For example, hurricanes, we see a lot,
fires. And you and I was talking about the apartment housing and buildings,
so we will be able to partner with the industry leaders on that,
on the building material, for example, to be carbon free and at the same time, a
hurricane proof and then also fire proof, for example. So and then with some other
quiet technology or our technology, we can provide independent green energies into it.
So with that, that we fundamentally change a lot of the things happening in the
disaster event. So you would no longer have power shortage. You'd only catch fire,
right? And then, hurricane -wise, when that happened, then you would not lose all the
livelihoods because of those technologies. So that's one of the area in terms of
commercial residential buildings. So we're enabling them to able to sustain,
sustainable living, right? So I would talk about farming and then also clean water
and internet. So same thing for farming verticals and also for data centers.
We talk about AI, the enablement of data centers to be able to have capacity to
support your AI model training. So that was another area we focus on next year or
the next 10 years, I would say.
Excellent answers. This is really great.