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

Family Office Leaders on Navigating Uncertainty & Spotting Opportunities

Family Office Investor Panel

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In this panel segment, seasoned family office investors reveal how they approach turbulent markets, rising interest rates, and global instability — and why chaos can be a prime time to invest.

Key Takeaways:
• Uncertainty can create the best deals — savvy investors profit while others hesitate.
• Real estate and ancillary businesses remain hot targets during market volatility.
• In tech, initial seed investments are “toe in the water” opportunities — follow-ons are where big gains happen.
• Strategic involvement (board roles, connections, guidance) is as valuable as capital for early-stage companies.
• Liquidity is power: cash reserves allow nimble moves when valuations correct.
• Diversification across real estate, operating businesses, and liquid portfolios ensures long-term stability.

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going back to, you know, the uncertainty question. You know, I'm sure you guys hear
from a lot of family offices, you know, some family offices here on stage directly.
You know, what are some worries? What keeps you up at night? And what are some
opportunities as well that you guys are seeing right now with interest rates, with
the global issues happening in the world right now? I know Brian had mentioned India
earlier. So what are some worries and what are some opportunities?
Well, I actually don't have any worries. I mean, I sleep quite well at night. And
again, as I said earlier, this is a great opportunity. And when we've done
collectively as a family office, the best is in an uncertain time. So I say,
you know, bring this on, this is, you know, we're very bullish, you know, on
investing in real estate, investing in companies that are ancillary to real estate as
well. But, you know, I think we're going to have a period in our estimation of
another two to three years of this kind of uncertainty and chaos. And in the
meantime, you know, we'll profit on that. So I prefer that we didn't have this.
I'd prefer that we, you know, as a family office, we're not benefiting from people,
you know, being distressed. But, you know, we have an obligation to my family
office, an obligation to our investors and, you know, we have to strike. I think
we've had the most difficulty making money when times were strong. If you look at
our, you know, what we're doing now and what we've in the last year, how well
we've done. This was our best year. So if we look over the last 12 months, 18
months in our history as a family office, We look at times where everyone was
succeeding, that is when we not struggle, but didn't do as well.
So I think for everyone out there, this is the time where this should be happening.
This is the time to approach offices like ourselves. We have collectively held on to
a lot of cash and are now in a place where we we see opportunities to really
heavily allocate. Might have some Irish in you as well. Perhaps.
Anyone else want to answer that question? I'll offer a quick answer.
One of the greatest opportunities-- again, I'll speak on the tech investment side
here. But one of the greatest opportunities for us is not really that first
investment, but the subsequent investments that we end up making in a company. We
kind of view the the seed investment opportunities which are often just a few
hundred thousand dollars as putting a toe in the water it's giving a company an
opportunity to grow to get to the next level to see how they develop and mature.
And as they do well we have an opportunity then to typically to reinvest and
contribute more capital and increase our stake in the company and that can lead to
some tough decisions because sometimes the company is doing well it becomes a very
simple proposition to reinvest and contribute additional capital. Sometimes the company
is really struggling. And for that reason, we do like to try and play an active
role in the tech investments that we make. We do like to at least participate as a
board observer if we don't actually have a board seat to make sure that we are
able to provide some guidance, some connectivity. I firmly believe that a family
office that's serious about monitoring their investments is doing more than providing
capital alone, but is also providing connections, is providing strategic insight, and
is really in a lot of ways helping the founders by holding their hands to help
bring their company to the next level. Absolutely. Yes, I agree with you 100 %
because most of the time for early startups, connections and the knowledge that
investors are bringing, it's more important than capital. Some startups come to me
like to raise funds and ask them, what did you do? Have you pre -sale? I'm building
startup. I pre -sold. Why not to do it? Maybe I can do connection. It's much
valuable, especially in today's market, when economies and wars are over there,
as an immigrant, as a global entrepreneur, I can say, when you do business in
technology, especially, where do you, where are you located online? It's a huge
opportunity to do business from anywhere globally.
You're right, Bill. I get paid to worry for clients. So my job is to be a
sounding board for when anyone is fearful, whether they're your average Joe or your
wealthy billionaire, I have a couple of hedge fund guys that keep me on Rolodex
just to argue with me because they say, "Bill, if I didn't have you to argue with,
I have nobody to argue with." But if you want to look at markets traditionally,
when you get compression, when everything is valued very high, that's when you tend
to want to raise cash to your point because because you're gonna get some sort of
correction. When seven stocks were carrying most of the market last year, on January
one, I was holding 28 % in cash, which went into the market at the bottom in
March, and I did the same thing in 2020. That's, and you have to give your money
manager some wiggle room. If I had more than 3 % in cash, 20 years as an
institutional, 20 years ago, or even 15 years ago as an institutional money manager,
I had gotten fired for cash drag. Now it's considered an asset class and people
want managers that are nimble. That's the favorite word since 2008.
I want nimble. So when might you accelerate, put your foot on the gas. When you
get dispersion, high dispersion between opportunities in both pricing and valuations,
And you saw that the market lifted off the bottom this year, but the dispersion was
very wide and only recently are you now getting price expansion or PE expansion as
the rest of the market is starting to catch up. You also want to look between
asset classes. You know, the Chinese three -legged stool is always the best for
family offices, right? A business or a job making money, real estate making money in
a capital market portfolio, making money, and even if you're a real estate biased
family office, I tell them you need at least 20 % of the value of your real estate
in a liquid portfolio, even if it's short duration bonds, to simply operate your
estate. This is the same thing I did with one of the most famous casinos in Las
Vegas in 2007. I came in and they said, "Okay, we're only meeting with you because
our account sent you to us. What do you want? I said, "Well, I'm here to help
your business." They gave me 10%, but they were still open in 2008 when Las Vegas
Sands went into bankruptcy. Trump had to redo it, and they redid their casino,
doubled the bonuses to their employees, and they carried on. So whatever your bias
is, I try and help people figure out a way to be stable. Yeah, that makes a lot
of sense.