
Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights
The Family Office Podcast released 3-7 episodes a week of interview mandate interviews, private investor strategies, innovative investment structures, and wealth management related insights.
We use this podcast to interview billionaires, centimillionaires, investors, and family offices and help founders, entrepreneurs and investors scale their platforms and invest more effectively.If you are looking to grow your business, get sharper at investing and scale you are in the right place.
Our program provides investors with insights on setting up their own single family office, virtual family office, or selection of a multi-family office to help them manage their wealth.
We cover private equity, real estate, income investments, commercial real estate, hard money lending, private loans, and innovative structures such as performance-fee only and Co-GP investment opportunities.
The Family Office Club has over 7,500 registered investors and our online investor community has over 700 recorded investor mandates, with a normal 15 live events hosted a year with 6,500 participants at those live events.
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Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights
The #1 Question Top Investors Ask Before Funding a Deal | Family Office Club Panel
In this candid Family Office Club investor panel, leading family offices and venture investors reveal the first question they ask when vetting a CEO or deal — and why it can make or break an investment.
From uncovering hidden debt to testing a founder’s execution plan, these seasoned investors share the sharp, direct questions that quickly separate great opportunities from time-wasters.
What You’ll Learn:
- Why undisclosed debt can instantly kill a deal
- How to spot red flags in founder relationships (including co-founders who are secretly married)
- Why “real revenue” beats letters of intent or purchase orders every time
- The critical importance of use-of-funds and 5-year execution plans
- How to pressure-test competitive strategy in markets dominated by giants (e.g., Elon Musk)
- The fastest way to save time in due diligence and avoid dead-end meetings
📌 About Family Office Club
The Family Office Club hosts 30+ live events annually, connecting investors, founders, and dealmakers worldwide. Learn more: https://familyoffices.com/
So for each of you, for investors here in the room who need a good sharp question
to ask when they're vetting somebody or for someone raising capital just to know
that they might get this question, what is the one question you ask up front?
Either you're asking yourself and you're looking for it or you ask the CEO when
you're vetting something like maybe in the first meeting with somebody? What would be
the one question that you would ask first or focus on? There's so many questions.
Do you have debt? That's a good one, because a lot of people do and they don't
want to tell you about it. What was the question? Do you have debt? Do you have
debt? Right. Because that will really blow a deal for us, right? If there's debt on
the books, then we need to know it right up front because we're second in line to
debt as an equity investor, and that's really important. And people don't really
understand that and they'll also put their own owner's equity on the cap table as
debt and we have to dissuade them of that idea and so there's there's a lot
involved right up front on that. I think that's smart because a lot of times you
get deep into diligence before someone reveals there is a massive lawsuit or judgment
or dad and you're like well if I wouldn't own that up front we wouldn't be in
meeting number five maybe or maybe not right? Yeah another good question is are you
your co -founder, are you guys married? A lot of people present as if they're not
married and they're married and it's funny. And you're like, why would you not be
upfront about that? Like you guys have the same last name. It's very curious.
- Right. - My first question is always, do you have a real revenue, not letters of
intent, not purchase orders, not, I mean, but actual checks that have been written
that you've cashed. - Right, right, yeah, the graph always goes straight up, even if
they've done 200K in revenue for five years, right? - To me it's all about execution
and I ask them use of funds where they see themselves in five years and how are
you gonna get there? If they can't thoroughly answer that question, I'm out of the
room. - Yeah, for us, it's always who is your toughest competitor and how are you
going to beat them. Again, we're going for the utterly asymmetric. So in a recent
deal, how many of you have ever heard of a company called Figure AI? Yeah,
Humanoid Robotics. Think of the movie with Will Smith and the robots taking over.
Well, they're a number one competitor, of course, is Elon Musk. So we had to have
a conversation about how is what you're doing actually going to compete with that.
Got it. Yeah, it makes sense.