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

Live Q&A: How to Get Investor Responses, Use AI for Outreach, and Build Credibility Fast

• Richard C. Wilson, Founder of the Family Office Club

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In this rapid-fire Q&A, Richard C. Wilson answers key audience questions on how to connect with investors, build pitch credibility, and use AI tools for smarter capital raising.

💬 Questions Answered in this Session:

- How can AI help find and target the right investors on LinkedIn?

- We launched in 2019 — is that enough history to build investor trust?

- What’s the best way to get responses to cold outreach?

- How do you stand out when pitching busy billionaires or family offices?

Richard shares real examples, cold email strategies, and insights from interviewing 40+ billionaires — including how his team secured investor meetings with Mark Cuban and others through humor, value, and patience.

📈 Ideal for:

- Capital raisers

- Startup founders

- Private equity and venture funds

- Family office professionals

🎯 Learn the psychology and strategy behind investor engagement — and what not to do when following up.

🔗 More strategies: https://FamilyOffices.com

#investorrelations #capitalraising #founderfundraising #familyoffice #coldoutreach #aioutreach #pitchstrategy #qandasession #richardcwilson #startuptips #investorcredibility #dealflow #raisingcapital

https://familyoffices.com/

So we're gonna be opening up cocktails here in about two or three minutes. I have
time for a couple quick questions. We could bring a microphone over to you. And
then otherwise, there'll be cocktail networking, and then we'll be seeing you tomorrow
at 10 a .m. So we have one question up front, and then maybe we'll have one more.
- Hi, Richard, thank you so much. - Sure. - Amazing weekend. I was just wondering
what you think about AI searches now on LinkedIn and other places to pinpoint
investors aligned with one's theses. - Right, we're experimenting with using AI in
many areas of the business, like analyzing due diligence documents, analyzing
materials, summarizing real estate inspections, experimenting with chatbots and custom
GPT boxes, et cetera. There's a Y Combinator company called Gumloop that allows you
to put into place half a dozen to a dozen different template AI processes and
automate different processes within your company. So Gumloop is on my list to
investigate. And so those are the areas we've been diving into. We haven't found a
slam dunk amazing LinkedIn tool. I know of many. I've tried many, tried many plugins
that claim to have the emails of LinkedIn people, et cetera. And data enrichment is
something valuable. And I think that it's something that we're trying to figure out
who to trust in data enrichment for our CRM, et cetera. But if you find one
specifically for LinkedIn, that'd be amazing because finding investors local to you
that know your industry or where you travel most, where you're buying an asset, or
just how to navigate the family office space even better on LinkedIn. We're always
trying to sharpen that saw. So definitely let us know if you stumble on something.
We're trying to be in the top 10 % of AI. We're not AI tech super nerds, but
trying to be a little bit of that. I think we have one question up front here.
Maybe I have time for one more quick one if there's another hand.
Appreciate you doing this as our timing is perfect for our company. My question is
we're relatively new like 2019 start dates so if we put a timeline on our pitch
deck is that enough time to be credible to investors?
What year did you say you started? 2019. 2019. Yeah I mean The, I think it is.
I mean, it depends how much you've done in five years, I guess, right? I mean,
sometimes some projects take so much research and development, and to outsiders,
it may or may not look like enormous steps are taken. So I guess that would be my
response is like, it depends if you can mark two, five different stages you've
gotten to to show how de -risk it is today. 'Cause you're in the storage or flex
space, is that right? Yeah, so if in five years you've done more than like one or
two deals and you've like built out some full -time W2 employees, the good news with
acquiring assets as a sponsor or syndicator is you need employees at each of those
locations. So it can add up to a lot of employees relatively quickly and an
entrepreneur will respect what it takes to have 30 employees under you or 60
employees under you. And I think those are some tangible numbers you could talk to
>> Yeah. Was there one more hand up that we can see? Yes.
>> So for the follow -up to get responses, how can you have the most impact? >>
Yeah, great question. So one of the hardest people to get cold email responses from
are like Uber big celebrities, Elon Musk, Taylor Swift, heads of state, and
billionaires, I think, they just get pinged the most. And we have cold emailed every
billionaire on planet Earth that we can identify via LinkedIn, Facebook, email many
times. That's how we've interviewed 40 of them. About 30 of the interviews came from
cold emails and we've learned a lot of lessons from that. So keeping the email very
short, offering to add value to them first by connecting them with others or buying
500 copies of their book. Having a sense of humor with Mark Cuban. We use a sense
of humor and on my 14th pitch to him, he replied, but I also don't follow up 14
times a day. It was 14 times over more than two years. The busier the person is,
the more I space it out by six to eight or 12 weeks, and the less busy I guess
they are, the more I might follow up by six or 10 or 12 or 15 days instead of
that many weeks. But I'm not an expert on it, or we've interviewed 100 billionaires
already, but adding value first so that your message to them, they should feel like
they're losing and they're missing out and they have to reply to you because it is
more valuable than every other email that hit their inbox that day. So when I moved
to Arizona, I went and got my car service somewhere that had a subscription model.
I was like, well, that's pretty smart. So I looked at their website and they had
like 13 locations. I was like, whoa, these guys must be doing big business. So I
emailed them and said, I bet each time you open a new location, you are having to
raise capital, give investors equity in each of those locations, and you not only
have to raise a capital, but now you're diluted in each of those locations, I could
design for you a gross revenue royalty structure potentially that could help you
raise the capital, give investors a good return, but in the end you retain 100 % of
the equity and still have them leave with a smile on their face and a great return
as a passive investor. And I said that like in I was sentenced in a half, and I
said, and I'm local, would you guys like to meet? And it was two people that owned
it. I independently linked in them. They both gave me positive responses from that
cold message. And the first 10 days I was in Arizona, I met a centimillionaire
family, got to meet with their board, meet with them in person several times, and
now it's completely cold, 'cause I offered them something, they're like, oh, I have
to have that. Like, I have arthritis, and you have arthritis and medicine for my
knee. Like, it's in my best interest reply to that. I didn't pitch them, "I'm gonna
join my investor club. "Do you wanna pay me to be a consultant?" And we don't
really do consulting, but that's the opposite. A lot of people who email are
pitching, "Hey, you wanna invest in this? "You wanna invest in this? "Wanna invest
in this?" It's not even customized to them, the pitch. So the opposite end of the
spectrum is it's nothing about your pitch. It's not about you. They're out there, so
their kids go to college to secure their family's future. They're not out there to
look as many random pitches as possible. And they don't owe people a reply. They
owe themselves to be a good steward of the capital that they worked 40 years to
make. And so they want to act in their best interests. So when you serve their
interests first, then your interests can get listened to more natively. And that
takes some patience. So like somebody said yesterday, I think Dean, he said like, if
you're stressed out over a two -week capital raise and you need my help, this is
what Dean said. He's like, we're not the people to help you because you need to be
planting seeds before you expect to pick the fruit. You haven't even watered the
seed a single time and you're wanting to pick the fruit already. You know, and
sometimes it happens. Sometimes we meet someone and they called the principal of the
family office that told them to turn the private jet around and come back to New
York to look at a deal that they had to see. And Ira who spoke at our event this
summer, he had that happen once at one of our events and he told the head of the
billion dollar family office, "You have to come back here to New York. It's exactly
what we're looking for. So sometimes things move really quickly.
That was kind of a long answer. So I think I'll let everyone enjoy cocktails now.
I hope everyone had a great time. We'll see you at 10 a .m. here tomorrow for
Investor Day. Thank you.