How to Stand Out to Billionaires, Family Offices & High-Net-Worth Investors

Aviva (00:00)
This week's listener of the week is Jack Jams. Jack, thank you so much for leaving us a five star review. And for those of you listening, if you leave us a five star review below, you might be next week's listener of the week, week, week. This week on Commercial Real Estate Secrets, we have Richard Wilson. Richard is the CEO of

The Family Office Club. Richard, thank you so much for being on the show today.

Richard C. Wilson (00:30)
Thank you for having me here. Appreciate it.

Aviva (00:32)
Yeah, Richard, for the listeners, who are you? What do you do? And how did we get here today?

Richard C. Wilson (00:38)
Sure. I started an investor club 18 years ago. It's called Family Office Club. We have a thousand plus active ultra wealthy investors like decamillionaire and centi Millionaires in the club.

In the last 18 years, we've posted 300 live events. We have 17 million social media group members and followers, and about 40 % of our activity is real estate related in terms of, you know, like at our next event, we have 100 speakers on stage. It'll be like probably 40-some that are real estate related. So real estate comes up constantly with what we do.

Aviva (01:14)
Sure. How did you get into the this business?

Richard C. Wilson (01:20)
I started with just a blog 2006, 2007, I started blogging about

investing, family offices, capital raising, hedge funds, and then it turns out people mostly just wanted to hear about family offices. And so I started blogging about that and then the website took off and I bought familyoffices.com and got invited to speak in many places and wrote a few books for Wiley. And we started hosting our own events and then it became more of a formalized family office club at that point.

Aviva (01:48)
So tell me about your events.

Richard C. Wilson (01:52)
Sure, yeah, so a lot of times when people hear about events...

They think of a local cocktail mixer or an angel investor event where everyone comes for free and there's 40 people sitting around here in pitches of startups or real estate deals. so our events are very different. We have four big investors, summits per year. So we'll have, let's say 450 to a thousand people at these events. We'll have 75 to 125 speakers on stage over two to three days. And it's strictly members only. So.

It's a community. get to know everybody. We'll do fireside chats on stage. I've interviewed a shark from Shark Tank. We've had 75 NBA players and NFL players on stage. interviewed Mike Tyson. I've interviewed Mark Cuban and Tony Robbins for our website, billionaires.com. The event is all about hearing from the winners in the game of business, whether it's real estate or manufacturing or auto dealerships and just trying to learn what

deal structures they use, how do they negotiate deals, how do they think, stuff like that. Yeah.

Aviva (03:00)
That's interesting.

I'm curious, so say you're someone who doesn't have any affiliations with the family office, but wants to get involved. What's the best way to go about doing so if you're a young gun coming up in the biz?

Richard C. Wilson (03:21)
Yeah, well, one thing is just to study and learn the industry, right? So you can listen to, you know, podcasts like yours. You can read books. You can study what they're doing and how they're thinking. So, you know, how to add value to them. we're not the only family office game on planet earth, but you can go to family office events, whether they're ours or someone else's and hear them speak on stage. And then, whether or not you meet an investor at your first event or even your fourth event, just knowing how the industry works and flows.

and

what gets their attention and what's unique and what's not is really important. And likely, if you want to work with family offices, you need to figure out like what is your niche? What are you amazing or world-class at or could focus on and become world-class at so you stand out from everybody else in their email inbox. And that's really important because otherwise, you know, if you're just doing what everyone else does, nobody's going to reply to your emails or want to meet with you. So figuring out that focus is a second step after you kind of learn the basics.

Aviva (04:17)
Sure. And do you find at your events, it's the family office personnel or it's the people who are being served by the family offices themselves?

Richard C. Wilson (04:31)
It's really a mix of both. So if somebody is worth more than two or $300 million or much more than that, they're going to have a professionalized team on some level and someone who can travel to some events on their behalf. like at our last event, we had the founder of Keller Williams Real Estate, we had the founder of Gold's Gym, we had the actual, a lot of the actual Ascent to Millionaires and Billionaires and Deca-Millionaires there. But also, the other thing is that our community is not only focused on people worth hundreds of millions

We like to interview some of those on stage and invite as many as we can. But a lot of our investors are someone who sold their dental practice for $7 million, or it's someone who sold their dad's auto dealership got sold. And then now they're trying to manage the money for that or a manufacturing company they sold for, you know, five, 10, $20 million, or they're a doctor and they're making seven figures, but that's new to them. They're trying to figure out how to invest. you know, it's not all these kind of almost seemingly impossible

to reach, ridiculously ultra-wealthy, It's also just the bottom level of ultra wealthy or just normal private investors. So we like to have all types come into our events.

Aviva (05:39)
Wow, that's interesting. So say I was a commercial real estate broker and I had an off market property that I think would fit a family office. How would you pursue a family office that say you'd never connected with

Richard C. Wilson (05:42)
Yeah, it's fun.

Sure. what I would first do is try to find any strategic buyer for that off-market property, whether they're a family officer or not. And, you know, I would look at data sources, big data, I would ask AI, ⁓ et cetera. I would also look for the ones that are right in my backyard or, know, within, ⁓ a one hour drive or flight from that location of that off-market assets. They're more likely to be able to conduct due diligence and actually close on it swiftly. if I was actually trying to get the attention of a family office specifically,

I would come up with a single sentence that summarizes the merits of the deal and is very clear about where it is, why they should care, and then craft that sentence to send them over via email. It also leave a voicemail. So I get a thousand, over a thousand emails per day, but I only get six to twelve voicemails a day. Nobody wants to leave a voicemail. They'd rather blast out an email to 10,000 people. So I definitely thought

up with that one-liner via voicemail and most people don't take the time to really narrow down why someone should care about their deal to a single sentence and if you're not willing to take that time why should someone else spend the time to try to figure out why they care about your deal if you haven't figured out why they should care it's like you know they're not gonna take it too seriously

Aviva (07:11)
Yeah

Hmm. So, okay, I mean, I ask this question every day, right? Email versus call. You know, I get these emails. I'm the same way. I get emails. like, I can't actually take all this seriously. I can't even take 2 % of it seriously. Does picking up the phone still work in 2025?

Richard C. Wilson (07:33)
Right.

I think it does, but a lot of times it just shows a deeper level of conviction that there might be a connection here, or they took the time to reach out. So when I do that, or when I encourage other people to do it, I'll say, well, you can look up my email if you want more details on this by going to richard@familyoffices.com and you can find it in your inbox. So it's almost like the voicemail almost, almost guarantees that they're going to hear your one sentence.

Aviva (08:05)
Yeah.

Richard C. Wilson (08:05)
And that might get them to open your email and then they might reply via email or you can offer them to text message you back Perhaps even if you left them a voicemail, they could text you so that can sometimes get the conversation going

Aviva (08:21)
Okay, so pick up the phone. Or does email work? mean, email does work.

Richard C. Wilson (08:28)
Yeah, we've gotten, we email billionaires and sometimes get cold emails to billionaires like Mark Cuban. It was a cold email that got him to reply and answer our interview questions. So, if cold emails will work with Mark Cuban, who's a very well-known billionaire, I'm sure you can convince family offices to reply to you, but you have to have something that stands out in their inbox against everything else that they're seeing that day. It should be in their best interest to reply to you because what you're offering is so valuable.

it's amazing compared to what everyone else is trying to do.

Aviva (09:01)
How do you find these people's information?

Richard C. Wilson (09:04)
I mean, Mark Cuban's pretty public about his email on his blog and some of his websites. Other people are more private. ⁓ There's family office databases out there. There are live events you can go to and then meet some of these family offices and follow up over email, ⁓ et cetera. So, you know, nowadays there's many different ways to get that. You can also approach family offices via LinkedIn as well.

Aviva (09:27)
Hm.

Hm.

You brought up LinkedIn. Are there other social media sources or sites where you find the right people hang in the right places?

Richard C. Wilson (09:40)
I haven't had a lot of success with other platforms. I know a lot of family offices are on Instagram and look at Instagram. I think a smaller percentage Facebook and even smaller percentage, you know, TikTok. I think a lot of them do have a X account as well. But, you know, finding.

success in sharing thought leadership via some of those other platforms has been harder compared to LinkedIn. So we focus on YouTube. We've gotten tons of traction on YouTube and then LinkedIn is the number one, but YouTube's the second. And the other social media platforms, you know, we don't worry about too much just because we haven't had as much traction there.

Aviva (10:22)
I met somebody off of X and I got a $70 million offer from them. X is actually crazy powerful, specifically in this space, in my experience. it's like, it's just like these people, it's it's, you know, the whole point of what you do, it's like, these people are actually out there.

Richard C. Wilson (10:26)
Thanks.

Wow.

Yeah.

Yeah, that's awesome.

Right.

Aviva (10:48)
How do we bring them together? How do we bring value to each other? And how do we ultimately get deals done? So I'm curious to hear like your YouTube journey and how you've seen success from YouTube.

Richard C. Wilson (11:02)
Sure. Yeah. So I started out just whenever I'd get on an airplane to travel somewhere, I'd record a couple of the videos of what I learned at the conference I was at or what I learned by hosting a investor club mastermind somewhere, et cetera. And then that way the videos were more dynamic versus only me sitting behind my desk for every video for a thousand videos can be a little bit stale feeling. So that helped make it a bit more dynamic. And then we've done a lot of mini series. So I've got a, 17 episode mini series called a hundred million dollar rainmaker series.

And in that series, we provide somewhere between 30 and 50 capital reasons, strategies that no one else is talking about. And so on YouTube, that's been, that's been popular. And then we also have a series for investors. and it's a how to start a family office mini series, on YouTube as well. And that one, think it is 12 or 14 episodes long and that's been really popular. And so as we grow, what we're trying to do is keep our content relatively concise. Like I know you do a lot of the time as well. And then.

And make sure we're saying things that are unique and not just repeating what everyone else in the world is saying, of course. And then importantly, what we're doing over time is really trying to make it so that they get so much value from the videos and so many insights from that, that it de-risks coming to one of our investor club events or working with us in a greater way. So trying to add as much value as possible, knowing that someone might watch that video 10 years later, five years later, and then it's still working for you and adding value to people.

Aviva (12:29)
That's cool.

Richard C. Wilson (12:32)
Yeah.

Aviva (12:34)
You know, with commercial real estate, have found, you know, it's a largely gate kept industry. And the internet is changing that where, finally, we can have discussions about how to do deals and how to structure deals. And I'm sensing a similarity within the family office. And sort of starting to, it's like you said, like, talk about deal structure. How did we get there?

Are you seeing any form of adoption overall by family offices onto the internet or what are you seeing there?

Richard C. Wilson (13:06)
Yeah, we see a huge interest in that. So much so that we put out our first AI tool in January, and now we have a suite of 30 artificial intelligence tools. And I'll send you a couple of links to them after this. We call it investor super intelligence. we essentially ⁓ like one, you brought up structures. One of them is called deal structured Ninja and it's been trained on a thousand deal structures. So you tell it what you're trying to negotiate, what you're trying

to solve for, what your priorities are, what the counterparty wants, what could blow up the deal. It'll give you 10 deal structures. And you say, I like number two and six. Show me 10 more like that. It'll do that again and again. And then you say, I like number four in this fourth set. Just tweak this one last part. It'll do that. And then write the email for your attorney and the counterparty saying why that structure is good for everybody.

And like, that's just one of the 30 tools we developed and like, it literally could change your life. If you get a deal done versus not with a $70 million asset or something, right? It's like, you know, so that, that one tool to me, it just like kind of breaks my brain. That's even possible, you know? So we're, we're, I'm spending more hours per day on improving and building out those 30 AI tools than anything else right now, because, it's just exciting basically. Right. So.

Aviva (14:26)
Yeah, AI, you know, internet was like level two, AI is like level 20. What a crazy opportunistic time that we get to live in right now. So talk to me about the relationship you're seeing with family offices in real estate in 2025. Yeah.

Richard C. Wilson (14:32)
Yeah.

For sure.

Yeah, well,

you know, up until two years ago, everyone was saying, you know, including five years ago, seven years ago, even people are saying this market's been too good for too long. Something might happen, but

They kept on investing because they kept on making more money and more money. then like, I think we entered this world of a capital raising bubble a bit where people are just raising capital for stuff left and right. You know, even people with little experience syndicating this deal, syndicating that deal and investors were dishing out checks and getting paid back. but then interest rates go up. valuations are questionable. a lot of people have to recap their deals, replace, you know, variable debt.

that's now gone so high where they need to recap their whole project and bring their debt levels down to 50 % or 60 % to survive. A lot of rescue deals, ⁓ et cetera. And so I think what investors are seeing right now is they're getting spoiled by the fact that they get almost equity-like returns with a debt-like security. So a lot of them are, you know, if they're really informed and see a lot of deals, ⁓ they might be...

Aviva (15:25)
Hmm.

Richard C. Wilson (15:53)
making 11, 12 % backed by real estate and maybe even getting a point upfront for that. And their worst case scenario is a, you know, not fun process of foreclosing on something perhaps. And so that's what some families are seeing. And it just depends on who you talk to out there. Like when markets go down and everyone thinks, oh, real estate is doing poorly, you probably want to stay away from that. Like, well, if it's going down, you're going to get a better deal. So it might be a great time to invest.

Aviva (16:12)
Hmm.

Richard C. Wilson (16:22)
potentially and when markets are super toxic that might be as billionaire Howard Mark says it might be like the best time of a generation to be investing like, you know, everything's going great

Because that's when you should be more careful. Right. So the mood is the

Aviva (16:35)
Yeah

Richard C. Wilson (16:37)
mood of the industry is interesting. Right. It like, there's less money being raised right now successfully. some deals are shaky. Some deals are breaking. So the investors are bloodied and lost money. So they're not in the best mood of investing, but then at the same time, it's like, that's when the good deals start, start popping up. Right. So.

Aviva (16:54)
I heard it before. Yep. So, I mean, now that we're two feet into this conversation, where do think we're going? Do you think it's going to get uglier? Or better? we at the? Are we at the bottom?

Richard C. Wilson (17:09)
I mean, I think that Ray Dalio said it best. I think it was Ray who said, I don't pretend to predict like the exact point of where we are in the market, but I can stick my head out the window and give you an estimate, right? And so I think that Trump is determined to lower interest rates one way or another.

I think it's good that we don't burn billions of dollars on things that maybe are not productive. And so when you're not dishing out billions of dollars to things, and you were yesterday, there's less billions of dollars floating around, right? And high interest rates are a slow motion train wreck. And when variable rates reset, then pain comes, then there's forgiveness periods, and then people be less forgiving, and then assets get taken over by banks. And, you know, so I think it'll get worse.

Aviva (17:41)
Yeah.

Richard C. Wilson (18:00)
and then interest rates will get dropped much more significantly. And then things will improve again and go back up to record highs. And that's my guess, but where that exact moment is in the cycle, I do not know, but I would guess that Q4 to Q1 is when rates will probably go down significantly, would be my best guess.

Aviva (18:03)
Hmm.

Yeah, it's, it's like you said, like, five years, seven years, everybody was going, my gosh, this has been so good for so long. And then the pandemic happened and it was like, everybody hide under your desk and then it was still good. And then now we're all, you know, it's like you said, looking around going, what is going on? I see. Like, but when you find that the,

Richard C. Wilson (18:35)
Right.

Yeah.

Aviva (18:53)
the magic ball that tells you the future. You call me, you let me know so I can get one too. Richard, I could drill you with questions all day because I find this fascinating, but.

Richard C. Wilson (18:59)
Will do. Yeah, will do.

Aviva (19:10)
I don't think that the listeners would enjoy listening to me ask you selfish questions. Do you have, you know, normally we ask for a commercial real estate secret, but I will make an exception if you have another family office secret to share with our listeners today.

Richard C. Wilson (19:28)
Sure, I think the secret that almost every single person gets wrong who comes to our investor club, unless they've raised hundreds of millions of dollars, they get this wrong. ⁓ They don't understand that who you are or where they met you or who referred the deal to them matters way more than the details of your deal. Like the relationship with you and trusting your honesty and your team and your value add process.

Matters way more than whatever IRR you put down on your paper, whatever spreadsheet math promises, whatever payback period. I mean, you can, I can show you a spreadsheet that solves world peace, right? It doesn't mean anything. There's never a bad pro forma, right? So I think that, that's what people mess up and it shouldn't be a secret, but it is a secret. People pitch without building a relationship and then you're not going to get much done.

Aviva (20:21)
It's so funny you said exactly what I was thinking, pro forma. It's just like, what am I doing with this pro forma? Like, please, you know. right, exactly, exactly. So it's like, but that's profound, thank you. I know we're gonna clip that one for social media and people are gonna love it, so thank you. Richard, for the listeners who wanna learn more about you.

Richard C. Wilson (20:29)
Right. I'll show you what to do with it.

Cool.

Aviva (20:50)
your club, your events, your content, where can they find you, follow you, contact you, et cetera.

Richard C. Wilson (20:56)
Sure, the best place would be go to familyoffices.com and at the top of the family office club website there, my WhatsApp number and my text number is right at the top of the website. And we try to get back to everybody real quick with like links to any mini series or videos I mentioned or resources and the AI tool set, there's 30 AI tools. ⁓

are really not found anywhere else right now. So we're super excited just to share the word about that.

Aviva (21:29)
Richard, this is fascinating. Thank you for what you do for everybody trying to learn and understand deals from the top to the bottom. So we appreciate your time today. Yeah, and for everybody listening, we'll see you next week.

Richard C. Wilson (21:41)
Yeah, thanks for having me here.