246: How the Ultra-Wealthy Invest in 2025
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Welcome back to another episode of The Richer Geek Podcast. Today we are joined by Richard Wilson, CEO of Family Office Club, the largest investor community for ultra-wealthy families with over 7,500+ members and 16+ in-person events every year. Richard has spent 18 years studying how the richest entrepreneurs protect and grow wealth, building a global social network of 17M+ followers and interviewing billionaires to decode what truly moves the needle.
In this episode, we chat about…
What the ultra-wealthy are actually investing in right now
Why investors are moving away from “spray and pray” diversification
The rise of Bitcoin and collateral-backed deals
Avoiding crowded, boring, and mediocre capital raises
How mindset shifts as you level up net worth
Why investors want to know you personally, not as a number
The power of proximity and joining the right rooms
Family Office myths vs. reality (fewer Rolex flexes than you think)
Simple tools that make raising capital faster and more credible
Key Takeaways:
Trust beats hype. Today’s capital wants security, clarity, and in-person relationships.
Don’t diversify blindly. Smart wealth plays offense where they know the game well.
Alignment matters. Investors gravitate to founders with shared industry expertise.
Materials make you investable. One-liner. One-pager. One-minute pitch video.
Environment is everything. The right room can accelerate opportunity overnight.
Be uniquely valuable. Say what no one else can say, that’s how deals get attention.
Resources from Richard
LinkedIn | Family Office Club | Billionaires.com (interviews & billionaire book lists)
Centimillionaire Strategies YouTube channel
Resources from Mike and Nichole
LinkedIn | Gateway Private Equity Group | Barcelona Hotel Fund | Nic's guide
+ Read the transcript
Mike: Hi, everybody. Welcome back to another episode of The Richer Geek Podcast. Today, we have a very special guest, Richard Wilson, husband, adventure enthusiast, father of three girls. And most importantly this, well, I should not say most importantly because husband adventure and three girls is more important than what he does. But he is the CEO of the number one ultra-wealthy investor club with 7,500 investors called the Family Office Club, which hosts 16 in-person events in the year. He also runs Billionaires.com, his own podcast. This guy does it all. Welcome to the podcast. Richard. How are you doing?
Richard: Good, good. I appreciate being here. I'm a geek and I am trying to get richer, like most people listening, so I think it's appropriate.
Mike: It is, and that's why it's named that we are a bunch of geeks that just want to know how to diversify. How to go outside of our norm? Which is for most of us, the 401(k), the IRA and people are sitting there, it's like, "Man, how can I get this with the stock market volatility?" You know, what are you seeing today with the investing and with hosting your own, what's the vibe out there?
Richard: Yeah, sure. So, you know, we did 22 live events this year. We'll do 30 next year. So we just hear a ton of opportunity flow and most importantly, what investors are asking for or complaining about. So, the theme out there right now is every investor I know who's worth tens of millions of dollars, has a few assets where distributions are cut off a few assets, where all their equity is wiped out, or it's at risk of being wiped out. And a few where they don't know what's going on, they're not getting much communication, they know things aren't going super well, and then they have some investments that are going just fine. But it's like a real mixed bag right now. And up until two years ago, it seems like, you know, deals were going well for just about everybody. If you snap your fingers the right way, you could raise money for something, you know? And now, things are more challenging. So because of that, there's a little bit of a flight to quality. They want to meet someone in person, they want to walk the property. They need to understand what the company does and with AI displacing jobs and a little bit of lack of trust in just the amount of debt the government has and other things related to that, I do see an increase in allocation to Bitcoin, much more so than before. People bring up gold and silver, but I see 'em taking more action now on investing in Bitcoin than before. So that's just kind of like some of the threads of, like, things I'm hearing about, there are some niches within private equity, real estate that could go into well, but a really high level that's kind of like the theme of what investors are bringing up most often.
Mike: Yeah. And that is very, very true. And even with ours, I mean, we have some hotels are doing fantastic hotels that did fantastic and now, no one's going to these business park, you know, because everyone's doing Zooms, you know, businesses are cutting back. So you see that in every asset class. And it's just, it's very frustrating and hopefully the economy's going to turn around. But, you know, let's talk about, you hit a little bit about the kind of the stop and pause and the shifting. And a lot of people don't know how to do that. And that takes a different type of a mindset and some different strategies for that type of a performance. Talk to our listeners a little bit about what's the difference between someone who's kind of getting started, someone that's been there and they're making maybe six figures, and then the mindset of that deck of millionaires. What are some of the things that you've learned over time that you could share with the people that are just getting started?
Richard: Sure. Yeah. I think one thing is that whether you're worth $100 million or $2 million or $6 million, one of the biggest mistakes is to spread your money around in a bunch of different industries. A bunch of different startups and hope that you're diversifying. It's really diversification. The reason why most of all you hear about diversification is because wealth managers just know that one beats on their drum and they just hit the diversification drum all day long. Their job is to play defense for you. If you're on here, you're either a high earning W-2 or you're a business founder, or you sold a business, maybe you had inherited money. That's probably an exception to most of you. And so, you can have your wealth advisor playing for you, but then typically the sharp families I know, they'll look at real estate and say, "What are the one or two areas I want to start with in real estate?" "Who do I trust there?" "Where do I want to allocate? What states, what food groups of real estate?" And then, "Where do I want to play offense?" Meaning, "Oh, I made my money in tech." I think I could conduct due diligence better in tech, or I'm a doctor or a surgeon. Maybe I can invest in profitable medical practices that are already making money in my niche, and that's where you play offense. If you just listen only to the people who play defense for you, then you're just going to track inflation basically, right? 7% to 10% returns in the S&P. I think most of us know inflation is 7% or more. Right? Like real inflation. So I think that's like the one key thing is having those three different buckets and making sure you're not doing diversification across your direct investments and just spread it out in a whole bunch of risky deals and risky startups.
Mike: Yeah. And that's when these people are investing, what are they now wanting or looking for? Is it more of a cash flow or is it more of a hold? What are they looking for now?
Richard: They're looking for security. So they do not want, typically deal with a very high amount of leverage or something that's very speculative, at least not with most investors for most of their portfolio. They like cash flow, they like collateral or, you know, our money lending credit deals have been very popular, as of late. And so those are things that are popular, but also I think it's just they want to trust what they're investing in much more so than two years ago. So, seeing you in this video of the podcast is better than just listening to the audio and meeting you in person is a whole nother exponential level better. That's part of the reason why we still do in-person events, but even if you don't go to anyone's investor club event, just making sure that if an investor, you're walking through properties, you're meeting the people in person, and you're not skipping that if you're putting any meaningful level of capital to work. And so, investing with people who made their money in the niche and asking them for feedback on a deal could be a very helpful due diligence tip, asking if there's any collateral possible to put behind a deal. Or trying to find some affinity like investors groups like, the Doctors Investor Club is a group run by Kyle Stephenson, who's an orthopedic surgeon, and it's just exclusively for doctors. And the DEEP Due Diligence Investors Club is ran by Marc Halpern and it's basically a bunch of technology engineer, nerds to get together and do due diligence on deals together. And you never have to invest anything if you don't want to, and the groups kind of self form and five people say, "Oh, let's go. Dig into that deal." And 12 people say, "Oh, let's look into that oil and gas deal." And so, meeting in person, doing due diligence in groups, being thorough, those are all things that investors are realizing they need to do more of right now.
Mike: Yeah. And you know, some of my investors have said, you know that they don't like being just a number where
Richard: Right.
Mike: Three, four years ago, they'd go into these huge syndications where there's hundreds and hundreds of investors and they've made the shift in what they said they'd like, you know about mine and other people's that we actually have your cell phone we actually have, can meet with you in person.
How important is that? You've been hitting on it, but have you seen that people are kind of gravitating towards a smaller, long-term successful, but also, someone that's where you're just not a number.
Richard: I think it depends on the investor. Some find safety in being with a big name.
Others, I know some families or some of my wealthier families where they won't go into any deal where there's like hundreds of investors and like you said, they want to be like the only investor or one of 10 or one of 20. What I've learned from buying Billionaires.com and interviewing all these billionaires is basically that many of them say who you spend your time with matters more than what you do.
So, if you spend your time with people who are always teaching you new things and are deep experts in their niche and very high integrity, et cetera, then you're always going to be learning and new opportunities will come up from that. And so I think that in a community or outside of a community, there's this need to figure out things like, "Who am I comfortable being around?" And if you're an investor, that's why I think there's some attraction to podcast content like this, right? To figure out like, "Okay, that's what Michael's thinking. Here's how Michael's looking at the current challenges," and those who relate to that and how you think or who's attracted to it. Because trying to find a peer when you're a high net worth investor or someone who just sold their company. You might feel like you're on an island by yourself and your spouse may not be as interested as you are in managing the finances. You may only have a couple friends that you message now and then. And then, you're very isolated sometimes trying to figure out how to invest.
Mike: Yeah. You know, it's some good advice. So you kinda hit it on a little bit. I've been in a lot of masterminds. I know Richard, you have also. I don't even know if you said, you know, the least knowledgeable or the small guy in the room.
Richard: Right.
Mike: How important is it?
It's like, "Wow, I'm involved with people that are 10 times better than I am. 10 times wealthier, have 10 times more experience." How important is that for our listeners to sit there and say, "Don't be intimidated by some of these masterminds? See if you can get into them and just learn."
Richard: Right.
Yeah, for sure. I did, you can hear an interview with Tony Robbins at Billionaires.com and one of his top three pieces of advice was to remember that proximity is power. And he got a $400 million profit made off of one transaction by being in the right circles, able to put a deal together between people and then close a very large transaction.
So, it is super important, but also most deals get done because of people moving off one of three trust curves. It's usually trust in the industry, trust in the team, or trust in the opportunity. So, if somebody's known you for 20 years, Michael, and they live down the street from an asset that you're acquiring and they've invested in the industry before, they're very likely to invest with you if they have the money.
But if they don't know you, they're based in New Zealand and your deal is in Scottsdale, and they can't walk the property. It's like even if they were familiar with your industry. Like, they're probably not going to trust that deal, right? And so, trying to figure out who is further down the path, the very specific path that you're trying to go down.
And it's not just smarter, but just smarter in the way that you want to acquire those traits. And it could be that they're ultra healthy, it could be that they are very good at negotiating deals, or it could be that they navigate structure all, et cetera. But just try to be careful who you select, because what you take in is what you're going to put out in business, right? And so, one project I'm doing right now is trying to read every book ever authored by a billionaire. There's about 245 of those, and we're about 130 books into it now. I think that most people are not that explicit and they're not that regimented with what media they consume, what groups they're part of.
So the more you can do that, I think the better.
Mike: Yeah. And you know, Richard, you mentioned the books with the billionaires. And ladies and gentlemen, it's Richard Wilson with the Family Office Club. I know when I signed up to get your newsletter. And ladies and gentlemen, I'm a big fan of Richard and the Family Office Club, all of his social media, his daily newsletters that come out.
And I actually got a link from Richard on what was it? The books of the billionaires and what they read. And that was an email, and I just started reading those. It was like, "Wow, what an actual, these are the books that I need to be reading." And it was Richard, who sent me those via kind of like a welcome to the newsletter thing.
Richard: Oh, cool.
Yeah. I didn't know that. Yeah, it's like a, what I always try to point out is that most people are reading these books, you know, like Atomic Habits, which might be a great book. But you want to get ideas into your brain from somebody who's really good at marketing a book, or you wanna get ideas in your brain from the winners in the games of capitalism, you know, which are billionaires.
And so I just want to maximize those ideas. And like one thing that I did for myself, I created this one-pager that I read every day. So I mentioned this at our events quite often, and it has my monthly, quarterly, annual goals and has all these one liner mental programming statements. And then I start out my day reading that so I know how to navigate my inbox, I know how to navigate my time management, et cetera.
And I also made one for my kids, it has our family values, as well as a couple of books summarized here. And I'll have them read over this page like we did this morning. Pick a couple of those items and before they go to school, kind of remind them of what's important. And I just find that if you start your day with that, then it's like a compass and you're like, "Okay, this is north and this is how we want to go across the terrain on this adventure for today, right?"
And if you don't have that, you might not remember all the different priorities, all the different ways you need to act in the world, all of that. So I think that's super important as well, because then you attract higher quality people into your circle versus only you trying to seek out being in the right circle. Other people will also want to seek out to be in your circle 'cause they wanna be more like you maybe in a few ways.
Mike: Yeah. Now, let's kinda shift to the term family office.
Richard: Sure.
Mike: For a lot of, I'd say the majority of investors, they get all nervous. It's like, "Oh my God, you know, this family office, I'm going to have to have a 50-page deck and I'm going to dress in the suit and borrow someone's Rolex and I'm going to have to like the dress to impress."
What are some of the myths, you know, about family offices? Richard: Yeah, well one thing is like, you know, I'm borderline overdressed. Now, I actually was just going to wear my Black V-neck and then I looked at one of the previous pictures of your podcast and they had a suit shirt on that looked pretty clean cut. And it was like, "You know, I don't want to be too casual for Michael." So, but I would say that many times in a room, not everyone, but a lot of the people who look like they don't have the most wealth. And those that go around and talk loud, showing off and say big things sometimes have the least amount of wealth. It's almost like the person that goes in debt to get a Ferrari and the person is really wealthy, has a pickup truck or something.
What I find is that the people with funders, employees, they have no, they have so much going on every day and so much they already have to think about and so much coming at them. They don't need more attention and more people pitching them and more things coming at them usually. Sometimes they want to get deal flow in a strategic way, so they'll give a talk at an event or do something like that or be on a podcast, but they're usually not the ones running around beating their chest with like a six inch Rolex on. But that's just some people's style. There's nothing wrong with that. So that's one thing. The other thing is that I started this business and I didn't have enough money in my bank account to pay rent the first month, and that was 18 years ago.
Everything I've learned is just from interviewing family offices and interviewing the ultra-wealthy and family offices are really just super founders or super entrepreneurs that have grown to earn 7, 8, 9 figures a year, or they sold their business for 7, 8, 9 figures. And they're almost all just very entrepreneurial, very sharp founders. And so, when you negotiate with them, you have to talk to them like a sharp entrepreneur, and listen to their advice and custom structure deals the way that they will get deals done. But you can also just learn a ton from them and almost all of my success is from just learning from them, implementing the ideas. Then the business would grow further and they would interview more of them. And so, the family offices you see on stage when I'm doing like a fireside chat with a centimillionaire or a decamillionaire, I'm selfishly just asking what I want to know.
Of course I try to keep the audience in mind, but I'm asking people to come on stage who I want to interview, and then it keeps it fresh for everybody that's in our community as well as we're learning from them.
Mike: Yeah, you pretty much hit it. Probably one of the richest per people that I know, an F-250 Ford, F-250, cowboy hat, flannel shirt, cowboy boots, and he's hanging out at the five-and-dime, you know, having scrambled eggs and he is worth two and a half billion, you know?
Richard: Right. Yeah.
Mike: No, he does own, you know, 6,000 acres in Montana and he owns this, and he owns that. You'd look at him, I just want to go fishing and
Richard: Right. You'd have no idea.
Mike: They more down earth.
Richard: Yeah. That's an instinct. I'm based in Hawaii, on the island of Oahu, and people here especially are low key. Like one of my friends here sold his company for over a hundred million dollars and you would never guess it. I've never seen him in anything but a t-shirt. And you know, just a very laid back, low key person and some places like Miami and Key Biscayne. I used to live in Key Biscayne for five years. People are a little bit more show off, more Lamborghinis and stuff in South Florida.
But here in Hawaii especially, the wealth is pretty quiet, low key and people live here too, enjoy the mountains and the beaches of Hawaii and have a healthy lifestyle. They're not here to show off and try to close their next private equity client or something. You know what I mean? So, yeah, it's interesting.
Mike: Yeah. And I love that laid back. You know, I live in Scottsdale and it's like, yeah, okay. There's another 20-year-old in the Lamborghini, right? But he hasn't saved a dime. He's some influencer that hasn't saved a dime for his retirement, but he's driving around Lamborghini. Let's shift really quickly before I have to let you go.
We haven't really talked about how these investors, you're in front of all these founders and all these investors, all these people have been successful. What are some of the things that our listeners can do to raise more money than they can now in today's environment?
Richard: So there's a number of things.
One, if anybody wants to reach out directly, we have three free artificial intelligence tools to help you raise capital faster. So we'll send those over to you. Email just richard@familyoffices.com. But otherwise, there's some things that anybody can do and they don't need our help to do it. And that is to make sure that you look at what your competition is doing, look at what investors are asking for in large part. Look at what you are doing and refine it into a single sentence that hits people between the eyes, makes them move forward and say, "Whoa, I've never heard of someone doing that before."
Or like, "Oh, that's so refreshing. That's different, that's unique, or that's exactly what we've been looking for." And if you're saying something that somebody else can say. It's not very good. You should say something that no one else can possibly say and no one else is currently saying. So having a one liner costs you nothing. It's just being intentional. And if you can't summarize what you're doing in one sentence that's super compelling, then no one's going to be able to tell their spouse or their business partner what you're doing in a compelling way. Either they're not going to do best with you, so you have to have a one-liner. I would say you have to have a pitch deck that's not 44 pages long or 70. I would keep it to 12-15 pages long, ideally. Have a one-pager that summarizes your pitch deck and like a one page PDF, one-sided. And then a really important piece is to have a one-minute pitch video from you as the founder. Maybe walking through one of your properties or showing pictures of all the different properties, portfolio or private equity deals you have done, et cetera. Introducing yourself first so they know who they're dealing with. Maybe showing off your team a little bit. The assets explain your strategy, so it's clear you only have three or four sentences to fit in one minute.
But then in that one-minute video, it may be more likely to convince an investor to speak with you and meet with you than a long pitch deck, because if you're articulate and you're doing something unique and you've scripted that one-liner that really grabs them, then you usually would start that video with that one-liner and can send that video as like a Dropbox link over text message.
You can embed it on your one-pager. You can put it in your pitch deck, you can put it on your website. And I just see so many people raising capital and they might have a great idea, but they have a long pitch deck. They have no one-pager, they have no one-minute video. They have no one-liner. Many times they have no website. And so, everything about their communication is not doing their experience level justice. Those are the things that just about everybody messed up when raising capital, I think. And it might not be messing up. You might get all the capital rates that you need, but if you're not getting enough momentum, you should put these things in place 'cause they cost almost nothing in today's world to at least get a basic version of them in place. You know? So that would be, that'd be something really at the core is like, don't do anything that's crowded, boring, average, mediocre, like in any part of your life. But like, make sure that you figure out the unique way to explain it and then align up all those materials to drive at home.
Mike: Yeah. That is perfect. Before I let you go, let's talk about the Family Office Club and the website. What is the Family Office Club?
Richard: Yeah, sure. So it's an investor community, an investor club. I started 18 years ago. We've hosted 300 live events now. What we've found is that it's easy for people to come to our events no matter where you are in the United States because we host them in Los Angeles, Dallas, New York City and Fort Lauderdale. Because we're hosting two events to year 30 events next year, 2026, every quarter, we have multiple events in each part of the country and our model is to do a couple of dozen investor access series events, which are one day, 10:00 AM to 4:00 PM events.
And those are 55 to maybe a hundred participants. So, you really get to network with everybody in the room. We have an AI tool that's done deep research on every person in the room. And then we'll connect you to the top 15 to 20 people who are from the same area, the same industry, are interested in investing in your area, and this AI networking tool you can use and look at their picture on LinkedIn to find that person in the room during the event. And go over and introduce yourself to Sarah, John, or Michael and make connections. So that's our investor access series events that we do a couple dozen times a year. And then we do five investor summits a year that are typically 400 person up to a thousand person events. And so our next one of that nature is the Family Office Super Summit.
And that's going to be a850 to 1,000 person event for three days and we will have 125 speakers on stage. So, there'll be more ultra-wealthy family offices speaking there than any other event globally. So, I've been doing that event for 12 years and been running our live events for about 15, 14 or 15 years out of our 18 years since we started.
And essentially, what we're offering people is a set of 40 plus ready to use artificial intelligence tools. We've got a couple core tools everyone loves most and then all of these live events. Then our web portal with 1200 videos of investors that you can stream, kinda like a Netflix app on your mobile phone is your traveling or walking the dog, et cetera.
So the people who join are either investors or people raising capital, running a fund, private equity, real estate. So that's essentially what Family Office Club is. And our website is just familyoffices.com. If you're raising capital, we've got a free book and then we are partnered with the Doctors Investor Club, they mentioned earlier, and the DEEP Due Diligence Investors Club for investors who want to do due diligence with each other.
Mike: Perfect. Richard, you know, I thank you so much for having this access for investors. You know, if I had it when I first started, I got started in what I call the pre-Google Days. Yeah. That's how long I've been doing it. And my God, the things that I could have learned if we had people like Richard, you know, ladies and gentlemen, it's Richard Wilson.
There very few times on our podcast, we have people that I would say look. Check out the website, check out the educational materials, all the different things.
Sign up for his newsletter and just learn from this guy and everyone that works with him. I follow him on a weekly basis. I get all the newsletters, even an old guy like me can learn a lot by listening to Richard.
Richard: That's the key, right? To always be learning. Like high velocity entrepreneurs are who other people want to invest in 'cause you're always making progress, you're always pivoting, you're always coming up with new ideas. And I don't want to get bored at my own events. And I think that's one of our secrets is that I didn't hire some cubicle jockey person to manage our events and hope they do a good job. It's like I'm keeping it interesting for myself.
And then just like you running this podcast, it's like you can just do it for the good of mankind. You're also doing it 'cause you have to learn and get to grow your network. And so I think that you and I think quite a lot that way and appreciate you being part of the community and what we often find is that people are very skeptical and they come to one event and they're like, "Oh, okay, now we get it."
"Yeah, I like this."
And the one thing that's been tipping them over recently that I'm surprised by. That's very similar to your podcast on our YouTube channel. It's called Centimillionaire Strategies. And under the playlist, there is a playlist called the $100M+ Rainmaker Series, and 17 little short videos and a playlist all on raising capital. And then there's another one for, How to Start a Family Office, for investors and what we find is that if people take the time to watch the miniseries. They're either going to think my voice is too monotone and boring and not like it or they're gonna hear ideas no one else is telling them and they're like, "Oh, okay, it's the real deal. We should go to the events, meet Michael in person, and meet Richard."
And so I definitely appreciate your support and having me on here and appreciate your time, to do this today.
Mike: Yeah. You're welcome. And Richard, hope you have a wonderful afternoon and thank you for coming on the podcast. Take care.
Richard: Thank you. You too.
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ABOUT RICHARD WILSON
Richard C. Wilson is a husband, father of three girls, and a third-generation Eagle Scout.
He is the CEO of Family Office Club, the largest investor community for ultra-wealthy families with 7,500+ members and 16 in-person events each year. The club operates the most-listened-to podcast and most-watched YouTube channel on family offices, with 1,000+ videos published.
Over 18 years, he has spent $25M hosting 300+ investor events and built a social media network of 17M+ members and followers. Richard also owns Billionaires.com, where he is interviewing 100 billionaires to document their scaling strategies and mindset.