

17 Oct 2026 · 21m · 9 chapters

A Silicon Valley Summit talk on family office investing amid tighter capital, higher return requirements, lower cold-email reply rates, and why investors increasingly rely on trust, domain expertise, and deal structuring (e.g., seller financing, creative collateral, and “clarity multiplies action”).
boost “family office IQ” continuously; ask many questions and present custom deal structures; compete via “co-opetition” (go to “Titans”/competitors as co-GPs/JVs); AI tools can speed execution; patient, long-term persistence wins (deals may take 6–12 years); health and energy support performance.
a last-minute seven-figure position filled by approaching three competitors; seller financing to avoid bank covenants; adding collateral (real estate, medical equipment, IP/patents) after asking; a Google-search tweak leading to operational family office work; “hair vs mess” accounting arbitrage.
Saeed (fireside chat; previously at PwC for 15 years; niche domain expertise), Dr. Robert Cialdini (influencing/persuasion interview referenced), Kevin Harrington (1,000 deals; energy/health referenced), David Goggin (quote referenced), plus “twin brothers” managing $13B (Boston; jiu-jitsu/crossfit referenced).
Written by AI. May contain mistakes.
Discusses the decline in capital raising and the impact of AI on fundraising.
“These are the four cities we host events in all the time.”
Emphasizes the need to constantly improve financial intelligence to protect net worth.
“ball without notice with a defender right in your face, or you won't be able to navigate it, right?”
Highlights the importance of structuring deals effectively to meet investor needs.
“What 1 % of what you're doing do they actually care about?”
Explores the necessity of trust in gaining investment and nurturing long-term business relationships.
“So now I get why people are paying for your app, right?”
Stresses how personal health and extreme focus contribute to success in business.
“And we said, okay, yeah, well, we're happy to change that.”
Explore the relationship between health and business success and how prioritizing health can enhance life experiences.
“The other thing I see, and I have Kevin Harrington's picture up here, which I always do even if he wasn't here today, is just that if you are ultra healthy, you have more energy.”
Discuss the introduction of guest Saeed and the value of networking with impressive individuals at events.
“We try to get you in close proximity with folks.”
Understand the benefits of Family Office Club membership, including networking and resources.
“We are going to be transferring over how a few of those tools work.”
Information about future events and networking opportunities for founders and investors.
“And then next month we'll be in LA, Dallas, and Fort Lauderdale in New York for our deal structuring mastermind.”

Get the gist, explore an idea or ask about something said.
On Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights, what are the key points of this episode?
Automatic transcript. May contain errors.
0:02I appreciate you being here. I'm going to go through my slides here for just about 10 minutes, and then we're going to wrap it up and do some networking. So I appreciate everyone's attention. We, on purpose, try to fit a lot of things on stage in one day. So there's multiple people to connect with in the audience and the peers. You can network through the mobile app. Hopefully, you get some new investment ideas, learn from a speaker or two just on how they present, how they structure deals. So you're learning on multiple levels. I'm going to go through a couple case studies and just insights of family office strategies on how to do more business in the industry real quick.
0:37But those of you who are here have heard me talk about this a million times, but it's just putting you in the right room, hearing from people that you can do more business with or think like Saeed and listening to how he does business. These are the four cities we host events in all the time. In case you'd like to get more plugged into our network and come to these more than just here if you're local and it's your first event you've been to with us. One thing that's challenging for a lot of us is that there is way less capital being raised today than before. The required return and cost of capital is higher.
1:09Usually banks will give you less percentage of debt on an asset or you can afford, you have to have less debt because the cost of debt is higher. And meanwhile, cold email reply rates have dropped from 8.5 % to 1.9 % last year. And I'm sure they're under 1 % this year. And it's only going to get way, way worse than what this is because of AI, right? So all these things are making life a little bit harder for most people raising capital. So you need more and more strategies. And one thing I keep on finding is that you have to constantly boost your family office IQ, your business IQ for multiple reasons.
1:41If you don't, your net worth will come down to wherever your financial IQ is after you make a lot of money. You might make high income and then you're overpaying for things all around you. You might have an exit and then you lose it from two bad investments, right? So you have to be constantly boosting your IQ to play defense, but also to play offense. If there's a hockey puck flying by 70 miles per hour in front of your face, you need to know how to catch that without breaking your fingers and then create an opportunity out of that. And if you don't have the strategy, the deal structure, the method to do that, then you won't be able to, right?
2:11So even if you're off balance and you're busy doing something else, if something happens and you notice that that is a pattern in front of you that equals opportunity, then that is something you just have to run with and go with. And you have to very dynamically be able to jump up and lean backwards and catch the ball without notice with a defender right in your face, or you won't be able to navigate it, right? And that's what Sayid was talking about, about two people had been at PwC for 15 years, and they had the niche domain expertise that's required, not just a fancy AI tool, right? So many times, it is a form of almost judo of like listening first, asking lots of questions, seeing what somebody is all about.
2:50Somebody might be obsessed with getting an 8X EBITDA multiple in their plumbing company or a certain NOI multiple on a real estate property. You might be able to give them exactly what they're asking for and then structure a deal that makes it way better than if you got it at a 5X, but then you had to put all the money up front and deal with a bank. Like, yeah, if you do seller financing and carry some and do this and that, we'd be happy to do the 8X. And they get to tell everyone at the golf course they sold for 8x and then you do right by them and everybody's happy right so many times that is the case people will say no under the right structure they say yes many times folks look at everyone else in the industry as competitors like we have to go get them but you're really just competing against your own self and many times we had a member actually emailed me two days ago he said hey richard at our your last mastermind i asked you for advice because somebody bailed on a deal.
3:40And last minute, we had to fill a seven-figure position. And you told me, go to the gorillas in your space, the Titans. And if your deal is really good, they'll recognize it as good and say, hey, this is what happened. Do you want to step in and be a co-GP, JV on this deal? And he said, I don't want you to share my name on stage because what happened was kind of private. And one client pulled out the last minute. But because of what you said, we went to three competitors and we got the deal done. And they funded it with a seven-figure check and it saved the deal. And it was a win instead of a complete loss.
4:08so he just randomly emailed me two days ago thanking me for that so looking at other people as coopetition not competitors that's why we have 30 to 40 different investor clubs on stage at our events we don't see bay area angels as a competitor right they're not doing what we're doing so we have those folks here so you can meet them and meet their 400 investors but also so that we have more investors at our events and then we can get more flexible things done together so it's really critical in every meeting you're at that you ask a lot of questions first. What 1 % of what you're doing do they actually care about?
4:41And then just focus only on that and give them exactly the flavor of food they said they like to eat every single day and forget all of the rest, which is noise to them, but also know what keeps them up at night, what they're excited about, and then you present a custom structure that's super dialed in to exactly who they are. One of my favorite quotes is that clarity multiplies action. If you're super clear with yourself about what you're trying to do, then you can be lightning fast. If you are really clear with other people, they know whether they're interested or not pretty quickly. If you're really clear about your priorities, your team knows what to prioritize.
5:13And other people can help you get to where you're going. If it's not clear where you're going, you might not ever get there. And other people don't know how to help you. And so I started the day with this. If you want to be quick, you need to figure out how do you have context engineering, prompt engineering, how do you get this dialed in for your team using what's available to you in the member portal. We have these tools. and if AI is bigger than the industrial revolution, bigger than mobile phone revolution, and that's coming from someone who's done 2 ,500 investments, then you need to be on top of this and really be leaning forward on it and making your business more lean and more strong.
5:51And you can be, with AI, you can be faster and more accurate. Usually you have a big trade-off between those two things. So trust and a flight to trust is what's happening across our industry. Those who have the most trusted deals are sometimes raising more money than ever before. And we see some of those in our club. Those who have a blind pool fund without a track record have the hardest time because direct deals on average are more popular than a fund. And folks want to find someone who's been doing something for 10, 20, 30 years, or you have that domain expertise or some edge they can see so clearly that combined with this structure, it makes a whole lot of sense, right?
6:26So they need to trust the industry and understand it, trust the leadership, meet you in person, trust the opportunity and go walk the manufacturing floor, use the product, see that it works, see that the value is real, and have a triple confirmed trust of meeting in person, seeing it, like using the app. And wow, it was amazing. So now I get why people are paying for your app, right? That's what's required to really get stuff done. And if you want to watch my interview with Dr. Robert Cialdini, it came up a few times today. It's on YouTube. I interviewed him on how to do deals with family offices, how to grow your balance sheet, how to invest, how to raise capital, using influence and persuasion.
7:02So you can see that interview within our member portal or on YouTube. And you really have to position yourself so you are attracting opportunities and seeing a thousand opportunities. So you can pick out the one out of a thousand. And if you're not doing that, it might just be because other people aren't clear on how you add value. But if you can add massive strategic value, then folks want to show you things and they'll think of you first. And what I told Centimillionaire, they'll talk about in a couple of minutes here the other day, is like, it's not how big your network is. Like, oh yeah, I met this person once.
7:31I met Saeed 18 years ago. It's how much of your network has you top of mind all the time. How many people in the world think of you first for your niche because there's great clarity about what you do. It's not how big your network is. It's how many people think about you first when it comes to things they want. You want them to be referring you to. And many times people who are new to investing and came up on the Dr. Cook interview, may only want someone with no hair on it. The financials are amazing. It's dropped by an investment banker. 22 different bidders are chewing on it to get a maximum valuation.
8:04But like all those things, except for the maximum valuation is what some investors want. It's like, oh good, everything's in a pretty little package. But sometimes the fact that there is hair on it, like Dr. Cook said, as long as it's not like a fraud or something, it's just the accounting's a little messy. She loves a mess. That's where there can be an arbitrage in adding massive value, right? So if there's no hair, then like why do you need a barber right sometimes you can't even see the skin there's so much hair on a deal right i need to figure out what's what and de-risk it to add value many times on structuring deals we've found that we'll go over this next month but you can ask for different forms of creative collateral and have part of your investment backed by real estate assets by medical equipment by ip by patents so at least you're not left with nothing if the deal doesn't go well and for investors here in the room it costs almost nothing to ask the answer might be no but over a dozen times have had family offices ask if there's any type of collateral and they've come up with creative ways to have some sort of collateral so they're at least not left with nothing if the deal doesn't go well but it wasn't baked into the deal to begin with but by asking for it they got it included so i would keep that in mind the other thing is that family offices are patient if you want to raise a thousand dollars from an investor you can do a crowd fund they don't need to meet you in person that might not even do a second of due diligence on you it's the opposite if you want to get funded from a publicly traded company, a billionaire, a sovereign wealth fund, a family office, et cetera.
9:25So you need to be patient. And one of our biggest clients, it took six years to get one deal done. And now I've done 19 deals, right? And so another one that we started working with just this week, we helped create their family office 12 years ago. And now they're coming back and want to work together on a more operational basis. So sometimes you have to plant seeds that you do the right thing and add value, even if it might not pay off for six years or 12 years. And others might pay off in six weeks or 12 weeks. But if you have the attitude of being frustrated at someone because they don't close right away, and then now it's upsetting, then it's not being politely persistent.
10:01And you're not going to get a lot done in the family office space. And that's one of the challenges of the space. The people that come here that do well have a medium to long-term perspective. People that just come and say, oh, I didn't raise$10 million from one event I went to. Like then they almost never do well in the family office space because they're not playing a medium to long-term game. And family offices want to do long-term business with long-term minded people. Many times if you can structure a deal so they can sleep at night, get their initial investment back, and then they get profits up to a 2x or 3x plus, investors are generally happy.
10:30Many times if you can structure a deal to avoid having to use a bank, so it's just seller financing, way less likely to have a foreclosure or have some random covenant on page 92 called on you because the bank feels like it or is being acquired, that can be a good thing. So keep that in mind. Also, we've had a couple times where, like one in particular I'm thinking of, where a centimillionaire reached out just because they wanted a tweak to how they were represented on a Google search finding based on our website. And it was from like a decade ago. And we said, okay, yeah, well, we're happy to change that.
11:04We can fix it. So we did that, asked what they were up to, saw there were some strategic choke points they should probably be acquiring in ways that they could be navigating their niche industry and presented those over. That led to wanting to get on a phone call. And now we're helping with operating their family office. And the point of that is it's related to the football picture. If you just fix the website and moved on, that would not be a smart thing to do if you didn't have ways to add value. So like Brian, for example, looks at a lot of VC deals. He has ways to add value to folks. He's got a network.
11:33He introduced me to a technology person that's in the Bay Area just a couple days ago randomly being helpful. He has ways to add value and everyone needs their arsenal of ways to add value. So when the hockey puck comes flying by, you can say, oh, I can grab that and help. And here are five ways to help. They cost nothing. You can go and do that without me. You don't need to ever talk to me again to do it. But if you want, this is how we operate and this is what we think about. David Goggin says, the worst thing you can do is become too civilized, too comfortable. Oh, I'm successful now. I don't need to make phone calls.
12:04I don't need to meet in person ever. I don't need to show up. I don't need to walk it and do in-person due diligence. And David Goggin says, like, you have not arrived. You have never arrived. Like, don't get too comfortable civilized. You're not willing to actually go and make a sale or to get things done or to ask for something. And I think that when Brian says you need to pivot your business, maybe recreate some stuff and burn some stuff, I think it's, like, related to this quote kind of, like, you know, you might have to, like, shake up how you're normally doing things because the world's changing faster than it ever has before.
12:34and it'll never move this slow again as it is today. We'll see if this video plays. It'll be a little bit of an experiment.
12:41Richard C. Wilson: If you're hyper-focused and you really invest the time and the effort, you can make really, really fast progress. So one of the things that I always... I've believed in for a long time is that if you overdo things, invest lots of time, lots of effort, you go the extra mile, you go the extra 10 miles, and you're like constantly overdoing things, then you will improve faster than anybody else by many times. And a lot of other people, maybe they're just not going the extra mile, or maybe they're just not as focused, or, you know, they're like meandering a bit more. For me, I think a lot of what I attribute being able to accomplish so much to is really about focus and overdoing it, going the extra mile.
13:31Richard C. Wilson: That's what I think it boils down to. so that's the billionaire founder of scale sold his business for billions of dollars at age 27 and he was basically asked like why are you successful and as you heard like extreme focus and then overdoing it massively overdoing it with extreme focus other people don't even want to focus and they don't overdo it here's how you talk about like working very hard as a requirement right it's not just because you have a good focus and now you can do a four-hour work week right so So this video is one of the videos that I watch each morning because I think it's so important and critical to what I see in the family office space.
14:05The other thing I see, and I have Kevin Harrington's picture up here, which I always do even if he wasn't here today, is just that if you are ultra healthy, you have more energy. Kevin stopped drinking alcohol over 20 years ago. I stopped 15 years ago as a three-month experiment because I figured I'm about to have my first kid. I probably need maybe caffeine versus alcohol, if anything. I want more energy, not less. and the twin brothers up here that managed 13 billion dollars in boston they're in their late 40s they do jiu-jitsu um every morning uh they're black belts ricardo there's a national champion jiu-jitsu judo competitor from brazil goes to crossfit like five days a week dan sull then burns a thousand calories before breakfast every morning he's 82 years old he says if you want to beat your peers just keep on running your business at 82 years old because most of them are in a nursing home and not even walking a quarter mile a day.
14:56And he is super healthy. Even for someone who's 62, he's very healthy. And so I try to think about it as, you know, if you communicate to those around you that you'll sacrifice your health and fun, not going backpacking with college friends, not going and having fun experiences with your family, not taking care of yourself, not enjoying life then you're basically communicating people with your actions that you know in this house we worship money and it's more important than any of these other things the whole point of life is money money money and if you talk to family offices they will not tell you that that is the case sayid was showing me uh wedding photos from someone in his family he was showing me his wife uh etc and like the personal things that he obviously cares about without me asking about that he shows that right so um when you get to a certain level of wealth on the maslow hierarchy of needs, you realize it's all about novel experiences, health, family, having fun.
15:55Why would you not want those things once you become successful? It's not about having Lamborghini number 19 and money is all that matters. And you can become wealthier faster by being ultra healthy. It's not choosing being healthy over wealthy is what I believe. So at Family Office Club, I hope you saw it today. We try to get you in close proximity with folks. I did not know Saeed's name or know of him before today. I'm embarrassed to say, no, we were hosting in his facility. We were nice enough to be introduced by someone at a large investment bank that was kind of helping us get this co-hosting arranged.
16:28And then I found out who he was and how impressive his platform was. So I'm glad we got to add him for a fireside chat today. I thought that was great. Super intelligence, our AI tools. If you want to learn more, you can go to hyperintelligent.com or just look in your member portal to get the deployment kit for some of our AI tools, links to 50 of our AI tools. We are going to be transferring over how a few of those tools work. There are some of them in motion right now on how they're operating through our portal. So in the next 30 days, they'll be changing slightly on where they're hosted and how those operate.
16:57And then helping you with scaling strategies. How do you close deals? How do you structure deals? What's a choke point? How do you do co-GPs? How do you negotiate with family offices? How do you close them? How does Dr. Cook think about things? How has Kevin Harrington done 1 ,000 deals? How does he have so much energy and get so much done seemingly, right? And so that's what I think keeps things fun and dynamic so that you get an ROI here by meeting peers or like Neil saying he'd put$5 million into a water company he met that's in Texas at our Super Summit last year. We've had$1 billion worth of transactions closed within our membership, and that's just that I know of as well over a billion dollars, but no one's required to report anything to me, right?
17:37So it's just things we hear about and know got done. We had someone on stage earlier this year that does$800 million in revenue in the egg business. We've had the founders of Barefoot Wines, how they started it in their laundry room. We've had a founder, Marcus, who founded F6. He got backed$5 billion from Blackstone, took a company public, got backed with another billion dollars, and now manages$700 million. How do you do that? How did you get those institutional deals done? If you want to shortcut the most value in your membership portal, just stream the fireside chats because I think those are some of the most amazing pieces of content we have and no one's going to watch all 2 ,000 videos in the portal.
18:17If you want to become a verified member, we do a background check. You get the check mark on your name badge and on the portal. We help you with your one-liner. My video editors on my team, my W2 employees help do your one-minute pitch video and we throw in an exhibit table and two discussion panels because those are worth more than the$10 ,000 a year verified membership anyways. Try to make it like a super a no-brainer if you're a sponsor with us you might as well get the blue check mark go through this process and everybody needs a one-minute video and a one-liner it includes annual membership and three guest tickets a year if you're a verified member and we're basically on whatsapp together so if you have trouble deploying one of the ai tools if you need help with some of the ai stuff you just shoot me audio notes and i'm usually shooting something back to you like five or ten minutes later or five or ten hours later uh to be helpful to you so just talk to daphne or jennifer on our team.
19:06If you're interested in doing a verified membership with us, if you'd like an exhibit table or a discussion panel slot or a standalone five-minute deal flow talk at our annual Super Summit, that's going to be 700 people in Fort Lauderdale, December 15th to 17th. And it's our biggest event of the year. And we have as many, if not more, family offices on stage there than any other family office event globally. It's super fast moving, 110 speakers over those three days. And then next month we'll be in LA, Dallas, and Fort Lauderdale in New York for our deal structuring mastermind. So I hope to see a lot of your faces there because that'll be a lot of fun.
19:42And we've got some great guest speakers coming in for those mastermind events, which are just 10 a.m. to 3.30 p.m. or 4 p.m. each day. So if you have any questions for me, my email is hidden behind these chairs, but it's richardatfamilyoffices.com. And I'll be sticking around for a little bit for networking and we have networking space available here in the room and back out by the exhibit tables so if you have feedback for us would love for you to fill out at least part of this form because i'll read these all on my flight home on the airplane and see how we could do a better job next time around and serve you better or change how we do things within our club including if you have anyone you want to refer over to us or any things good or bad that you think we should know i read all these myself and then have my team help me with the various types of follow-up that's needed based on what you say there.
20:28But we appreciate your attention and being here all day. I know it's a lot of sitting in one day, but we try to keep it interesting and dynamic and fast moving. So thanks again. We'll see you next month at our Masterminds.
20:42If you are a founder, raising capital, developing real estate, or you're an investor, we'd love for you to get involved in the Family Office Club. I've run this community for 18 years now. We've hosted 300 live events. We have 17 million social media group members and followers. We have the number one YouTube channel on Family Offices. We have the number one most popular podcast on Family Offices. You can learn more about us and our membership options at familyoffices.com. We have 30 in-person events planned in 2026 and another dozen events this year. Please go to familyoffices.com to learn more.
What can entrepreneurs and investors learn from how family offices build wealth, evaluate opportunities, structure deals, and develop relationships?
After 19 years of working alongside family offices, centimillionaires, billionaires, investors, and entrepreneurs, Richard C. Wilson shares 10 lessons on building wealth and getting more deals done.
These lessons cover creative deal structuring, raising capital, building trust, positioning yourself to attract better opportunities, turning competitors into partners, using AI to move faster, and developing the long-term mindset that sophisticated investors expect.
One of the biggest lessons: **it’s not how big your network is—it’s how many people think of you first.**
In this presentation, Richard shares why family offices often take a different approach to wealth and deals, including how to:
• Structure deals around what the other side actually wants
• Turn competitors into partners through co-GP and JV opportunities
• Build trust before asking for capital
• Use creative collateral and seller financing to reduce risk
• Position yourself to see more—and better—deal flow
• Become top-of-mind within your niche
• Build relationships that compound over years
• Use AI and specialized intelligence to move faster
• Recognize opportunities others overlook
• Think long-term about wealth, health, relationships, and business
Family Office Club gives members three core advantages: proximity to family offices and ultra-wealthy investors, superintelligence through applied investor knowledge and AI tools, and scale through better deal structures, capital, relationships, and strategic chokepoints.
Subscribe for more family office, capital raising, deal structuring, investing, AI, and wealth-building strategies.