
Ron Diamond is the Founder and Chairman of Diamond Wealth, a syndicate of more than 100 family offices ranging in size from $250 million to $30 billion, with whom he has invested for more than 20 years. The firm focuses on private markets, including private equity, real estate, venture capital, credit, and special situations. He is also the Founder, Host, and CEO of Family Office World Media and helped create the Family Office Program for TIGER 21. Ron currently serves on the Advisory Board and Steering Committee for the University of Chicago Booth School of Business Family Office Initiative and has taught family office courses at Oxford, Stanford, Harvard, and Chicago Booth.
Earlier in his career, Ron founded Pinnacle Capital, a $250 million hedge fund, and held roles at Bear Stearns and Drexel Burnham Lambert. He graduated Magna Cum Laude from Northwestern University with a degree in Economics.
Insights from Ron Diamond on Professionalizing Family Offices
Ron Diamond has spent more than 20 years investing alongside family offices, and he believes the model has an advantage traditional private equity cannot fully match. Family offices can hold assets longer, avoid the pressure of a fixed exit timeline, and make decisions around long-term compounding instead of a fund clock. The problem is that too few family offices currently have the governance, infrastructure, and execution needed to make that advantage meaningful.
That gap is a big part of what Ron is working to change. Through initiatives at Stanford and the University of Chicago Booth School of Business, he has helped build family office education around governance, investing, succession, and best practices. At Booth, that work has grown from a family office course into a broader initiative with an advisory board and conferences designed to bring families together around education rather than pay-to-play deal flow.
In this episode of The Dealmakers’ Edge, Aaron Strauss and Ron Diamond discuss why family offices are becoming more important across private markets, how professionalization could help them compete more effectively with private equity, and why better governance and education matter as more wealth moves to the next generation. They also get into the longer-term impact Ron believes family offices could have on how companies are financed and how philanthropic capital is deployed.
1:48 – Starting at Drexel Burnham and launching a hedge fund after its collapse
3:08 – Getting into the family office space
4:39 – How Diamond Wealth aggregates capital across more than 100 family offices
5:53 – Matching investment opportunities with families by asset class
6:40 – How larger family offices source and diligence deals
7:55 – Why family offices can compete differently than private equity
11:10 – Giving business owners a third option beyond private equity or strategic buyers
14:21 – Why professionalization is critical to the future of family offices
15:41 – Building an education-first family office initiative at Stanford
18:10 – Creating the Family Office Initiative at Chicago Booth
21:21 – How family offices could change philanthropy and real-world problem solving
26:12 – Governance, succession planning, and what should happen after a liquidity event
28:35 – How much capital it takes to make a single-family office economically viable
30:22 – The Go-Giver, gratitude, and advice for the next generation
Mentioned In Family Offices & Purpose-Driven Capital: A Conversation with Ron Diamond
Aaron Strauss: You're listening to The Dealmakers’ Edge with A.Y. Strauss, diving deep into stories behind commercial real estate leaders.
Hello, everyone. Welcome to The Dealmakers’ Edge. Today we have an exciting guest, Ron Diamond, who's the founder and CEO of Diamond Wealth. And Ron wears many hats, serving on the advisory board for multiple privately held companies and nonprofits and serving as chairman for a number of them. He's also on the steering committee for the University of Chicago Booth School of Business Family Office Initiative. He's a former hedge fund owner, he's a savvy investor and he is the man who is certainly in the know in many ways in the family office community. And we'll talk about the disruption of family offices, the future, the present, how they distinguish themselves in the market and his illustrious career. So without further ado, here's the conversation. Hope you enjoy.
Hello, everyone. Welcome to The Dealmakers’ Edge. Today, we are excited to have Ron Diamond on with us, who's the founder and chairman of Diamond Wealth, which is a syndicate of over 100 family offices, ranging in size from 250 million to 30 billion, who he has invested with, for over 20 years. The firms focus exclusively on private markets, including private equity, real estate, venture, credit and special situations. And there's divisions which focus on philanthropy, wealth transfer, investment banking, social impact and governance. Ron's going to share his story. We're going to talk about a lot of cool things today and it's been a pleasure getting to know you in person a little bit, over the last year. Thank you for being on today, Ron.
Ron Diamond: My pleasure and it's been great getting to know you as well. Thank you for having me.
Aaron Strauss: Of course. So your background is unique and what you're doing is unique. Maybe for the listeners, you can kind of give the origin story and the career arc and then we can get into the present day.
Ron Diamond: The origin story is not what I had initially planned out, which I think is true with a lot of people in life. I graduated from Northwestern in 1987 and I got a job at a firm called Drexel Burnham, which at the time was the most profitable firm on Wall Street. And I was there and two years later, Drexel Burnham went bankrupt. And I was in a room with a lot of people in their 60s and 70s and many of them lost most or all of their money. I moved back to Chicago, started a hedge fund, before I really knew what I was doing, and scaled it, grew it, had some tailwinds, had some success, sold it, and started investing. That's the really quick version of it, but it was not what I had planned after college.
Aaron Strauss: Definitely sometimes going through the rockiness and seeing what challenges look like up close inspire you to figure out your own success. So congrats on the entrepreneurial bent and platform and trajectory you've taken. And you've also founded the Family Office World Media, which is a platform for sharing information among family offices. And you've created a family office program for Tiger 21, where you've been the chair. How did you kind of get hooked and started in this family office space, which is really a real niche, obviously, in the investment world?
Ron Diamond: I'd love to say it was a well thought out plan, but it was a bit serendipitous. I used to run a hedge fund and in my hedge fund I had clients and back in… my hedge fund was from 1990 to 2000 and in the 90s they didn't call them family offices. They used to refer to them as rich people. So I had a bunch of rich people who are now called family offices. That's kind of how I got into the space. And what I realized is that this industry, this family office industry, there's currently $10 trillion in capital in family offices, but there's $124 trillion that's being transferred from the baby boomers to the next gen in the next 20 years. So we're about, we are starting now, we are experiencing the largest transfer of wealth in history. So this is massive. Having said that, the model itself, the family office model, does not work. Only 25% of families make it to the second generation, 10 make it to the third, and five make it to the fourth. The industry is fragmented, siloed and inefficient and I'm doing everything I can to try to change that.
Aaron Strauss: And maybe you talk about some of the particulars. I mean, it's obviously hard to deal with one family office and you're touching dozens of them and everyone is different and everyone has their own mandates and they have so many nuances. So how do you kind of take this global approach and run your company when you have so many key stakeholders? And maybe you can even talk about kind of governance, you know, how you're set up, what the operation really looks like to flow for people who, you know, just want to learn about your organization.
Ron Diamond: Well, first of all, it's not really a business. This is a way for me to take a finite amount of capital that I accumulated, aggregate with very, very wealthy families and get better deal flow and execution. So don't look at this as a business. Look at it as a way for me to take a finite amount of capital and aggregate it. And that's basically what I've been able to do. We've got about 130 families, anywhere between $250 million to $30 billion and we've been investing together probably for the last 20 years. We don't charge anything. It's not a business, but I'm not doing it for selfless purposes. I do it selfishly, because I don't have enough capital to put $100 million in every deal. Now I do. So I call it First Call Alpha. I wouldn't look at this as a business. I would look at this as a way for me to deploy personal assets. From a business side, I chair some advisory boards and that's kind of what I do. And I put together the Family Office Initiative at University of Chicago, Booth and Stanford. So those are two other things that I focus on. But what I'm doing here is just deploying my own capital.
Aaron Strauss: Exactly. But even to orchestrate that, that's a huge amount of effort and energy and needs some infrastructure. So maybe you could just describe how that works in practice. A deal comes across your plate. It's exciting. You love it. It needs X amount. So you just have a system to reach out to all these other investors.
Ron Diamond: So basically, it's very informal. It's a very tight group of people. We've been together for a long time. And I know if it's early stage venture, there's of the 130 families, there might be 13 like early stage venture. If it's multifamily realty, there might be 84. If it's health care, there might be 57. So I kind of know who likes what. And when I see a deal that is attractive, I invest in every single deal. And when I see a deal that I'm going to invest in, I will then go to the people who invest in that asset class and see if they want to come in. If they do, great. If they don't, that's fine too.
Aaron Strauss: Got it. And how are you set up on the personal side to analyze all these deals? I'm sure every day somebody's pitching you 10, 20, 30 opportunities, because when you're an investor, everybody wants to collaborate. So how do you set up your own filtration system and analytics to figure out what's the best use of your capital?
Ron Diamond: First of all, most of the deals we get come specifically from larger family offices. So we might have a large family office that's taking down $200 million of a deal. They'll lay off $50 million. They've already done the due diligence. They've already negotiated better terms than I could do myself. And they'll say, do you want to come in for the other $50 million? And we'll come in and pair or pursue with them. That's a lot of how we do it. We've got a team of analysts who will look at the deals, but most of the deals that we get, come directly from these large family offices, who've got teams of sometimes 50, 60 people who are vetting the deals and then we'll do a final gut check on it. But again, we've got an unfair advantage of the people that we get the deals from.
Aaron Strauss: That makes a lot of sense. We've also talked about how family offices are kind of almost disrupting private equity. Private equity is very powerful, obviously and the family office market has expanded, as we've talked about. Maybe we can talk a little about how that disruption has occurred, what the nuance is, how families are in a position to invest differently, different metrics, different return profiles and perspectives. And maybe the overlap where you see the separation, where you see that disruption and how people should think about pursuing a private equity investment or a family office investment, the pros and cons of each, if you will.
Ron Diamond: So I graduated from college in 1987 and this is when private equity and venture capital weren't even industries. They were inside banks at the time. And I used to run a hedge fund. So if you had to report, if you have a company and you had to report to me or somebody on Wall Street every 90 days, it's a very challenging and not an efficient way to run your business. You're basically managing your earnings. Private equity and venture capital in the late 80s came out. It was a better model. 2% covered the overhead. 20%, I make money if you make money. It was a better model. You don't have to report every 90 days. And you could do diligence. You could do as much research as you needed to without worrying about quarterly earnings. It became a multi-trillion dollar industry, private equity and venture capital and extraordinarily lucrative. And we're at a point now, though, where as private equity and venture capital disrupted the public markets, because it was a better model, we're at an inflection point and we're starting at a period where family offices will never ever replace, but they're starting to disrupt private equity. And here's the reason why. Today, if a private equity firm buys a garage door company in Toledo, Ohio, I could tell you pretty much within six, 12 months when they're going to sell it. Not because I'm so smart, it's because I know how they're compensated. They're going to typically sell that company in five years, maybe five and a half years. They might sell to a strategic, they may sell to another private equity firm. And I could tell you when they're going to sell it. Again, not because I'm so smart, just because I know how they're compensated. So if you look over the course of 20 years, this one company, this one garage door company in Toledo, Ohio, is going to change hands, let's call it four times. If you look at the taxes and the friction and the disruption in business, versus a family office who has the ability, if they want, to hold it, let it compound over 20 years and grow it without having to sell it, it's objectively a better model. The problem is, we don't have enough family offices that can execute. So right now, in many instances, it's a moot point. That's starting to change. So I put together a program at Stanford and I'm working with several people to put together a program at Booth, because as soon as family offices get the execution right, they will be able to disrupt Carlyle, Blackstone and KKR. Some can now, but very few, more and more will. So we're at an inflection point. And like I said, with $124 trillion in capital coming downstream from the baby boomer to the next gen, This is going to be a game changer. And it's going to do two things. It's going to fundamentally change the way companies are financed. And it's going to also fundamentally change the way a lot of philanthropies are funded. And that's kind of my North Star.
Aaron Strauss: And presumably be ready for the companies and entrepreneurs themselves have greater optionality. If it's only go to PE and that's the only option, like you said, but all of a sudden there's other markets to explore, they get a better return. They have different options for their potential successors in these businesses and whatnot. It could be better for the impact, how they're run, if it's not necessarily IRR driven, but more longevity, compounding, or relationship upside earnings, et cetera. So it seems like that's a very positive thing overall.
Ron Diamond: Before family offices became and again, it's very fragmented right now, but it's starting to change. Before they came in, if you had a business before family offices, you had two options. You could either sell to a private equity firm, or you could sell to a strategic, which is in many instances a competitor. And if you're in the same area, usually sometimes you don't get along great with your competitor. There's ego involved and everything. So they had those two choices. So family offices now give you a third option. Now, you can do private equity, you can do strategic, or you can invest with family offices. Now, having said that, we're still very early in the evolution of family offices. Again, I argue, I used to think we're in the second inning, then third inning, sometimes I think we're in the first inning. This is going to fundamentally change how companies are financed, because if you look at it from the lowest common denominator, go back to alignment of interest. How are interests aligned? This is a better alignment of interest, if the family offices have the team that can execute. If they don't, then it's a moot point. We're trying to change it where more and more family offices have the ability to execute. And if you have a team of 75, 80 people that can execute and they work for a family office and they don't have a shot clock, like Carlisle or Blackstone or KKR, it is objectively a better model. We're just very early in when that's changing. So I look at this as almost 1987, 1988, when the private equity firms were just lifted out of the banks and just became. That's really where we are right now. So it's a fascinating time. And my world is changing literally in real time on a daily basis.
Aaron Strauss: Fascinating. Maybe you can talk about that change, because obviously the one thing that those behemoths like the KKRs and all those massive shops have is, they do have that scale. So if you're a family office and it's 500 million or a billion, or even if it's 2 billion, you still need this huge army of people. And ultimately, while those kinds of long-term compounding opportunities exist, it does seem like everybody has their own massive infrastructure that's got to get fed, which could be also fairly inefficient. Like you said, combining the resources, who's diligencing, you're going to spend an army of 50 people in one company and 50 in the next. It could be combined. Figure, you know, if you're rolling up in private equity, a hundred car dealerships. You do get those economies of scale. Family offices, by definition, are not rolling up, but yet they still have all those independent infrastructures. So maybe you could describe how that economies of scale could be better. What you're seeing shaping the future of family offices, I guess, is a ton of collaboration, of course. There's pros and cons for how they're situated and then there's the inevitability of, all right, what does the next gen look like? In fact, the founding fathers of these family offices may have totally different determination as their kids or grandkids, if it even exists. Maybe you can talk about how all that is changing in real time, if at all and what you see as the future of it.
Ron Diamond: It's changing in real time. And again, we're at the very, very beginning. So right now, if I'm KKR and Blackstone or Carlisle, I'm not really that concerned about most family offices being able to compete with me. There are some that can. And those that can, I think, have a better model. I think that's going to change. And I think it's going to change as soon as the family offices start to become more professionalized. I mean, first of all, I have written and spoken Ad nauseum. 85, 90% of the family office that exists currently shouldn't exist. In my opinion, I don't judge anybody. You sell your widget company for $100 million. You want to start a family office? God bless. Do whatever you want. I don't judge anybody. But there's no metric. So what we're trying to do is put together an industry where we basically educate people. I keynote a lot of conferences and the investors who invest alongside me will always say, hey, I see you're keynoting this conference. Should I go? And 99 times out of 100, I'll say no. Because the model in general, not all, but most of these family office conferences, are it's pay to play. If you're speaking, it's sponsor-driven. You're spending $25,000 and that's the reason I'm listening to you. It turns into service providers pitching to service providers, family offices stop going to these conferences and it's not even a good use of time. I wanted to put together a conference that… I chaired the Instructive Technology Center at the Advisory Board at Stanford University, this is during COVID. And I wanted to put together a family office initiative and I got that green light from the dean of Stanford. And I said, let's put together a conference. But I said, for the conference, I will do two things. I will get you world-class speakers without an agenda. We're not selling anything. And I'll pick the content. So I went to Kirkland & Ellis. Ryan Harris runs the family office division for Kirkland & Ellis and Bobby Stover ran the family office division for EY. I went to Kirkland & EY. I said, you guys do the heavy lifting and I will get you world-class speakers. And we'll have a conference that will actually be beneficial for the family office to attend, because right now, most of these family office conferences are just pay-to-play. I'll give you three quick examples. First guy I called is a good friend of mine, Paul Carbone. Paul runs or ran the family office for Tony and J.B. Pritzker. He was talking about diligence. He was not trying to pitch a fund. He wasn't raising any money. He was saying, here's how we've done fairly well. And they've actually done extraordinarily well. But they start with 200 companies. It goes to 50. It goes to 20. Paul comes in here. They have an investment committee meeting. They decide if they want a board seat, not a board seat, minority, majority, et cetera. And they voted on it, they have two-thirds majority and then they decide. There was no ask at the end of that. It was just, this is how we do due diligence. Second example is… to give three. Tim Callahan, who is Sam's Else partner. He wasn't raising fun for fun vibes. He wasn't raising anything. He was simply… and he made a fortune in offices. He was simply opining on what he thought was going to happen to the office market during COVID. Because remember, during COVID, we didn't know if we'd ever go back to work. And he was just giving his thoughts. And there was no, oh, and by the way, I'm raising a fund. No agenda, just education. And the last example, Denise Illich, good friend. They own Little Caesars and a couple of sports teams in Detroit. She, along with Dan Gilbert, pretty much turned Detroit around. And it's really starting to thrive more now. And she wasn't asking people on the call to donate to her charity to make Detroit better. She's saying, I don't care what your philanthropy is. You need to run it more like a business. And here's what we got right. Here's what we did wrong. And she was just educating. And there was no QR code at the end saying, if you want to invest to make Detroit better, here's how you do it. It was purely educational. We had 880 families from six continents on a Zoom call during COVID, 420 over a billion dollars, like tenfold what Kirkland or EY expected. I had no idea. It was certainly more than I expected. But that was like, check the box, it works. And then fast forward, I think that in order to get this, to have this industry become more efficient and less siloed and less fragmented, it has to be done at a university level. So I live in Chicago and we've got one of, if not the top business school in the world, in the University of Chicago Booth. So three years ago, I was having lunch with Michael Milken, who was my first boss at Drexel Burnham and Steve Kaplan, who's one of the top professors at Booth. And I told him what I did at Stanford. I said I wanted to create one at Booth. He said at the same time, Paul Carbone also had approached him, wanting to do something. So the three of us, three and a half, four years ago, kind of whiteboarded this together, put it together and we put together a program. Because we want, if this is an industry that's just changing, remember this is, in 1988, private equity was not an industry. They used to call it leveraged buyouts and they changed the name to private equity. So now, how do we get, if this is objectively a better model and it is objectively a better model, because there's no shot clock, how do you educate the people? And I think it's got to be done in a university system. So what we did at Booth, the first thing we did is we put together half a credit course on family offices. And we had no clue if people would buy it. Personally, you have to be a full-time MBA student at Booth. So it's the first one in the country to do that. We did a half a credit class. We had no clue if anyone would sign up. It actually sold out quicker than the private equity class, which was shocking. Then we did a full credit and now we're doing two classes. So that did really well. Check the box. There's huge demand for it. Then we put together an advisory board. We got 35, 40 families. These are $5, $10 billion families and larger to be on the advisory board to work with us kind of learn best practices, govern, et cetera. And then we put together a conference. And the conference, again, we've got a huge advantage, because we don't have to make money. We've got… somebody donated $5 million for the naming rights of the professorship. Somebody's donating $30 million for the naming rights of the program. And we could just have Nobel Prize winners from Booth talking about geopolitics or tariffs or interest rates, behavioral economics, without having to sell anything. And we've had two conferences right now. We had about 175 at each conference. We're going to do one probably…. We do it in Chicago right now, we're going to probably do one in Asia, probably do one in Europe as well and expand this. And this was just the first. I mean, Booth is the first to really do this and scale it. But it's not going to be the last. I mean, I've gotten outreaches from other schools, MIT, Harvard, Northwest. I mean, other schools are reaching out. And in five years, more and more of these schools, I think in seven to 10 years, most of these major business schools will have family office initiatives. And I think that's a good thing. I think that's a very good thing, because the industry needs it. But right now, again, we're still in the infancy of this.
Aaron Strauss: Really exciting. And it's honestly really rare. It's hard to someone like you who really deeply is so interested and so understanding of the nuances, because it's kind of this mysterious murky world that it's almost like kind of like shadow economy, if you will. So it's nice to see some light shined on it from the inside out.
Ron Diamond: Well, it's very opaque, but there's two things. First of all, what we see in society, the rich getting richer and the poor getting poorer is a bad thing. Without a sustainable middle class, bad things happen. You can go back in history, always. And what's happening now is the wealthy are getting a lot wealthier and the poor are getting a lot poorer and the middle class is going down. That's a negative thing and that's why there's a lot of people who are complaining about the wealth disparity. And it is a fundamental problem. It is wrong for that disparity and it's not a good thing. The positive, however, is that I do think that it's going to change how companies are financed, I think, which is a better model. But the real impact in my North Star is from a philanthropic standpoint. So my father, who was my hero, passed from prostate cancer when he was 57 years old. At the same time, Michael Milken, who was my first boss at Drexel Burnham, developed prostate cancer. What my dad did is he went to two, three, four top doctors, got second, third, fourth opinions, lived three and a half years, and then he passed away. And that's what most people would do. What Michael Milken did and Michael was a visionary financier, he basically created junk bonds at Drexel. He did what my dad did, but he also built it like a VC fund. He put $250,000 in this crazy idea, $2 million here, $3 million here, up to $100 million. And because of Michael Milken, you, I and most male listeners will die with, but not of, prostate cancer if we live long enough, that's one. Two, Eric Lefkowski, he's founded a company called Tempest. Tempest is a multi-billion dollar publicly traded company. He did not found Tempest to make money. His wife had breast cancer. He didn't like the data. He wasn't a doctor. He did some research. And as a result of his trying to save his wife's life, a company was born. And again, now there's more and more people that are putting money into that. Third example, Sergey Brin. He has a predisposition for pancreatic cancer. Is he going to solve it? I don't know, but I put my money on him over the American Cancer Society. Bill Gates, irrespective of what you think of him personally. I would argue did more for COVID than the US government through his family office. So it's not a panacea, but I do think that a lot, the positive of this is that a lot of these real world problems, not all, but many of these real world problems are going to get solved by these family offices, because I've got two beautiful daughters, 22 and 25. If God forbid they had a disease or something, I would be passionate about it. So if you look at these philanthropists and these entrepreneurs who have the means to do it and they're entrepreneurial and their kid has diabetes and their kid is blind or their mother has dementia or whatever it is, if you take the, the passion, the fact that they've got the wherewithal to fund something and the entrepreneurial spirit to do it. Again, it's not a panacea, but I think it's going to solve a lot of these real world problems, because it's not going to come from corporate and the government's not really good at that stuff. So while it is negative that the rich are getting richer and the poor are getting poorer, I will agree with that 100%. The positive that's coming out of this is from a philanthropic standpoint and I do think a lot, again, it's not going to solve everything, but many of these real world problems are going to get solved, because they're going to run it more like a business.
Aaron Strauss: That's really well articulated, as always. And I know when we were together, was it about a month or so ago, we had talked about, with a larger group, how philanthropy ties into a lot of these growth opportunities and how to set a lot of these platforms, for lack of a better term, up in a way where you really could have a win-win. Obviously, that K-curve economy showing a lot of breaking signs, all that negative, but a lot of resources, a lot of brains, a lot of initiative, a lot of passion. Historically, a lot of great things can come. So thank you very much for articulating that. I think that's very important to hear. Maybe we'll talk a little bit about the market and obviously it is an interesting time, right? As we speak, there's wars going on, there's the Iranian issue, there's interest rates, there's constant, constant change geopolitically, domestically, everywhere. Family offices traditionally are setting themselves up, hopefully, to be around a long time. So a lot of your peers, yourself included, I know obviously diversification and all those core themes, but maybe you could talk a little bit about some specific things, some things in the economy, some things you see are opportunistic, that are exciting, that is motivating you to jump on investment as you see it in certain industries in real time.
Ron Diamond: Well, remember, let me preface it by saying today the model doesn't… the family model doesn't work. Only 25 percent make it to the second gen, 10 to the third and five to the fourth. So the model itself, as it is today, doesn't really work. And why is that? What happens is somebody has a liquidity event. And again, the first family offices, at least in the United States, probably Rockefeller and Vanderbilt, back in the late 1800s, it took generations to create that kind of wealth. With the internet and now with AI, you can create an app and become a billionaire literally almost overnight. So the time, the speed at which you can create wealth is changing rapidly. And I think you see more and more of these families, they have a liquidity event, what do they do? They start investing. Well, that's not the first thing they should do, but they don't know any better. What they should do is, they have a liquidity event. They should do something called governance, which they don't even know what governance is. They should do something called have them put together a mission statement. They should put together a succession plan, a next gen, family dynamics and talk to a state planning attorney who's more important than any asset manager you have. And then after 12, 14, 16 months, then start investing. But it's all done backwards. And there's no game plan to do it. So what we're trying to create at Booth is, OK, you have a liquidity event. The first thing you do is X, which is governance. The second thing you do is Y. We also need to have a platform for how much money do you need to have a family office? I had five billion dollar families and multi-billion dollar families at a conference I keynoted at Stanford. And I just asked each one, I said, what's a family office in your opinion and why did you create it? And I had five totally different answers. And nobody was wrong. Nobody was right. It's just that's where we are. I think we're in a fascinating time right now from an economic standpoint, both from the way companies are financed and the way philanthropies are funded. Because these family offices, there's $124 trillion that's being transferred from the baby. That's not theoretical. That is actually happening and it's starting to happen right now. So something's going to happen. And unless we educate these families and give them a playbook, it's going to be rinse and repeat. They're going to make the same mistakes. 25% will continue to make it to the second gen, 10 to the third, 5 to the fourth. I want to change those odds. In order to change those odds, you have to have a playbook. The first question is, how much do you need to have a family office? The answer, we've done a lot of research on this, if you're going to invest in the private markets and you have a deal team, you need $500 million. There's a ton of family offices that are under $500 million that they call themselves family offices. And again, I don't judge anybody, but in order for it to make economic sense, you need $500 million. Otherwise, you're better off at a multifamily office like a Crescent or some of these big multifamily offices, where you're sharing the cost of everything. So right now, again, it's changing in real time. The growth, I think, of many of these single-family offices are going to morph into the multi-family office and the crassest of the world. And the big family offices are going to become more sophisticated and compete directly with the KKR, Blackstone and Carlisle and will have a better model. We're still very early, but I'm extremely excited because, again, I know I could see what's going to happen in the next three, five, seven years directionally. I'm not sure the exact timeline, but I'm sure the trend and it all comes back to alignment of interest, which this is a better model to do it with families, if they have the ability to execute.
Aaron Strauss: Let me ask you one more question. Somebody's meeting you for coffee, some young up-and-comer, doesn't matter what industry they're in, real estate, private equity, who knows? They want to be successful. This is a very dynamic time, like we've talked about, between the way technology is advancing so rapidly. There's so many things competing for your attention. It's just almost insurmountable. So you've been around a lot of wealth. You've been around a lot of leadership. You've led companies, been successful yourself, what is a principle or two you'd want to kind of indoctrinate in next gen that they should carry with themselves, as they sort of progress through these future times, present times we're in?
Ron Diamond: There's a book called “The Go-Giver”, which I give to everybody who's younger than me that talks to me about wanting to do anything. And basically the premise is pretty simple. The more you give, the more you get. And I think right now we live in a society, where everyone's looking to get something. They're looking to, they want something. If you give, you're doing something that 95% of the people aren't doing. And again, I think that as I've gotten older, the more you give, the more you get. It's not logical, it's not intuitive, but it actually works. So the first thing I tell people is be giving, be thoughtful and also pay it forward, because I think you have to do that. And with that mindset, I think that's the most important thing to do. Look, AI is going to fundamentally change the world. There's no question about it. There's going to be bad actors. There's going to be good actors. Good things will happen. I think it'll be most beneficial in health care. So maybe we can cure diabetes and take care of cancer and some of these things. There's also going to be bad actors and doing some bad things. So we're at the very early stages of this. But it's a fascinating time to be alive. And again, I'm an eternal optimist. And I just think that the other thing I tell people is just focus on gratitude, because there's five things that suck in everybody's life. And there's five things that are incredible in everybody's life. And we're wired as a species to focus on what sucks. So the sabor toothed tiger doesn't eat us. If you focus on gratitude, good things happen. So you need a growth mindset. And that's the second thing I tell people, tell younger people.
Aaron Strauss: Ron, I love it. I really do. I really appreciate the time you've given everybody here today to listen to these valuable ideas, concepts, history and where we're at. And of course, our friendship. Hope I'll see you again in person sometime real soon. And I hope you continue to be successful, inspire the next generation and continue to educate and all the great things you're doing. So again, thanks for making time. And really, really always appreciate being around you and learning from you. And I'm sure everyone is listening to you as well.
Ron Diamond: My pleasure. Again, thank you very much for having me. It was great seeing you last month.
Aaron Strauss: All right, Ron, to be continued and we'll talk soon. Thanks again.
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The Dealmakers’ Edge with A.Y. Strauss highlights the stories, successes, and struggles behind major commercial real estate investors. Each episode offers a behind-the-scenes look at commercial real estate leaders and their unique edge.
Hosted by Aaron Y. Strauss, Managing Partner at A.Y. Strauss
Aaron Y. Strauss is one of the leading legal advisors in the commercial real estate industry, providing insight and guidance for billions worth of transactions during his career. As our firm’s founder and managing partner, he has positioned A.Y. Strauss as one of the region’s most respected law firms for commercial real estate owners, lenders and sponsors, serving the needs of our clients with the utmost in care, integrity and transparency.


