← White Coat Investor Podcast
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This is the White Coat Investor Podcast where we help those who wear the white coat get a fair shake on Wall Street. We've been helping doctors and other high income professionals stop doing dumb things with their money since 2011.
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Hey, welcome back to another episode of the White Coat Investor Podcast. Full disclosure, what I'm about to say is a sponsored promotion for locumstory.com but the weird thing here is there's nothing they're trying to sell you. Locumstory.com is simply a free, unbiased educational resource about locum tenants. It's not an agency, they simply exist to answer your questions about the how to's of locums on their website, podcasts, webinars, videos, and they even have a Locums 101 crash course. Learn about Locums and get insights from real life physicians, PAs and NPs@Whitecoatinvestor.com locumstory all right, we're sure glad you're here. It's not much of a podcast without you and we try to meet your needs, meet your desires. With regards to a podcast. Hopefully it's a little bit entertaining. Probably not. I'm not that funny of a person. More importantly, hopefully it's both educational and inspirational to help you to improve your life so you can make a big difference in those things that matter most in your life. Maybe that's your medical practice or your other profession that you do. Maybe that's your family. Maybe it's just having a little more free time and crushing your burnout. I don't know what you're dealing with out there. I thank you for dealing with it. I know everybody has a struggle. I've got my own. Everybody I know struggles with something. So whatever you're struggling with today, thank you for fighting the good fight, number one. And number two, may you find success in doing so. We've got a guest today with a decently long interview, so I wanted to get a few things out of the way before we got into that discussion. The first one is our quote of the day. This one comes from Plato said, the harder you work, the luckier you get. Now, I've heard that for years and years and years. I didn't realize that came from Plato, but apparently he said it first, or at least he was the first to record it, saying that. Now in today's interview, we're going to be talking a lot about estate planning. Really gathering documents to make other people's lives easier for the most part is what we're going to be talking about. But I want to let you know about another service that we've brought on. I've had people asking me for years and years and years and years for referrals for estate planning. You know, they need a trust, they need a will, et cetera. So we have partnered with a new partner. It's called Trust and Will. If you go to whitecoatinvestor.com trustandwill you'll see there's a discount of 20% off for our readers. And you can do a lot, a lot online these days thanks to the assistance of AI and all the advancements that have been made. Basic wills, basic trusts. You just need a simple revocable trust. This is a great way to do it. Very inexpensive. Way cheaper than finding the nearest estate planning attorney in your state. Check it out. Take a look. Whitecoatinvestor.com trustandwill let us know what you think about it. Now, if you've got some complicated estate planning situation, you really need to sit down with somebody and go over things and weigh your options and put together some DECA million Trust. This might not be the service you want. You probably need to sit down with a good estate planning attorney in your state. But for the vast majority of white coat investors, especially relatively early in their career, I know there's tons of you out there that don't even have a will. Despite having kids, nobody knows who's going to be taking care of those kids if something happens to you. Go to Trust and Will and get this sorted out as soon as you can. Okay? Tonight. See this drops on June 11th. So tonight, June 11th there is a Financially Empowered Women event. It's at 6pm Mountain. These are live. Ashley Shaw is going to be talking to us about contract negotiations. I say us. I should say you. I'm not going to be there. I'm not allowed to the Few events. That's not true. I did get to speak at one of them one time about backdoor Roth IRAs, but otherwise I haven't attended any of the Few events. I haven't been invited to them, nor to the socials at wcicon for the Few. But if you are a member of the Few or would like to be a member of the few, register@whitecoatinvestor.com. And that'll get you signed up for the event tonight. Even if you're not able to watch it live. I think they probably send you a video of it and check that out. Okay? If you need help with disability insurance, I know a lot of you do And I feel like I talk about it all the time. But the truth is, the people who most need it are those who just found White Coat investors. So if you're somebody who actually needs this, maybe you've never heard me talk about it, but if you depend on your income, you need disability insurance. And the best place to get it is to go to whitecoatinvestor.com insurance or you can just go to whitecodeinvestor.com, go into the recommended tab. And we have insurance there as well. Okay. My guest today on the podcast is Josh Kantor. I'll be introducing him on the podcast. The feedback I've gotten from the annual survey is always make sure you guys know when there's any sort of financial conflict of interest with any of our guests on the podcast. So I'm letting you know right now there is potentially a financial conflict of interest with this guest. You know, we were just lining him up because I thought he was doing something really interesting. And then somebody at the company said, well, maybe we could have some sort of affiliate relationship with him. So we actually put one together. If you hire Josh's company, after coming through the links we give you in this podcast, we might actually get paid. We've never actually been paid at the time I'm recording this, but it's possible we could get paid. So be aware that we may have a financial relationship going forward. I'm not sure we're really going to send him a lot of business given what he does, but I think what he does is super interesting and I think you need to do it in some form, whether you hire his company to help you do it or not. And that is mostly to aggregate and communicate with your family about all the different accounts and people and things that are going on in your financial and non financial life and get it together in one place so that if somebody ends up having to be your executor, they'll be able to find all this stuff and it won't be tortured for the next 18 months dealing with it. So let's get into that interview now. Our guest today on the White Coat Investor podcast is Josh Kanter. He is the founder and CEO of Leaf Planner. Josh, welcome to the podcast.
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A
Thanks for having me. I'm excited for this conversation.
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B
Yeah, this is really exciting for both of us because we discovered after lining this up that we only live like a mile apart. So we're very much neighbors. We've never met prior to doing this, but we probably run by each other's houses Multiple times. So it's great to have you on the podcast and talk to you a little bit more about you and your career and what you've done and your company and even your family. A little bit.
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A
Yeah.
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B
Thank you. Before we start talking about Leaf Planner, let's talk a little bit. Let's talk a little bit about your dad and then we'll talk a little bit about your career. Tell us what your dad did for his career and some of the things that he came up with that maybe listeners would find interesting and relevant in today's estate planning world.
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A
Yeah, so my dad. Thanks for asking. I love talking about my dad. So my dad was a fascinating, fascinating guy. All of my grandparents were from Eastern Europe, emigrated to the United States, God knows when, and my mom and dad both ended up on the East Coast. My dad was born in New Jersey, ended up in Chicago in the 1950s for him to go to University of Chicago undergrad and then law school. And he became a wildly, wildly well known and successful tax lawyer, probably of his era, which is now back into the 1960s through the, through 2000 when he got sick and then passed away. And I'll come to that part of the story. He really was the preeminent tax lawyer in the country to some extent around the world, developed many of the estate planning techniques that we all continue to use today. His client roster was kind of anybody who was anybody of multi generational family wealth of that era. The projects he touched were just remarkable. Everything from helping to build Ticketmaster and Cablevision and the film industry and represented Santana and Credence Clearwater Revival and like just crazy career, just crazy, crazy career. His fingerprints are still on all the things that we do in the tax world today. And again, you know, just touched all these kind of iconic projects. He turned into the venture capital space in the 1980s. So started, I wouldn't say a different career, but like a whole other aspect of his career, building businesses and running two venture funds. The downside to all that is one gets the attention of the Internal Revenue Service when you're that good at what you do. And so he was audited every year from 1964 to 1994.
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B
That's a lot of audits.
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A
That's a lot of audits. He was charged criminally in the 1970s and acquitted. And then the IRS started a civil case against him in 1979 that went to trial in 1994, ultimately went through three circuit courts, up to the U.S. supreme Court, back to three circuit courts, back to the tax court. And back to three circuit courts and not ending until 2012, 11 years after his death. And so, yeah, it was quite a fascinating career.
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B
Yeah. So, I mean, you know, he's coming up with new stuff and it sounds like he's relatively, you know, for lack of a better term, aggressive when it comes to seeking out, you know, tax deductions. And that will attract attention at times, won't it? It will, especially if you're publicizing it. It widely. You know, give us an example of a technique he came up with that's still being used today.
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A
Yeah, so one of the ones that I love is for. And I don't know if any. If your listeners will understand what these are, but I'm happy to describe it a little bit, but there's a trust structure called the intentionally defective grantor trust.
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B
Yeah, I've got one of those myself, so I know very well.
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A
There you go. Okay. Well, I've got the first private letter ruling approving an intentionally grant. Intentionally defective grantor trust on my computer because that was something my dad dreamt of. I think it was like 1974, 1975. And so, you know, many of those techniques, again, were things that really came out of his, his practice and his work. And, you know, and it's interesting because you make the comment about, if you're, if you're public about it. And my dad was very, very public about what he did and was very, you know, there are many of our generation, right. Has grown up in an era where you could pick up the New York Times or the Wall Street Journal and you'd see that law firms and accounting firms were asking their clients to sign NDAs and all these other kind of things. Right. And my dad was out writing law review. I think he published one. Articles, law review articles about the things he was doing. And he, his attitude was, this is what I'm doing. This is why I think it's legal. Come copy me, and if you don't think it's legal, then come challenge me. And they did.
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B
Do you get a sense he ever regretted being that outspoken about it?
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A
I don't think so at all. I think underneath it, he was a teacher.
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B
You don't think he minded the audit?
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Right.
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Like, this is my 27th year of auditing. Bring it on. Right.
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Yeah. They had, in their law firm, they had a, an office set up basically for the IRS auditors because they knew that we're just there full time. And so. No, I think he really loved it. I think he loved it. I think he loved the Game. But I think he loved the education about it. I think he loved teaching people, including people at the irs.
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B
And it's true, right? Because sometimes they do need to be educated. You know, I found myself over the years, you know, I'm not professionally trained in finance by any means, but I have found myself teaching a lot of accountants about accounting just because things that they just didn't have a lot of clients that were dealing with this issue. And I happen to have a big part of my audience dealing with that issue, so I know it very well. And so it's, you know, sometimes the teaching goes in a direction that people don't expect it to.
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A
You know, I'll tell you, there's a new book that just is coming out. It's coming out actually in a week that I've been given a pre publication copy of that's got a chapter about my father. And one of the things that the author uncovered or came up with was a conversation with an IRS agent from back in those days who basically, I think very begrudgingly has to say and acknowledge Burt Cantor worked within what Congress handed him. And that if you want to blame anybody for this, right, you got to go back and blame Congress.
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B
You can't blame or ate the game, not the players. Yeah, yeah, yeah. Very cool. So what was it like growing up in that shadow?
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A
You know, it's. It's funny. I mean, I think for me, one growing up, certainly the criminal trial in the mid-1970s, which was, you know, kind of my early teen years, that was rough, right? That was rough on our family. I think after that happened, my dad really protected us from it. Like, we didn't really know. I didn't know until I came back to law school that then the civil case had started back in 1979, and I came out of law school in 1987 and then was carrying briefcases for everybody when that thing went to trial. So he did a pretty remarkable job of just kind of protecting us from knowing that this was continuing in some different format. But then there's the side of it, of just growing up in the shadow of kind of this giant. And my dad was nationally recognized, internationally recognized, but certainly in the Chicago community. Nobody didn't know my father. So I remember coming out of law school and interviewing at different law firms, and there wasn't a firm in Chicago until the one I went to who their first question wasn't, you're Burt Cantor's son. Why would you want to come here? You're not going to stay? And so it was really, you know, I think there was some difficult, there's mostly pride, I would say. I would not say I, you know, have any. Do not shed a tear for me whatsoever. But, but it was interesting growing up in the shadow of kind of this, you know, remarkable human.
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B
So you, you talk about going to law school now. Tell us about your career.
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A
Yeah, so I, I went to law school. I became a corporate insecurities lawyer. Started in actually commercial real estate and then in one of the real estate downturns turned into a corporate and securities lawyer. And my family was engaged in venture capital work by then. So I ended up doing a lot of work with my dad and my brother worked with my dad on the venture side. So the three of us were kind of loosely working together. I was still out with another law firm, so I was outside counsel really in that respect and really enjoyed being a lawyer. I was good at it. I had fun. I was doing well and building my own career again, partial connection to the family. And then in 2000 we found out my dad had cancer and was going to pass away. He was 70, so still young guy, deal junkie, globe trotting really, I'd say still somewhat at the prime of his career and his life. And again, we knew he was going to pass away. So I left my practice to come help our family navigate through all that. And obviously, as you might imagine from the description I gave you of who my dad was, there was a lot of complexity surrounding our families. So we had, we were filing 750 tax returns a year. We had a complicated balance sheet. He was in all kinds of deals. We had the venture business, obviously ongoing IRS litigation, as I mentioned, family dynamics. We were three generations, three branches. And so I came in to basically help navigate through all that, which was, I think for me it was the right thing to do. I knew I had to come help my family. But again, I enjoyed being a lawyer. This was not, I'm not the guy who walks into a room and says, I'm the recovering lawyer. And so I left, I did that. I spent 18 months with my dad before he passed away and then really jumped into the family office world and had been leading a single family office for our broader family for the last 25 years, which led me to then doing a lot of consulting with other families because I saw among the families I worked with and nearby all the kind of problems that families of multi generational wealth face. And I, and I really enjoyed talking about those issues and helping families think through those issues, especially first generation wealth creators who don't even know what the questions are to ask. And so I, I jumped into a consulting practice of helping families go through those issues. And then ultimately that led to the creation of this company, Leaf Planner. So it's all connected. It's one, you know, winding path like so many of us have had.
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B
Now, I didn't run into you on a run. I became aware of your work after taking, I think it was a qu quizzes you put together for Relief Planner, which was basically designed to help somebody decide if they would benefit from having a family office, I think is essentially what it came down to. And of course, I was pleased to see that after I got done taking the whole quiz, it said, you probably don't need one at this stage. But it was a fascinating process because there was way more involved in the quiz and the things it was asking me about than just level of assets. Because that is what it so often comes down to when people start talking about family office. It's, do you have 30 million? Do you have 50 million? You know, if you, if you have 50, but not 30, then now you need a family office. But you, you started asking about other things. You started asking how many businesses, how many generations, you know, questions like that. Where, where the, the financial life just became, just becomes a lot more complicated. When did you start thinking about that sort of level of complexity, you know, and designing something like that tool?
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A
Yeah, that's been, it's really been in the background the whole time. So if I go back to my dad's death again, when he died, as I mentioned, you know, 750 tax returns, complicated balance sheets, on and on and on. And what I realized quickly after he died, and I spent, as I said, 18 months with him before he died. I'm a lawyer. I took his estate planning class in law school. I knew where the documents were, I knew where the balance sheets were. It was all the complexity, all the context that was missing. And so we started building this thing for our family 25 years ago that we called the family owner's Manual. I'm sure you remember the old adage of you get an owner's manual with a toaster and not with a kid. And we said, well, guess what? You don't get one with a family of wealth either. And so what would that look like? And it was really about that complexity. And so complexity has kind of been at the forefront of the way. I've thought about this for 25 years, long before Leaf Planner came along. And what you took was our complexity Calculator, I think. And there's also then a free quiz on there about just kind of family readiness. And there's another EQ quiz that really is out there to talk about do family members understand sort of the emotional side of the family as well. But the idea of complexity that you're talking about in that complexity calculator that's out there, anybody can go take it. And it's not even really about, do I need a family office? It's really just to get people to focus on how complex we really are. And I think your audience is the perfect audience for this, right? Because you've got, you know, physicians and other professionals who are high income earning people who have who, you know, my neighbor puts me in this deal and I've got now my vacation property down in Cabo. And, you know, whatever it is, it doesn't matter, Right. People tend to grossly underestimate their complexity. And one of the ways I say that all the time is like, you could be worth, who cares? Make up a number $10 million and have a couple of homes and a couple of kids and a couple trusts and a couple cars and a couple insurance policies and a couple of private investments. And you start thinking about all these things and you're really complex. And alternatively, conceptually, you could be worth a billion dollars of Bitcoin on a USB drive. And I keep saying to people, don't lose that password. And you're not that complex at all. And so again, I think the idea of that complexity calculator was to say, we all have a tendency to say, oh, I'm not that complex. And that's because it's all rattling in our heads. It's not in my wife's head, it's not in my kid's head, it's not in my lawyer's head, it's not in my accountant's head, it's not in my wealth advisor's head. Little pieces of it may be in all of those heads, right? But again, it ends up being this really gross miscalculation of how complex we are. And so I'll say often, I think there is a correlation between wealth and complexity, but it's not a correlation of 1. That correlation is much, much different. We did that because it's important and you got a kick out of it. That's all that matters, is that people, it opens their eyes a little bit to say, this is more than the size of my balance sheet. And you said, there's a lot of things we ask about. Yes, it's things like generations, because you look, you're young enough to. Your parents may be alive. Mine are gone. Right. But that means people who are in that sandwich generation who have parents above them and kids below them. That adds complexity. If you add another house, that probably adds 15 new relationships between the landscaper and the utility accounts and maybe a property manager, whatever it is. And people don't think about that. So you start thinking about all those moving pieces and it gets really complex really quickly.
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B
Yeah, the classic MO money MO problems, for sure. We'll include in the show notes a link to that complexity calculator. If you're wanting to learn more about Leaf Planner, by the way, probably the easiest way to go there is just go to whitecoatinvestor.com leafplanner and you can check out the services available there, which we'll get into more as we go along. But I noticed when I go to the website, the first phrase on the website is identify, aggregate and communicate. Why? Tell us about those three things and why they're so important for somebody with a relatively complex financial and family situation.
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A
Really. I think that again, the problem I had when my dad passed away, and I've seen it now over and over and over again, literally in hundreds of families and family offices, is that there's so much information that's rattling around somewhere, right? Information is one of the phrases I use is information is everywhere or nowhere. When I came at this 25 years ago, you know, there was no box, there was no Dropbox, there was no Google Drive. Right? But nevertheless, it was the same problem. Information was scattered. Different systems, different file drawers, different people. That's all still true today. Even if you're really well organized around a Dropbox folder, Right. You still have. Somebody's got to understand the architecture of that. You still have to know, are your private investments over at Juniper Square, do you have documents over in DocuSign? It's endless. The more systems we add, the more complexity we continue to add as well, even though they're designed to simplify things. And when you think about educating, whether it's your spouse, your partner, your kids, whoever it is, your advisors, your trustees, your guardians, how do you educate them? How do you give them what they need to know? How do you communicate that to them? How do you share your values with them? Right? These are all the things that people, I would say, tend not to appreciate. So they say, oh, I've named somebody as my trustee or my guardian and they know where to find my balance sheet. Okay, that's Helpful. That's great first step. But that's not really how you get them prepared to have conversations with your kids or with whoever you know you're supposed to be doing this with. So, and the communicate part, I would say is, is really, to me, you know, I'm. I'm sure you've got some real estate investors in your audience and, you know, there's that old real estate adage, location, location, location. And when I talk about families, I say it's about communication. Communication, communication. Because you don't end up on the front page of the Wall Street Journal in the New York Times because you were looking for 10 more basis points of performance. You end up there because sister and brother are suing each other because they don't know why mom and dad did this, that or the other. It's all about communication right now. That's not going to always solve everything. There certainly are problems that communication can't solve. But I think that in my experience and what I've seen in all the families that I've worked with and worked alongside and studied, so much of this just comes down to preparation, communication, saying what you mean, all these kinds of things. So that's really where that came from on the website.
- [24:50]
B
Identify, aggregate, and communicate. Okay. So I mean, people are hesitant to talk to their kids about how much they have for lots of reasons. They're worried they will ruin them if they'll quit working if they know they have this big inheritance coming or they just tend to be private. Right. There's some things you don't talk about. And so I think communication is challenging for families not only from, you know, generation one to generation two, but between, you know, members of, of generation two. What problems have you seen in this work you've been doing for the last 25 plus years with families that did not communicate? I mean, tell us a few horror stories that could have been solved just really easily if people would just communicate.
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A
Yeah. So let me answer first from a different perspective, but then I'll come back to answering what you specifically asked. First of all, people tend to really confuse, I'll say communication with transparency. And what I mean by that is people tend to think transparency is a binary issue. I'm going to show you the balance sheet or I'm not. And I think that really harms people because that's not what transparency should be. Transparency should be a continuum. And you can have a conversation with your kids about your values, you can have a conversation with your kids about your investments or your structures long before you're revealing the balance sheet. So I get that there's families out there that don't want to talk about the balance sheet or don't want to talk about how much they're worth or whatever. Whatever those things are. But there's a lot of preparation you can do leading up to that sort of reveal, if you will. And that, I think, is one of the things that people need to really focus on. Because if you don't do this, then back to your horror stories, right? I mean, again, you're leaving your kids. I mean, obviously things can happen when you don't expect them to, but let's say things even go in the. In the most normal of kind of processes in the way it's supposed to go, right? You outlive your kid. I mean, you. God forbid you outlive. I do not want to outlive my kids. You die before your kids, right? And now your kids are adults, and they've got their own careers and their own lives and their own kids and their own homes and their own complexities. And now all of a sudden, they gotta unwind your crap. Is that fair? Is that really what you want to do to your kids? Like, one of the things I keep saying is if it takes me 20 hours to put this together in my leaf plan, for example, it doesn't matter how you do it. It's gonna take my kids 200 hours, 400 hours, I don't know. By the time they have to go do all the forensic work to figure this out, it's not fair. It's not what I want for my kids. I don't think it's what my dad wanted for me. And so I think the horror stories are. I mean, the worst horror stories, of course, are lawsuits, right? The second level of horror stories are ruined relationships. Because, again, kids don't understand, why did Susie get more than I got or why didn't, you know, whatever. And if you're not communicating about these things, again, you're not helping anybody. We had a very open communication in our family, for example, that. And I mean, our broader family. But it doesn't matter. It could just be our little nuclear family. Education was such an important value to our parents. And so we just. And so, like our parents, we all came out of school with no student debt. Like, really, really fortunate, right? We understood the gift that we were given by our parents to be able to do that. And we said, we want to do that again for the next generation, but we want to do that in a way that didn't matter whether you went to, you know, Georgetown or the University of Utah. It didn't matter if you went through college or to vocational school or to law school. Whatever it was, it was getting paid for. Didn't matter if you had three kids and I had two kids. And so that was important to communicate to all of the cousins, I'll say at that next generation or to my kids, that that was never going to be equalized. And that's intentional because this is based on the values that we hold. So to me, again, that's about the communication side, not about telling them how much we're worth, not about revealing that balance sheet. And so if you think about communication about your values and why you're doing these things, then worrying about whether you're going to ruin your kids becomes much more secondary to those lessons that you're giving them.
- [29:12]
B
Okay, so let's talk for a minute. I think this is the first time we've probably talked about the concept of a family office on this podcast. Can you describe for us what is a family office? What kind of services do they offer? You know, how does. How is that distinguished from a typical, you know, financial advisor that's a financial planner and an investment manager? What am I getting with a family office that I'm not going to get from, you know, even a good financial planner?
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A
Sure. So, you know, the reality is the words family office have, I'll say, kind of been bastardized over the last 20 years, and now they mean whatever you want them to mean.
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B
That's the problem with the term financial advisor, too.
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A
Yeah, true. Exactly. Exactly. So I tend to think the best definition of a family office is a structure. I mean, forget legal structure, but it's a structure that's set up to really be able to look holistically at everything the family is doing and involved in and wants to accomplish and is really there to serve to the best interest of the family. So that can mean, I mean, most people, I think, think immediately. If you think family office, you think, well, I'm going to have a bunch of investment professionals and I'm going to bring that function in house. I would argue that's fine. You can. Lots of family offices do it. You're not going to do that. You're not going to go hire a chief investment officer if you're worth $50 million. If you're worth $1 billion, you might. So there's, there's clearly scale around some of those decisions. But the most important function, from my perspective, is that holistic picture. How does this all fit together. How do we think about this in that holistic nature? Then you can start thinking about all the services. Right. It could be, I mean, for us, I would say it started around, Remember I mentioned we were filing 750 tax returns a year. That takes a number of accountants who are on full time. That's all they did. Right. For years. And so that was kind of our core function. Some family offices are focused on investment. Some family offices are going to be focused on tax and compliance. Some family offices might offer concierge services, some family offices might offer financial planning, as you said. Right. So lots of different things that they can do. And typically I would say the family office is deciding what do we want to do in house and what's better outsourced. Right. Most families, even family, even really, really large family offices, tend not to hire in house an estate planning attorney because you don't, you can't use one full time. You gotta be a really, really big family to need an estate planning attorney on full time. Right. So you gotta just be looking at what is it that I want to do? Well, internally and what do I want to do externally? And you'll start to get, you know, conversations about am I, am I a single family office, am I a virtual family office, am I a multifamily office? Right. All these different variations that are starting to pop up. But ultimately I think it's, what do you, what do you need at the core to serve your family and your legacy? And if you're building wealth, and especially if you're compounding it, you know, I'm sure you've got listeners who are still in debt from school, but they're going to be off into a high income career, they're going to build wealth. And you know, if they, I, I doubt there's a class in medical school about compounding. There should be.
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B
There certainly. There certainly is not, I assure you.
- [32:31]
A
So there should be. Right. Because, you know, I run into lots of people who all of a sudden wake up and realize, oh, I'm in my 30s, I'm in my 40s, I'm worth 5 or 10 million dollars. Compound that out for a few more years or a few more decades. Right. And you know what that does. Right. And so the notion of thinking about how do I want to think about the legacy I'm building, what do I want to do for my kids, all these things, those are to me at the core of that family office conversation.
- [32:59]
B
And of course, the cost of a family office is highly variable based on how Much you bring in house.
- [33:05]
A
Yeah.
- [33:06]
B
I mean, I think there probably aren't very many family offices at all that are going to cost you less than $100,000 a year. But I'm sure there are seven figure family offices as well.
- [33:15]
A
Yeah, easily. I mean, you know, big, big, big family offices can easily run into 10, 20 million dollars a year or more. Right. Because they're bringing in really, really sophisticated professionals on the investment side, on the tax side, you know, on the accounting side, on, on all these different things. I would again argue, you know, you could conceivably be a family office of one and be the person who's really acting as that quarterback, conductor, whatever you want to call them, if you like sports metaphors or music metaphors or whatever you like. Right. But it is that coordination that to me is really the value. And Maybe that is $150,000 person.
- [33:55]
B
Probably.
- [33:55]
A
It's probably still a little higher than that, but nevertheless. Right. It doesn't have to be the billion dollar family and the multimillion dollar budget. I think you can start at scale, so to speak.
- [34:07]
B
And I've even seen, you know, businesses out there offering, you know, kind of a shared family office experience where maybe this family office is taking care of, I don't know, four or five or 10 different families. What do you think of that model? Do you think that's possible, that they can do that in a way that's really adding value?
- [34:26]
A
Yeah, absolutely, I think so. There's really, I'd say, and I don't know if you mean the distinction, but I'll make a distinction. There are a few models out there that are truly what I would call what you just used, the shared family office. That's really 4, 5, 6, 10 families coming together and saying, we're going to hire the staff and build out the family office to just serve us. Then there's the multifamily office that really is a commercial business that is out saying. And there are a lot of these popping up who are saying, hey, the, let's call it the 20 to $100 million family that's unlikely to go start their own true single family office, but needs that level of service and attention. And those, I think, can be great. I think they're a really, really good offering. And they're very different than walking down to your typical broker, dealer, you know, your Merrill lynch office, your Wells Fargo office, your UBS office, whoever it is. Right. That's a very different service level and a very different component of services that they're offering. You And I think those can be great. I think it's hard to go sort of, I'll say, I don't mean this to sound badly backwards. Like for me, the problem for us to go now, after having run a single family office for so long, to go into a multifamily office environment. For example, I don't know who wakes up every day like I do and thinks about what does the cancer family need today. That's hard, right? But if you're growing into this, I think the multifamily office, the shared family office, they're great models and you can get really good talent these days. You know, there's, there's a fight for talent, but I think as opposed to 25 years ago, you can outsource a lot more. This is more like there's a, there's a real conversation about this and how to do it, which 25 years ago you couldn't do. So there's, there's much more opportunity, I think, for families that, that don't want to build all this infrastructure themselves to go share it or to go find it now.
- [36:17]
B
I think a more typical story for our audience is someone that's going to retire with 2 to 6 million dollars. Maybe they die with 8, 10, 12 million dollars. Maybe. Is there a role in that sort of a family as it becomes multi generational for this sort of a structure, or are they kind of stuck with, you know, use a financial planner, diy, see your estate planning attorney and do the best?
- [36:43]
A
No, I think there definitely is a role. I mean, I, I again, like they're firms that are going to cater to the, the 20 to $100 million family. But there are firms out there that are offering, you know, something akin to a family office service to the two to $10 million family. And so it's just a question of, you know, I, I think you have to be careful of your expectations. If you're bringing $2 million to a firm that offers something akin to family office services, you're not going to get the same service that if you had $100 million, right, you got to be honest about that. But I think you can go find the services that you want matched to your wealth level and what you're hoping to accomplish much more so than again, you could in the past.
- [37:27]
B
Now you've been, you know, running this family office essentially for, for decades and you know, obviously come from a fairly well to do family and, but at some point in the last few years, you became very passionate enough to start a new company, enough to start Leaf Planner, what need did you see that you felt like you could fill with Leap Planner?
- [37:51]
A
Yeah, I mean, we mostly saw. So what Leap Planner essentially does is what were the words? Identify, aggregate, communicate. You got to remind me of my own words. It really takes everything there is to know about you, your family, your family enterprise, if you will, your family business, your investments, your really everything. And maps it out into a giant kind of mind map or owner's manual again of all these things that we do and how does that all interconnect? So you're talking about documents, you're talking about balance sheets, you're talking about deals, you're talking about relationships, you're talking about eq. Why is this painting behind, behind me important? Why do I care about it? Where did it come from? I don't want to just know the basis record. I want to know why is it important to me? Not even is it important in the art world. Why is it important to me? Right? So it's aggregating all of that kind of information in a way that nothing else on the market was doing. And so for me, I'm 63 years old, so I started this at 59 years old. And I jokingly say it doesn't change the beach I retire on. It might change how close to the beach my last house is. But I do this, it's out of passion. It's out of passion of helping families because nobody else is doing this. Nobody else is really guiding families to say this is the kind of thing that's important. And in many respects that makes your audience perfect for what we're talking about. Because again, they're high, likely high earning, first generation wealth creators. Nobody's sitting down with them. I mean, their Merrill lynch broker is sitting down with them and saying, let's talk about your portfolio. Nobody's sitting down with them and saying, let's capture how your family's going to find that, you know, when you're, when your neighbor and your fellow doctor and oh, you bought your, you bought your medical office building and nobody knows where the information is about that or the utility accounts or whatever it is, or where your dog goes to the vet. I mean, it's literally all encompassing or why do you support this charity? All of these different things that aren't explain that aren't brought together into that again, that holistic picture. And so for me, the passion was saying, how do I really, again, to your point, how do I help everybody, not just the $100 million plus family, how do I help everybody Understand how to ask those questions. And that became Leaf Planner. And so it's, it's very much a. Sure. Of course I'm trying to build a business and check a box to say I went and built something. But it's, it's very much how do I take what I've experienced For the last 35 years of variations in my career and help your audience and the people I work alongside and do it more than. Because I'll do this, I do this on a consulting basis with four or five families a year and that's awesome. I love helping four or five families a year. But Leap Planner gives me an opportunity to say, how can I go help hundreds of families a year? And that's really, really meaningful to me at this point in my life.
- [40:44]
B
Yeah, very cool. And this is a real issue. My wife's grandfather died recently. I wrote about it in a newsletter for the White Coat Investors. And he died as wealthy as he'd ever been in his life long career as an educator and then a superintendent and just always a saver and never got around to spending as much as he certainly could have spent. And so he built some wealth in his 94 years. And now in the last few months there's this scramble, even though this was foreseen and he essentially was able to choose when he died, that still a scramble to find information and look at intent and these discussions that started before he died and continue after his death of what he wanted to do and so on and so forth and how his trust he wanted to set up is going to be administered. There's a lot here that is not covered just by setting up an asset allocation for your investment plan. There's a whole lot more to it. And having this information in one place would be miraculous for I think most families going through it. So tell us how this works a little bit. And for those who are not aware, we wanted to kind of have this conversation. Of course I bounced it off. Anytime I do anything like this, I bounce it off. Our coo Brett, and his job of course is to make sure we make payroll every month. And so he's running the business of White Coat Investor. He's like, well, we should set up an affiliate agreement. So we did. We set up an affil affiliate agreement with Leaf Planner. So if you go there from whitecoatinvestor.com LeafPlanner we can get paid. I don't know that anybody, I don't know. We're going to send you a single client. I think it's an interesting conversation, even if we never do. But listeners should be aware of that. But knowing that, tell us how this works, like somebody decides, okay, I'm going to make a leaf plan. How does it work? What happens?
- [42:39]
A
Yeah, so, and first of all, thank you for the partnership and my conversations with both you and Brett. And really important to us that you guys get paid for that and that we're putting deals together specifically for White Coat Investor members. And that's really important to us to be able to offer something of value to your members. And again, if this doesn't make sense to anybody, I hope everybody will just learn something and think about it differently whether they come to LeafPlanner or not. Honestly, not the most important piece. The most important piece for me is to educate people that there's a lot of little nuance that they need to be thinking about if you do come to Leaf Planner. And if you don't, by the way, there's again, some of this is available on our website as free tools or as free quizzes. The one, for example, that you talked about earlier. And so we really just want to help people. If you do become a Leaf Planner client, we have a, a team that you work with. You get actual people. You don't call a 1-800-Leaf Planner. You call Susie and Diane and Josh and whoever. Right? Everybody's got my phone number and my email address and we train you, we onboard you onto the platform. We have different plans where people can choose how much of a do it yourself do they want to be. But obviously, as you can imagine and certainly within your audience, again, you've got people who are working six, seven days a week and eight, ten hours a day and say, this is great, I see the value of it, but I don't want to do it. I don't have the time to do it. Or I don't have a family member who wants to do it. And we'll come in and do that for you. So it's really a very curated experience depending upon what it is that you and your family need and want and what's the right fit for you guys. So we work that out with each family and get them up and running. It's an annual subscription. People can, there's no commitments. People can move, can leave, they can stay, they can move from plan to plan from year to year. We really try to make this as client friendly, which again comes from, you know, let's go Back to, I'm 63, I'm doing this to help help our clients. There Are a lot of things that we do that, that I've seen in the industry that really bothered me. There are no data limits, there are no user limits. Like, kind of a lot of things that just bother me as a buyer of these kinds of things we, we don't do. But anyways, it's a very streamlined process. We try to make it as easy as possible and we're there with you along the whole journey.
- [45:01]
B
Okay, so what does my leaf plan look like? I mean, is this 20 pages long? Is this 800 pages long? Does it list everything I have and why I own it and who it's supposed to go to and what the passwords are to get to it? I mean, what's in this plan? I guess is my question. If somebody wants to try to DIY this thing, what do they got to do?
- [45:22]
A
Yeah. So you're going to be guided through all of that, but it is literally every. First of all, you don't have to do everything. But if you, if you went into my leaf plan, for example, and you zoom in on a person because this is, you're capturing again, documents and contacts and I'm describing relationships and all these different things. Right. And all the little tidbits of knowledge that come out of your head. So a simple example of this out of my leaf plan is if you went in and you said, oh, here's this person, Barbara, and she's my, she's, she touches these 17 different things. She's a trustee, she's an investment advisor, she's a confidant, she's whatever. You're going to see that. Then you're going to see, oh, I want to come in on this trust. Well, okay, now for the trust, I'm going to see here the documents and here's why we created this trust. And here's where this trust has a bank account and here are all the parties to the trust. And here all the documents for the trust. And oh, that trust owns my house a mile away from your house. And by the way, if you look at my house, my house has these utility accounts and this is how you get into them. And this is the passwords and this is the, they're on autopay from my bank account. And oh, if you go into the house, well, there's this art collection and the art collection has basis records.
- [46:32]
B
Sure.
- [46:32]
A
But it also, we have a deal at one auction house different than a deal at another auction house. Or you should know that this painting hung in my dad's office and now it's in My office. So it means a lot to me. Or again, whatever. Here are people you can trust in the art world if you're going to go to them. Or then you might zoom out into a deal that I did and why did I do that deal and who did I do it with and where are the documents and what's it worth? And we're not a financial aggregator, by the way. So, you know, we don't, we don't replace the general ledger system, we don't replace the portfolio aggregation system. We're about all that connective tissue in between the hard data, if you will. And so it is. Yeah. And when you say, like, what are you going to. You're going to get down to utility accounts, you're going to get down to your charitable donations, you're going to get down to your housekeeper, you're going to get down to your dog and where they go to the vet and do they have pet insurance and do they have a chewy account? I mean, if you want to do this stuff. And so then it's, it's really, it's an app, obviously. It's a, it's a web app. And you're going to see this all mapped out. At a click of a button, you get a book of the whole thing. So to your number of pages, depends how complex you are, but. But yes, you're going to see everything there is to see. So that. And in my leaf plan, for example, the first instruction to my wife and kids if something happens to me is just print and read our leaf plan, because that's going to give you the picture of what the next 18 months of your life is going to look like. Right. And it's a tool I can use to educate my kids along the way. My kids have their own access to it. They can go in. You know, one of my kids is in college and his car wouldn't start and for the first time he had to call aaa and God bless him, he actually went into his leaf plan and found his AAA card and did it all without me. So, you know, there's a, there's just like teaching kids about adulting, if you will. That's kind of baked into it. There's a lot of education in it. It's kind of what you make out of it.
- [48:27]
B
But this doesn't replace an estate planning attorney. You're not going to draft a trust for me, Correct? This is, this is, I don't know,
- [48:35]
A
it's not going to replace your financial advisor. It's not going to replace it really is not designed to replace people. It's designed to help everybody do their job better, more efficiently. It will save you money on your estate planner, especially when you return to your estate planner because somebody died. You know, now when they start asking you all those questions to fill out a 7 of 6 and estate tax return, it's all there. But no, it's not going to replace those people. It may ask you questions about why you're doing what you're doing. It may ask you questions if you look at your house, house, it's going to ask you who owns your house. And if you say, Josh and Catherine own our house, it may trigger the thought, is that intentional? Or did my estate lawyer tell me I should move my house into a revocable trust? So you're going to see a lot of blind spot identification. But it's not going to replace the actual estate planning, the actual financial planning. It's going to ask you to build out the context again, that connectivity, that connective tissue around those things.
- [49:34]
B
Well, I'm a big fan of planning. White Coat investors know I've been preaching have a plan, have a plan, have a plan for 15 years now. And that includes not just when you're, you know, trying to get back to broke as a young attending physician, but also, you know, a little bit later in life when you need this sort of a thing and your heirs will certainly appreciate it.
- [49:57]
A
Okay.
- [49:57]
B
I think Brett worked out some sort of a discount for white coat investors. Is that right?
- [50:02]
A
Yep. When you come to us, we will offer you the white coat investor discount. And we're really excited about that.
- [50:08]
B
Yeah. So you can go, you can go through whitecoatinvestor.com leafplanner to get that. But what sort of range of fees are people looking at for an ongoing subscription to have access to leaf Planner?
- [50:23]
A
Yeah, ongoing subscriptions. I mean, usually our first year is a little bit more expensive because of the setup and the work with our team. And ongoing subscriptions can be as low as $3,000. And I've got to look at, actually, I don't remember off the top of my head what we agreed to do for white coat. So we'll figure that out. But yeah, it's designed to be very accessible for really anybody who wants to do it.
- [50:45]
B
Yeah. Very cool. Very cool. Well, I think this could be very useful for, well, pretty much everybody. Right. I mean, having this information in our lives certainly become more and more complex as I look at my life. I think this year's tax return had 21 K1s on it. You know, I filed in nine or 10 or 11 states or something like that. It's just life starts getting more complex, especially the more successful you get, especially if you're successful in creating a family as well. Now we've got multiple generations, and they've got, you know, they've got their own spouses and eventually their own kids and their kids will have kids. It just gets really complicated. So I think having something like this just to keep track of it can be very useful. Obviously, this isn't for every listener of the White Coat Investor podcast, but if you would find this useful, be sure to check that out again. That's whitecoatinvestor.com LeafPlanner all right, so your son has used Leaf Planner to hook himself up with aaa. What other. I don't know if success stories is the right way to phrase this, and maybe the big success is after generation one kicks the bucket is where it really becomes successful. What can you us about experiences some of your clients have had in the past with.
- [52:03]
A
With leap planning? Yeah, we've seen really all kinds of things. I mean, everything from. We had a. A guy whose daughter was passing through o' Hare and lost her phone and had one of those credit card sleeves on it. So she lost her license, her passport or her credit cards, her phone, everything. And, you know, he was literally in between his three houses and was able to pull up all the information he needed for her. We've had a parent go into. In another state, go into the hospital, and all of a sudden the kids are all traveling and need access to the healthcare power of attorney and the medication list and the doctor list and the Social Security number and the health insurance card and all that stuff. And it's all right there. We've seen families take this into family meetings, talk about the communication side that we were on earlier. We have families all the time using this as the educational tool to help bring the kids into the picture. I share it with my dog sitter so that they have constant updated information about our dogs. You know, it's really.
- [53:07]
B
Now, now we. Are you able to just share it, like just a part of it with somebody?
- [53:11]
A
Yeah.
- [53:11]
B
Okay, so you can, I mean, obviously you don't want to give the dog sitter.
- [53:15]
A
Correct.
- [53:15]
B
A list of your portfolio assets.
- [53:18]
A
No, Highly, highly structured in how you share things. And then there's a whole workflow management piece of it. So it's all integrated into obviously, the single system. But so whether, you know, I'm sure many of your listeners have done Grantor trusts that require crummy letters, for example, or insurance trusts that require crummy letters. So it's going to remind you about the crummy letter. It's going to remind you that your passport's due. It can remind you that your boiler maintenance is due at your house. It can remind you that your insurance policy needs to be reviewed. So there's a huge amount of workflow management built into it to make it a day to day family operating system, if you will. And so, yeah, I think success stories are sort of all over the board, which I think speaks to our retention rate, which is super high in the 90s.
- [54:02]
B
You know, I, I feel like I've tried to do this myself over the years at times. Right. I have written down, you know, a death document, what you should do if I die. I've written a letter to my executor, you know, and I don't keep it up to date. Right. You know, we've got, now we have a password manager, which I think helps with the passwords anyway. But you know, what else, what else have I done? I have tried to, you know, I've taken everything out of my wallet and made a photocopy of it before. Right. But the last time I did that was 10 years ago. Right. It's different stuff in my wallet now. And so I think a lot of people have tried to do what you've done, you know, in this incredible way. They've tried to piecemeal it, DIY it, you know, in the past, you know, and I've seen a few other products where you just kind of write down a few things on a few pages and put it in your file cabinet. This is dramatically more comprehensive.
- [54:57]
A
Yeah, more comprehensive and really designed to avoid that problem. Right. Both the garbage in, garbage out problem and the. Oh, I forgot. Well, I guess garbage in, garbage out is the same as I forgot to do it for 10 years. Right. Or whatever it is. So again, it's really baked into taking a multidisciplinary approach. We've got on our advisory board, so a lot of this obviously comes from my 35 years. But we've got insurance people, lawyers, accountants. But then we've moved to the softer side and we've got family dynamics experts, we've got religious leaders, we've got doctors, so that everybody is asking the questions that matter from their perspective. So we had a question in there originally, for example, that just said, do you have long term care insurance? Well, that's a great question. Most people forget to ask that question, but it was only until one of either, either the doctor or the insurance person, I don't remember, which said to us, well, but you need to ask the follow up question, which is do they want to be cared for at home or do they want to be, are they okay going to a facility kind of thing? Right. I wouldn't know to ask that question. Your audience would, but I wouldn't. And so again, it's. Even if you try to DIY this, you're only as good as the number of questions you know how to ask or the prompt that you give. ChatGPT.
- [56:09]
B
Right.
- [56:10]
A
And so what we've done is take that guesswork essentially out of it and then systematize it, if you will, in a way that, that avoids that neglect or garbage in, garbage out.
- [56:22]
B
Yeah, very cool. Well, thank you for developing this to start with. You know, the world is constantly looking, you know, for lack of a better term, entrepreneurs, but problem solvers. Because this is a problem, this is, I mean, evidence. Looking back over the years, I'm like, oh yeah, I understand why this is need it because I've made a mess of things and despite doing my best to have a plan and to write it down and keep it up to date and that sort of stuff, and you've come up with a solution to that. So thank you for doing that. Whether I actually send you a single client, I have no idea. But thanks for what you've done because you've seen a problem and you've gone to solve it and hopefully you've created some jobs and, and created a successful business along the way. So well done. In that case, what have we not talked about today with regard to estate planning, leaf planning, whatever you want to call it. What have we not talked about today that our audience ought to know?
- [57:21]
A
Yeah, well, I think the obvious answers is, as you said earlier, have a plan. I just saw a Chubb report that still said, and Chubb is not exactly dealing with the mass population. Right. They're dealing with a pretty upper end clientele. And even their latest wealth report said 74% of people don't have an estate plan. So get your plan done.
- [57:43]
B
And we're just talking about like a will. We're not talking about somebody who actually
- [57:46]
A
knows where the accounts are. Exactly. Right. So basic estate plan, just chip away at this. A lot of people just don't take this on because it seems overwhelming. One I would say it's not. And you can do it over a long period of time, but everything you do is going to make your Family's life better.
- [58:03]
B
Now, one of the downsides to doing this, to having a leaf plan, is you have to do it right. It's a fair amount of work. How do you get people to overcome our natural laziness and actually do the work?
- [58:18]
A
To some extent, you can't. Right? I mean, that's always going to be a problem. If it weren't, then 100% of people would do it. If it were easy, then 100% of people would have an estate plan. But we've done whatever we can to make that easier. So it's a very guided process. Our team will do it for you. We'll hold your hand, we'll do whatever you need us to do. And so we're trying to reduce that friction. Obviously, AI is making that easier as well. So lots of things that we're trying to do to reduce friction. But to your point, there's always going to be friction. The only thing I would say about it is if there's friction to us, us, there's going to be multitudes, exponential multitudes of friction to our kids. And if that's not what you want to leave them with, then accept that there's a little bit of friction in life. There was friction in life to get to where you got right.
- [59:05]
B
Fair point. If you love your kids enough that you have bought a term life insurance policy, at some point, you probably had to love your kids enough to put together some sort of a leaf plan, whether you hire a leaf planner or not, for them to help help sort through this stuff. Because it is complicated after you go in particular. But, you know, you may not even go before this thing's needed. You might just become a little bit demented or disabled or just be in the hospital for a while, or maybe your kid just needs aaa, you know, whatever it might be. Awesome. Well, Josh, thank you so much for your time. As I mentioned before, that link, if you're interested. Whitecoatinvestor.com LeafPlanner thank you so much for your time today, Josh.
- [59:46]
A
Thank you. I really enjoyed it. Thanks for letting me share it with you. All right.
- [59:51]
B
I hope you enjoyed that. That was a lot of fun for me. It's fun not only because we're neighbors and didn't know it, but because it's just something that I've dealt with for a long time kind of in the background and never even thought about hiring out. Probably because there never was anybody to hire this sort of thing out. Well, now there is. In our world, in our AR world and our world of app. You can actually keep this stuff up to date and move forward with it. So if that service is right for you, hire them. If it's not, figure out how you're going to do it yourself. But either way, you need to aggregate some of this information. You definitely need to be communicating with your family. Our sponsor for this episode is locumstory.com and full disclosure, this is a sponsored promotion forum. But the weird thing here is there's nothing they're trying to sell you. Locumstory.com is simply a free, unbiased educational resource about locum tenants. It's not an agency, they simply exist to answer your questions about the how to's of Locums on their website, podcasts, webinars, videos, and even have a Locums 101 crash course. Learn about Locums and get insights from real life physicians, PAs and NPs@whitecoatinvestor.com locumstory okay, don't forget about the few event tonight. You can sign up whitecoatinvestor.com Few contracts Ashley Shaw is going to be talking to the financially empowered women about contract negotiations. Get paid what you're worth. Okay, we hear a lot about gender pay gap and we're not going to get into a big deep discussion about that today. But you know how one of the methods for eliminating is making sure you're getting paid what you're worth by negotiating, getting your contracts reviewed, et cetera. So learn more about that tonight, 6pm Mountain. Also, don't forget if you still need disability Insurance, get it whiteconeinvestor.com Insurance is the best place to do that. Thanks. For those of you leaving us five star reviews and telling your friends about the podcast, a recent one came in said the best medicine the principles of WCI are the best medicine for physician burnout. With all due respect to wellness talks, yoga and meditation, taking care of your finances is by far the most beneficial burnout. Buster, Dr. Dali and the WCI team will show you the simple steps necessary to control your financial life. Rather than having money problems control you burned out physicians. You need this podcast and wci in general. 5 stars. That was really nice. Appreciate those reviews not only because they make us feel good, but more importantly, they help spread this message to others. Help others find this podcast. There's somebody listening to this right now that has never listened to this podcast before because somebody put in a review. So I thank you for doing that. I thank you for what you're doing in your daily work. It does matter I want you to optimize your career for longevity so you can do this important work you're doing as long as you possibly can. But also you got to find balance. Balance in your financial life between the needs of current you and the needs of future you and balance between having purpose in your life. Eudaimonia is the Greek term as well as pleasure or fun in your life. Or hedonia. You got to balance it all and I know you can figure it out. The more intentionally you live, the happier you're going to be. Keep your head up and your shoulders back. You've got this. The whole White Coat Investor community is here to help you. See you next time on the podcast.
- [63:10]
A
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