What happens when entrepreneurial success results in a web of investments, assets, and stories that grew too complex for any one person to manage? This episode of The Angel Next Door Podcast dives into the often-overlooked challenges of building and preserving a family legacy while maintaining clarity and order for generations to come. Our guest, Josh Kanter, brings firsthand experience from growing up as the son of a legendary tax lawyer and later managing his family’s highly intricate financial affairs. His journey through the legal, venture, and family office worlds inspired him to create Leaf Planner—a tool designed to help families and entrepreneurs untangle their personal and financial complexities. Listeners will gain a high-level playbook for managing investments, capturing important family stories, and laying the groundwork for true multi-generational success. Josh Kanter and Marcia Dawood offer practical steps and compelling anecdotes, making this a must-listen for anyone looking to streamline their legacy and protect what really matters.
What happens when entrepreneurial success results in a web of investments, assets, and stories that grew too complex for any one person to manage? This episode of The Angel Next Door Podcast dives into the often-overlooked challenges of building and preserving a family legacy while maintaining clarity and order for generations to come.
Our guest, Josh Kanter, brings firsthand experience from growing up as the son of a legendary tax lawyer and later managing his family’s highly intricate financial affairs. His journey through the legal, venture, and family office worlds inspired him to create Leaf Planner—a tool designed to help families and entrepreneurs untangle their personal and financial complexities.
Listeners will gain a high-level playbook for managing investments, capturing important family stories, and laying the groundwork for true multi-generational success. Josh Kanter and Marcia Dawood offer practical steps and compelling anecdotes, making this a must-listen for anyone looking to streamline their legacy and protect what really matters.
To get the latest from Josh Kanter, you can follow him below!
https://www.linkedin.com/in/joshua-kanter/
Sign up for Marcia's newsletter to receive tips and the latest on Angel Investing!
Website: www.marciadawood.com
Learn more about the documentary Show Her the Money: www.showherthemoneymovie.com
And don't forget to follow us wherever you are!
Apple Podcasts: https://pod.link/1586445642.apple
Spotify: https://pod.link/1586445642.spotify
LinkedIn: https://www.linkedin.com/company/angel-next-door-podcast/
Instagram: https://www.instagram.com/theangelnextdoorpodcast/
Pinterest: https://www.pinterest.com/theangelnextdoorpodcast/
TikTok: https://www.tiktok.com/@marciadawood
Marcia Dawood: Josh, welcome to the Angel Next Door podcast.
Josh Kanter: Thank you for having me. I'm so excited for this conversation.
Marcia Dawood: I am so excited for this conversation. We met recently and I was just fascinated by the story of your family and then how you created this amazing tool called Leaf Planner and why and all the things behind it. So start off, tell us a little bit about your background, and we have to get into this whole story about your family. It's awesome.
Josh Kanter: Sure, sure. Well, thank you. First of all, I'm just thrilled that you were intrigued by the story and everything else. So my background, I'm originally from Chicago and I grew up in a household. A friend of mine wrote a book that was really predicated on this idea of growing up in the shadow of giants. And I feel like that definitely describes my life. In growing up, my dad was in his era, I would say the world's most renowned tax lawyer, super famous guy, most brilliant person I've ever met to this day. Love him to death, but was really a giant to grow up in.
And he had a fascinating career. He's passed away. I'll get to that part of the story. But he really fascinating career representing a who's who of corporate industrial America and across the world. His fingerprints on all the estate planning that most planners continue to use today. So again, just really interesting. He ended up going into the venture capital space. My brother ended up joining him in the venture space.
And so we were, I would actually say, given your background, we were probably in those days, much closer to angel investors than professional venture capital investors. We made that transition at some point and had a couple of venture capital funds. And my brother joined him, my dad on the venture side, and I became a corporate securities lawyer. So coincidentally, by the way, but ended up doing a lot of the work for our family and our venture funds and our portfolio companies. And that went along all pretty nicely for about 15 years. And with the three of us loosely working together, my dad and I were at different law firms in Chicago and my brother was in Washington, D.C. and. And then in 2000, unfortunately, as these things go, we found out my dad had cancer and was going to pass away.
And so we had, as I'm sure we'll come to in this conversation, a tremendous amount of complexity surrounding our families, our family. And I guess it's families because we were three generations and three branches of the family. So families, I guess, but one big family. And. And so I left my law practice to come essentially work exclusively for my family and to help us navigate through all of this. And that ultimately led me very different path than I expected to. I loved. I'm not one of these people who walks into a room and says, I'm a recovering lawyer.
I actually liked being a lawyer. I loved advising clients both on the security, the corporate side and the security side. And obviously you've got a deep background on the security side of that. And so for me it was a big detour on my path to say, oh, I'm going to leave and go into the family. And that set me off in this whole new family office arena, which are words that I think I would have said back then. I didn't know how to spell, let alone what they meant. Right. And I got introduced into the whole family office world and the idea of lifelong learning and family dynamics and all the things that come along with this.
And here I am some 25 years later, still doing it.
Marcia Dawood: Amazing. So I remember you telling me that your dad had all of these clients, but then they become friends and then in some cases they ask him, hey, do you want to be in on this deal? And all that. So, so tell us a little bit more about those stories.
Josh Kanter: Yeah, so really incredible. And I don't think I'm. Most of this is on the Internet. I don't think I'm saying anything. I'll try not to use any names that I shouldn't use. But he was very close friends and client. His clients were people like the Pritzker family and Sam Zell and Mel Simon of Simon Properties and Chuck Dolan of Cablevision. And so this really fascinating kind of group of icons or titans of industry of that era.
And some of them still. Right. And to your comment, yes, A lot of these people were either offering him an opportunity to co invest. So in those days, certainly angel investing in a sense. Right. To co invest with them in some of the things that they were doing or asking him to help them raise money for certain things they were doing or even frankly using tax structuring as the fundraising vehicle of some of these things. So I think if you go back to the early origins of Cablevision, which was the country's first and probably at the time most important cable network or cable system, it was all, all the money was raised, I think through essentially tax structured financing. So really interesting.
Anyway, so my dad ends up in all of these different kinds of deals. And so of course then later when I come into it and they're picking up these balance sheets all over the place. There's, oh, there's, we have this tiny interest in a real estate Deal from Sam Zell here and from this one there and from that. And it's just, it's just incredible. He ended up involved in the film industry and the recording industry. He was instrumental in bringing Second City to Chicago from when they couldn't open because there was Cabaret tax that they were. Because they were live theater in Chicago at the time. So just the stories and the things that we were.
Had interest in Ticketmaster. I just crazy pedigree of or portfolio of things that he was involved in in our first venture fund. And my dad also, he's really, he's the most brilliant person I've ever met. And I think that the venture industry went through this from I guess what I would consider as generalist to specialists. And now maybe we're trending back toward generalists or something. But in his day he was definitely a generalist. We had a pasta manufacturer in New Jersey, we had a chip manufacturer in San Jose, California that made the first guidance chip for the cruise missile. So it was like across the spectrum, crazy number of things.
Like just so cool.
Marcia Dawood: Amazing.
Josh Kanter: Yeah.
Marcia Dawood: So, all right, so then your dad gets sick. It's what, 2000?
Josh Kanter: Yeah, yeah.
Marcia Dawood: And you have time with him though before he passes to maybe start to get a handle on all the things he was involved in.
Josh Kanter: Yeah, that was so the good news, right was, was we had some time. So he, my, my dad passed away of cancer. And so unlike the heart attack at the desk or whatever or the bus or the plane or anything else, we got some notice and so we, we thought we had six months notice. I actually ended up getting 18 months with my dad before he passed away. And, and from the day we found out he was sick, he was 70, so he was still, I would say young. Deal junkie, globe trotting. This is a guy that Concord was flying. This is the guy who thought London was a day trip.
Really crazy. And we knew there was so much complexity around our family. We were filing 750 tax returns a year for our family alone. We had five full time accountants who were doing nothing but file tax returns. We had obviously a complicated balance sheet because a lot of these interests frankly at the time were small. Right. These weren't my dad. A lot of this stuff goes back to the 60s.
My dad is 10, 15 years out of law school. So he's getting little pieces of lots of things. And you obviously, again as an angel investor, know how you quickly accumulate lots of small pieces of lots of little things.
Marcia Dawood: That's right.
Josh Kanter: And it's a lot to keep track of and back in those days too. Remember, there's no portfolio aggregation, there's no QuickBooks, there is no add a par. None of this stuff exists. Right. So it's just balance sheets all over the place and whatever. And then we were in the middle. The irs, shall we say, was not a fan of my father's. And so we were in the middle of what would turn into a 33 year battle with the IRS.
Went up to the US Supreme Court, started in 1979. My dad dies in 2001 and the case continues until 2012. So 33 year battle with the IRS. So anyway, all that to say I left my job as soon as we found out my dad was sick because we did have an understanding of the complexity that this was going to result in. And I spent 18 months with him literally every day. Now obviously that's a lot of doctor's appointments and a lot of he's dying of cancer. There's a lot of bad days in there. Right.
But the thought was that I would get this tremendous education about what I needed to know. And I've got two siblings, so there's three spouses, the three of us, three spouses. My mom was still alive at the time. There's grandkids. And I thought I would get everything I needed. And within, I like to say within minutes of his death. That's obviously not minutes of his death. Within minutes of his death.
The lawyers are asking me questions, the accountants are asking me questions, family members are asking me questions. And I'm quickly realizing how little I actually know. And that was this huge wake up call to say, frankly, oh my God, if I don't know, and I'm a lawyer and I took my dad's estate planning class in law school and I just spent 18 months with him. If I don't know, who knows?
Marcia Dawood: Right?
Josh Kanter: And that's a problem.
Marcia Dawood: That's a problem, yes.
Josh Kanter: And I think it's a problem at levels of far less complexity. Like I tell my story and it people's eyes balls out of their head. Like when you say 750 tax return spite people don't, I would say, give credit to how complex our lives really are. And it's not about zeros, it's about complexity. And if you're a family that owns a couple of homes and has a couple of kids and has a couple of cars and has a couple private investments and has a couple insurance policies and maybe a trust or two and you start thinking about all the connection points. We are wildly complex. And that's not just a United States thing. Right.
That's a worldwide problem. Right. Complexity. And you've said to me in one of our conversations, like, technology is just making that, it's making it better, but it's also making it worse.
Marcia Dawood: Right.
Josh Kanter: It's just now think about how many accounts you have. And anyway.
Marcia Dawood: Yeah. How you get into those accounts. How would somebody get into those accounts if you weren't around? And. Yeah. So that leads you to start thinking, hey, we need a better solution for this.
Josh Kanter: We need a better way. Yeah. So really, right after my dad died and I. I have this, that's probably the year or two after his death and I'm having this epiphany of again, oh my God, I don't know anything. And now I'm the one, I don't want to say in charge because my brother, sister and I are like equal owners of the Cantor enterprise, if you will. But I'm the one in charge. Right. I have the most information.
My brother ran our venture capital arm, but pretty much everything else falls into my kind of portfolio, if you will, of work. Right. And so to your point. Yeah. We just said there's gotta be a better way. So 24 years ago, we start building this thing that at the time, I call it the family owner's manual. And you probably remember the old adage of, you get an owner's manual with a toaster and not with a kid. Oh, right.
Guess what? You don't get one with a family of wealth either. And so how do you build an owner's manual for a family? So this was not in a case of emergency file this, that had a few documents and a few contacts and stuff. This was an owner's manuals. How do you pick this thing up and make it work? What do we do? How do we do it? Who do we do it with? Why do we do it that way? Where do we do it? Anything you could imagine. And how does it all interconnect? And so we started building that for our family and did that for years. And family members had a copy of it and trustees and executors and advisors could pick it up and read about it and understand our family in a way that was much more comprehensive than you would ever get in kind of a single conversation or, or forgetting to share details. And that if I Fast forward that 20 years after having taken a number of families through this process and realizing this was a universal problem. Right.
There are no solutions for the complexity. There's great solutions these days for consolidated general ledgers and for portfolio aggregation and for alternative investments and all the hard data, if you will. But nobody had really tackled. And of course, there's a million digital vaults in the world. Right. But nobody had tackled this idea of how does it all fit together? How do you look at the tapestry of all this information together? And so four years ago, we set out to say, how do we help as many people as we can in this problem? Because again, I'm going to say it's about complexity, it's not about wealth. And that became this product leaf planner that you alluded to, that we decided to go build this as a repeatable process that anybody could take advantage of and learn from.
Marcia Dawood: Yeah. I remember one of the stories you told me before was, and you don't have to say any names, but there was an investment that your dad had made years ago, 50 years ago almost, and then it was nothing. And then all of a sudden it became something. But, like, how would you even know? Like, how did he. Why did he make the decision? Who invited him into the deal? There's so many things, like, we all think about, oh, well, you just need the paperwork. You need the paperwork to prove that you made this investment or whatever the story is. But there's actually so much more to it because you just don't even know who it could transfer through all kinds of different people that are administering. There's so much complexity just to one.
One investment, let alone lots of them.
Josh Kanter: Yeah, yeah. And I think there's. So that, to me, is really about how do you contextualize all this stuff? Right. And again, my dad, in some ways, I hate the word unique. So, like, he's not really unique. There's a lot of complicated people in the world who have lots of different moving parts. But again, I'm going to say we all have more complexity than we likely give credit to. But to the example that you're talking about, and there's a couple of them that I think are really interesting.
There's one, for example, where we say, you put it in my head not to use names, so I won't use names, but we get a check. My dad was involved in a particular project in San Francisco in 1970. We get a check from that project every year. And since 1970, so now it's 55 years later, we're still getting a check.
Marcia Dawood: Amazing.
Josh Kanter: This is with a major US Corporation. Right. We're a tiny. Like, it's a knack to these guys. Right. But that check has to show up every year. We don't do anything. We just get, get the check.
It's like clipping a coupon, right? And so within our leaf planner, within the owner's manual was a how did we get into this deal? Who are we in this deal with? Who's on the lookout for this check? Because you can imagine over 55 years, there's a couple of years where the check didn't show up. Or think about the personnel turnover at that corporation, right? Who I don't even know who to call anymore. And they have probably tens if not hundreds of thousands of employees. So how do we, again, to your point, cut and track all of that? The example that you were talking about, which is a story that I just love, is when I took this over and was collecting kind of all these balance sheets from all these different entities. One of them, there was like a K1 interest on the balance sheet because we were all tax based, right? I mean, everything was tax information. So on the balance sheet is essentially the K1 value of, I think it was $8,000. So one is, it's good it didn't get lost because I don't mean to demean $8,000, but it's like, okay, I could have easily lost track of that. So I'm coming in again in 2001.
This was a real estate deal. And back in those days, I don't know if people still do this, but back in those days, right, People did nested partnerships in real estate deals. And so we were three partnerships deep in the deal. We had no transparency to what this deal was about, who the real partners were, anything else. We're just like this tiny piece of this tiny third level. It's on the balance sheet for $8,000. And so I keep saying to people like, you could imagine an unscrupulous partner coming to me. And this just goes back to trust, right? Who do you trust? Who did your dad trust? So this, I could see the fictional, unscrupulous partner coming to me and say, hey, Josh, I know you're carrying that for $8,000.
Do you want 50 grand to make that go away and clean it up? And I could easily see saying, that'd be swell, right? Probably great. And in fact, our not unscrupulous partner, our very trustworthy partner came to us, I don't know, I think it was like two years ago and said, hey, you probably don't know anything about this partnership because it's three partnerships deep. This was a real estate deal that your dad and me and some third guy put together. And now it's 50 years old. And we needed to either sell it or rehab it. So we decided to sell it. And by the way, your little $8,000 K1 interest was worth $1.5 million.
Marcia Dawood: Oh my gosh.
Josh Kanter: And it was like, oh my God, we had no idea. And so it's again, it's not only how do you not lose track of all these little things, but how do you again, how do you contextualize it with the who do you trust? Who do you not trust? We have, we're art collectors. We have a deal at one auction house. Very different than a deal at another auction house. Like you could figure that out if you read all of our consignment agreements. But who's going to think to do that if I don't leave a proverbial post it note on the art collection saying don't forget. Right. In big flashing lights.
So it's yeah. This notion of how do you capture not as you're saying, not just the documents. I always argue like people will find the documents. That's almost the least of my concerns.
Marcia Dawood: Right, right.
Josh Kanter: It's how do I say I did this deal because I went to college with this guy, but oh God, don't trust him when he shows up on your door or God forbid, don't do the next deal with him.
Marcia Dawood: Right, right.
Josh Kanter: Or whatever it is. Right. There's so much context that people don't think about.
Marcia Dawood: Yeah. We as angels, we dream about the $8,000 turning into life. That's all we dream of.
Josh Kanter: Exactly.
Marcia Dawood: Someday.
Josh Kanter: Exactly.
Marcia Dawood: Oh my gosh. But you're right, there is so much that people don't think about. Just when you were saying that little bit about art, I think as we get, as we start to accumulate other alternative assets, a lot of times people are thinking, oh well, I have a brokerage account, I own public stocks, or I have a 401k and it's now on an IRA or whatever. The story is. Like those things are pretty, they're not simple, but they can be simpler than if you have private investments where you really have to keep be keeping up with who's managing this, where am I going to get information from? Are there updates? What happens if there is a liquidity event? How will I actually find out about it? Where will the money go? How will they know who to contact? All those things, especially if many years have passed. Right.
Josh Kanter: Yeah. And I think even the brokerage accounts is interesting. Right. Because again, given the level of complexity that we all manage, your 401k is somewhere and your IRA is somewhere and you're right. And all of a sudden you realize, does my wife really know all of that? And is it really aggregated somewhere? And would she have access to it even if she knows that it's there? And I'm sure you've been through enough experiences to know what a problem it is if you actually don't have access set up and things like that. And then, and to your point, whether it's on the angel investing side, and you've probably been in a situation where you've been asked to join a board as an angel investor, and maybe you were given a stock option granted. And maybe that stock option grant has to be exercised within a certain period of time after your death, if you were to die. But that's not, you're probably not maintaining a system that is your family going to know, oh, somebody's gone, and now I've got X period of time to exercise a stock option grant.
Or I was on a call on a leaf planner call with a gentleman who was sitting in front of a bookcase like you are, and accept that instead of being an author, he was a collector. And he literally says to me, while we're in this kind of conversation, nobody in my family would know which of the books behind me is the first edition, such and such, and which is the $29 book that came from Barnes and Noble. And if I don't tell them, they're going to box it all up, take it to the library or Goodwill, right? And there goes the $10,000 first edition.
So again, there's just, there's endless examples. When my dad died, I found an undated safe deposit box receipt that had no date and no bank name on it. And I'm like, to this day I jokingly say, I don't know if there's a million dollar gold. With gold now at $4,000 an ounce, maybe it's $4,000,000. I don't know if there's a million dollars of gold sitting somewhere.
We're juice from Eastern Europe, so I know it's not family recipes. I have no idea if there's a safe deposit box out there somewhere that we'll never find. It's just, it's so crazy.
Marcia Dawood: That's crazy. And so we're talking about a lot of things that are at a very finance level and stuff like that. But a friend of mine went through something recently and like all of the things that she was trying to get information from related to her mother's and for her, not her estate, because she wasn't, she hadn't passed yet, but she was in a coma, couldn't communicate. So all of the things that were related to her life, they couldn't even. They didn't even know the WI FI password to. Once they were in the house, they couldn't get into any of her accounts. They didn't know if the H Vac had ever been updated. There are just like so many things that people don't really think about, related to our everyday life that I know when my H Vac was last updated, I.
But how would anybody else know that? Because maybe if I. But they. I'd have to tell people who the company was.
It's just. There's so many details, right?
Josh Kanter: There's so many details. And very much to that point, like I'd say it's both. It's the detail side of it and then it's also the storytelling side of it, right? And on the storytelling, I want to come back to the details, but on the storytelling side, I shared with you, for example, a story of There's a. My parents were art collectors. We're now art collectors. There's a sculpture in my front yard I love, isn't worth anything. It means the world to me because it was a close friend of my parents. That sculpture was in my parents driveway in suburban Chicago for my entire life and now it sits in my driveway.
And so I'd like to say I see it every day, but I don't leave the house every day like any of us post Covid. But when I leave the house, I see it, right? And I think about my parents. So that story, how do I capture that and share it? And so Leaf Planner again is designed to. And the owners may not care if it's Leaf Planner or not, but the owner's manual idea was how do you capture that EQ as well as the iq, right? How do you capture. Why did you choose me as your trustee? Why did I make one of my kids? I've got two kids, so this story doesn't work. But why did I make one of my kids the healthcare power holder, one of my kids, the power of attorney holder and my third kid who I don't have is nothing, right? How do you share and be. And I'll say all the time to people like you don't end up on the front page of the New York Times and the Wall Street Journal 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 understand what mom and dad did and why they did it.
Marcia Dawood: Yeah.
Josh Kanter: And then the detail signed, really, to your very story. We had an early client who. Exactly. The situation you're describing. Right. Somebody. It was a. He had agreed to be the trustee and executor for a friend.
The friend went in for some surgery, routine surgery, went bad, ends up in a coma. So to some extent, I hate to say, the bad news is he's not dead. So now you've got this, like, limbo situation. Right. Which you understand how troubling, how difficult that is. Like, people also tend to focus on, I'm alive or I'm dead. Well, there's a lot of middle ground. There's a whole different set of problems.
But anyway, he goes into this guy's house, and almost, I'm going to say, worse than the not knowing the WI fi password, he sees three checkbooks in the kitchen. So first of all, who has checkbooks anymore? But he's got three checkbooks in the kitchen, and it's Covid. So he has to make an appointment to go in to see the banker on one of these checkbooks to try to figure out, like, I'm now the power of attorney on this guy. It takes him six months because it's Covid. He gets an appointment. He goes to see the banker, and the banker says, thank you so much for making an appointment and waiting six months to get in and see me. That account was closed three years.
Marcia Dawood: Oh, my gosh.
Josh Kanter: So talk about the just sheer waste of time and mental energy.
Marcia Dawood: Right.
Josh Kanter: And.
Marcia Dawood: Yes.
Josh Kanter: Just. Yeah. So to your point. Right. I mean, it's just. It is endless details. It's endless access, and it's endless questions that we don't. When people are gone, you can't ask those questions anymore.
Marcia Dawood: Right. Right. Yeah. When my mom got sick, she had ALS for two years before she passed. And toward the end, she couldn't really communicate with. And then there's also the thing that a lot of people don't think about, too, which is when I knew that I had a limited amount of time to ask her questions. When I started to ask questions like, who gave you this? Or where did this come from? Or whatever it would get her. She would get so upset that she didn't want to talk about it.
And then I'd be like, okay, well, I need to know, and I want to know before something bad happens. So. But it was, like. It was very challenging. I can see there's the emotional part for the families can be very bad.
Josh Kanter: Yeah. Yeah. I think that's so true. And I think that we've spent a lot of time within Leaf Planner. And again, I did this owner's manual concept for 20 years before Leaf Planner existed. So it can be done. Right. It doesn't require Leaf Planner.
But the idea was to say we don't want people to think about this essentially as a death product because. Exactly. For the reason one, either that we don't literally want people to die, and then that's when it's valuable.
Marcia Dawood: Right.
Josh Kanter: But putting people in a position to have conversations like you and your mother had to have at a time when that may be uncomfortable or remind people about death or anything else is sad. Right. It's not necessarily what we want to do. And we've really worked hard to make this an idea that people understand. This is about life management. It goes back to your comment about the H vac. This is as much about making sure that I remember to get the boiler checked as it is to make sure that if I'm dead, my wife knows who to call to make sure. Right, Right.
Right. So the more we can get people to think about. This is about your daily life. This is about the deal that you did yesterday. This is about the check that you should be collecting next week or reviewing the insurance policy or whatever it is. Right. That this is an active life management process. It's not about preparing somebody for death because nobody wants to look.
That's human nature. Why do most people not sign their estate planning documents?
Marcia Dawood: Yeah.
Josh Kanter: Because they don't want to admit they're going to die.
Marcia Dawood: That's right.
Josh Kanter: Right. And so. And this is the same thing. So we want to make sure people understand this is this process, and it can be. It can bring families really close together because you are getting to tell that story, and you're getting to tell that story at a time when it doesn't feel like it's being driven by an event like in your mom's situation, which. Which just focuses on the event and I'm so sorry.
Marcia Dawood: Yeah. In fact, I just thought of a story the other day after we talked before. My mom had. I had a pair of earrings made for my mom when I got married, and they were from a clasp in a bracelet that had been my grandmother's. Absolutely worthless to anybody else. Right. But to us, because it had been passed down in the family, and now I had it made into earrings. Awesome.
Right. My dad didn't know. Hopefully he won't listen to this episode. So my dad didn't know that those were the earrings that had the sentimental value. And what does he do? He takes it and gives it.
Josh Kanter: Oh, no.
Marcia Dawood: Yeah. So there are certain things that I was like, oh my goodness, nobody knew the story. Right, so. Right, it does matter.
Josh Kanter: Yeah, it sure does.
Marcia Dawood: Yeah. So what are some. If you had to give three pieces of advice to people right now, like what should they start to do in order to make. Get to a little bit more clarity with all of this?
Josh Kanter: Yeah, that's a great question. I think I, first of all, I'd say take a deep breath because this can feel overwhelming.
Marcia Dawood: Right.
Josh Kanter: It's something that can happen over a very long period of time. Right. I would say think about this first and foremost. Again, as we've been talking about from the contextual side of it, what are the stories that matter? What matters to you? Not where. The documents. Yes, again, that matters. But like where are the documents? What's it worth? Think about what do people really need to know? What's meaningful? So again, maybe putting in that human or emotional intelligence into the equation. If you're going to do something like this, whether it's with leaf planner or otherwise, start with something that you feel comfortable with.
Don't start at the hardest thing, start at the easiest thing. Right, right. There's some people who are really comfortable around their balance sheet. There's some people who are really comfortable around their estate planning or something. They collect. Start with your house and your car, like it doesn't matter. Start easy, it doesn't have to. And then you can build in.
I keep saying that the best way to do this, we always talk about peeling the onion. I don't know what putting the onion back together, but think about it as building the onion back together. So start easy, start with things and involve your family.
Marcia Dawood: Yes.
Josh Kanter: I think this can be a really rewarding thing to do for families that have wealth. It's actually a tremendous way. Families of wealth, I would say, are always looking for ways to get that rising gen engaged in their wealth and their. And so this is a really, actually brilliant way in my view of getting people engaged. But even if it's not about the wealth, if it's just about the stuff.
Marcia Dawood: Right.
Josh Kanter: It's a great way because I say all the time, if this is going to take me 20 hours to put together, it's going to take my kids 200 and my kids are going to be raising their own kids and buying homes and in their first jobs and whatever else that they're doing in their lives. And the last thing I want to do is Burden them with the complexity of my life.
Marcia Dawood: That's right.
Josh Kanter: And so think about it as a gift that you're giving to your family and use it. I don't know if I came up with three, but I'll stop there.
Marcia Dawood: No, that's excellent. Yes. Because it can be very overwhelming. I could see where people be like. And then just to your point about the estate planning, I remember we went through it and then the conversations you have to have, like, for all of the scenarios that they make you run through, and everybody's, oh, I don't want to think about that. But when kids are younger, it's, I think, something you're forced to think about because you're like, oh, dear, I need to make sure you're taken care of. Right. Who's going to take care of them? And all that kind of stuff when they're younger.
But then as they start to age, then you get to a point where you're like, okay, what happens once they turn 18? What happens once they would turn 25, 35. Like, all of these things, like, you're trying to think ahead into the future, but all of you know, can all be very daunting.
Josh Kanter: Yeah. And I don't want to. I was never practicing trust an estate lawyer, and I am not one. I would remind everybody, first of all, it's interesting because I would say most people first get tripped up, as you were alluding to, because they can't decide on the guardian. And so when kids are little, nobody signs their estate plan because they haven't decided who they want to be the guardian. And then as you're saying, as kids get older now, you gotta make some really hard decisions about how you want things divided up or whatever else it is. But what I keep trying to remind people is every state in the country has an estate plan for you if you don't do one. And so it's not that you don't have one.
What I can promise you is you don't have the one you want. Utah or Illinois or wherever you are has got a plan for you, and that's what you're going to be stuck with if you don't do it. So sign the documents and you can almost always change them. Better to change them than not having signed them to begin with. But anyway, yes, my push for estate planning for people.
Marcia Dawood: Yes, excellent advice. Well, Josh, thank you so much for coming on the podcast today and sharing all of this great wisdom with us and all of your fun stories. And we will definitely put all the links in the show notes so that people can find you and they can find Leaf Planner.
Josh Kanter: Awesome. Thank you so much for having me.