The WealthTech Podcast

Creating the Owner's Manual for Your Family | Josh Kanter, leafplanner

Mark Wickersham Season 2 Episode 13

What if your family had an owner’s manual?

In the latest episode of The WealthTech Podcast, we sit down with Josh Kanter—family wealth executive turned fintech founder of leafplanner—to explore the personal story that inspired him to build a tool that helps families preserve and share critical knowledge across generations.

Josh shares:
✅ Why information—not just data—is the missing piece in wealth transfer
✅ How leafplanner helps families prepare for succession, not just react to it
✅ What advisors need to know about delivering true “family office services”
✅ The role of transparency, complexity, and emotional intelligence in legacy planning

As always we end the podcast on a personal note with three questions that have nothing to do with wealthtech.

🎥 Watch on YouTube: https://youtu.be/4-qabV4ONUc

About Josh Kanter

Josh started his career in 1987 as a lawyer focusing on corporate and securities law, mergers and acquisitions, real estate, venture capital, private equity, bankruptcy, commercial lending, and more. 

Josh founded leafplanner, a digital document and information sharing platform designed to replicate the creation of his own family’s “owner’s manual,” a tool to identify, collect, organize and communicate information from the disparate parts of a family’s ecosystem in order to identify blind spots, share information, educate family members and advisors, and provide a more holistic succession of information for families. 

Josh received his J.D. from the University of Chicago in 1987. He earned a BA/BS in Economics (magna cum laude) and Political Science from Emory University in 1984.

About leafplanner

Humans aren’t as good as we think at identifying unknowns. leafplanner enables your family to get and stay organized, educate family members and advisors, and discover planning gaps that could influence your family’s desired impact, both financial and non-financial. Whatever your goals may be, taking a proactive approach presently and in the future is imperative to allow you to focus on what matters most. 

About The WealthTech Podcast:
The WealthTech Podcast is a bi-monthly interview series hosted by Mark Wickersham. Each month we present conversations with various industry leaders that focuses on the challenges family wealth firms face with technology, people and process. The podcast is produced by Brad Oliver.

The WealthTech Podcast is brought to you by the generous support of Risclarity. Risclarity fills the technology gaps family wealth firms face when serving the complex needs of ultra-high net worth families.

Disclaimer
Information provided is for educational purposes only. Opinions expressed and estimates or projections given are as of the date of the presentation there is no obligation to update or provide notice of inaccuracy or change.

The WealthTech Podcast Transcript

Host: Marke Wickersham

Guest: Josh Kanter, Founder leafplanner

00:00:34.010 --> 00:00:55.240

Mark Wickersham: all right, Josh, it is great to have you on the podcast. Thanks for coming on. It's been, I've enjoyed kind of getting to know you, since we've done that panel. And I think you have a really interesting story and background. I think there's gonna be a lot of great information in this, podcast would you mind kind of giving a brief introduction of yourself and leafplanner.

00:00:55.850 --> 00:01:03.369

Josh Kanter: Sure, thanks, Mark and I very much enjoyed getting to know you as well. The panel was a lot of fun, and thank you again for having me on the podcast

00:01:03.590 --> 00:01:11.879

Josh Kanter: so I think we'll get into a little bit later. Maybe the story behind leafplanner itself. So I'll, I'll do more of a kind of service level. But

00:01:12.390 --> 00:01:19.440

Josh Kanter: I started my career as a lawyer, mostly corporate and securities kind of work, and in Chicago, and then.

00:01:19.690 --> 00:01:23.750

Josh Kanter: for reasons that I'm sure we're going to get into ended up transitioning

00:01:23.940 --> 00:01:30.020

Josh Kanter: into a family office role with my family, which was a 3 generator, or is a 3 generation, 3 branch

00:01:30.350 --> 00:01:35.179

Josh Kanter: family, and so kind of had a family office career in there, which I still do, and then

00:01:35.400 --> 00:01:38.489

Josh Kanter: decided that I really liked helping other families, and so

00:01:39.090 --> 00:02:01.370

Josh Kanter: started a small consulting practice, helping other families as well. And then leafplanner is sort of the latest iteration that brings many of these things together, as I'll hopefully describe in a few minutes and leave Planner itself is really the idea of creating an owner's Manual for a family or a mind map, if you will, of all the things that families really need to know. So think about

00:02:01.630 --> 00:02:06.479

Josh Kanter: executors and trustees and rising Gen. Family members and spouses and partners and

00:02:06.590 --> 00:02:08.979

Josh Kanter: outside advisors, all of whom are

00:02:09.250 --> 00:02:20.530

Josh Kanter: have some piece of the puzzle, but nobody, except usually well, I'll actually say nobody has the full puzzle, because there's always information sharing between different people, whether that's

00:02:21.100 --> 00:02:24.980

Josh Kanter: spouses and partners, whether that's property managers or

00:02:25.080 --> 00:02:50.180

Josh Kanter: chief financial officers or executive assistants, or, again, outside trustees, executors and advisors, and all these things. And so leafplanner is really a platform designed to help families bring all of that information together, share it, learn from it, look for blind spots, educate family members manage workflows, and then ultimately, of course, really efficiently manage successions and transitions.

00:02:51.923 --> 00:03:07.240

Mark Wickersham: I'd love to talk to founders about their founder journey, especially when that when it's kind of born out of a an experience within the family office. You don't see it often. It could be difficult to commercialize

00:03:07.768 --> 00:03:11.990

Mark Wickersham: products, as you know that the software business is a bit of a messy business, and

00:03:12.130 --> 00:03:30.549

Mark Wickersham: you don't normally fit the mold of a young entrepreneur. So I'd love to hear about your founder’s journey, and how you kind of started leafplanner, why did you start leaf, planner? What was the experience like? And then also just kind of looking back on your kind of founders. Journey. What have you learned.

00:03:31.110 --> 00:03:49.730

Josh Kanter: Yeah, I appreciate that. So obviously, I don't know if we've never talked about whether there's a video component to this or not. And so anybody who maybe sees me obviously will see quickly that I am not the young 30 year old entrepreneur probably don't sound like it either. So to your point, you know it's definitely a different journey

00:03:49.730 --> 00:04:02.009

Josh Kanter: coming at this much later in life than earlier in life. And I'm not the serial entrepreneur who's just been doing this over and over again. So you know, I mentioned the idea of the Owner's Manual a second ago, and

00:04:02.580 --> 00:04:13.769

Josh Kanter: I know you've already heard this joke, but hopefully your listeners have not, and remembering the old adage of you, get an owner's manual with a toaster and not with a kid, and about 25 years ago.

00:04:14.196 --> 00:04:24.420

Josh Kanter: As I said, I was practicing corporate securities law, and we found out fairly suddenly. I mean, these things are always unexpected, right. But we found out suddenly that my dad, who at the time was 70,

00:04:24.880 --> 00:04:37.620

Josh Kanter: had a cancer and was going to die, and I would say my Dad was kind of the quintessential patriarch of the family. He was a brilliant tax lawyer world, renowned, represented a fascinating set of characters and

00:04:37.800 --> 00:04:44.049

Josh Kanter: multifamily multigenerational wealth and in different industries, and across America and across the world.

00:04:44.190 --> 00:04:59.260

Josh Kanter: and then had turned into the venture capital business. And so we had a wildly complicated balance sheet. We had a wildly complicated enterprise structure. We were filing 750 tax returns a year. We had a small staff of accountants who were doing nothing but file those tax returns.

00:04:59.650 --> 00:05:01.680

Josh Kanter: We weren't boiled in. What would

00:05:02.220 --> 00:05:17.240

Josh Kanter: end up turning into a 33 year battle with the Internal Revenue service that went to the Us. Supreme Court. Just really, you know, a mess and a half, and finding out all of a sudden, of course, again, that my dad was, had cancer and was going to pass away. I left my

00:05:17.600 --> 00:05:29.350

Josh Kanter: private practice to come essentially help my family figure out. How do we navigate through all of this, and in that process, and I've got I mentioned we're 3 branches, so I've got a brother and a sister, and my mom was still alive at the time as well.

00:05:30.400 --> 00:05:35.350

Josh Kanter: and as I was as we went through this process I ended up spending 18 months with my dad.

00:05:35.850 --> 00:05:59.319

Josh Kanter: I'm a trained lawyer. I took his estate planning class in law school, which is a huge mistake for a whole host of reasons. But nevertheless I did, and ended up again with that 18 months with him, I would say, most families don't have somebody with the capacity that I do. And I don't mean that, obviously, egotistically, it's just, you know, by luck of training, and most families don't get 18 months of notice and time to prepare for these things.

00:05:59.480 --> 00:06:01.460

Josh Kanter: And yet I was really in the dark.

00:06:02.170 --> 00:06:14.100

Josh Kanter: and so realizing that I was in the dark, and if I was in the dark, what did that say about my mom, my sister, my brother, my wife. You know my kids weren't born yet, but ultimately my kids. And and what does that really say? And so

00:06:14.330 --> 00:06:18.059

Josh Kanter: one of my 1st reflections was, there's got to be a better way to do this.

00:06:18.110 --> 00:06:27.540

Josh Kanter: And so we started building for our family. Now I guess it's 23 years ago an owner's Manual, and the idea, again was, how do you better

00:06:27.570 --> 00:06:54.219

Josh Kanter: educate family members? Engage them, empower them. How do you bring together? What do we do? How do we do it? Where do we do it? Who do we do it with? Why do we do it that way? So I'm sure you know, you certainly are familiar with the old in case of emergency file, and those are great, like I, jokingly or disparagingly sometimes say, you know, that's cute, but those are great. You should have that. But that's only going to get you so far as opposed to all the context and emotional intelligence that goes into these things.

00:06:54.350 --> 00:06:57.020

Josh Kanter: And so that's what we built for our family. And then

00:06:57.510 --> 00:07:01.339

Josh Kanter: did this for a host of other families through my consulting career.

00:07:01.560 --> 00:07:09.899

Josh Kanter: And ultimately, I'm really one of these kind of happenstance conversations at lunch one day, and somebody said to me, Why don't you turn that into a platform?

00:07:10.050 --> 00:07:12.179

Josh Kanter: There's nothing like it in the industry.

00:07:12.420 --> 00:07:16.680

Josh Kanter: and I was like, Oh, well, that's a that's a cool idea. And unfortunately I had a

00:07:16.820 --> 00:07:36.516

Josh Kanter: colleague at lunch with me because I would have again being at that time I was 59, so I would have easily said, Oh, that's a cute idea. I should do that. And then that would have been the end of that conversation, and a colleague at lunch really kind of pushed me to do it. And so that became leafplanner. So it's now this platform that's been live for.

00:07:37.540 --> 00:07:40.770

Josh Kanter: I guess we're about 3 and a half years with clients.

00:07:40.970 --> 00:07:47.230

Josh Kanter: and the goal is to help as many families as we can, and let them kind of go through the same process.

00:07:48.060 --> 00:07:57.860

Mark Wickersham: Yeah, I really do think leafplanner is unique. I mean, do you have a sense of what kind of category would fit in? I don't know if it does. But do you.

00:07:58.110 --> 00:08:18.730

Josh Kanter: It's an interesting question. To some extent. I kind of think we're creating a category. And when I say that I mean I don't, it's hard to obviously say there's so many things out there. So I would say, we're not really strictly a digital ball. Obviously, there's a million digital vault products, whether they're specialized products or whether they're.

00:08:18.960 --> 00:08:23.529

Josh Kanter: You know the box and dropbox or Google drive, or onedrive, or any of these kinds of things.

00:08:23.960 --> 00:08:34.527

Josh Kanter: There. We were part digital vault. We're part. CRM, we're part relational database. So ultimately I would say, no, there's nothing really specifically like it. What I like to

00:08:35.260 --> 00:08:59.410

Josh Kanter: if I had to define the category. I guess you know, we've gotten used to there being this idea of data aggregation which, typically, in my view means portfolio reporting, or, you know, financial aggregation, whether that's on the GL side or the portfolio side. I look at Leafplanner as sort of being the corollary to that is information, aggregation. And so it's really everything about your family

00:08:59.530 --> 00:09:04.030

Josh Kanter: again, all of that context, and bringing it all together in a single source of truth.

00:09:05.350 --> 00:09:09.109

Mark Wickersham: That makes sense. Who is your ideal client profile?

00:09:10.510 --> 00:09:16.819

Josh Kanter: So it's that's a really difficult question for us to answer, because I think when we look at our client base

00:09:17.300 --> 00:09:28.840

Josh Kanter: right now and you know, again, we've been around for about 3 and a half years. So we're starting to really see some trends and kind of who our clients are. But the reality is, it's all across the board. We see

00:09:28.970 --> 00:09:43.459

Josh Kanter: everything from kind of the mom and dad and some kids in the high net worth category, certainly an abundance of families that are in sort of the ultra high net worth category. And then even really significant 1 billion dollar plus family offices. So

00:09:44.320 --> 00:09:57.089

Josh Kanter: to me, the common denominator, if you will, is about complexity, and it's really about a desire again, to kind of educate family members, and to for people who are

00:09:57.730 --> 00:10:08.452

Josh Kanter: again. I don't. I don't want this to sound the wrong way, but a little bit more self aware of the problems that families are going to face when there's multigenerational wealth at stake. And so

00:10:09.460 --> 00:10:17.329

Josh Kanter: again, I really look at it as a complexity issue. But it really is anywhere in, you know, kind of the sub 10 million dollar

00:10:17.450 --> 00:10:24.380

Josh Kanter: net worth range all the way to the 1 billion dollar plus range just depending upon the circumstances that family is facing.

00:10:24.820 --> 00:10:36.210

Mark Wickersham: Yeah, it doesn't take a whole lot of significant wealth to add that complexity right in terms of multiple properties, accounts. Different legal agreements. I mean, my wife just

00:10:36.440 --> 00:11:01.919

Mark Wickersham: settled her mother's estate through probate, and it wasn't a complicated estate. But still it's it's a process, and it's complicated. You don't actually know where everything, and she had a plan. Chance to plan with her mother. A lot of folks don't have that opportunity like you did, or she did, and are suddenly left with trying to figure figure out what's going on. What are some without naming names? Kind of how wealth transfer could kind of

00:11:02.620 --> 00:11:11.180

Mark Wickersham: go wrong, and and how you know, maybe a client success, story or 2 with with how leafplanners help kind of prevent some of those horror stories.

00:11:11.500 --> 00:11:32.909

Josh Kanter: Yeah, so it really is. Again, it's the stories are all across the board. We've seen family offices use leafplanner as a transition tool between a retiring executive and an incoming executive. There have been a couple of instances of that that's been super cool, and there's 1 family in particular, one family office in particular, that I, every time I see him. The incoming guy.

00:11:32.960 --> 00:11:51.499

Josh Kanter: you know, keeps telling me how much it accelerated the learning curve for him as he came in, which is so great. We've seen rising Gen. Family members take on leafplanner as a wealth engagement tool. You know. I think families of wealth, obviously, as you well know, are sitting around often thinking about, how do we

00:11:51.650 --> 00:12:00.789

Josh Kanter: engage the kids in this wealth? And sometimes that may be putting the kids on an investment committee, and sometimes it may be doing this, that or the other, or getting them involved in philanthropy or some different

00:12:01.000 --> 00:12:03.530

Josh Kanter: aspect of what the family is up to. But

00:12:04.320 --> 00:12:11.139

Josh Kanter: this was an instant or a couple instances where a rising Gen. Family member again kind of took on building the leaf plan as their

00:12:11.360 --> 00:12:15.780

Josh Kanter: engagement. And then we've really seen a lot of things that I'm

00:12:16.190 --> 00:12:26.510

Josh Kanter: are, as you said, really, the roadblocks or mistakes or problems that come up. So whether that's just finding documentation, although again, I don't want to over

00:12:26.520 --> 00:12:46.310

Josh Kanter: emphasize the value of that. I mean, any digital. Vault will do that. But the reality is, you know, family members who have come across. Oh, we can't find the healthcare power of attorney, or we can't find this, or we can't find that. So there's that aspect to it. There's been a lot of, I'll say again, built into the emotional intelligence. That can really cover a lot of

00:12:46.860 --> 00:12:58.949

Josh Kanter: a lot of different ground. That may be explaining, you know, in my family there's 3 kids at my generation. I'm 1 of 3, right, and so I was named executor and trustee and power of attorney.

00:12:59.090 --> 00:13:06.869

Josh Kanter: and to some extent there was an obvious understanding of why that was the case. Right. I'm the trained lawyer. I spent the 18 months with my dad, etc.

00:13:07.830 --> 00:13:23.649

Josh Kanter: but often we're looking at a situation where a family, or maybe the Matriarch and Patriarch haven't described. Why did you choose this kid as this thing and that kid as that thing? And, by the way, Kid number 3 wasn't named as anything at all, and those are the things that really hurt feelings, and.

00:13:24.010 --> 00:13:36.770

Josh Kanter: you know, leave problems between siblings or the time that goes into these things, as you said, just the administrative burden of of probate. I can't imagine how many hundreds of thousands of dollars I spent

00:13:37.180 --> 00:13:44.910

Josh Kanter: on administrative Bs on my dad's estate, that had I had a leaf plan to be able to say, Boom! Here it is.

00:13:45.330 --> 00:13:47.630

Josh Kanter: and I understand all these pieces.

00:13:48.140 --> 00:13:58.940

Josh Kanter: How much simpler, you know, that would have been so. All kinds of different things. One last example I guess I give you. For example, I talk all the time about. We've got a

00:13:59.120 --> 00:14:07.789

Josh Kanter: really significant spread in our relationship between the 2 major auction houses and our family are big art collectors. And

00:14:08.110 --> 00:14:15.589

Josh Kanter: you know, you can imagine that that's got a that's got a lot of value to it at the end of the day, and if and I don't know how many people in the family know that.

00:14:15.760 --> 00:14:16.970

Josh Kanter: And so

00:14:17.370 --> 00:14:38.989

Josh Kanter: again, if I'm not here and somebody is selling some of the artwork in the family collection, you know what? And they go to the wrong auction house. There's 24% down the toilet that they didn't know they were sending down the toilet. So it's again. They're just all these different kinds of things to think about that you don't think about until

00:14:39.160 --> 00:14:51.239

Josh Kanter: it's a too late right? And and then you're in the throes of making decisions. You know, there's I think there's some psychological stuff around you don't make major decisions within 90 days of a trauma.

00:14:51.650 --> 00:15:01.550

Josh Kanter: Somebody said to me recently, I love this quote of Don't make decisions at dusk. It's the time when you think you can see everything, but you can't and I thought that was really like a brilliant

00:15:01.690 --> 00:15:06.040

Josh Kanter: phrase for kind of when we're typically put into these situations to make decisions.

00:15:06.520 --> 00:15:34.140

Mark Wickersham: It's that context as you talked about right like in once the family member has passed it. You don't have a chance to understand that context unless it's been documented in some sort of way. I think it. You know. Obviously, American culture has a tough time with 2 things. Talk about death and money. How can the next Gen. Be better prepared? What are you seeing as in terms of the work that you've done with families in terms of.

00:15:34.290 --> 00:15:46.299

Mark Wickersham: When should these conversations begin with the next? Gen. How can these conversations be more productive? And how do you? How do you bring along that that next Gen.

00:15:46.440 --> 00:15:52.720

Josh Kanter: Yeah. So the good news, I'd say, is, you know, in our lifetimes, right over the last 2, 3,

00:15:53.070 --> 00:15:55.150

Josh Kanter: maybe even 4 decades.

00:15:55.390 --> 00:15:59.609

Josh Kanter: The trend has been towards certainly more transparency.

00:15:59.740 --> 00:16:08.899

Josh Kanter: more conversation. You know. Money is kind of coming out of the closet, if you will, and we can talk about it a little bit better. There's still our families that I'll come across where

00:16:09.600 --> 00:16:26.670

Josh Kanter: the 96 year old patriarch is like my kids can find out when I'm dead, and all that kind of stuff that still exists. But it's not nearly as prevalent, obviously, as it was in prior generations. And, you know, given all the work that Jay Hughes and so many others have done on talking about these issues and getting families to talk about these issues

00:16:26.810 --> 00:16:30.810

Josh Kanter: that's really opened up. I think that conversation but to your point as well.

00:16:30.940 --> 00:16:36.750

Josh Kanter: Still, nobody wants to talk about their death. Nobody wants to face mortality, so I think

00:16:37.130 --> 00:16:41.589

Josh Kanter: the more positive you can, or the more you can approach these issues from a

00:16:42.110 --> 00:16:51.630

Josh Kanter: position of I'll say positivity, as you know, that sounds like hoity toity, whatever. But is that? Think about it through education. Think about it through.

00:16:52.450 --> 00:17:06.250

Josh Kanter: really. I want my, I want my kids to know what they're going to have to be dealing with. I want them to be good stewards. I don't want this to land in their laps and ruin their lives like all those kinds of things right? So thinking about it much more from a positive

00:17:06.500 --> 00:17:26.829

Josh Kanter: psychology kind of standpoint. And then often we have, especially with leafplanner. We've got rising. Gen. Family members who realize to your point like you, you mentioned your mom's probate right? And you're gonna we know that we're the ones are. Now, now, I'm the senior generation. Suddenly we became the senior generation. So

00:17:27.050 --> 00:17:31.929

Josh Kanter: those kids know they're the ones who are going to have to step into this and sort it all out.

00:17:32.390 --> 00:17:35.909

Josh Kanter: and they understand the complexity. And they understand that there's wealth.

00:17:36.050 --> 00:18:00.549

Josh Kanter: and they understand they're going to have to do it at a time when they've got their own careers, their own kids, their own homes, their own lives, their own, everything. And I gave up 10 years of my life to come have to do this right. So a lot of these conversations are starting, I think, with that next generation, saying, Hey, I want to be educated about this because I want to be a good steward, or I want to be able to efficiently run this process when it happens so

00:18:00.760 --> 00:18:11.430

Josh Kanter: again to me. I think if if you can start these conversations from a position that it's about communication, it's about education, it's about engagement and empowerment.

00:18:11.830 --> 00:18:13.640

Josh Kanter: and it's not just about death.

00:18:14.152 --> 00:18:19.399

Josh Kanter: That that's that's super super powerful to me. The families that do this the best from my perspective, do this

00:18:19.610 --> 00:18:21.770

Josh Kanter: for decades before there's a death

00:18:22.592 --> 00:18:24.530

Josh Kanter: and it's really not it. The

00:18:24.640 --> 00:18:27.490

Josh Kanter: that's an end result. But that wasn't the

00:18:28.130 --> 00:18:33.360

Josh Kanter: the driving force or the driving factor in why, the family was having those conversations.

00:18:34.160 --> 00:19:01.749

Mark Wickersham: Sometimes you hear about these families, and and they're, you know, the the Patriarch are not letting the kids know about the situation at all where the kids gotta they gotta know that. The you know they're not like, like everybody else, that there is significant wealth in the family. But they don't have these honest communication and help prepare them for the for these type of events. It's really like, I said. It's some of it's just cultural right. It's just so hard for.

00:19:01.750 --> 00:19:02.270

Josh Kanter: Yeah.

00:19:02.270 --> 00:19:05.480

Mark Wickersham: Have those kind of conversations, but I think that's great advice to try.

00:19:05.480 --> 00:19:20.950

Josh Kanter: And and there, by the way, I would say, you know, it's interesting because one, I'm often saying to families, and I kind of think that this should have passed already with the Internet age, but that for the families that do think their kids don't know like you're saying really right.

00:19:20.950 --> 00:19:35.363

Josh Kanter: I mean, there's this thing called Google. It's been around for a little while now. There's Chat Gpt, and everything else right? And I mean, I asked chatgpt for my own history, and I mean I was blown away by what it told me about myself. Right?

00:19:36.520 --> 00:19:46.859

Josh Kanter: zillow, you know, and kids are can look up, obviously what their homes are worth, and it's not like they can't look up. What 1st class tickets, or God forbid! Your family's flying around on a private jet, so.

00:19:46.860 --> 00:19:49.520

Mark Wickersham: It has a Wikipedia page. Maybe that's a clue, right.

00:19:49.520 --> 00:20:00.719

Josh Kanter: Yeah, exactly right. So I'm often telling families to really be careful about how much they think. And by the way, kids guessing wrong, whether they're guessing wrong up or down. Both have dangers.

00:20:00.720 --> 00:20:01.040

Mark Wickersham: Yeah.

00:20:01.040 --> 00:20:06.529

Josh Kanter: And so. And the other thing that I talk to families a lot about is the idea that transparency

00:20:06.820 --> 00:20:25.839

Josh Kanter: is not a binary topic right? And and I think that a lot of families come into a transparency conversation and think transparency means. I tell my kids nothing, or I'm showing them the balance sheet, and I am often having conversation with families, and I think Leafplanner is an interesting play into that. That transparency can be a lot about

00:20:25.950 --> 00:20:34.519

Josh Kanter: structure. It can be about understanding financial literacy. You can do a lot of things between nothing and showing them the balance sheet.

00:20:34.520 --> 00:20:35.030

Mark Wickersham: Right.

00:20:35.030 --> 00:20:39.579

Josh Kanter: And and that continuum of transparency doesn't have to be totally binary. So

00:20:39.980 --> 00:20:51.250

Josh Kanter: I hope families will think about that and and share more, even if it's just from that education standpoint and not put numbers on it. If it's inappropriate at that particular time for the kids, or whatever.

00:20:52.090 --> 00:20:54.846

Mark Wickersham: I think that's that's good advice.

00:20:55.370 --> 00:21:10.729

Mark Wickersham: you serve both families directly, and you you serve wealth manager so kind of a b 2 b channel as A, B to C channel. Can you talk to me a little bit about how the challenges that you have, or or just the you know, being able to

00:21:11.450 --> 00:21:14.959

Mark Wickersham: service both those channels as an entrepreneur.

00:21:15.580 --> 00:21:19.799

Josh Kanter: Sure. I mean, I I think, for us. And with leafplanner, it's been

00:21:20.450 --> 00:21:27.180

Josh Kanter: an interesting journey of of learning, I guess, about what are the pain points on both sides of that wall, if you will.

00:21:28.140 --> 00:21:34.129

Josh Kanter: And also what's really the value proposition? I think we we really well understood from the outset.

00:21:34.290 --> 00:21:40.570

Mark Wickersham: What the value proposition was on on that family or the B to C side the family. The family office.

00:21:41.110 --> 00:21:47.970

Josh Kanter: You know I lived it right, and that's the world I've lived in for the last 25 years, you know, either for myself or with other families. So I watched it.

00:21:48.120 --> 00:21:50.250

Josh Kanter: I think, on the b 2 b side.

00:21:50.380 --> 00:22:05.229

Josh Kanter: It took us. I think we're a little behind in understanding that value proposition story, but I think we really do see it, and especially in today's day and age, when so many wealth advisors are moving toward the the multifamily office or the fractional family office

00:22:05.370 --> 00:22:08.769

Josh Kanter: model, and want to offer a family office service

00:22:09.430 --> 00:22:18.729

Josh Kanter: kind of offering, and particularly because, you know, to some extent there's a race to the bottom on aum fees. Right? I mean, it's been going on for decades. And so

00:22:19.010 --> 00:22:33.950

Josh Kanter: wealth advisors are seeing the need, for there was just another article. A couple of days ago I saw that was about inheritors firing their parents. Wealth, advisors, right? The cost of acquisition is a lot different than the cost of retention.

00:22:33.950 --> 00:22:38.319

Mark Wickersham: And it's so common, right? I think it's like 75, 80% do it. So.

00:22:38.320 --> 00:22:43.349

Josh Kanter: Yeah. So if we can, if we can show a value proposition around

00:22:43.990 --> 00:23:04.420

Josh Kanter: deeper conversations and deeper relationships with your client, getting to that next generation and establishing that relationship having a more holistic picture. If you're going to hang the words Family office services on your website, do you really know how to deliver it. And can we help you deliver it? So a lot of those different kind of value propositions

00:23:05.000 --> 00:23:12.180

Josh Kanter: somewhat different than the b 2 c. Side. But I think we're I think we're serving it. Well, we're getting really good reception on that side of the wall as well.

00:23:12.669 --> 00:23:14.369

Josh Kanter: It just has been a

00:23:14.520 --> 00:23:20.410

Josh Kanter: it's again. It's a little bit of a different pain point and a different value proposition that we've had to come to understand.

00:23:21.080 --> 00:23:41.830

Mark Wickersham: Different buyer, obviously. But I just think to your point, if you're going to be a true wealth manager or family office, as you know that those terms get used and abused. This is such a critical component that people are looking for their advisor to be kind of a life coach in a lot of different ways, right?

00:23:41.830 --> 00:23:42.350

Josh Kanter: No idea.

00:23:42.870 --> 00:23:50.360

Mark Wickersham: You know, picking stocks or managing the investment performance and don't get me started on Aum based pricing and how broken that is.

00:23:50.600 --> 00:23:51.080

Josh Kanter: I was.

00:23:51.080 --> 00:23:52.610

Mark Wickersham: Not tied to value at all.

00:23:53.090 --> 00:24:09.520

Mark Wickersham: You can deliver a lot of value to a family, and probably one of the most important aspects with leafplanner. So I really think like, the more I learn about leafplanner, obviously, I think it's really unique. But I just think it fills such an important gap.

 00:24:10.191 --> 00:24:28.909

Mark Wickersham: When you take a look at innovation on your product roadmap, just talking to you as a tech entrepreneur. Now, where do you see innovation coming from? How do you balance innovation with other functions? And obviously, it wouldn't be a wealth tech podcast we didn't have a chance to talk about AI, and how AI is impacting your business.

 00:24:29.770 --> 00:24:39.919

Josh Kanter: So I think so. Innovation for us or the roadmap. I'll I'll say that because I'm not sure I want to call it innovation at the moment. But I'll get to that, I guess. On the AI side, on the roadmap side.

 00:24:40.160 --> 00:24:47.419

Josh Kanter: you know, we had a pretty good again. Obviously this comes from somewhat 25 years of my own experience, or even 35, if I include some of my

 00:24:47.610 --> 00:24:49.710

Josh Kanter: law practice in there and things like that.

 00:24:50.790 --> 00:24:53.279

Josh Kanter: And so we had a pretty good understanding

 00:24:53.480 --> 00:25:10.439

Josh Kanter: of what we wanted this thing to do. But you know, that's never. That's never gonna end. Where there's always something else to add to it, or things that change, or things that are different in different regions of the world, and and those kinds of issues. So there's roadmap. That's just about the product as we come up with it.

00:25:10.580 --> 00:25:38.509

Josh Kanter: Our clients are obviously a huge source of feedback. Right? It's a great feedback loop to be able to listen to your clients and say, Okay, that's a great idea. Let's go do that. And then there's regulatory changes, you know, a couple of years ago we were really focused on making sure we're ready for the Corporate Transparency Act, and we adopted some stuff within the platform to deal with the Corporate Transparency Act. And personally, I'm not convinced it's really dead. So we'll see, you know what happens later in this Administration or the next. And

00:25:38.890 --> 00:25:44.640

Josh Kanter: whether the Cta comes back. So there's there's those kinds of roadmap issues and then

00:25:44.800 --> 00:25:50.460

Josh Kanter: there also are, you know, just constant. Obviously, as I'm learning now as a tech entrepreneur, there's constant

00:25:50.838 --> 00:26:13.430

Josh Kanter: new technology coming out. And and how do we integrate with other systems? And when when I go back to your question about the b 2 b side. You know the b 2 b side is very interested in. Where does this? How does this integrate with the rest of my tech stack, right? Because they're already using a port of a portfolio aggregation system. They're using a Crm, they're using a document management system. They're already using these disparate pieces.

00:26:13.520 --> 00:26:21.239

Josh Kanter: And we have to be ready to say, Okay, this is how you know you're gonna integrate this into what you're already doing. So integrations are a big

00:26:21.370 --> 00:26:24.179

Josh Kanter: piece of where that innovation is is going.

00:26:25.050 --> 00:26:26.150

Josh Kanter: And I was in.

00:26:26.150 --> 00:26:28.089

Mark Wickersham: How? How is the AI impacting? What?

00:26:28.090 --> 00:26:41.260

Josh Kanter: Yeah, the AI question is definitely out there. I mean for us in fairness, I'm gonna say honestly, at the moment there's not a lot of it going on in the system. I jokingly like to say, our AI is human intelligence being built by our concierge team, which is.

00:26:41.260 --> 00:26:41.990

Mark Wickersham: There you go!

00:26:41.990 --> 00:26:45.460

Josh Kanter: Group that works with our clients. But there's definitely going to be application

00:26:45.750 --> 00:27:00.100

Josh Kanter: of AI, whether that's document ingestion, document summarization and ultimately, where I'm actually really excited as we envision, maybe as early as later this year. But we'll see where the where this comes up is that your leaf plan

00:27:00.790 --> 00:27:22.169

Josh Kanter: ultimately becomes, I may use the words wrong, but ultimately becomes your family's own private small language, model or large language model, whichever the right terminology is, and you'll be able to query your leaf plan and just be talking to your leaf plan to say, Hey, tell me about this. Tell me about that. Maybe even having conversations with your ancestors that are stored, you know, if all that data is stored

00:27:22.260 --> 00:27:41.839

Josh Kanter: in your leaf plan being able to have a conversation with past Josh. And you know all these things. So we're pretty excited about where it's gonna go. I I think we're not as excited about. Oh, we have to make sure that we can use the words in conversation, but we are excited about where where it's gonna go.

00:27:42.020 --> 00:27:45.020

Mark Wickersham: Not worried about trying to get a 10 x multiple by slap in it.

00:27:45.020 --> 00:27:46.560

Mark Wickersham: We are not the name of leaf plan.

00:27:46.560 --> 00:27:47.370

Josh Kanter: Exactly.

00:27:47.370 --> 00:27:56.520

Mark Wickersham: Whatever. Yeah, I think that makes sense. I think you just want to do it right where it makes sense. It's not this be all. I do think in terms of, you know.

00:27:56.590 --> 00:28:21.320

Mark Wickersham: document interrogation, summing lots, large amounts of unstructured information being able to have a conversation with your data, hey? Can you find that will for me? Or can you tell me about how this asset transfers, or whatever it is that to have a normal language conversation with it, figures out where that data is and does that for you is really powerful.

00:28:21.821 --> 00:28:45.620

Mark Wickersham: We had a chance to be on a panel together for the family wealth report around post implementation best practices. And we thought, revisit that a little bit. How confirms better adopt new software. And then how is leafplanner kind of increased client adoption. You've talked about your your concierge service, but you could just tell me a little bit more about that.

00:28:46.190 --> 00:28:55.179

Josh Kanter: Yeah, I mean, I think you know to me, and I'm I'm not. I would say, certainly an expert in this and that that panel was a lot of fun to hear different perspectives on it. I think

00:28:56.350 --> 00:29:04.449

Josh Kanter: the difficulty with adopting a lot of these things is becoming an expert in them right, and if you don't have the personnel to become an expert in them

00:29:04.916 --> 00:29:11.780

Josh Kanter: you know, I think I think the post implementation review question is sort of dovetails nicely with the in-housing or outsourcing

00:29:11.890 --> 00:29:14.050

Josh Kanter: of some of these different things. So

00:29:14.160 --> 00:29:16.979

Josh Kanter: you know, some of these systems are so complex

00:29:17.150 --> 00:29:27.029

Josh Kanter: and constantly being added to. I mean, even with leafplanner. We're talking about a roadmap, right? We're constantly adding things. Now, I would argue, leafplanner is ridiculously simple to use, but

 

183

00:29:27.430 --> 00:29:35.619

Josh Kanter: it still takes time and effort to stay on top of what's coming out and what the new features are, and things like that. So I think as as

 

184

00:29:35.870 --> 00:29:39.329

Josh Kanter: people, families or family offices or firms look at

 

185

00:29:39.970 --> 00:29:46.270

Josh Kanter: in sourcing or outsourcing some of these technologies, you know, that's that's got to be

 

186

00:29:46.550 --> 00:29:58.530

Josh Kanter: something that they're thinking about. And how do we come back on a post implementation review basis and say, is this meeting our needs? Do we understand how this is being developed. And how do you do that? And some firms don't offer

 

187

00:29:59.010 --> 00:30:23.220

Josh Kanter: that implementation service. And so you're really relying on your own personnel or outside consultants to do it. So one of the things Leafplanner did very intentionally for a host of different reasons, not just because of this. But again, we built this internal concierge team or implementation team, whatever you want to call them, and they work alongside every advisor, every family member, and are really there to to say, Hey, this is how you can

 

188

00:30:23.340 --> 00:30:39.909

Josh Kanter: best get this out. So if we have a real estate family, then they're going to say, Well, we've worked with dozens of real estate families. This is how they've approached it, you know. Do doing this a private equity family, or this or that, or whatever. So it's it's been, I think, a real benefit for leafplanner to have that team

 

189

00:30:40.040 --> 00:30:43.169

Josh Kanter: who's been seeing all these different implementations

 

190

00:30:43.740 --> 00:30:52.719

Josh Kanter: and work with families and firms to be able to say, this is how we see you get the most value out of this and and do that on kind of a post implementation

 

191

00:30:52.860 --> 00:30:59.959

Josh Kanter: basis as well. But I think, yeah, people have to really think about what's that? How do you stay on that education curve

 

192

00:31:00.610 --> 00:31:05.880

Josh Kanter: with with software and and all the things that are changing and how you're gonna get

 

193

00:31:06.170 --> 00:31:10.350

Josh Kanter: the best value out of what we're doing, especially because change is hard, right? I mean

 

194

00:31:10.530 --> 00:31:19.380

Josh Kanter: shifting systems. If you all of a sudden see something over on your right. That that wasn't, you don't think is in the system you're using.

 

195

00:31:19.540 --> 00:31:24.720

Josh Kanter: But making that kind of shift is really really complicated, costly time consuming.

 

196

00:31:25.760 --> 00:31:34.530

Josh Kanter: And so the more that you can, you can be on top of what your own systems are doing, you know, obviously the better, that is. And I think for some of the smaller firms like us.

 

197

00:31:34.710 --> 00:31:44.150

Josh Kanter: it's great to know that our clients can come to us, and really do get, you know, a service level of being able to say, Hey, we'd like to see you do this, and we can go do it.

 

198

00:31:44.310 --> 00:31:46.700

Josh Kanter: and that's that's important to us.

 

199

00:31:47.180 --> 00:32:03.354

Mark Wickersham: I I think you know you have the benefit of obviously seeing multiple family offices and having that true best practice. What works, what doesn't work where obviously, family offices, they're not gonna be implementing systems, especially leafplanner and not, you know, that's that's gonna be an implementation of one for them.

 

200

00:32:03.660 --> 00:32:20.899

Mark Wickersham: They don't have a chance to see these multiple reps. They they have obviously limited resources and a high complexity portfolio to be able to manage of services that they provide to the family. And, like you, said, change is just hard. I don't care what it is. It's just a human

 

201

00:32:21.010 --> 00:32:43.110

Mark Wickersham: component to it, and often that it has nothing to do with the technology vendor. Sometimes it's just the change management component of it. Is your staff ready for the change? Do they understand why that change is going to take place? Also to your point. I think you know it needs to be managed, and and you need to be engaged with your vendor to be able to say, Hey, am I doing things right?

 

202

00:32:43.110 --> 00:32:43.540

Mark Wickersham: Getting them?

 

203

00:32:43.540 --> 00:33:08.199

Mark Wickersham: What's new with you guys? Let me explain what's new with us, so you can better serve us, and to just be engaged as a partner with with your vendors. I think a partner relationship is always much better than a vendor relationship. And having that that kind of mindset, because for the most part, you know, you want to help your clients, and you want to help your clients succeed. The more value they get out of the system. That's a win for both sides. Right.

 

204

00:33:08.630 --> 00:33:09.420

Josh Kanter: For sure.

 

205

00:33:10.100 --> 00:33:22.579

Mark Wickersham: So, Josh, I love to end these wealth tech podcasts on a personal note with 3 questions that have nothing to do with wealth. Tech, I think, with this one I got a tough time kind of keeping it down to 3. But.

 

206

00:33:24.310 --> 00:33:34.479

Mark Wickersham: you're from Chicago. I love Chicago, one of my favorite spots on the planet. What do you love about Chicago? And what's a great spot some of you might not know about.

 

207

00:33:34.800 --> 00:33:53.420

Josh Kanter: So I moved to Salt Lake City, almost 25 years ago. And so it makes you appreciate the things that I've always loved Chicago, and I still do love Chicago. So I would say. 1st and foremost, the restaurants food in Chicago is just amazing. I in some ways I even think it's better than New York. So.

 

208

00:33:53.420 --> 00:33:53.980

Mark Wickersham: Really this.

 

209

00:33:53.980 --> 00:33:57.339

Josh Kanter: Really kind of. I think the food scene in Chicago is just incredible.

 

210

00:33:58.080 --> 00:34:16.839

Josh Kanter: Obviously the architecture in Chicago is unmatched. And and it's just a great city, and on the 3 good days a year you can look out over the lake and just really see how beautiful a city it is. It's really pretty pretty spectacular, you know. Really cool spot.

 

211

00:34:17.920 --> 00:34:33.040

Josh Kanter: you go down toward the shed aquarium, and you're sort of out a little bit jutting into the lake, and and you can see the skyline in just a way that is just magical. And so used to go just park there and look at it. It was really.

 

212

00:34:33.040 --> 00:34:47.809

Mark Wickersham: It's certainly cool seeing the lake and then having this, you know, skyscrapers behind you. And yeah, it's quite a different view. I would highly recommend anybody that the architectural tour that goes on the boat. I think that was because it is really amazing city for for architecture.

 

213

00:34:47.810 --> 00:34:48.460

Josh Kanter: Yeah.

 

214

00:34:48.823 --> 00:35:04.009

Mark Wickersham: You're an art collector. What are some of your favorite art museums? And I'll throw another one in there if I, if I was. Go to the Art Institute in Chicago like, how do I get the best? Because it's so big?

 

215

00:35:04.150 --> 00:35:08.299

Mark Wickersham: How do you, Ferris Bureau's day off in the in the museum and get the best experience.

 

216

00:35:08.300 --> 00:35:13.870

Josh Kanter: That's a great question, and I don't even know if I know the answer to that. I mean, you might, you know, have to pick

 

217

00:35:13.990 --> 00:35:22.669

Josh Kanter: what you're really into. If you're into contemporary art making sure that you're going to the contemporary wing. You know the Art Institute's a hard place to

 

218

00:35:22.850 --> 00:35:28.809

Josh Kanter: consume in a day. But certainly in Chicago, I would say the Art Institute is

 

219

00:35:29.120 --> 00:35:39.520

Josh Kanter: got to be at the top of the list. And you know there's so many little gems around the world. I'm such a huge fan of the Albright Knox Gallery, up in Buffalo that's just like this

 

220

00:35:39.650 --> 00:35:47.040

Josh Kanter: little gem sitting in the middle of nowhere. You know not that buffalo is in the middle of nowhere. Sorry any buffalo listening.

 

221

00:35:47.040 --> 00:35:49.050

Mark Wickersham: About going to Buffalo for an art museum. But yeah.

 

222

00:35:49.308 --> 00:36:02.750

Josh Kanter: We just one of my kids was studying in Europe this summer, and we went over to visit and took him down to the south of France, and I had actually been there before. But it's a little town called Antibes, and there's a beautiful Picasso Museum sitting on the water.

 

223

00:36:03.170 --> 00:36:18.829

Josh Kanter: And it's just, you know, these little places all over the place. There's another town down there that has a whole Lege museum, and the entire Museum is a lege mosaic on the outside of the museum. I mean, there are just so many great places.

 

224

00:36:19.420 --> 00:36:24.150

Josh Kanter: as long as you kind of ask around and and are open to these smaller

 

225

00:36:24.350 --> 00:36:27.589

Josh Kanter: kind of non. I mean, I love the Art Institute, but it but at the same time

 

226

00:36:28.050 --> 00:36:29.810

Josh Kanter: it's easy to go find these little

 

227

00:36:30.180 --> 00:36:34.359

Josh Kanter: kind of off the beaten path places that are just gems in the art world.

 

228

00:36:34.780 --> 00:36:42.130

Mark Wickersham: Nice. Yeah, I think that's that's great advice. Alright, Josh, I appreciate you being on the show. This has been a great conversation.

 

229

00:36:42.130 --> 00:36:44.620

Josh Kanter: Thank you. Mark, really appreciate being here.

 

People on this episode