Whose Trust Is It Anyway? The Intersection of Family Wealth, Estate Planning and Improv with Mark Shiller

Mark Shiller
mshiller@certuslegalgroup.com
Certus Legal Group
Fishsticks Comedy 

Mark works with business owners, professionals, senior executives and other individuals, couples and families who appreciate his thoughtful and creative approaches to their often complicated personal, estate, trust, tax and wealth planning challenges. His deeper engagements involve the identification and leveraging of a family’s personal, financial and moral capital, and family system strengths and weaknesses, to inform and direct the achievement of multigenerational planning goals. Success in this effort is not just measured in taxes avoided or how long the money might last, but in the support and mentoring of productive “Next Gens” and effective and efficient succession of ownership and management of family businesses and wealth.

Mark seeks to educate, inform and empower others, as represented by his inclusion as a faculty member of the National Trust School of the American Bankers Association and as an adjunct professor at the University of Wisconsin Law School. He is a sought-after speaker, consistently receiving high marks for his humor and ability to engage professional and general audiences on complicated technical and personal topics alike. In 2024, he released “How to Not Ruin Your Kids with Money,” an outgrowth of his speaking and work on the topic. In addition, as a part of Mark’s 20-year plus career as a professional improv comedian, he also consults and provides training for organizations, including Fortune 100 organizations, on developing a collaborative
culture, addressing intergenerational communication issues, and many other topics.

Kirby Rosplock

Welcome to the Tamarind Learning podcast. I'm your host, Dr. Kirby Rosplock, and today we are talking with Mark Shiller. He is an estate planning attorney. He's been doing this 30 years, and he works with ultra high net worth individuals and families. And he plans on all different kinds of issues, from business succession to estate and trust administration to family wealth counseling. But that's not all. I mean, Mark is an improv and stand-up, a little stand-up comedian, so he does some of that. He's also a speaker and an author. So he's written a book, which you can see right behind you, How to Not Ruin Your Kids with Money. And he's genuinely a wonderful gentleman. I've gotten to know him over the last several months, and we're doing some other work together on another webinar. So welcome to the podcast. It's so great to have you here today, Mark

Mark Shiller

It's really nice to be with you. I'm looking forward to this.

Kirby Rosplock

So one of the things that really fascinates me is how you have been able to weave improv and estate planning together. I mean, those are two things that I don't typically see going together in somebody's practice. So tell me, how does that work?

Mark Shiller

Yeah. When I started doing it, I started doing improv, comedy, based on getting a Christmas gift from my wife to an improv workshop. Okay, I'll try that. The way I would talk about it with people is, it was a way for me to exercise the other half of my brain. There's an element to that. But over time, it's really become very clear that the lessons that you learn in improv, which is a very personally revealing art form, it causes you to learn about yourself in ways if you do it for long enough anyways and are serious enough about it, you start to realize, Oh, I have that tendency. That's something I like, or that's something I don't, or that's something that has been sort of kept under wraps for a while, but that just came out. Well, that's interesting. You also learn about how to work with groups. Well, as you and I both do, Kirby. We work with certain types of groups of people, and those dynamics do play out in ways, and you can learn from both to have a better experience, I think, in both.

Kirby Rosplock

I think it's really important to distinguish improv is not comedy. Comedy is not improv. Can you just unpack that a little bit for folks that might think it is the same?

Mark Shiller

Yeah, it's actually in some ways, most of the time when people think of improv, they are thinking about improv comedy. That is generally what I do, is improv comedy. There is an element to it, but it is a different target of laughter, at least when I think it's done at its best. It's a different target. So just take you back. This was in my first session, that first session that I mentioned that I went to based on that Christmas gift. I was in a scene, and we were just doing a, it was a petting zoo was the suggestion. I'm with my friend Matt, who I still know to this day, and he and I were in this, and we were feeding the goats. It's just all mimed or whatever. He has his hand out, and he has his thumb in his hand. For those of you who have little kids who have ever been to a petting zoo, you do not want to have your thumb out because the goats can't distinguish between the food and the thumb. I just said, Hey, you got put your thumb to the side, and it got this laugh.

Mark Shiller

Now, it's not funny. There's nothing really funny about that. But what it was, it was a recognition moment. All of a sudden, everybody's like, Oh, this is a real place that we're at. We're playing now, and we're laughing because we feel safe with each other. We're recognizing something at the same time. And that laugh is a bringing together, connecting laughter. And that, like I said, is, I think, what the goal of really really quality improv comedy would be.

Kirby Rosplock

Yeah. I always think of like, Whose Line Is It Anyways, where they are just given something to react to. And you know that they're coming up with something spontaneous. It's not like something where they've crafted a very smart, comedic, tailored, funny bit, which took them hours and hours to come up with jokes. And I think that's also something, especially when we work with families, you can't really script a family meeting. You can't really script how some of those discussions are going to go, right?

Mark Shiller

Right. Because one of the light bulbs that goes on for somebody when doing improv is you realize if you plan it, it will go poorly. It just does. So one of the things is to come with an empty, open mind ready to just take things as they come to you and react to them, hear them, listen to them, respect what you're hearing, and then contribute and build on what others are offering in a way that accomplishes something.

Kirby Rosplock

Yeah. Well, I would love for you to just give us a little bit more clarity about how you are bringing improv to some of your practice. What does that look like? How do you weave it in?

Mark Shiller

Well, as you and I talked about, this is in some ways reverse engineering how what has evolved over time in the improvisational work that I do, which always was pretty separate, but it starts to bleed into things as you start to realize some things. Our approach in part of a group called Fishsticks Comedy, and it's got people in not only Milwaukee, where I'm from, but also in Atlanta, Chicago, Dallas, Denver, and Nashville. We have people all over the place. But how do you do that together? Our flavor of it is something we call other-centered improv. And most improv, I think you could say, has that element to it. You're doing it not as a solo sport, at least not typically. So how do you do it in a way that is going to have some benefit for others? That cleverness aspect that sometimes... Some people are quicker than others, and that can sometimes be a way to overwhelm someone in a scene. They may get all kinds of laughs, but it tramples the group. I hosted an improv podcast called Improv Comedy Connection, and I had an interview with somebody who had played with Robin Williams at his very first improv experience.

Mark Shiller

At least it sounded like it was his first. In one of their shows, he was just a whirling dervish back then, too. They talked about how they were doing this scene that involved a baseball game. Robin's on stage, and all of a sudden, there's a fly ball, and he runs out through the crowd into the hallway. I don't know if he caught a fly ball or whatever. But the picture of this was the whole crowd was turned, and the rest of the cast was on stage looking at the back of everybody's heads. The crowd is enjoying that moment, but the rest of the troupe is like, the word sometimes used is you're shining. You're the one who's taking the glory and it's to our detriment or we're being minimized in part of the process. If you're going to be other-centered, even though that might get a laugh, you're going to think pretty hard about whether you make a move like that because of the impact it has on the others on stage with you.

Kirby Rosplock

That's a great example. Now, tell me how other-centered might show up in a family? Because I can tell you a lot of others that are in some of these families that I work with. What does that look like for you?

Mark Shiller

When you look at the course of time, I mean, family cultures are all different, right? Everybody comes at it at a certain point in time and in their own personal evolution. If you're working with someone who is in the then senior generation, they have gone through the raising of their kids. They may have started to see the grandkids, and maybe the grandkids have already gotten raised. Then they're at a point in time where you've got to figure out what are they really trying to accomplish? Or if it's a couple or a cousin group or whatever it is, whatever that grouping is, what is it that they're trying to accomplish? And they're doing so at a certain point in time, like I said. They may have come to the point where they had built enough up or had managed things for a period of time that now they want to see the next generation take things on. It's a move from mine to ours, from individual to group. The further you get in the generations, hopefully that hour is mentality starts to be more natural in the background music from day one. But if you're at Gen 1 to Gen 2, that's a shift that families need to make.

Mark Shiller

That's not always a spoken or understood thing. But in that position, the senior generation member has a decision about how much they want to accomplish of what their goals are versus what their overall family goals are. They should also be honest with themselves about how much they could accomplish with their goals versus what the family goals might be if we want to have long term multi-generational success. So part of how to move into other centeredness in a family context is trying to place yourself where you're at and understand, am I trying to accomplish things for the group, myself? Is that balanced in the right way? Do I need to drop something that I'm holding tight to? Or do I need to hold on to something or elevate someone who might be pushed to the side in Gen two or three, all those kinds of things.

Mark Shiller

A simple rubric that I think can be helpful in that is to go through and decide in a family, how are we going to set up our priorities and how we work together? We sometimes talk of it in the improv context as having an order of honor. It's just a real simple thing. If we're being brought in, we'd want to honor our show host, and we want to honor our audience, we'd want to then honor each other, and then lastly, ourselves. That's a shortened version of it. If the audience member, if we're asking for a suggestion, they flub their words or whatever, we're not going to go for a cheap laugh at their expense because we're honoring ourselves over that audience member. If we do that, the audience member starts to close up and you start to lose that experience.

Mark Shiller

That can happen in families, too. If someone is starting to push their own agenda and devaluing or heightening their value over someone else's, that starts to tighten the group, and the group isn't as able to accomplish group goals in the same way. If you're a senior generation member, do you want to honor your goals above those of your Gen 2s, for instance, or do you want to match your goals to what you think honors them most? Just having that language. You mentioned the book. One of the examples I use in the book is a pretty simple one. It happens multiple times. This is not a single story.

Mark Shiller

But if you've got somebody who's worried about how they might ruin their younger kid, if they've got some wealth in their family system, they might have have something like, Well, we don't want them to be spoiled by the fact that we're able to have these two-week vacations in Europe and bring our nanny or whatever, because that's not the environment they're trying to raise them in, let's say. There's nothing necessarily wrong with any of that. But if your goal is really primarily how your kid turns out, then whether you go on that particular vacation in that particular mode should run through the filter of, is this going to be a positive or negative for my kid, as opposed to, am I going to enjoy the trip?

Kirby Rosplock

I love it.

Mark Shiller

Yeah. We don't like having those conversations internally, necessarily, but it does give us some alignment. When we have alignment, then we have clarity. When we have clarity, we can get to accomplishment. If we lose something along the way, then we're fighting through a sloggy mud to get somewhere, but we might not even know where we're heading because there's so much mud on the wind shield, right?

Kirby Rosplock

Yeah. How do you use the metaphor and how do you use the practice of improv? It sounds like this use of ensemble and the dynamic of a family is something that's really relatable. I could see how the idea of good and bad actors is something that I would think families could gravitate towards. Do you bring that in to the family system?

Mark Shiller

When you and I were getting to know each other and we started talking about the improv stuff, and like I said, it was reverse engineering it a bit and realizing that in many indirect or indirect unspoken ways, some of these tools and techniques and observations were coming out into the way we were talking with families. As you've encouraged me a little bit more just to engage in this conversation with you, I realized that being more direct on these things, I think, can be very helpful. When you say improv, improv-comedy, those things, it may sound like, Oh, that's a parlor trick, or that's cute that you do that. But if you really see it as a type of study of human behavior and human systems, then there is some real value to it. When you get into scrapes within families or points of disagreement, if you do have the ability to refer back to this is how we want to conduct ourselves in terms of that order of honor, that can be helpful. Or if you're able to get people to listen well as opposed to try to look for spots to insert their own opinion and position.

Mark Shiller

There is aspects of learning the art of listening, which is in very short supply and takes a different mindset than you might be used to deploying. If you're an entrepreneurial family and you're used to running in a very authoritative way and structure. That's not how families always operate. I guess sometimes they do, right? Sometimes they do. But once If you replace one authority figure, which eventually will happen, then what is left behind? Is it another authority figure? And does that authority figure follow a certain pattern or not? If you're going to have an authoritarian approach, you've got to also understand the rest of the family as well, because ultimately, it's got to be for everybody's long-term good.

Kirby Rosplock

Well, and I look at this wealth transfer event that's happening over this string of decades, and we're in the thick of it right now. And as silent generation boomers are retiring 10,000 every single day, which is pretty mind-blowing, we're moving into this democratic shift, where a lot of families are trying to go from that matriarch or patriarch who really held the reins, which is pretty normal, to a more democratic ruling thought process. And I see a lot of families who are trying to build systems of governance that are somewhat like concessions. We're making concessions. We're trying to get to decisions. And if you think about the word improv, improvisation is a counterpoint to concession. So that is about a group improvisation. Is how you make... It's a difference from concession where you're conceding and you're giving up, but it's how you're working together to adapt and change. And it's not necessarily like somebody's conceding, but you're working together to manage the change. I think that's a really important distinguishment.

Mark Shiller

I think it is because if we do try to find a center of where everybody's position are, that's certainly going to be an unsatisfying result, probably to everybody. It may be livable, but it may not be something that anybody feels like, We got to make this go another generation or two or 10. If you build it together and have some openness, then I think you often can surprise yourself where you land. But it... I do think there are senior generation members who will end up playing the role sometimes of the concession makers, and the next generations are moving forward in a way where it's trying to set the stage because it's now our time. And that never hits just perfectly, but there's always this generational tension, which showed up in a very odd way for for me because I do some improv-based teaching on intergenerational communication as well. The day before I was going to deliver this to a group of people, I had recorded this goofy show, you may be familiar with it, Mystery Science Theater 3000. Silly show, stupid. Basically, you have these two robots and somebody making comments over a film. Well, the film they chose for this particular regular recording was too short.

Mark Shiller

So they also did this treatment to a 1940 Chevy dealer training video. So this is 1940. So it was a father who looked like he was in his 80s, talking to his son, who was probably in his 50s, about the 20 something who wasn't working hard enough, and was this, that, and the other and was complaining about X, Y, Z. The conversation was the same as we've had. The 25-year-old was something before the silent generation, probably. His dad was before that, and the older person was born prior to the Civil War, probably. And it's a human dynamic that we have. And so rather than getting caught up in it and not realizing we're falling into the same ruts as everybody else, why don't we take a step back and try to figure out how can we do this in a way that is affirming and growing for all of us? And I think there are societal shifts that are making that more fertile soil because today's 70 somethings are much more likely and interested in sharing some of what it is that they've built up or including the next gens into the conversation than would have been true for the 70 somethings 15, 20 years ago.

Mark Shiller

I think we're on a hopeful trend, but we also have just human nature challenges to that, that if we're aware of them, which is one of the things that I think improv does give you a little bit more of a sense of, here is our human nature, and here's how it gets in the way, and here are the pathways that we always seem to walk, and how can we have divergent thinking as a way to get us to better results that we will naturally just shepherd ourselves into.

Kirby Rosplock

I love it. I want to jump over to your book for a minute because I love that you wrote a book, and I know you were inspired probably by your many, many clients and the many, many families that you saw struggling with raising children, young adults, teens. Tell us more about how to not ruin your kids with money and some of the stories that you put in there. And what's one of your favorite parts of the book?

Mark Shiller

Well, I'll tell you my favorite thing so far about the book is that it has engendered conversations and given people some language and handholds to have them. Because the inspiration for the book, first and foremost, was people really do worry about how how their kids and grandkids are going to be impacted by their wealth. It just feels like you're spinning the wheel and hoping you land on the right spot when all is said and done because people don't typically talk about it. They don't have people in their lives that they go to. Now, that's not true across the board, but wealth has an isolating factor to it. And if you're isolated and alone, then you really just feel like you're adrift in many ways. And so you have resources. I mean, having conversations on podcasts like yours, having books and other resources that people can go to is helpful, but ultimately, you got to get your hands into it and move on to actually achieving success. In terms of favorite stories or not, I may, more often than I was originally thinking, start with a story from very early on in my career, because when we think about how to not ruin your kids, we usually think about either where they're at now or when they were really little.

Mark Shiller

But my first story that got me thinking this way happened to be an interaction with someone who was in their 80s. This was about 30 years ago, give or take. I was going along to witness some changes for an estate plan with a partner at the firm I was at at the time. This woman was not long for this world and needed to make some changes, and so we went to her home. We had this lovely conversation. She was delightful. She was engaging in her conversation and just very pleasant to be around. But at the end of our time, after we had signed up the documents and had our conversation, she asked a question about getting some additional funds out of a trust that her grandfather had set up for her in the '20s or '30s or something like that. In that moment, she became this little eight-year-old girl, it felt like, asking for money from grandpa as represented by the partner and the Old Line Trust Company that were trustees of this trust. It just felt like something less than she had all the capacity to be when it came to finances. I'm not saying she was a bad person.

Mark Shiller

I thought she was great. Can't remember her name, couldn't place her, and it was a long time ago. But that moment of feeling that this is, what do we want at the end of the story? We're raising adults. We're not raising children. So what do we want those adults to look like and be, and how can we empower them? We're not going to get the results just the way we want them to, but we can think a little bit differently and maybe be a little bit more motivated to do things in a different way.

Kirby Rosplock

I love it. You're speaking to my heart and soul. I'm so on board with it, and I'm so glad you wrote this book because I had the opportunity to page through it, and there's so many great, wonderful stories in there. So I do encourage everyone to pick up a copy. If you have clients who are dealing with these issues, if you yourself have a family and you're picking your brain, I mean, Mark, you really have a very thoughtful approach to getting into the weeds, but speaking to the layperson. So I really appreciate that you took the time to put pen to paper and share the stories and bring your insights. You have a very thoughtful, level-headed, no-nonsense way of bringing truth to the masses. So thank you so much.

Mark Shiller

That's very you to say. I think it helps when you have certain goals in mind. And as a professional advisor, if you have a sense of what it is that you think your purpose is to help others, for me, and this is true in improv. It is a tie, is that I want people to experience authentic connected lives with each other. And if that's how you're going to approach things, then you measure your results in your success in different ways than how many millions or billions of dollars of estate taxes have I avoided? It's a very different way to look at life, and I think it's been more rewarding.

Kirby Rosplock

So Yeah. I do feel that oftentimes when we leave the financial assets to another, we miss sometimes communicating the why of what we really wanted to do for that beneficiary. And that's actually what they're craving. That's what they really need help with, more so than sometimes the money itself. But is the why it's so important?

Mark Shiller

It is completely the why.

Kirby Rosplock

The why.

Mark Shiller

Because as you look at the way these things move generationally, the wealth came from somewhere. Almost always it came from some concentrated special skill, special business, entrepreneurial success, whatever. Somebody loved the game and they were good at it. And then it's there. And then the next generation, sometimes lightning strikes in the next generation, too, and you have somebody who is very enterprising and they know how to grow it. In fact, that's pretty common, actually, for the families that continue to progress. You'll have that extra second stage booster that happens. But at some point, everybody has to look at it and say, What are we doing with this? Because when you start getting into the family office space, that usually means that there is more wealth connected in this family than is needed to supply the personal needs of each family member. If the only reason to grow it is because we have it, then at some point, it's like, What are we doing? The current upcoming generations, more and more, I don't know if you're seeing this, too. I'm guessing you have. More and more of the members of this rising generation are being like, I don't need it.

Mark Shiller

Let's send it to charity. Let's push it away. I don't want to hold it. And so then your wealth as a gathering point is no longer sufficient. So if you don't have that why, it ultimately is going to fail because it just doesn't create its own why. The why comes from outside of the wealth. The wealth should support the why as opposed to be the why. So if you back up and realize, Oh, we've just been talking about the stuff on the page or what's in front of us. We've kept ourselves busy, and we haven't done the family work. Well, then what do we have? We don't have anything.

Kirby Rosplock

Yeah, so true. It's so true. Well, this has been such a fun conversation. I think I could talk to you all day. Mark, if there's a couple of things that you want to leave us with related to improv, your book, your practice, othering, anything, what would it be?

Mark Shiller

Well, I guess the one other aspect of the other-centered aspect, which I think is a foundational, is we call it the principle of the one versus the 99, is to try to avoid the trap of listening only to the majority or the loudest voices. Try to pull those on the sidelines, including those who might not be in the room with you in the way that you make decisions as a family. I think that works in improv. I think that really works in families. That could be its own episode, probably in and of itself. But I do think just that little tidbit, if you start thinking that way, I think if you're in a family of wealth, I think you will serve your family well by going that route. In terms of the rest, I'm not that difficult to find. You can find the book anywhere. You can go to markshiller.com. Schiller doesn't have a C if you're looking at it. You can find the book and some other resources there. certuslegalgroup.com is the law firm, and fishstickscomedy.com is the improv troupe.

Kirby Rosplock

That's awesome. And we will have all of these links included with this podcast at tamerindlearning.com. So please like us. Please subscribe to our podcast. Mark, thank you so much for being our guest today at the Tamarind Learning podcast. We loved having you.

Mark Shiller

I loved being here. Very much. Thanks.