Common Mistakes During Family Business Estate Planning | The Family Biz Show Ep. 128
Estate planning is technical.
Family business estate planning is emotional.
Because in a family enterprise, wealth is never just capital.
It represents identity. Sacrifice. Legacy. Control. Protection.
And when estate planning is driven by fear instead of preparation, families don’t just protect assets — they unintentionally weaken the people who must steward them.
In this episode of The Family Biz Show, wealth psychologist Jim Grubman, co-author of Wealth 3.0, challenges the most common assumptions shaping multi-generational estate planning.
What he reveals reframes everything.
The 70% Myth That Built an Industry
You’ve heard it:
“Seventy percent of wealth transfers fail by the second generation.”
It’s repeated in boardrooms.
It’s cited in advisor presentations.
It’s used to justify complex trust structures and control mechanisms.
But where did it actually come from?
Jim explains how limited, narrow research became accepted as universal truth — and how that narrative shaped decades of defensive estate planning.
When founders believe generational decline is inevitable, they design structures around protection instead of development.
Fear becomes policy.
Exposure Is Not Preparation
Many G1 leaders assume:
“My kids grew up around this business. They’ve seen it. They’ll figure it out.”
But as one next-generation leader put it:
“Just because I was along for the ride doesn’t mean I know how to drive.”
Estate planning often transfers ownership without transferring capability.
Preparation is not passive.
It requires:
Intentional financial education
Decision-making responsibility
Governance participation
Clear communication
Without these, wealth transitions become fragile.
The Hidden Estate Planning Variable: Parenting
The quiet truth behind most generational breakdowns?
It’s not tax law.
It’s not structure.
It’s not even governance.
It’s parenting.
Jim calls it the “hidden dirty little secret” of wealth.
Families often assume they can raise children the same way they were raised — even when their economic reality has completely changed.
But wealth changes context.
Context requires adaptation.
If parenting doesn’t evolve, tension accumulates.
And no trust structure can fix that.
The Language That Shapes Legacy
One of the most powerful insights in this episode is linguistic.
“Shirt sleeves to shirt sleeves in three generations.”
It’s not even a complete sentence.
There’s no verb.
No inevitability.
Just assumption.
Yet families internalize it as destiny.
And when inevitability is assumed, estate plans become restrictive.
Control increases.
Trust decreases.
Narrative drives structure.
Structure drives outcomes.
Adaptation Is the Real Strategy
Successful multi-generational families ask three questions:
What should we keep?
What should we let go?
What must we learn?
Estate planning is not static.
Every generation faces:
Different markets
Different personalities
Different spouses
Different pressures
Replication does not guarantee continuity.
Adaptation does.
Key Takeaways
• The “70% wealth transfer failure” statistic is often overstated and misunderstood.
• Fear-based estate planning leads to over-control and restrictive structures.
• Exposure to wealth does not equal readiness to manage it.
• Preparation for generational transition must be active and intentional.
• Parenting and communication are central to long-term wealth continuity.
• Language and inherited narratives shape governance decisions.
• Estate planning should focus on developing capable stewards — not just protecting assets.
The Real Purpose of Family Business Estate Planning
Estate planning is not primarily about minimizing taxes.
It is about aligning:
Wealth and capability
Structure and trust
Protection and preparation
Family identity and future leadership
When estate planning is fear-driven, families fragment.
When it is preparation-driven, families flourish.
This episode is a masterclass in reframing estate planning from defensive preservation to intentional generational development.
Because wealth doesn’t fail.
Preparation does.
Transcript
Michael Palumbos (00:21.366)
Welcome everybody to the Family Biz show. I am your host Michael Palumbos with Family Wealth and Legacy in Rochester, New York. And today we've got a treat for you. Jim Grubman, who has been a long time mentor of mine. A lot of the work that we talk about today came from Jim and Jim's work with the Ultra High Net Worth Institute and the Wealthesaurus and
Michael Palumbos (00:46.496)
If I looked at all the things that you've done in your career, and we would be here spending the whole hour going through that. And of my mentors, of the people that I've learned from through the years, you're probably one of the only ones that I haven't had on the show. So I'm so excited to have you on the show today. Welcome Jim Grubman.
Jim Grubman (01:05.004)
Well, I'm excited to be here because yeah, we have been in the same circles and known each other and various sorts of things, but we haven't actually sat down to have this conversation. I'm looking forward to it.
Michael Palumbos (01:16.142)
Good. So Jim is the author of the book Wealth 3.0 along with Dennis Jaffe and Kristen Keffler. And it was, you know, when it came out and when you started talking about this, it ruffled some feathers in the industry. And in a good way, in a really, really positive way, because you, the three of you made the shift.
Michael Palumbos (01:46.562)
to thinking about things in a positive light and thinking about from a strengths-based, you you don't get out to three or four generations without doing some incredible things. And most family businesses were beating the, you know, the beating the S &P 500 businesses by five, 10, 15 years in terms of their longevity. So it was due, it was due. Thank you.
Jim Grubman (02:16.376)
Well, thanks for pointing that out, because yes, we did ruffle a few feathers and a few people were a bit unhappy of how we were objecting to the status quo. But that's the nature of what happens in paradigm shifts and the need to grow beyond what has been to something a bit better.
Michael Palumbos (02:38.018)
Yeah. And, you know, so for those of you who haven't heard it, let's just go through the old paradigm and what you might've heard when it comes to family businesses is that, you know, it's shirt sleeves to shirt sleeves in three generations. The third generation is going to lose the family wealth and the family business or the collapse of the family will happen. Rice patty to rice patty. it's, you know, here's what I, you know, I would say, and this might be a good time to, you know, just
Michael Palumbos (03:07.254)
Debate it a little tiny bit. I don't know. That's not the right word, but discuss is You know physics and entropy it does kind of have this cycle that matches that shirt sleeves the shirt sleeves and three generations and the the the families that that don't think about it from a strength space that aren't open to emotional intelligence and growing
Michael Palumbos (03:36.238)
these human beings, at the end of the day, this is all about people, right? And that's where I think, you know, we could probably, you know, stop to say, you know, I hate the carrot and stick, but I don't know how else to say it, but it's like, for some people, and then we, you know, when we started, we're going to talk about this a little bit, but for some people, that it's going to be, they're stuck in their ways.
Jim Grubman (03:40.512)
Absolutely.
Michael Palumbos (04:05.582)
And so it's, know, wealth 3.0 and I've got one that I'm thinking of in my head right this second. Man, I could open up his dialogue, his emotional ability to say, you're saying that the way I'm talking about the family, the way I'm talking about G3, the way I'm talking about our family wealth and what I'm doing with it is actually doing more harm than good.
Michael Palumbos (04:34.872)
That's what you're saying is let's focus on how do we get them thinking in the right direction, right?
Jim Grubman (04:41.55)
Absolutely. know, for some people it just sounds like, oh, positive psychology of rose colored glasses, but, know, things can happen. And I was dealing when, and maybe what we should do is pause for a second and just for those people, go back and review sort of what wealth 1.0, 2.0 and 3.0.
Michael Palumbos (05:01.902)
Michael Palumbos (05:02.286)
No, no, I appreciate that.
Jim Grubman (05:04.782)
Essentially, I was asked to do a retrospective on the field of wealth management back in 2019 at a certain conference. And I was racking my brain and having been in this business for back into the dot com era. What sort of settled out for me was most people do not realize that the modern wealth management industry is only about 45 years old. They think, well, it's always been this way.
Jim Grubman (05:32.846)
But before the 1980s in the US, was wealth 1.0. It was all about the money. There was no mutual fund industry. It was very simplified, and there was very little written or very little attention to the family issues of wealth. It's hard to believe that everything that we've been, you're talking about discussions of family entropy and sure safe to sure safe. All of that.
Jim Grubman (06:01.888)
starts from around the 1980s. And that's what I then called, well, Wealth 2.0 began around then. And we have been in and are still are in the Wealth 2.0 era in most places. And it was...
Michael Palumbos (06:16.078)
Can I ask a question? think I want to go back to that. When we look at what was happening up to the 1980s and he may be even into wealth 2.0.
Michael Palumbos (06:27.502)
One of the, you we said it's always been this way. Where did the feudal, if we look at feudal times and look at, you know, the Lord's passing their castle, the Lord's passing their kingdom to, you know, the next generation, that's really how old, if I'm thinking is about the family business.
Jim Grubman (06:44.974)
Yeah.
Jim Grubman (06:48.754)
Absolutely, you probably know, but not many people know that although we can trace the concept of trusts back to Roman times, it was really during the Middle Ages that the concept of a trust and a trustee and what a trust is about happened exactly for what you said, which is people had to go off to the Crusades. What are you going to do with your castle and your family and whatever? They would go to a friend and say,
Jim Grubman (07:17.91)
I am going to have you take care of my family, but I'm not giving you my family. And the idea of splitting the role of somebody who cares for is a steward of, which interesting also comes from that era as a word, but does not own the trustee, does not own the assets. That is from the same era. And so yes, there is this long history of family and wealth.
Jim Grubman (07:47.214)
ownership, things like that. What I'm talking about for 1.0 though, particularly in the US, 17, 18, 1900s, was people who dealt with very rich people were pretty much supposed to just manage the money. There was very little education to the family. It was very paternalistic. And again, I mentioned something. There was very little writing or discussion of
Jim Grubman (08:16.738)
very little teaching and training and passing on of to the wealth advisors, an understanding of the family issues. And so it was all, you know, apprenticeship of sort of, you know, be by my side here in this trust company and watch what I do. This is how you take care of really rich people. It was in the 1980s, the two things happened in the nineties. One is
Jim Grubman (08:46.638)
the voices of inheritors started to come out. Often a lot of these people were from the 60s and you know, we know what that was like. But the idea of in 1988, for example, Joni Bronfman of the Seagrams Bronfman family did a dissertation for the first time talking about the title of the dissertation was the experience of inherited wealth.
Jim Grubman (09:13.838)
There were other things. So voices of the family side, what it's like to live with wealth, the challenges of wealth, the fact that wealth is not all, you know, as we say now, unicorns and rainbows and whatever. And people say, you know, this is a lot harder than people think. That started to come out. And then with that, certain other voices, Jay Hughes, other people started to talk about it. But you got to remember Jay Hughes' book,
Jim Grubman (09:42.808)
Keeping the Family was first published in 1997. People think it's been around like forever. That's not that long ago. And so 2.0 basically did wonderful things of bringing out the voices of families and wealth, the challenges of wealth, the fact that it's not just about the money, there needs to be financial education, attending to governance.
Michael Palumbos (09:50.718)
Right.
Michael Palumbos (09:53.464)
Yeah.
Jim Grubman (10:13.28)
All of that has only been built in the last 45 years. The problem and why I wrote the manifesto that was 3.0 based on the original talk and then and Kristen were joining me in that was exactly what you said, which is a lot of it got codified as fear and catastrophe that
Jim Grubman (10:43.404)
We only talked about the challenges of wealth. only talked about that wealth doesn't survive easily. And then unfortunately, terrible things happened in research. And if you're watching this on YouTube, you know I'm using air quotes. If you're only listening, I'm using air quotes. That in the early 1980s, there was actually some really
Jim Grubman (11:12.768)
not bad research by John Ward and some other people saying, you know, there's some studies looking at a very limited way that says some family businesses don't seem to survive that well past about the end of the second generation. Unfortunately, that's all. And that that became gospel. Yeah. And it was been repeated. William's Impressor and their books and lot of bases and
Jim Grubman (11:42.7)
I mean, how many websites have we seen and how many PowerPoints have you and I seen in presentation after presentation that says, you know, 70 % of well transfers failed by the end of the second generation. And I got fed up and I said, really? Like, and I went back and I tracked it all down to one small study that is not widely applicable.
Jim Grubman (12:12.62)
and that everybody is just keep referring. All of this is background to your client.
Jim Grubman (12:21.152)
your client and the patriarch of many enterprises have been hearing that and having it confirmed by saying, I worry that the wealth is going to ruin my children. And the advisor will say, well, actually you should be worried. Have I told you that 70 % of wealth transfer has failed? We have data on that. It's true.
Jim Grubman (12:43.854)
And essentially what Wealth 3.0 has been about is saying, wait a minute, first of all, we actually have no data. There are no real data in the modern world other than anecdotal to know what happens to wealth over time. Number two, shirt sleeves to shirt sleeves is a really nice adage. And that's about it. And a lot of advisors will say, well, I've seen
Jim Grubman (13:13.646)
sure sleeves to shirt sleeves. Right. I often have to say to them, okay, can you think of three families at least, where actually they were doing okay in the third generation or beyond. And they usually stop, look up, think about it and said, well, actually, yeah, I've known some families like that. There's a confirmation bias and a hindsight bias about what we think is the story.
Jim Grubman (13:41.026)
Finally, what back to your client, a lot of it is this reciprocal conversation where somebody in G1 expresses worry, the advisor confirms it as true. And then what they do is they build it into the wealth plan. Okay, we got to protect the family from the money. Let's put it all in trust.
Jim Grubman (14:09.774)
keep it away from them, tie them together so that they cannot destroy it, and that's it. And what I and Dennis and Kristen have been talking about is there's a better way that having a different conversation, pointing out the flaws in some of that thinking. We have research with the 100 Years Family Project that says many families actually do well.
Jim Grubman (14:37.942)
And we move away from the very binary, do you succeed or fail to the idea in reality, there are actually many possible outcomes. For families of wealth. Pass or fail. So
Michael Palumbos (14:55.326)
Evolving. We just evolve and it needs to be different and there is nothing wrong with, know, Tom Deans talks about, you know, every family's business that in his theory is that every generation should sell the business. And if you want to be in the next, you know, if you want to own it, that's fine, but buy the business and do it. And that's a form of evolving. That's not right for every family either.
Jim Grubman (15:21.208)
Right. basically, we were very locked in the sort of simplistic thinking to the pass fail nature of wealth. And it just so much stuff around that. But that was 40, 50 years ago. Yeah. The demographics have changed. A lot of things have changed, including the rise of understanding new techniques to deal with it. The bottom line is we now are beginning to move into and need to move into
Jim Grubman (15:51.512)
Wealth 3.0, which is leaving some of the bad stuff that grew up in Wealth 2.0 behind, keeping the good stuff and having better, newer techniques. And ironically for advisors, being able to say, we don't know. And somebody says, well, you know, I've heard wealth is going to ruin my family. And say, well, actually we don't know what those statistics are.
Jim Grubman (16:18.292)
It's a much bigger question than that. Let's talk about what you can do and maybe what you already have done to make it come out well.
Michael Palumbos (16:28.514)
Yeah, it's time to get curious.
Jim Grubman (16:31.978)
Yes, to be curious rather than judgmental. And the other thing is to make room for stories and techniques that actually do work. You know, and in my career and yours too, we've worked with families who actually are, they want to be proactive. They're doing fine. They have strong things. But maybe now at this point we get back to...
Jim Grubman (16:58.85)
when you were talking about, because I've seen many of those people too, usually the patriarch who says, nope, I've seen it, it's not gonna happen. I wouldn't say it's sort of like, how many movies and books have you seen and read and TV shows that show that rich people all basically go down the tubes? And so, nope, we gotta protect the money from the family and make sure the family, we may not even tell them that it's there.
Michael Palumbos (17:17.411)
Right?
Michael Palumbos (17:28.109)
Let me tee that up just a little bit. before the podcast started, before we start recording, we were talking about the families where it is typically the patriarch.
Michael Palumbos (17:41.826)
who wants to control things, knows better than everybody else, is afraid of the wealth either ruining people or the fact that, you all have to work together. This is how I'm gonna keep the family together and I'm gonna advise beyond the grave. then the impact that that has, there's a ripple effect. That's bigger than a ripple effect. It's more like a tidal wave.
Michael Palumbos (18:10.078)
of what happens, know, as Jay said, it's the meteorite, right? Yeah. It slams into the family because this is what you're going to do. So I think that that's really important. And I think a lot of people, when we set that stage, many people that are going to be listening to this are experiencing that exact thing right now. So.
Michael Palumbos (18:36.344)
What are the questions? are the conversations that they should be thinking and talking about with the family to ease that, to have a different discussion, to open up a different door, especially when there's damage that's already been done. I already have a son who split off and started his own business or won't come to Thanksgiving giving dinner table any longer because...
Michael Palumbos (19:02.956)
You know, he was told that from a young age, this one day this will all be yours and you'll be the president. And when there was multiple siblings and multiple cousins that came into the business, that wasn't, you we need to work together and it didn't happen the way he wanted. How do we open that door to those families? That's, I think would be really powerful.
Jim Grubman (19:25.294)
But it's funny because I've encountered that very often, you know, and that either pushback or somebody saying, don't know. I mean, I've seen surest of this, surest of this. And, know, I don't know a lot of wealthy families that are doing well. you know, but again, the confirmation bias and, know, as Daniel Kahneman said, people don't believe facts. They believe stories. Yes. the success.
Michael Palumbos (19:51.63)
Michael Palumbos (19:52.371)
Yellowstone, know, just dynasty. It goes on and on forever.
Jim Grubman (19:58.958)
And a story like succession has had so much more impact than people saying, actually, you know, sure, there is no evidence one way or the other on shirts, sleeves, the modern world. But it's like, yeah, but have you seen succession? And it's funny, because I once read an article about a psychotherapist in New York City. And I had to like smack my head and shake my head a few times because he said,
Jim Grubman (20:28.084)
all my clients are billionaire children. And yes, succession is true. They all are like that. Succession is a true thing. And I thought, that's funny. You haven't met my clients and who actually they're doing fine. But to your point.
Michael Palumbos (20:43.446)
Yeah.
Jim Grubman (20:47.842)
When I talk with somebody who expresses concern about their children and grandchildren, and that they're not quite sure what to do and that they think they need to lock it down or do something, I don't take a frontal approach and say, well, actually, you're thinking is really old and it's a lot better than you think. What I say is, I agree.
Jim Grubman (21:16.322)
that actually it sounds like you see risk in what's going on with the family and you see risk in some of the ideas of having, for example, family meetings, more communication, teaching them about the wealth. That actually it sounds like you see a lot of risk in that. And what happens next is the most important thing because
Jim Grubman (21:44.136)
Usually they'll say, absolutely.
Jim Grubman (21:48.814)
So notice it's like, I don't contest the risk, because actually there is risk, it's legitimate. And so they say, yeah, I mean, there's a lot of risk to this and I just don't think it's a good idea. I will then say, I agree there is risk. I have some ways of handling that risk that may be a little different than what you're doing. Would you like to hear about?
Jim Grubman (22:20.266)
And what I then do is watch and listen, because it's an assessment of the degree to which somebody is open or closed. If they say, okay, yeah, like what is it? What do you do about it that I haven't heard about or whatever? If they say, no, I'm good. Like, yeah, I'm pretty comfortable with what we're doing. And I think we'll just keep doing it.
Jim Grubman (22:50.006)
I don't go any further because that tells me they have no interest in hearing it anymore. They are completely closed and I'm wasting my breath and potentially damaging the relationship if I just go in head to head with them and say, no, you really got to hear this and you're wrong and whatever. And so think of these things. I agree there is risk because that's what they're focused on.
Michael Palumbos (23:16.6)
Right.
Jim Grubman (23:18.452)
I ask if they're interested in hearing how to handle the risk other than what they're doing, the method. If they express interest, we then start talking and I tell them about the bogus research and many other sort of things. And I watched to see, you know, is the light bulb going on, but to go head to head with somebody who is pretty convinced they know the story and that what they're doing is good.
Jim Grubman (23:48.91)
Don't even waste your breath.
Michael Palumbos (23:51.2)
-
That well that makes all the sense in the world. I