The Mistake That Breaks Family Business Growth | The Family Biz Show Ep. 81

More than 70% of family business problems stem not from financial mismanagement—but from breakdowns in identity, communication, and generational alignment.
 
On this episode of The Family Biz Show, Michael Palumbos sits down with Dr. Jamie Weiner to unpack one of the most overlooked sources of family business problems: the internal pressure experienced by children of successful parents.
 
This is not a conversation about balance sheets or structures. It’s a conversation about identity, legitimacy, and the emotional weight carried by rising generation leaders inside family enterprises.
 
The Hidden Identity Crisis Behind Family Business Problems
One of the most misunderstood family business problems is the belief that success transfers seamlessly across generations.
 
Dr. Weiner challenges this assumption by introducing a critical distinction:
There is a difference between being successful and feeling legitimate.
 
Many individuals growing up in successful families experience persistent family business problems tied to identity:
  • Feeling like they are living in someone else’s shadow
  • Questioning whether their achievements are truly their own
  • Struggling to define purpose outside the family legacy
As Michael shares from his own experience, he was often known not as himself—but as “his father’s son.”This subtle dynamic becomes one of the most common yet unspoken family business problems across generations.
 
The Journey That Shapes Family Business Problems
Through global interviews and decades of advisory work, Dr. Weiner outlines a consistent developmental path that explains many recurring family business problems.
 
  • Awareness: Recognizing You’re Different
  • Tug of War: Expectation vs Identity

  • Exploration: The Most Critical Phase

  • Ownership: Taking Agency

The final stage is ownership—where individuals take control of their decisions, direction, and identity.This is where many family business problems begin to resolve—not because systems changed, but because the individual did.

 

Breaking Moments: The Turning Point in Family Business Problems

A defining insight from the episode is the concept of “breaking moments.”These are pivotal life events that often feel like failure but are essential for growth.Examples shared include:

  • Being fired by a parent
  • Career setbacks
  • Personal struggles
  • Unexpected life disruptions

These moments often represent the peak of family business problems—but they are also the gateway to purpose.One powerful metaphor shared is the butterfly:If you remove the struggle too early, the butterfly never develops the strength to fly.In family systems, overprotection can unintentionally create deeper, longer-term family business problems.

 

Parenting and the Creation of Family Business Problems

Many parents in successful families believe they are reducing pressure by saying:“You can do whatever you want.”But this often creates a new layer of family business problems.Why?Because children still see their parents as giants.Even without explicit expectations, they internalize the need to measure up.This leads to:

  • Silent pressure
  • Internal comparison
  • Fear of disappointing the family

Dr. Weiner emphasizes that addressing family business problems requires:

  • Acknowledging the “giant effect”
  • Creating intentional space for independence
  • Encouraging real-world exploration

Without these, family business problems don’t disappear—they compound.

 

Cultural Complexity and Global Family Business Problems

In today’s global environment, family business problems are increasingly shaped by cultural differences.One story highlights a daughter seeking independence through employment, only for her father to ask:“Where’s my face in it?”In his worldview, success was collective—not individual.This highlights a growing category of family business problems:

  • Conflicting definitions of success
  • Cultural expectations vs personal autonomy
  • Global exposure reshaping identity

For modern family enterprises, understanding these dynamics is essential to navigating evolving family business problems.

 

From Pressure to Purpose: Resolving Family Business Problems

When individuals move through awareness, struggle, and exploration, something powerful happens.They don’t disconnect from the family.They reconnect—with clarity and intention.Dr. Weiner found that individuals who resolved their internal family business problems:

  • Desired stronger family relationships
  • Wanted to contribute meaningful value
  • Sought to create impact beyond themselves

This is where legacy becomes real—not through wealth transfer, but through identity and purpose.

 

Redefining Wealth to Solve Family Business Problems

Michael reinforces a critical framework:There are three forms of wealth:

  • Financial
  • Values
  • Knowledge

When asked which matter most, the overwhelming majority choose values and knowledge.Yet most families focus primarily on financial systems—creating misalignment and long-term family business problems.Solving family business problems requires shifting that focus:

  • Investing in conversations
  • Developing human capital
  • Building clarity of purpose

The Real Work of Solving Family Business Problems

This episode makes one thing clear:Family business problems are not operational—they are human.They require:

  • Curiosity
  • Communication
  • Space for growth
  • Permission to struggle
  • Intentional development of the next generation

Because the goal is not to replicate the previous generation.It’s to empower the next generation to stand on their own.That is how pressure becomes purpose.That is how families build enduring legacies.And that is how the Family Business Flywheel continues to create momentum across generations.

 

Key Takeaways

  • Most family business problems are rooted in identity, not finance
  • Success does not guarantee a sense of legitimacy for the next generation
  • “Breaking moments” are essential for personal growth and purpose
  • Overprotecting children can create long-term family business problems
  • Exploration is critical for developing independence and confidence
  • Cultural differences can intensify modern family business problems
  • True legacy is built through values and knowledge—not just financial wealth
  • Solving family business problems requires intentional human development, not just systems
Transcript
Michael Palumbos (00:59.506)
welcome everybody to the Family Biz Show. I am your host, Michael Palumbos with Family Wealth and Legacy in Rochester, New York. Welcome. Today, we have a really cool show for you talking about a topic that we've touched on. 
 
Michael Palumbos (01:14.018)
throughout several episodes, but nothing that we spent the whole time talking about. So Jamie Weiner, thank you for joining us. 
 
Jamie Weiner (01:22.626)
My pleasure. We're to be here. 
 
Michael Palumbos (01:24.736)
And the book that you have just written and it's out on Amazon right now is called The Quest for Legitimacy. 
 
Jamie Weiner (01:32.611)
Absolutely. It's for legitimacy how children of prominent families find their unique place in the world. It's a mouthful. 
 
Michael Palumbos (01:40.49)
 
Michael Palumbos (01:40.63)
love the website right now and growing up in the shadow of a giant brings unique challenges. I will throw to you that, you know, it definitely happens when, when, you know, you, you have great wealth and you, and you've amassed great wealth being the child of a mother or father who's super successful. My father, you know, I've lived this my whole entire life. 
 
Michael Palumbos (02:08.618)
So I'm really excited to talk about this because my father was one of the top 100 people in the company that we're with. that was the company that I decided to run just based on the training that they had and what I had learned from my father. I was never Michael Columbus, I was Marty's son. 
 
Jamie Weiner (02:24.494)
 
Jamie Weiner (02:36.462)
There you go. 
 
Michael Palumbos (02:39.52)
And so, you know, it's very funny. And to this day, dad's retired now. You know, it's we have the same thing. Hey, Michael, how you doing? Say hello to your father. It's 
 
Jamie Weiner (02:51.19)
Hey! 
 
Michael Palumbos (02:56.061)
never how are you first? you've talked about it. So, Jamie, what we have a tradition on the show, we ask people to to share with us your journey. 
 
Michael Palumbos (03:09.23)
There are several universities today that have family business and family wealth studies within their campuses. Many years ago, 10, 20, 30, 40 years ago, that didn't exist. So for guys like you and I, people like you and I who ended up working with either family businesses or families of wealth, 
 
Michael Palumbos (03:38.126)
There had to be a twisting turning road to get there in my opinion. Not always, but we'd love to hear your background. How did you know, where did you start? How did you end up doing the work that you're doing today? 
 
Jamie Weiner (03:49.39)
So Mike, it's a great question because you and I are both so used to being in the space and thinking about these kinds of things. And it's important for us to realize that it's a relatively new thing. I was born a rabbis kid, so it's a little bit different, but it came from a prominent family. I start the book actually with a cute story. 
 
Jamie Weiner (04:17.262)
about being in the sanctuary and somebody, a little kid popping up his head and saying, mom, is that God? And crawling under the seat behind me and going, well, no, that's my dad. And so I can understand what it must have been like being Marty's son. 
 
Jamie Weiner (04:43.598)
About 15 years ago, my wife who came from a business-owning family, her parents died 35 days apart from each other. And there had been a generation before that had a family business. When that business ended, everybody stopped talking to each other and nobody went to the funerals. And we had to make sure we were going to have that happen in our family. So that was really the beginning of the work. 
 
Jamie Weiner (05:12.606)
And as I began to work with Rising Jen, I always noticed that there was kind of, know, a psychologist, by background, you sort of pick up on things even before people start talking. And I always noticed that there was some impact of growing up in a prominent family. And I figured, might as well ask. So I started, I met Russ Hayworth. 
 
Jamie Weiner (05:44.818)
And for the UK, who's also got a podcast, everybody's got a podcast. And Russ and I started interviewing Rising Gen family members and asking them a simple question, which was, what's it like growing up in the land of giants? And guess what? Nobody asked us what we meant by giants. They immediately said, yeah. 
 
Jamie Weiner (06:12.382)
know, Marty's my giant. You know, and the rage was huge because it was, the oldest was about a 450 year old company. And there still were giants along the road. So, so that's kind of how I got into this whole pursuit. 
 
Michael Palumbos (06:34.318)
And so your background, you come from a psychology background psychiatry background is that that I get to catch that. 
 
Jamie Weiner (06:42.89)
Yeah, I'm a psychologist by background. And the last, I think it's almost 20 years, I've been doing family business consulting. 
 
Michael Palumbos (06:56.398)
Got it. Okay. I love it. Thank you. So how many, we talk about doing interviews, approximately how many people did you interview? Do you mind me asking? 
 
Jamie Weiner (07:09.07)
Well, let's not do approximately. It was 25 people from around the globe. So Indonesia, Chicago, Costa Rica, and I don't know if I did anybody from Rochester, New York though. Anyways, the range. So the oldest person that I interviewed at the time was 75 years old. 
 
Michael Palumbos (07:12.674)
Okay. 
 
Jamie Weiner (07:38.72)
And he was looking back on the experience. He was part of the Kaiser family, which at one point was one of the largest and wealthiest families in the country. 
 
Michael Palumbos (07:49.334)
Okay. When you're in talking to these people, what did you find? You know, what were some of the unique challenges that that you were hearing? What were the themes that you were hearing? 
 
Jamie Weiner (08:04.375)
So there's a difference between feeling successful and feeling legitimate. And we interviewed people even who were successful at a point in their life but still didn't feel in relationship to the giants that they were born next to, that they have established a sense of their own legitimacy. So the 
 
Jamie Weiner (08:32.641)
The biggest one was the whole thing about whether you felt you were enough, whether you measured up. I think that's a somewhat universal feeling. But I think when you have the experience of growing up with somebody who's built something or been part of something that's very large, and it could be the... 
 
Jamie Weiner (09:01.228)
the general store in the town. So I'm not making it that you gotta be a multi-billionaire to be a giant. And I think that was the primary thing that we found. 
 
Jamie Weiner (09:23.694)
You know, the other things that I'd love to talk about is I'd love to talk about one, how everybody we interviewed had breaking moments. And then from there, we probably should touch on the fact that we discovered a path and that by discovering that path, we really think we can make a difference in the lives in a way that... 
 
Michael Palumbos (09:33.582)
Okay. 
 
Jamie Weiner (09:51.114)
in modesty. don't think anybody else has been done before that would be able to change people's lives. 
 
Michael Palumbos (09:59.758)
I love it. Well, let's dive in. Tell me a bit more about it. 
 
Jamie Weiner (10:04.918)
that. 
 
Jamie Weiner (10:07.948)
Breaking moments is a very interesting idea. When I look back at my own life, I can identify a chain of breaking moments. And it's a very important concept that's worth thinking about because parents, when somebody has a breaking moment, sometimes in this... 
 
Michael Palumbos (10:19.822)
Okay. 
 
Jamie Weiner (10:36.278)
current world jump in and want to do this repair scene. But I wouldn't encourage, I'm not looking for people to have breaking moments. But for example, Rishi, one of the people we interviewed in the book, and it's a longer story, got fired by email from his father. Stopped talking to his dad for two years and during that period of his life, 
 
Jamie Weiner (11:05.678)
figured who he is and what he wanted to do. So it was a couple of years, he was crushed at first. And two years later, he hit a point where he had a position as a professor at a university. His dad was Indian, his mom was not. He hadn't spoken to his dad for two years. And he took the risk and decided that before he would start, he would go home and knock on his dad's door. 
 
Jamie Weiner (11:35.566)
It was greeted by his dad and his dad said, I'm so glad you did this. I wouldn't have done it. And there was a cultural thing going on in the background of that. From that point on, it changed Rishi's life and it changed his relationship with his father. So there are less dramatic examples in the book. 
 
Jamie Weiner (12:02.318)
But that's a pretty dramatic example. I call that period that he was struggling being in a period of liminality, a feeling betwixt and between. So I'm a psychologist. I'm not calling it depression. I'm making a distinction and trying to emphasize. there were a couple of cases where I think it was depression. 
 
Jamie Weiner (12:30.178)
But I'm trying to emphasize that people have hard times in their lives. And that's not exactly what we would think about in terms of clinical depression. It's struggling. And that it can be the beginning of the quest to figure out what you really want to do with your life. 
 
Michael Palumbos (12:48.494)
When you think about it, Maslow did a pretty good job of putting together a formula years and years ago of am I safe? Can I take risks? Do I have my autonomy? And do I make a difference? Or how did my life matter? What's my purpose and am I going to matter? 
 
Michael Palumbos (13:14.126)
And one of the things that I've been playing with and trying to help families to understand is that we put all these systems together for the wealth. We, know, how to create wealth, how to, you know, how to manage wealth, how to pass wealth. you know, but there's, there's not a ton of systems for families to be putting into place. It's, we know in our industry that there's a lot of people like you and I that are, it's this 
 
Michael Palumbos (13:43.97)
burgeoning quest out there like your quest for legitimacy to help people to understand. There should be a system in place that the parents understand that really their job is not to be the giant. Their job is to help their children stand on their own pedestal and find out what they're passionate about and how they're going to make a difference in the world. Because if we're all cut exactly like our fathers or our mothers, 
 
Michael Palumbos (14:13.814)
It's going to be a really boring. 
 
Jamie Weiner (14:15.662)
When I absolutely love that you know about Maslow and more and more people that may mean something, may not mean something to your whole audience, but it was really the idea that development happens over the course of lifetime. And I think rising happens over the course of lifetime. 
 
Michael Palumbos (14:39.566)
That's a great way to talk about it because it's not something like, okay, you're a teenager now, you're 13, you you go and get your bar and bar mitzvah, you go get your confirmation, whatever, you you become the, you become a teenager for the first time. Now you're self-actualized, not a... 
 
Jamie Weiner (15:00.046)


Jamie Weiner (15:00.387)
Wouldn't it be nice? 
 
Michael Palumbos (15:06.998)
It would be 
 
Michael Palumbos (15:07.538)
super nice. you know, there had to be for the people that you interviewed, you know, there had to be some awareness to what was what they were feeling and what was going on. What did that what was like that like for them? 
 
Jamie Weiner (15:26.744)
So yes and no. When you have a breaking moment in your life, could be a divorce, could be whatever, you're not thinking about, my God, this is an opportunity. You're thinking about, my God, I just got kicked in the teeth. you're going, a lot of people, it's self pity at that point. 
 
Michael Palumbos (15:54.742)
Okay. 
 
Jamie Weiner (15:56.898)
and it's only through that process of, of sorting, sorting stuff out, do you begin to maybe be able to look back and go, God, I wish that didn't happen. But, and I think it's that, but that's very important. and that's part of the message that I'm also kind of giving about. 
 
Jamie Weiner (16:26.35)
parenting because somebody sent me this wonderful little two minute video about a butterfly and a young man walking and discovering a cocoon and deciding to sit down and watch the butterfly emerge, which doesn't happen real quickly. And the butterfly's halfway out and seems to be stuck. So the young man cuts off the cocoon and holds the butterfly and waits for it to fly. 
 
Jamie Weiner (16:55.084)
Well, that last period is when the butterfly releases what needs to be released in order for the wings to work. And it just it touched me. Because it was in two minutes, it sort of captured the whole thing and the whole transition to becoming to rising and taking it being able to have some to fly. 
 
Michael Palumbos (17:23.628)
So walk me through, I'm trying to make the connection between the breaking moments and the quest for legitimacy. take a step back for me for a second, just, and I apologize, but I'm like, I'm somebody that you've interviewed. I'm feeling that I'm looking for this quest for legitimacy. What I guess. 
 
Michael Palumbos (17:51.586)
Where am I? What's happening? What's through the interviews that you did? What's the theme before the breaking moment and after the breaking moment? So I guess am I missing that? 
 
Jamie Weiner (18:03.576)
So let's do before. I'm gonna do it very quickly. Before you all of us, you you kind of have these moments and Henry Kaiser was a good example. Henry Kaiser and you know, got sent to a private school. early on, there was this message that he'd better prepare because it's someday in his life, something important was gonna happen. 
 
Michael Palumbos (18:06.082)
Yep. 
 
Jamie Weiner (18:33.282)
and got sent off to boarding school. I don't think he really wanted to go to boarding school. And that was kind of the beginning. And the beauty of what happened was along the way I picked up a research team from the University of Adelaide. I met the researcher in an elevator and we got off the elevator and he said, God, that's great. 
 
Jamie Weiner (19:01.794)
do some journal articles together. And so was one of those magic moments for me where all of a sudden I had a practitioner research team. And what we discovered is whether it was Indonesia, Chicago or Costa Rica, that there was a pattern. Wasn't linear, so it wasn't like you did step one and then you did step two, but it started with awareness. And... 
 
Jamie Weiner (19:31.116)
I don't know for you if you remember the early moments of awareness of growing up in a prominent family, but even the story of being the sanctuary and having that little boy say, is this God, his mother? Sort of that one of those moments where I went, there's something a little bit different about who my dad is and the world I was born into. It moves from awareness into what I call the tug of war. 
 
Jamie Weiner (20:01.518)
because you grow up in a culture and your family and you're aware of it. And lot of the families you and I work with have family governance. They have all kinds of things going on. They may not be aware that somebody's already doing estate plans for them and figuring out what's going to happen to them later in their lives. But as you go out into the world, you begin to discover 
 
Jamie Weiner (20:30.414)
other things and what you were brought up in. And at first you come home and parents go, God, that's so great. Where did he, learn this? A little bit later you come home and they go, Oh my God, where did he and she learn this? And it's a tug of war between two being in two worlds. It moves on and with COVID I hope is still the same, but 
 
Jamie Weiner (20:58.764)
The next period is a period of exploration. One of the people I interviewed, father's business failed during her adolescence. And she managed to convince her parents to find a way to have her, there's a Mexican background to go. 
 
Jamie Weiner (21:24.846)
explore other cultures, travel, insights. And she never lost that connection to the culture she was brought up in, but she also became rich by what she experienced and used that period to sort out the different, the world she brought up and what she was learning to form who she was. Cause the last period is taking ownership of your life and 
 
Jamie Weiner (21:53.26)
the word that is more of a psychological word, but having agency, feeling like you have some control over the decisions you're making. 
 
Michael Palumbos (22:03.63)
Okay. And so that really makes an awful lot of sense. I can only look at it from my experience. My awareness was the first time I got interviewed at the company that my father works for, the manager said to me, Michael, just based on your name. 
 
Michael Palumbos (22:26.124)
I'll bring you in tomorrow. And I was one of those non-traditional students. So I had not finished my college education. had gotten an associates, but kept pushing it off. And he said, when somebody asks you, where did you graduate from? What are you going to say? Your father graduated from X, Y, and Z. And so what are you going to say? And I'm like, OK. And that was enough to get me to go back to school. 
 
Michael Palumbos (22:56.13)
but it was that comparison that happened. And then the first time you're walking through the office or walking through a company event that's outside of the office, it's even bigger. you've got the name tag on and, you're Marty's son. And so then there's this awareness of that you didn't have at home. What an impact dad had made in the world outside of the house, if that makes sense. 
 
Michael Palumbos (23:24.974)
And then there was that, you know, I don't want to, think the tug of war was a little different for me than, what you were talking about, but I think the tug of war was this is the way dad did things. I don't know if that's the way I want to do things, if that makes sense. I, you know, so for me, the exploration was like finding the purposeful planning Institute and, having a conversation with Jay Hughes and. 
 
Michael Palumbos (23:53.772)
And just starting to look at this thing and say, there's more to wealth than just money. There's wealth in the knowledge and the values and whatnot of the family. And I wouldn't have discovered all of that stuff and gotten to the point where I have my own podcast and I'm like, I am and I just like doing this work, you know, but as you were going through those pieces, I can doubt, know, in the, different steps, I can definitely feel how that was my life. 
 
Jamie Weiner (24:24.908)
You know, I'm so surprised. just assumed you did everything the way Marty did it. 
 
Michael Palumbos (24:32.75)
Right. And you know, we have, we have, we have an even closer connection that you don't know this, but my father, his mother had four boys and she put all four boys into the seminary. Only one came out of priests, but she knew that if she put four in, there was a pretty. 
 
Jamie Weiner (24:50.304)
And, you know, it's not uncommon for people who grow up in prominent families to struggle with school. So it's a great example. I did. Right. I didn't go, great. I'm going straight for what I want to do. It took a long time to kind of sort it all out. 
 
Michael Palumbos (25:17.774)
Yeah. And I think, you know, in hindsight, I can look back and say, you know, dad was successful. He was a, you know, the first generation wealth creator. Again, not, you know, I mean, super proud of dad. He's done incredible, but we're not talking, you know, Walmart, know, Walton wealth, but definitely, you know, top 3 % of America kind of a thing, you know, done really, really well for himself. And. 
 
Michael Palumbos (25:48.27)
I as the oldest, I watched it to go from point A to point B. I was in the very first house that was, you know, very blue collar, very. And in the second house where it was very, you know, middle, middle America. And then watch them the year I went to college for the first time, they, you know, moved into this neighborhood and into this house that I was like, 
 
Jamie Weiner (26:00.814)
You 
 
Michael Palumbos (26:18.668)
Man, my sisters have got it great. And my brother, know, they're loving, 
 
Jamie Weiner (26:24.91)
I couldn't march now. 
 
Michael Palumbos (26:27.566)
That's fun. that the breaking moment now is, know, this makes it to me, this is making more sense. I've gone through this journey. I've done these things. Where does the breaking moment talking about, that, you know, like you mentioned the one story. Can you give some other examples of other people that have had, you know, they've gone through being in the shadow of the giant through the breaking moment. What were some of the other breaking moments that people had had? 
 
Jamie Weiner (26:58.656)
So the one I'm gonna share is may feel kind of different, but somebody who grew up in Costa Rica, grew up in a family that played tons of tennis and fairly early on in his life, he had an injury. So it was a literal breaking moment. And... 
 
Jamie Weiner (27:26.446)
The injury from that point on meant that he was not going to play tennis at the level that his family played tennis. And he started to form other friendships different than the family's friendships. This was such a fun interview to do. He had a guitar hanging on the wall. You could tell that there was something different about him. 
 
Michael Palumbos (27:56.238)
Bye. 
 
Jamie Weiner (27:56.566)
And he really decided that what he wanted to do primarily with his life is play tennis and make music, surf and make music. And he did really well at making music. And at some point realized he needed to make a little bit of money. So dad had a chain of probably, they weren't 7-elevens, but that kind of store. 
 
Jamie Weiner (28:23.982)
And he created a business making sandwiches. Who could do in a much shorter period of time. He actually at one point had a hundred people working for him making sandwiches. And all of that was really designed to support his ability to surf and make music. So it was a literal breaking moment, but it clearly changed his life. And for a while, it was really a struggle with 
 
Michael Palumbos (28:27.288)
Okay. 
 
Jamie Weiner (28:52.942)
who had this idea of where he should be going or what he should be doing. And a lot of people assume you're to end up in the family business. You did. But not everybody ends up in the family business. And not everybody should end up in the family business. 
 
Michael Palumbos (29:09.326)
you 
 
Michael Palumbos (29:13.932)
Yeah, you know, it's funny that you say that because I haven't had these specific conversations with my siblings, but I do feel there are times when, you know, they may feel, and I should reach out to them and have these conversations that they may feel, boy, weren't you lucky working with dad all those years and... 
 
Michael Palumbos (29:40.974)
You know, just some, you know, the fact that they didn't take that path or go down that road, just a different experience for them. Still, every one of my siblings, I still think that they feel the shadow of the giant because dad, you know, was successful and did have, you know, some wonderful experience. I have a sister, my youngest sister, she's one. 
 
Michael Palumbos (30:10.272)
two or three Emmys. And, then she just won just this year won the South African equivalent to an Emmy. She's a producer for Sesame Street. so she's the TV land before she, and then now she's a producer. She produces Takalani Sesame, which is Sesame Street in South Africa. And, and she just downplays her success. It's one thing with your, friends and fam, you know, friends. 
 
Michael Palumbos (30:39.32)
But with your family, you should be like the people that you trust and your closest people. And sometimes she still downplays it. And I'm curious if there's any of the, I'm just not sure the difference I'm making in the world, if this is exactly where I want to be. And if there's any comparison to the amount, mean, was, did a great job and success in his business, but then also. 
 
Michael Palumbos (31:03.402)
in the community, he was on every board and everybody in the, you he made a difference in a lot of charities and a lot of people just knew who he was. You can't really walk through the town without knowing who he is, you know? And so I wonder if that's, that'd an interesting conversation, I think, for us to have as siblings. That's pretty neat. 
 
Jamie Weiner (31:23.832)
So if you ever need me to, you know, lead that conversation with your family, you know, one of the things that we really discovered is that the rising gen grows up with a sense of isolation. They don't quite understand. And so we're actually starting to do one year experiences called the rise where we're going to gather groups of rising gen. 
 
Jamie Weiner (31:51.598)
And I use that as a broad range in terms of ages, but people with that sense of being part of something that there's a giant and they're sorting out who they are with. And we're doing the first one in Oxford because those kinds of conversations that you're talking about happening don't happen. And what your sister is doing sounds real cool. 
 
Michael Palumbos (32:23.616)
You know, I'm, I'm brag on her for two seconds. She just got married and the cast and crew in South Africa put together like a five, six minute video with all of them dancing and wishing her good luck on her marriage and with, with, with, you know, the Muppets in. 
 
Jamie Weiner (32:43.223)
jeez. my God. 
 
Michael Palumbos (32:46.85)
Then, 
 
Michael Palumbos (32:47.37)
you know, one of the artists then drew a picture of her and her new husband. You know, it really cute, you know, both in their 40s, and neither of them had been married, neither them had kids. And they found each other during COVID. And just super sweet, you know, that they found all that stuff. I want to get back to you. So enough bragging on my sister. 
 
Michael Palumbos (33:15.726)
Love you, Andrea. 
 
Jamie Weiner (33:19.02)
You 
 
Michael Palumbos (33:20.826)
So now we go through this journey, know, the kind of that questing of these things. We have the breaking moment. And then you alluded earlier to some, I don't remember exactly the words you used, but some steps or some path forward from there. Did I catch that right? 
 
Jamie Weiner (33:40.81)
And 
 
Jamie Weiner (33:41.11)
so the steps are awareness, tug of war, exploration. Exploration is one probably the most important to spend some time on. And that moment, and I'm not sure everybody gets there, where you really feel like you've taken agency of your own life and done in all kinds of ways. Clearly for me, writing a book was like, okay. 
 
Jamie Weiner (34:10.622)
You know, I wish my dad were here because I think he would be, you know, I think we could have different conversations than we had before he passed away. 
 
Michael Palumbos (34:22.232)
just resonated with me so incredibly much. I wish my dad was here to see this because I can't tell you the amount of people that those words, I've heard them before, my mom or my dad. And I've got one in particular that I'm thinking of as a family member that I happen to do, you know, I manage their investments. It's a older relative. 
 
Michael Palumbos (34:51.296)
And I remember looking at him and saying, you know, my, my, grandfather was a saver. There's one of my uncles and I, you know, my uncle had been saving and doing a really good job in saving. you know, and I just looked at him and I said, man, pop pop would be so proud. 
 
Michael Palumbos (35:15.57)
And it was almost like, you know, you could just like his heart just soared hearing those words. And to your, you know, I think you're breaking moments, you know, when you talked about the first story of the son going back to the father. Don't wait. If you have those moments, don't wait. 
 
Jamie Weiner (35:40.398)
Yeah, well, thanks for sharing a little bit about your family, because then this stuff comes alive. And I have stored away every sermon my father wrote. I have a photo album that traces his history from Dresden to Palestine through India. I have all these memorabilia. For a long time, I couldn't look at them. 
 
Jamie Weiner (36:09.378)
because they were so overwhelming in terms of how big the journey was for him. And now one, I've done something that feels like if he were here, we'd have a conversation about it. And two, now I'm really excited to go back and at least organize and have some idea what all that stuff was about. And you're doing it in real tangible way. I mean, 
 
Jamie Weiner (36:39.796)
I see the backdrop, you know? So it's very powerful because at some point our parents continue to live inside of us. And making peace with that experience is pretty powerful. 
 
Michael Palumbos (37:03.436)
Yeah, there's probably a lot of, how do I say this? 
 
Michael Palumbos (37:13.598)
generational pull on that giant shadow. Explain what I mean. know, it's, it's probably, you know, it's possible and tell me if I'm, if anybody experienced this before, but it's like the way that regardless of, regardless of the wealth or regardless of the success, there's still that I want to make my mom, I want to make my dad proud. 
 
Michael Palumbos (37:42.734)
of who I am, I want them to see me for me. And then the wealth just magnifies or the success of the father or mother that's successful magnifies that even bigger. Is that resonated on with you? 
 
Jamie Weiner (38:02.506)
It sure does. 
 
Jamie Weiner (38:15.385)
J use mean mean nothing to your audience. Maybe you may have talked about J so it may mean something to your audience. 
 
Michael Palumbos (38:21.934)
Jay's been on the show before, they may know if Jay Hughes is kind of like the, you know, I know he's the godfather of all a lot of this work for many of us. 
 
Jamie Weiner (38:35.062)
Well, yeah. So, you know, Jay talks about all the different kinds of wealth. And for my dad, I didn't get the financial, but I got all the others and Jay did the, the intro to the book and, Jay, I love the intro cause he talks about his own experience growing up with a prominent dad and prominent attorney. 
 
Michael Palumbos (39:01.198)
Okay. 
 
Jamie Weiner (39:04.194)
and recognizes, and we all look up to Jay, right? And he recognizes that he grew up in the shadow of somebody who was extremely prominent and the power of doing that in the introduction of the book. And I go, what better introduction for what this book's about? 
 
Michael Palumbos (39:28.568)
Yeah, and to my point, Jay's grandfather was a prominent attorney. 
 
Jamie Weiner (39:34.892)
Yeah. 
 
Michael Palumbos (39:35.534)
So it's kind of passed on. So I guess that's where I was wanting to ask you is from a parenting perspective, you know, this, if I have young children or even grown children, if I'm, you know, their father today, you know, I'm talking with my kids today, what are some of the conversations that I should be having? 
 
Michael Palumbos (40:03.85)
with them to make sure that they maybe that the tug of war that they might be having in their heads, I can lessen that and let them know that, you know, I really just want them to be happy and follow their own path. 
 
Jamie Weiner (40:22.606)
So that's a great one to talk about because I know parents who've said, do whatever you want to do. And they forget the part of acknowledging that in their kids' eyes, they may be seen as a giant. And so even though they say, do whatever you want to do, the person growing up is saying, yeah, sure, but I got to measure up. And so that part of the conversation is really important. 
 
Jamie Weiner (40:51.022)
The other one, and it's probably even the bigger one, is allowing room for a rite of passage and allowing that next generation, maybe even encouraging the next generation to do some exploration. And I know people now talk about gap years and all that kind of stuff. They talk about working for your and somebody else's business. 
 
Jamie Weiner (41:20.702)
It's those are tangible manifestations of something that needs to happen inside. And it's really that thing that needs to happen inside that is what's going to help transform somebody into believing that they too can stand and walk in the land of giants. 
 
Michael Palumbos (41:45.1)
I it. Yeah, I'm looking at my daughter that is taking a gap year this year to, you know, she's doing, wants to go to medical school and she now has three interviews. So she probably has a pretty good shot of making it in and doing what she's doing. But that process, you know, the gap year is a lot for a lot of parents to take on to say, 
 
Michael Palumbos (42:13.046)
Really, shouldn't you just like be doing your applications in your senior year and whatnot, it's doing those app that application process is ginormous. But what I'm, what I'm watching as the parent is exactly what you just said. She's living on her own. She's not being covered by mom and dad and the family. She's figuring out the expenses on her own. She's working. and you know, having some struggle. 
 
Michael Palumbos (42:42.914)
Which I think, you know, a year from now, or five years from now, or 10 years from now, she'll look back and as that was one of those defining moments for me to say, I can do this. You know? 
 
Jamie Weiner (42:55.694)


Jamie Weiner (42:58.075)
I think that's really powerful because medical school, know, once you step on that conveyor belt to become a doctor, right? It's a conveyor belt. You know, once you start, it just keeps going and going and going. Depending on how much you specialize or what you end up doing at the end, it's not a 
 
Jamie Weiner (43:25.39)
Oh boy, I can take three weeks off or a year off in the middle of it, you know, and so having that moment is pretty powerful. 
 
Michael Palumbos (43:36.194)
Yeah. What are some of the other things that you've found or maybe some of the things that surprised you in this discovery process and interviews that you did that just really stood out that you want to talk about? 
 
Jamie Weiner (43:55.318)
Yeah, probably the one that popped in my head. We interviewed a woman from Indonesia, Chinese family. right now is not a great time to build wealth and wasn't her parents was not a good time to build wealth in China. And so they came to Indonesia, they made money, they sent the daughter off to the States. 
 
Jamie Weiner (44:18.646)
So all the children's daughters, so there was no son to set that role. And she goes off, she's got two instructions. One, you gotta get an advanced degree. And two, you have to come home. Right? So she comes home and her dad's business is mushroomed. And so she helps dad build a factory, but they don't get along all the time. 
 
Michael Palumbos (44:35.886)
Okay. 
 
Jamie Weiner (44:47.918)
And, you know, in her culture, you're supposed to honor your father. And so one day she decides, I'm going to go get a job. then before her interview, she sits down with her dad and she's, Dad, you're going to be so proud of me. I'm going be able to earn my own money and do all that kind of stuff. And her dad looks at her and said, 
 
Michael Palumbos (44:55.982)
 
Jamie Weiner (45:17.526)
which this threw us, he said, I don't get it. Where's my face in it? We're going, where's my face in it? What did he mean? Well, he meant, how in this are you honoring me? Cause you're supposed to be part of what we're creating as a family. And more and more, what we found is that people grow up in a world where they have more multicultural experiences. So the idea of 
 
Jamie Weiner (45:47.502)
getting a job and making money as being part of how you define your independence was foreign to him. And that is a much more common phenomena than a lot of it, because we live in a global world. And I think it's important for the people who are raising the next generation to appreciate that we grow up in a global world. 
 
Michael Palumbos (46:07.608)
Right? 
 
Michael Palumbos (46:18.318)
I love that. I love that. think, I can't remember who wrote about it, but there was somebody else had written about that. And it was really interesting because I've led a pretty sheltered life, you know, most of my time in upstate New York. so, you know, other cultures and how they do things like, you know, Eastern philosophies are just different than Western philosophies. 
 
Jamie Weiner (46:45.592)
Yep. 
 
Michael Palumbos (46:46.19)
And so, you know, in dealing with families and how you do things, think, you know, I don't have any families from other cultures in my, you know, in the work that I do right now, but we do live in a work, you know, upstate New York has many cultures in it. I ever to, if I was ever to serve another family from another culture, that's been one of the things that, you know, as the advisor side of it, you'd really need to look into 
 
Michael Palumbos (47:15.488)
What are the standards of the culture? What you know? How are things typically done so that at least you go in aware that the way you've done things with other families may not be the way that you need to do them for this family? 
 
Jamie Weiner (47:28.718)
What a great awareness because even I grew up in Skokie, Illinois, which, know, little suburb outside of Chicago, one point, it still has a Jewish community, but now there's Indian cultures in there. mean, it's more and more we live in a world that's multicultural and marriages produce, you know, bringing people in from other cultures. 
 
Michael Palumbos (47:49.432)
Yeah. 
 
Jamie Weiner (47:58.926)
And how we deal with all of that, both as advisors and as parents is part of this whole quest thing. 
 
Michael Palumbos (48:05.42)
Yeah. 
 
Michael Palumbos (48:10.102)
I love it. So we've talked about the journey. We've talked about the, come on. I just, I'm not the roadblocks, but the breaking moments. 
 
Jamie Weiner (48:27.223)
Right. 
 
Michael Palumbos (48:29.026)
We've talked about some of the surprises that have happened for, know, once somebody is through that awareness phase, you know, through those phases and now they have ownership, what's kind of, what are some of the results of, you know, for that rising generation, once they have ownership, what were some of the feelings and what were some of the things that, you know, you saw through that? 
 
Jamie Weiner (48:57.602)
You know, there's really an important insight that comes out of that question, which is a lot of people, lot of business families encourage the generation, the next generation, and it can go the opposite way, but a lot encourage them to come into the family business. Or in my case, I struggled with whether I was going to become a rabbi or what I was going to do with my life. 
 
Jamie Weiner (49:27.999)
and because of the power of and 
 
Jamie Weiner (49:37.152)
When somebody discovers who they are and takes agency, everybody that we interviewed wanted to have a stronger connection with their family. They may not want it, wanted to be part of the family business, right? But they wanted to bring the value back and they wanted to bring value back to their family. They wanted to have an impact on the world. 
 
Jamie Weiner (50:07.278)
Impact is a big deal. We could do a whole show on impact and what impact means. Even now we talk about impact investing, but impact is more than about investing. I just think that's such an important part of what we discovered. 
 
Michael Palumbos (50:09.794)
Sure. 
 
Jamie Weiner (50:33.61)
I think it's different for women. There's a whole chapter in the book about women. 
 
Jamie Weiner (50:42.51)
And. 
 
Michael Palumbos (50:44.91)
It's 
 
Michael Palumbos (50:45.19)
interesting that you say that because when, know, again, I, only thing I can do is relate my journey and my family to, you know, what you discovered. And as you talked about it, I started smiling because I'm like, I found out what my core purpose is. You know, my core purpose is to inspire change. And it's only been, you know, change is hard and difficult and 
 
Michael Palumbos (51:14.606)
Not fun, it's never fun. I mean, it may be fun along the lines, but it's usually comes with some amount of pain because you're going from someplace to someplace and that change process, like the butterfly that you talked about in the beginning, it's difficult. And so, you know, what I, for me, what was really neat was anytime, you know, once I learned that, 
 
Michael Palumbos (51:43.246)
I determined that it didn't matter where I landed in terms of the work that I did because I could inspire change as an educator or as a business owner or as a family wealth advisor, or if I was working for someone else, I'd still probably be working on my core purpose once I had the ownership of who I am and where I was going. 
 
Michael Palumbos (52:12.174)
And it was super helpful. so I, you if your process, know, as your process and you're having these discussions to help people figure out, you know, what do they value and what is their purpose to help them through that journey and have those discussions, man, what powerful work that is. 
 
Jamie Weiner (52:36.578)
Absolutely. And I understand that on a very personal level, because, you know, when you're younger, you think it's all about picking what you're going to do, what your job is going to be, what you're going to do with your life. Well, it is, but it's not really about what you what job you're going to choose. It's about finding the why. That you're here about. 
 
Michael Palumbos (53:01.218)
Yeah. 
 
Jamie Weiner (53:04.622)
And there are plenty of people to talk about finding the why now. But once you figure out the why, you also got to figure out the how. But you can't just sit around and think about the why. But you're right. I mean, I'm at an age that most people retire. What is that? What do you do when you retire? so... 
 
Michael Palumbos (53:08.067)
Yep. 
 
Jamie Weiner (53:33.294)
didn't learn how to play golf. have to do something with my life. And my part of my journey fits in with who I am. And it's about wanting to make a difference. 
 
Michael Palumbos (53:48.718)
I just was reading an article earlier this morning that was all about the seven ways to stave off. 
 
Michael Palumbos (53:55.982)
Alzheimer's and dementia. one of the top ones was to always be learning something new. you know, retirement, I think is going to become more and more a thing of the past. And we're going to be tired talking about not retiring from, but retiring too. So, you know, maybe you retired from a practice one time and now you're an author and that's a whole nother chapter in your book of life, you know. 
 
Jamie Weiner (54:20.814)
Yeah, and I thought it would be more relaxed. I'm working harder now than I've ever worked before. So I'm going to be speaking in Edinburgh and going to London and doing all this kind of fun stuff. And I'm going, OK, I'm on the ride. 
 
Michael Palumbos (54:40.172)
I love it. You know, I didn't ask you, do you have children? 
 
Jamie Weiner (54:45.11)
I'm a step dad of three. And one, I think they all like me. It's really a lovely thing. 
 
Michael Palumbos (54:47.299)
Got it. 
 
Michael Palumbos (54:55.886)
So 
 
Michael Palumbos (54:57.428)
the reason I ask is, you know, is there a message that you would, you know, in this talking about journey of giants and being in the shadow, is there a message that you as a stepfather, you know, would share with your kids to, you know, the message that you'd send to them? 
 
Jamie Weiner (55:16.974)
Yeah, I also got to tell you I nine grandchildren. So I'm now part of a multi-generational thing without any genetics involved in it. But it was very cute. have a 14-year-old granddaughter. And over the weekend, her and I had back-to-back many, many pettys with each other. And it was just, it was so delightful. 
 
Michael Palumbos (55:20.239)
my gosh! 
 
Jamie Weiner (55:46.05)
just to be there for her and to hear her curiosity about me, curiosity about the book, but also to hear about her playing soccer and her own, and it's allowing that space for those special moments. 
 
Michael Palumbos (55:56.908)
Yeah. 
 
Michael Palumbos (56:13.39)
love it. You use the word curious, which I think is the most powerful word that is overlooked in my opinion that I've learned through the last few years. Learn to get curious. Get curious about your spouse and what she's saying or he's saying. 
 
Michael Palumbos (56:32.222)
get curious about your grandchildren, about your children, and ask the questions that show that you care, right? And that probably, yeah, I can imagine if, you know, we're asking, why does that matter? Why is that important to you? Or what did you learn from that? And we got curious about these things. It probably gives that space for the growth that they're going through in their journey in your shadow. I mean, think about that. Your grandchildren are going to be sitting there 
 
Michael Palumbos (57:02.368)
saying, you know, my grandfather wrote a book. How do I live up to something? And so that journey of being curious and thinking through, you know, good questions and just being there for them, like you said, being with them, go do a mani-pedi with your 
 
Jamie Weiner (57:07.427)
I'm 
 
Michael Palumbos (57:29.67)
Allow for that to happen. love that. Jamie, I just want to say thank you. This has been awesome. The Quest for Legitimacy is available on Amazon and all the other spaces out there that you can purchase a book. And then I know that you and Russ are also doing 
 
Michael Palumbos (57:53.932)
some talks so like if you're listening to this and you wanted to have a more in-depth conversation or to have Russ and Jamie or either one or the other to lead a discussion for your family or for your business and whatever the case may be of what some of the family business centers might be interested. You go out to their website, I think it's thequestorlegitimacy.com. 
 
Michael Palumbos (58:21.248)
is the website to be able to find Jamie and Russ in these conversations. Thank you so much for your time. 
 
Jamie Weiner (58:29.358)
God, this has been a treat. I got to learn about you and not just talk about me, which is always a beautiful thing. So thank you for the opportunity. 
 
Michael Palumbos (58:38.638)
The one thing I, my wife wants to, you sometimes she'd like to take the, the proverbial hook and get me off stage. I wear my heart on my sleeve and I'm vulnerable and I've made lots of mistakes and I've done some good things. And so the only thing I have is the experience that I went through with my family. And it's probably one of the things that drives me most is that I made mistakes as a parent. I made mistakes as a son. 
 
Jamie Weiner (58:46.766)
You 
 
Michael Palumbos (59:07.926)
You know, I watched mistakes being made in the family, but there's also, if you look at the scale of justice, so to speak, there's way more good that has happened through all those things. But I definitely want to make sure that, you know, all of the bad stuff that as much as I can to the degree that I can, I want to let my kids know that there were some things that, you know, you don't have to do it that way. There's a better way of doing it. And as Jay says, I'm 
 
Michael Palumbos (59:37.026)
want to be an elder, not an older. 
 
Jamie Weiner (59:41.056)
I love it. 
 
Michael Palumbos (59:43.47)


Michael Palumbos (59:43.75)
And so, you know, I will always be learning and I will always be curious and, it's not my place to determine their journey. Right. And so this conversation for me just has been super awesome because I can't, I have not read the book yet. I'm going to read the book so that I can take the experiences that you've had from these other families and be able to apply it to my own family and how we do things. then obviously. 
 
Michael Palumbos (01:00:13.101)
the families that we serve. 
 
Jamie Weiner (01:00:15.144)
Absolutely. And you understand both the balance between financial wealth and that it's about a lot more than that. And that's really a beautiful lesson. 
 
Michael Palumbos (01:00:24.918)
You know, I know I'm over the time a little bit, but I just want to say I've asked this question to people all the time. We really, at the end of the day, you've got three things. You have your physical wealth, your assets, right? You've got your values and how you live your life. And then you've got the knowledge of how you put all of that stuff together. And I'm sure there's some people would throw in, where's the relationships in there? Where's the social and all those things. 
 
Michael Palumbos (01:00:52.824)
But if you just looked at it as three assets that we carry inside of ourselves, knowledge, values, and financial assets, wealth, if you could only pick two to give to your children, which two are you giving them? And I would say, way over 90 % say, I'm giving them my values and knowledge. But where do we put our financial assets? We always spend our time and our money on the financial assets and how we're going to move those over to 
 
Michael Palumbos (01:01:22.828)
the kids, and we really should be taking some time and some money to invest in how are we transitioning the knowledge and the values, and we should be investing in those things since that's what's really important to all of us. 
 
Jamie Weiner (01:01:36.526)
We could talk a lot more about that, but you just said a mouthful. And thank you for the gift. 
 
Michael Palumbos (01:01:44.108)
Yeah. Jamie, you have been, I'm so glad that we did this. I'm so glad to share this with the world. Everybody grab a copy of the quest for legitimacy and enjoy. Jamie, Jamie Weiner, I really appreciate your time today. My name is Michael Palumbos. This has been the Family Biz Show. I'm in Rochester, New York with Family Wealth and Legacy. And we can't wait to have you listening on the next episode. Have a great day, everybody.