Ep26 Octavian Graf Pilati—How a 25-Year-Old Saved His Family Legacy After Losing Everything

Ep26 Octavian Graf Pilati—How a 25-Year-Old Saved His Family Legacy After Losing Everything
The Pressures of Privilege
Ep26 Octavian Graf Pilati—How a 25-Year-Old Saved His Family Legacy After Losing Everything

Feb 23 2026 | 00:52:33

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Episode 26 February 23, 2026 00:52:33

Hosted By

Diana Oehrli

Show Notes

Diana Oehrli sits down with Octavian Graf Pilati, whose family owned the same Austrian forest since 1730, to explore what happens when privilege meets crisis. After his family lost everything to fraud when he was just 25, Octavian discovered something most wealthy families never learn: comfort creates fragility, and hardship builds strength.

In this raw conversation, listeners will discover how to prepare the next generation for real adversity through intentional discomfort. Octavian shares the framework behind antifragility for families, explaining why conflict avoidance destroys wealth faster than market crashes and how giving children early authority with guardrails builds competence instead of entitlement.

Diana and Octavian dismantle the myth of the three-generation wealth curse while exploring why CEOs and prison inmates share similar neurodivergent traits. They reveal how the stewardship trap robs heirs of agency, why trust funds often create the exact incompetence they're designed to prevent, and what families can do instead.

Listeners will learn practical strategies for building antifragility across five types of family capital, understand why productive conflict is essential for family innovation, and discover how intentional hardship retreats prepare families for inevitable crises. This episode offers a blueprint for raising competent heirs who get stronger through challenges rather than shattered by them.

Chapters

  • (00:00:00) - Under the Pressure of Privilege
  • (00:05:48) - The crisis management of a failed investment
  • (00:11:21) - The sale of the Palace and the forest
  • (00:17:50) - On Coddling Your Parents
  • (00:21:42) - The Secret Life of the Palace
  • (00:24:37) - The cabin where my dad used to disappear
  • (00:25:16) - Symptoms of Mast Cell Activation Syndrome (MCAs)
  • (00:29:26) - Have ADHD and Autism in the same group?
  • (00:33:11) - The Art of Re-thinking Yourself
  • (00:41:28) - An Age-appropriate Handover of Wealth
  • (00:44:22) - What is the biggest problem facing families today?
  • (00:47:43) - Five Types of Capital to Make a Family Antifragile
  • (00:52:08) - How to Manage Your Wealth
View Full Transcript

Episode Transcript

[00:00:00] Speaker A: A competent heir is made, they're not born. And it's the parents responsibility to make an heir competent. If you have been cuddled, you have decision paralysis. You don't know you can't make a decision because you have never had to make decisions. If I've never had to solve any problems, how am I going to solve a big problem? [00:00:19] Speaker B: I'm Diana Earley, and I've spent most of my life learning firsthand what privilege actually costs. The legacy control, the family expectations. The guilt of feeling trapped in a life everyone thinks you should be grateful for. If you've ever wondered why having everything still feels like something's missing, you're in the right place. Welcome to pressures of privilege. His father took him to a cabin in the forest when he was young. No food, no supplies. Want to eat fish, hunt, gather, Come back empty, you're hungry. Octavian learned to be hungry. His family owned that forest. In 1730 they had a palace, a thousand year name, everything privilege promises at 25 fraud, international venture gone wrong. Family lands leveraged as collateral bank circling responsibility with zero authority K he could have run. But instead he accepted the situation. He sold the palace his family held for over 300 years. And his body responded MCAS chronic fatigue. Information his immune system was giving him later, an autism ADHD diagnosis. That explains some things. Reality doesn't reward acceptance in the short term. But 10 years later, he's teaching families what he learned. Antifragility. Getting stronger through hardship, not despite it. This is a conversation about acceptance, about reality's timeline, about what hunger teaches. Octavian Grof Pilati. Welcome to the pressures of privilege. [00:01:56] Speaker A: Thank you. [00:01:57] Speaker B: You're welcome. I'm so happy you're here. And the story that, that I read on your substack, it reminded me of my old childhood where, you know, our mother would make us ride our bikes to. To choir practice instead of driving us. And I used to resent her for it, but now I'm so grateful that she made us kind of tough it out, you know, and it's. And it's also kind of European. In Switzerland, my children had to bicycle everywhere and walk everywhere. And it just, it toughens kids up. And I'm curious, like, how does that land with you? [00:02:32] Speaker A: Oh, yeah, my. My dad was very much of similar as you you mentioned with the cabin. I absolutely hated going to the cabin. I mean not, not every trip was as. As uncomfortable as you described it at the beginning, but it did sometimes go quite extreme and I really didn't like that back in the day. [00:02:54] Speaker B: Well, what did hunger teach you? [00:02:56] Speaker A: Well, it teaches you that, you know, not a lot of the things we take for granted, particularly in our European society, it's a privilege essentially, that we have them. You know, you can get strawberries all year round. That wasn't like this in the past. And we have plenty of food. You know, you have a warm, warm, flat, dry, dry, flat, things like that. In other countries it's different. In other countries, a lot of people don't have this. On the other hand, it teaches you how to handle situations like that. You know, if you have never been hungry and then there's a day where you are hungry, people panic. But if you have experienced it in, let's say, homeopathic dosages in comparison through your life, you're used to it and it's like, okay, I've done this before. Maybe not as big as it's hitting you right now, but it's not such a big deal. And you can more easily go into problem solving mode rather than panicking and freezing and entering fight or flight. [00:04:01] Speaker B: When the, the fraud happened and the, you know, what happened in 2015, it's like, it's almost like your body was primed for the, for the stress of it. [00:04:12] Speaker A: Yeah, in, in a sense it was, it was primed, but at the same time, it, as, as you know, it, my condition shows it was too much altogether. You know, the business situation taking over a lot of responsibility at a young age. At the same time, also, I talk about that a lot. We had a dispute that came about within the family that made it worse. And prior to that we had, you know, inheritance and succession discussions that didn't go that well while the, obviously the crisis kind of took things into its own hand then. But that was a challenge. That was a bit too much, probably, for my body at least. Yeah. [00:05:03] Speaker B: Because it's one thing to lose, to feel hungry in the forest with your dad, but at least you're together and you're in it together. But when there is a big family fight and everybody's sort of at odds with each other, it's almost like that sense of belonging gets comes into question in a way. That family unit starts to break up. [00:05:23] Speaker A: Yeah, I think actually the mental stress that situations like this bring, particularly within the family unit, they're much worse than the physical stress that you can come under. I don't know, it's like what they teach in the Navy seals or any, any special forces, is that your body usually tells you stop at about 30% of what you can bear and and if you know about this, you can mentally take yourself much further. [00:05:46] Speaker B: Interesting. But you didn't know that at that time when you were 25. [00:05:51] Speaker A: No, I did not. [00:05:52] Speaker B: Yeah, but you were also in a really difficult situation. You were as, you know, between a rock and a hard place. You know, you had a ton of responsibility, but you didn't have any authority. Can you explain? [00:06:05] Speaker A: I did have a power of attorney to act. However, the, and I was representing us, particularly because the estate is in the countryside and most of the, the discussions concerning the, the failed investment that we had, which caused a crisis were happening in Vienna. So I ended up as the crisis manager at some point. So initially my dad, with support of my older half brother and his wife, they were, they were handling the crisis. And I'll quickly tell the story because it shows how sudden it was. So the first thing I did when the crisis hit, when I realized, oh, okay, we might lose everything at the beginning, that's what it looked like. As a consequence of this, I got myself a job. I was a student and I, I landed a, a part time job in Vienna and the headquarters was in Munich. So once a month we were in Munich on like an all hands meeting and we would always go to the beer garden afterwards. And I remember our lawyer and, and at that time I was accompanying my dad to the meetings as a translator because everything was in English and my dad didn't speak English. And our lawyer called me when I was in the beer garden that I was, I saw the number and I thought, why on earth is our lawyer calling me? He never calls me. So I picked up the phone, I'm like, yeah. And our lawyer asked me if I had read the email and I said, what email? And his answer was read your email. Call me back when you have done. So I read the email, I looked for a wi fi spot somewhere in the beer garden. I read my email and my dad had written an email to everybody involved and said that my brother and him are going on a holiday to take a break from this for two weeks and they won't be reachable in that time and Octavian is going to be handling things for the two weeks. My first phone number and email address were in the email. I didn't know about this. Our lawyer didn't know about it. And then, so that's how I was thrown into this for two weeks. And after that our lawyer made the suggestion to hand the crisis management over to me. So it wasn't my idea, it wasn't my dad's idea, It Came from our, our advisor. [00:08:24] Speaker B: Wow. You were thrown into the fire. Literally. [00:08:28] Speaker A: Yes. Not literally, but yes I did have a bit, you know, I knew a little bit of what was going on, you know, translating documents and things like that. But you know, this was a very, from studying and you know, having like just my first proper job to doing this was a big step up. [00:08:47] Speaker B: So you were in charge for two weeks. Did you have the authority to act? [00:08:51] Speaker A: Well in theory I did. But our lawyer's suggestion, which I happily accepted was okay, he said okin for next two weeks the word yes is non existent in your vocabulary. Whoever calls you about this, you say maybe, you say no, you never say yes. That's how we're going to play this for two weeks. And that's basically what I did. [00:09:16] Speaker B: So you listen to the lawyer? [00:09:17] Speaker A: Yeah, yeah, of course. Because obviously what, what do most people if you're on the other side of Basically this was not a win win situation of any kind for everybody. Everybody, like every creditor, everyone in this whole thing was trying to fight to get as much out of this as possible back. Like everybody knew they were going to lose something but everybody was trying to make sure it's not the biggest loss isn't them but someone else. So when you read that a 25 year old who is still a student is going to be in charge, what you do, you invite me to meetings, you call me, you try and get whatever you can out of me. Essentially that's what happened. It's quite busy. Two weeks. [00:10:00] Speaker B: Wow. People are sharks. They just go for the, they go for the blood. Right. [00:10:05] Speaker A: Particularly in like finance stuff. Yeah, it's always like that. [00:10:09] Speaker B: So in that case the lawyer gave you good advice. [00:10:11] Speaker A: Very good advice. Yes. [00:10:14] Speaker B: Yeah. But how did you feel in those two weeks? [00:10:17] Speaker A: It was an interesting mixture. I didn't really have a clue what I was doing. I mean that not having a clue what I was doing continued. What I had going for me was I was young, I had energy and I was trying out a lot of things and I could put in a lot of hours with little sleep. I was writing my master's thesis, I had a 20 hours a week job and I was doing this at the same time. So I had to find time somewhere to put this in. You know, I felt important. Of course, you know you get this feeling of importance. You do have this feeling of maybe agency is the right word at this other, on the other end you're incredibly stressed, you are under a lot of pressure. There's moments where you, where you think I'VE got this. And then there's other moments where you think, I don't want this anymore. Can this please stop? I'm gonna fuck this up, basically. So this is like this weird up and down, but I can see that [00:11:14] Speaker B: even you rubbing your forehead. I'm like, even the memory of it probably brings up some stress. [00:11:19] Speaker A: Yeah. Yes, it does. [00:11:21] Speaker B: How soon after those two weeks did the sale of the palace happen? [00:11:25] Speaker A: We first sold the forest. That happened within two and a half years. The sale of the forest was at the end of the 2017. I took over in middle 2015, and the sale of the. Of the palace was concluded in 2022. The problem was, you know, when you're in. When you're doing a fire sale, which we had to do, and a legacy asset like a palace will never fetch a good price. So most of the people, when we tried to offer the forest and the palace in a package, people would deduct money from the sale price for the palace. There was very few buyers that really looked for a palace in the forest together. Most were just wanting to buy a forest. So I made the decision back then to say, okay, we'll sell the forest, because at the time, there was no other forest in our quality and size in all of Austria on the market. So we had a very. Even though it was a fire sale, we had a very strong selling position by leveraging that there's no one else in. In that category at the moment available, so we. We could dictate prices to a certain degree, which was, you know, luck in an unlucky situation. And then I said something like, a palace requires more time to find the right person. And it did take quite a long time to find someone who. Who then offered market value of the palace and bought it. That kind of played out. Well, [00:13:01] Speaker B: that's good. So you got market value for it. [00:13:03] Speaker A: Yes. [00:13:04] Speaker B: Do you know the new owner? [00:13:06] Speaker A: I know the. The. The new owners, yes. Two guys bought it together. It was a new year. One is an artist, the other one is an Austrian developer. But sadly, the Austrian real estate market has tanked in the last two or three years, so the developer has gone bankrupt. So we'll see what happens with the palace. But if you sell any asset, that's my opinion, you need to realize that you have to let it go and whatever happens, happens. Delete any, any kind of attachment that you have. Otherwise it just drives you crazy. [00:13:40] Speaker B: So I can imagine during, from 2015 to 2022, you were under a lot of pressure. [00:13:48] Speaker A: Yeah, yeah. And there's certain Things like, you know, we had the sale of the forest and then my dad split up the proceeds that were left after, you know, selling and paying off the debt. For tax reasons we sold the whole forest and for market reasons we could have maybe, you know, sold only a little bit and there would have been in between options, but we didn't go for them. And I was with two legacy buildings, the castle that I still have, the palace and some cash on my bank account because my dad split the cash that, that came in between the two of us. I got some of it, he kept the rest. That created some very toxic pressure. Cuz I was, I knew how much the palace and the castle cost every year. You know, it doesn't take a mathematician to, to, to figure out how long of a Runway you got with that cash. That led me to, you know, typical thing like going a bit more into risk when I do, when doing investments which didn't play out that well or everywhere, some things played out well. So it was a stressful time. Also when I, when I stepped up to handle the crisis, my primary goal that I set, which was very naive, was that I will save the estate. The estate will stay with us the way it is. We're not going to sell anything. We'll figure this out somehow. So I failed in my goal and we had the sale and everything. And I kind of from, from, you know, when you grow up as a young kid and the center of your family's identity is the estate. For some of it, the family history plus the estate makes a big portion of the family's identity and it's gone. I spent a lot of time in the forest with the cabin and there's a lot of time in the forest that I liked there. Even though the cabin. I built my own cabins all the time and spend a lot of time in the forest. It is like. It felt like a piece of myself was cut away and I fell for a part of the time I was in kind of, you know, the existential vacuum, as Viktor Franco would call it. What's my me, what's my purpose now? I don't know. Just looking after a palace or a castle is not something I would defined as a purpose for me in life. For some people it is, but not for me, which also happens a lot when you have entrepreneurs who in the founding generation, they sell their business and then they sit in a lot of cash and they don't know what am I going to do now? Is one question. And the other thing is you've just been Vastly successful. So being at the age handling this, selling for a good price, you are overconfident. Like, I don't need advisors to help me invest. I can do this myself. I just did this and that. And then you make mistakes, a lot of them, because you're suddenly in a totally different situation than you were before. And that was also painful to go through and learn and say, okay, I'm not going to do this anymore. Like this. So again, as I said, some things I did played out really well. Others were a disaster. So little in between. [00:17:22] Speaker B: So you learned a lot by doing? [00:17:24] Speaker A: Yes, I did. A friend of mine, I love the way he says it. He's like, you just paid for a very expensive. You just paid for a real life mba. [00:17:33] Speaker B: You did not learn this just theoretically. You actually pragmatically went through it. And it probably, your experience is probably more valuable than anything you could have learned in school. The theoretically, yeah. [00:17:46] Speaker A: A lot of the things that I learned you were not taught as an MBA course. [00:17:50] Speaker B: You mentioned Viktor Frankl and I love Viktor Frankl and I love his whole search for meaning. And I love the descriptions of the people in those camps that made it and the ones who didn't. And the ones who didn't were usually ones that were fragile psychologically. This is why I was really attracted to interviewing you and this idea of anti fragility which of course Nassim Taleb talks about in his book as well. But I like how you bring this to the, to, to wealthy families because there is a huge weakness sometimes in certain families who, where they think, well, I worked so hard for this and I went through such hardship and it was so difficult. I want, I don't want my children to go through that. And that's a huge mistake, right? [00:18:37] Speaker A: Correct. Yes. [00:18:38] Speaker B: And had you been coddled during your childhood, what would have happened with that? The problem with the palace, that whole from 2015 to 2022, like how would somebody who was fragile, how would that person have responded to that crisis? [00:18:53] Speaker A: People that are fragile, they kind of freeze in the situation. So in situations like this there is not, you know, the stakes are high, but at the same time it's a totally paradoxical situation. The stakes are high, but doing nothing is a disaster. So you have to do something. But any mistake that you make, any decision, failure can mean it's over. But not making a decision definitely means it's over. So you're stuck in between this paradox. The same as with like, you need more time to figure things out, but you don't have any time. So how do you go about that? How can you buy yourself time? And it's these, these, you live in these polarities in a situation like this where you need to figure out a way of doing it. And if you, if you have been cuddled, you have decision paralysis. You don't know you can't make a decision because you have never had to make decisions. Like if I've never been made allowed, if I've been never allowed to make the smallest decisions, or if I've never had to solve any problems, how am I going to solve a big problem? A competent heir is made. They're not born. And it's the parents responsibility to make an heir competent. Unless they are competing, you know, they have schizophrenia or some other clinical illness or something like that. They're not born incompetent. They have been made incompetent by their family. And this is something that families need to realize, that all of this fear of entitlement and incompetence, it's hope made. You're worried about your kids being entitled or incompetent. You probably made some mistakes because otherwise you wouldn't be worried. [00:20:50] Speaker B: Wow, that's really strong. So I guess you're very grateful to your father. [00:20:55] Speaker A: I am for certain things, very grateful to my father. And then for other things I'm not. But no one ever gets everything right. Of course. [00:21:03] Speaker B: Exactly. He's a human being like all of us. We're all fallible. But he made you tough and he made you strong. And you're trying to help others, which to me is a huge purpose. [00:21:13] Speaker A: Yeah. So to Victor Franco, find your purpose in suffering. One of his three pathways that he, that he defines. It's kind of there. I, I do, you know, the, the, I do enjoy parts of the wealth management that I, that I do for myself. There's a lot of parts I despise. They're boring as hell. But the antifragility part that I wanted, that I, that I work with, with families that I write about, that I speak about. That's fun. I enjoy that. [00:21:42] Speaker B: What I find really interesting is that some of your best memories that you write about is that cab. It was in a cabin, not in the palace. [00:21:50] Speaker A: Yes. Because the palace didn't play such a. It played a big role. And I might, I'll probably still touch on certain things in the future. So we didn't live in the palace, we lived next to the palace. So my great grandmother split up the wealth between her four daughters. And then my grandmother was one of Them. So that palace that ended up with us was not the palace our family actually lived in. It was a summer palace. It was built to host big parties. That was. So it was not. You couldn't live in it. Like, huge ceilings, huge rooms. You can't heat that place. We did have a. Like a private museum in it. So I would, you know, spend a lot of time doing guided tours from an early age. I think my first guided tours started at the age of nine, which is a tad early, and did get my parents into trouble with the authorities at some point. [00:22:48] Speaker B: Why? Is it child labor? [00:22:50] Speaker A: Yes, yes. But in Austrian and German law, if you're the son of the owner, child labor doesn't exist. You are kind of allowed to work in the business in. In a certain capacity. But people that came to visit and had me do a guiding tour, they don't know these laws. So some people, you know, went and complained that there is child labor going on. Yes, yes. [00:23:14] Speaker B: Yeah. Because I was thinking in the Swiss Alps, which is where I'm from, in Gstad, farmers bring their kids to work, and the kids are busy working with the cows. They move them around, they help with fences, they. They help cut the hay and raking the hay. I mean, people could say that's child labor. [00:23:29] Speaker A: It is child labor if you have a kid of your neighbor do it. But if your own kid is doing it, it's not like in Austria. Now, I'm digressing. But now if you. If you're doing like, something at home, only your direct neighbor or your brother's parents and kids are allowed to help you with it. If a friend helps you, you need to pay them by law. [00:23:51] Speaker B: It's silly because I would say that the. The work that my children did on the farms in Stad helped to make them who they are today. [00:23:59] Speaker A: Yes, that was a very good thing. Yeah. [00:24:03] Speaker B: I mean, I am so grateful for that. You know, my son would help the farmer, you know, move the. The cow milking machine from one cow to the next. [00:24:10] Speaker A: He probably enjoyed it, at least for a while. [00:24:12] Speaker B: Or he had. He helped feed the calves, and my daughter had also had calves up on the alp. And they helped with raking and moving cows around, you know, from one pasture to another. And they. I mean, those are part of their best childhood memories. But this is the thing. This goes into another topic of sort of when the state comes in and does these rules. [00:24:33] Speaker A: Yeah, yeah, it's a whole different topic. And. And also back to the cabin. The cabin was my dad's favorite place that Was like his, his refuge. When things got too much for him, he would disappear for a few days in the cabin. You can't even if he would have taken a mobile phone with him, there's no reception where the cabin was back then. [00:24:54] Speaker B: At least it was probably being in nature and it was probably helping with the stress. [00:24:58] Speaker A: Yeah, yeah. So he did that all his life. When he was or since he took over the estates, the cabin was like his refuge. He would go there whenever he needed a break of something. Either he needed a break from my mother or some work thing. He would just take his stuff and just disappear. [00:25:16] Speaker B: The physical problems that you ended up with, you know, with the MCAs, can you explain to our listeners what that is? I had looked it up but it's. [00:25:25] Speaker A: Yeah, it's, it's getting more and more known. It's called mast cell activation syndrome. And basically your immune system in the body. The mast cell is an immune cell goes into override and is overactive. So my immune system is current is. Is constantly kind of like in fight mode. We are where something's going on. So that leads to a certain to. So the mast cell controls about 200 different substance substances that your body produces. And if it's overactive some of these substances are overproduced and some are under produced and that leads to other problems in the body. Typically intolerances with like histamine problems and we don't really understand very much of it yet. And usually you have like there's some sort of root cause that triggers this and then your mast cells are due to this something happening. Your masters are kind of like reprogrammed to be a bit trigger happy. [00:26:30] Speaker B: How did that manifest itself in you? [00:26:32] Speaker A: Um, I started having regular anaphylactic shocks. Nobody knew what it is, what was going on. When it was really bad. I, you, you get like MCAs flare ups where it, your whole system goes into override and I, you know, there's, there's moments where you, where you lose your capacity to speak or your capacity to see. Those are like the really bad moments. It's pretty well under control now. There's more medicine. There's you know, medicine now that didn't exist back. It's been officially it's been a condition since 2015. That's when it was the first time, you know, made official. I had my first issues 2013 probably before that. When you go back in time you get like rashes as well and things like that. So most likely I had some sort of infection or something as a kid. That was the initial trigger. And then with every little bit that, that, you know, any stressor that you encounter in life adds to this problem. I lived in a flat that had a mold issue for a while without realizing that was that. That's probably. And that was at the same time as we had the crisis, the flat on a mold issue. So that. That probably made the spike or definitely not. Probably. Definitely. So. So that was the. And then mental stress and pressure doesn't, you know, adds to it. And I. I used to play competitive rugby or big sevens. Rugby sevens for Austria. That is a very physical sport. That adds to it as well. [00:28:17] Speaker B: Wow. So are you playing sport now? [00:28:20] Speaker A: Very little. I do something called functional patterns and I go hiking. Those are my sport activities currently. [00:28:28] Speaker B: What's the patterns? [00:28:30] Speaker A: Functional patterns. It's. It's a. It's a type of biomechanical training. I have a lot of injuries from playing rugby and a car accident, going to the gym and pumping iron. I used to do that. Like, it doesn't, you know, I make my injuries worse when I try. So now I. I've moved to. I have a coaching certificate myself, so I interior. I can make my own gym sessions and so on, the rugby coaching certificate here in Austria. But I just make it worse if I do it myself because I become too competitive. So now I do it. Yeah, it's an issue. I'm like, I want to lift more, I want to go faster, harder, stronger. And then I always break something in myself. So now I do it with a. With a trained physiotherapist who is trained in functional patents. And I do what she tells me and things work well. [00:29:26] Speaker B: You mentioned the autism ADHD diagnosis and you also have said that the people in, like, the people of wealth are like CEOs and people in prison have something in common. And I felt that was really interesting. [00:29:41] Speaker A: The most people with ADHD, you find them in prison or as entrepreneurs and CEOs. So that's where you find them. So, like, the wider population has. So 5% of the wider population have ADHD. And entrepreneurs, it's 30%. There's a. There's an interesting study on this and this, this goes for, like bipolar. It's 1% in the wider population, 11% in entrepreneurs, addiction, 4%. 12%. [00:30:12] Speaker B: Wow. Where are the stats coming from? [00:30:16] Speaker A: I can tell you afterwards. They are from a university in the us. I've written them down. I forgot to write down the source. And it's like 70% of entrepreneurs suffer from some sort of mental illness and in the wider populations it's 20%. And why, why do you find more people with ADHD? And there is no statistics for autism autism, but it's probably the same because if you have adhd, if you have autism, if you have bipolar, you don't function as an employee so well, so you end up doing your own thing. And adhd, autism, probably also bipolar, they are genetic. So your kids. And again, mind you that autism and adhd, we probably are still not, you know, diagnosing everybody. I Was diagnosed at 36. Would have been good to know as a kid. And there's many people out there who go undiagnosed their whole life and the diagnosis is becoming better. The likelihood that you have children in wealthy families with which at, at the onset is on. The wealth was made of entrepreneurial activities and then usually entrepreneurial families kind of like marry between each other as well. It's a, it's a gene pool of neurodivergent people. Probably. [00:31:41] Speaker B: Interesting. But also, also there's the pressure that you have that you experienced because whenever there's money, it's a magnifier for what's already there. [00:31:49] Speaker A: Exactly. Either it's like fuel, you know, you can make your car go faster or further, or you can set a house on fire with it. [00:32:00] Speaker B: Yeah. Now what's interesting is on the other end of the spectrum and our friend Dr. Paul Hochmeier, who I interviewed a couple of weeks ago, he talks about, he worked with people in the streets of la. They were like you mentioned, the people in prisons. They also have some similar traits because perhaps they're under a lot of survival pressure. [00:32:20] Speaker A: So. [00:32:20] Speaker B: So there's extreme pressures on both sides, actually. [00:32:23] Speaker A: Exactly. I mean, and there's a Nazism, Machiavelism and psychopathy. There's a similar. It's the same most of them you find in prison or in the boardroom. It's kind of like where do you make a wrong turn or which I think also which family are you born into? [00:32:39] Speaker B: Well, maybe that explains. I have a lot of friends who are very wealthy, especially in Europe, but they don't marry in the same class. They go off and marry a middle class girl who's probably healthier to be a better mother for their kids. [00:32:50] Speaker A: Definitely it, this brings other problems with it, but nothing that you can't deal with. [00:32:56] Speaker B: You avoid that genetic component that you're [00:32:58] Speaker A: talking about or it's more likely you avoid it. But the thing is, neurodivergent people are attracted to each other, so it's very unlikely that you marry someone who is neurotypical. [00:33:11] Speaker B: So you were, you accepted what, you know, the situation that you were, the cards that you were dealt with. And you have a quote that you really like. I'm so glad you're a Viktor Frankl fan, because I am too. You said you love the quote. When we are no longer able to change a situation, we are challenged to change ourselves. So can you explain how you've changed yourself as a response to what happened? [00:33:33] Speaker A: For me, the only way to kind of deal with this, the whole thing was to sit down and reflect. I, when, when the thing was done and I, I thought to myself, it's like, okay, where did we go wrong? Where did I go wrong? What could we have done better? What did we do? Well, what we, you know, and that's actually going on this path of reflection. That's what also led to kind of, you know, me starting the anti fragile family. When you have such a big challenge, you will hit walls constantly and you will need to find a way to get on the other side. And the wall is not going to change for you. And if you're not strong enough to climb the wall, you need to dig under it or you make yourself stronger. Whatever it is, you need to get to the other side. [00:34:23] Speaker B: You reinvented yourself. [00:34:25] Speaker A: Yeah. Gradually at least you don't control anything other than yourself. And also we can argue that a lot of, lot of things about yourself you don't control either. So the decisions you make is essentially you have a lot of control over the decisions you make. Not always, but most of the time. [00:34:45] Speaker B: I've read somewhere that when entrepreneurs make decisions, there's like, even if it's 50, 50% right. Like on average for every decision you make, you're still going to be successful. [00:34:56] Speaker A: Yeah. Because it's not so much about making the right decision. People fret a lot about making the right decision. And I forgot there's this Harvard professor who teaches about the aspect of making the decision right for you. You make a decision, you go on the path and then you need to figure it out. Rarely you're going to make the right decision from the onset because you don't have enough data, anything. But you know one thing, if I don't make a decision, I am screwed. [00:35:26] Speaker B: So how do you work with families now trying to help them avoid that three generation syndrome, you know the, oh, [00:35:32] Speaker A: the three generation syndrome. That's also a term just like entitlement that I absolutely despise because it's not true. Okay, Anybody that wants to read into why it's not true. Wealth 3.0 is a good book where they explain it. If you look at specific family names across Europe, you will see in each, in each country that the same last names have been successful for the last, I don't know, 500 years. And that certain last names have not been successful like more likely that they are in a job in the typical employee situation. If you had a recent iteration syndrome, that wouldn't hold true, most likely. And so it's a bit of a myth. And there's a study that always gets quoted from the US and that study only looked, they went into the company book and they looked at the owners and how long the same family owned a company, but they didn't look at why was the company sold, did it go bankrupt, what happened after the sale? So entrepreneurial families, they found companies, they sell companies. There's exceptions where the family companies held for 12 generations or something. But a lot of the families, if it's an entrepreneurial family, every generation is entrepreneurial. So the father might start the business, the son might start a business and then when the father is to like wants to stop, the children might decide, look, I've got my own thing going, I don't want to take over your business. So then it's sold. And then in the statistics it shows as the family failed after one generation. Well, it didn't fail because it. So that, that is like a typical study that was not done well and that's always with studies. The case you need to look into what, what was actually the research question? What are the data that is being used and how has it been analyzed? So they purely looked at. Okay, how long do families retain the business? [00:37:26] Speaker B: Ah, that makes sense. I have actually an ex boyfriend from Oberaldorf. His father was a collector of castles and I think he lost his fortune and remade it twice. But the son went off and made his own latex glove factory which is completely different than what his father did. And but the father hired an economist be part of his staff to teach his son business. I would accompany them on their business trips to East Germany to go visit, you know, these companies. And it would always be this like professor, Herr professor at the table advising the son on like even though it was, it wasn't on the son's own business, it was on the businesses having to do with the father. So he was expected not just to, he was expected to help the father and his fam. Family business, but also he ran his own thing which is hugely successful today. I don't Know if he's still managing his father's stuff or whether he sold it all. But I thought that was interesting to hire a professor and have him on staff at all times. [00:38:21] Speaker A: And one thing what I don't like about this regeneration myth is that it puts the third generation in families under huge pressure that they shouldn't be put under. [00:38:31] Speaker B: Well, in America, in my circle there, most kids are not trained to be entrepreneurs. They're more trained to don't spend too much and make sure you're well invested and hand it over to a financial advisor. [00:38:42] Speaker A: And then you land in the so called stewardship. Stewardship trap. [00:38:46] Speaker B: Okay, talk about that. [00:38:48] Speaker A: It's a bit more complex, but the stewardship trap is basically you. You breed airs that are very risk averse, that stop being able to make the hard decisions, that outsource decisions to advisers. Advisors will always make defensive decisions. So not good decisions on the long run because they have a job and it drops the family of agency. You know, there's a lack of urgency. And on the long run, this actually leads to, you know, slow, slow destruction of the wealth. Because if you look at it also from a per capita situation, how much wealth do you have in the family per capita with every generation that you pass it on, usually the per capita that the amount of people in the family increases. So you should look at the wealth needing to increase at the same rate as the family members increase. And the only way you can do this is by being entrepreneurial, by going into defensive things and you invest in bonds and get mediocre returns. This is the way to definitely lose your money. I know that that happens a lot. And that is because in the US particularly European families are different because we've been doing it for a longer time. But in the US the industry has established this mindset that you need to protect your children from the wealth or that you need to protect the wealth from the kids. Similar approach, different ends of the spectrum, but both are very extreme opinions that lead to very similar results down the road. You set up a trust fund where you have some professionals make the decisions. The heirs are completely robbed of agency. You throw money at them and then you are very confused why they are incompetent, entitled, end up in addiction, end up depressed. If that is what you wish on your kids, set up a trust fund for them. [00:40:50] Speaker B: So what would you advise instead? [00:40:52] Speaker A: Teach them, let them have a go early. Authority, power and money decreases in utility the older you get, the younger you are, the higher the utility, the more you learn, the more you can do with it. Imagine giving a 10 year old $1,000 to do something with. For a 10 year old, that's a huge amount of money if, if they end up investing it in the stock market because you teach them how to do it right? My dad did that with me, age 12 and it compounds. That's a lot of money down the road. Or they can, they can buy something that can help them do something. If you give a 60 year old $1,000, it's nothing. And the same is with the wealth you can. And the best way to have your heirs is a gradual handover of authority, power and money. So they can practice always in an age appropriate, you know, situation. Give you. With the example of my dad, I was given about €10,000 at the age of 12 to invest in the stock market. There were certain rules how I had to do it, and so on and so forth. For us as a family, €10,000 back then would not have mattered if I'd lost it at all. But for me, it was a hell of a lot of money. My dad gave it to me as a loan. So I learned the whole principle of debt and having to pay interest rates and everything when once I had paid back the loan, I liquidated the portfolio and bought a gaming computer. That was kind of not the whole point of it, but also my dad didn't stop me doing it because he said, okay, well, your money, you made it, do whatever you want with it. That's just one example. And you can gradually increase it. And I know some families who do this really well. I know you give them, you put your kids into an environment where they can make decisions, where they have to make decisions, where they have to suffer the consequences of their decisions. But it's at a size where they're not going to be shattered by any mistakes, but they learn from them. [00:43:01] Speaker B: And how does the parent let the kid know, don't be shattered, I mean, because, I mean, as you were saying, like a 12 year old gets that kind of money, they might get shattered if they lose it and they make a wrong mistake. [00:43:15] Speaker A: It's the intention you set behind it and the goal that you set and the structure you give them. If you give a 12 year old no structure to do this, it's going to go horribly wrong. I had to present every investment I wanted to make. My dad never said no. It was more about me having to think about why I want to invest here. He let me invest in a company which was obviously about to go bankrupt. He knew it. I didn't get it? But I had an idea and said no, no, they're going to do well. I lost everything but in that position. And then there was, I think I was never allowed to invest more than, I don't know, 20% in one investment or something like that. So there were rules around it and I couldn't invest into any foreign things. It had was only Austrian stock market so there were these guardrails so you [00:44:09] Speaker B: couldn't lose it all and have too much stress. [00:44:11] Speaker A: Yeah. And the night the Austrian stock market isn't very big so there was only a couple of companies. That's not too overwhelming for a 12 year old to look into. [00:44:22] Speaker B: So when you work with families today, what are people coming to you with the biggest problem? [00:44:26] Speaker A: Improving inter family communication is one thing that is usually something, something that brings people to me. I work with something called the GC index which is an organometric tests people on what do they enjoy to do. So if you use that tool you can figure out okay, which person is best put into which position in the family council or in the family or whatever. We work on, you know, crisis management plans for the family we work on. Conflict in the family is also something that people come to me because what makes an anti fragile family is to be able to have productive conflict. It's hugely important. Any antifragile individual is able to have conflict in a productive manner. Conflict is needed for innovation if you don't have conflict, which fragile families are all about conflict mitigation. I absolutely hate it. Because what people understand under conflict mitigation is let's not have conflict, let's not talk about it. And that's dangerous. First of all it's dangerous because without the friction, without this tension, you can't innovate properly in the family. And tensions kind of like they get bigger over time and then you have there's an eruption at the end of the day and that destroys the family. Usually of course there are different cultures that come into play. But at least in the European perspective there needs to be a way where the family can have conflict, where the generations are able to talk to each other about problems without the whole thing going peshipped. So that's something that's very big on the agenda and generally like air education. And I don't mean there's a lot of providers out there now that teach where you can get courses for your heirs, for your kids to learn stock investing, venture capital, private equity, what not. But it's more as I describe in my substack, there's Way more to it than just these technical fields where they should have some knowledge. [00:46:38] Speaker B: So you help families with crisis communication, estate planning, how do the governance issues. [00:46:46] Speaker A: My mission is to help families to be an antifragile family so that when, when shit hits the fan, they go through it and they come out the other end stronger than they went in. If the family is resilient, they can withstand, you know, pressure and at the end of the day, nothing changes. If they're fragile, a big event will destroy the family. Often like you go to a gym, you go to the gym, you put yourself under stress and at the end of the day you get stronger from it. Antifragility is a practice more than, than something that you set up once. You need to have an anti fragile practice in the family because like in, in performance sport, you need to train constantly. So when something happens, the step from where you are to the crisis isn't 200% but 10% and then you can handle it. [00:47:43] Speaker B: So what are some of the practical things people can do to become antifragile? [00:47:47] Speaker A: If you go into the five different types of capital, you have like the cultural capital of the family, some call it the spiritual capital, which is all about the culture that you have. You have what most people know about the financial capital. You have the human capital, which is the people. You have the intellectual capital, which is the knowledge in the family, you have its social capital, which is relationships within the family and relationships without, outside the family to others. And in each of the capitals you can do things to make this capital base antifragile. And as long as about three of these capitals stay intact, when you go through a crisis, you are going to bounce back from whatever has occurred. You can lose all your money when the other four are fine and an entrepreneur money, entrepreneurial family will make it back again. I mean, you can, you can destroy your body. That's your human capital. You have enough money, you can start to fix things again. Is that, that's the principle kind of behind it. And so the idea is to go, you know, if you look at the human capital, what can you do? You can do hardships, retreats, which I, which I talk about where you think of a way where the family encounters mental and physical hardship for the, for the day when you need it. Sports, you know, you can do all sorts of different sports, that is physically training the fitter you are physically, the more you, more pressure you can withstand mentally. And the other way around, if you're trained mentally, whatever that means, do some coaching, meditation, other types of exercises that increase your mental capacity, your psychological capacity. You can also withstand more physiological pressure than you know, it goes hand in hand. It's like the whole human capital aspect. Fragile families, you know, in fragile families you have things like depression, alcohol addiction go rampant. That those are not people that withstand, that can deal with adversity. They're already dealing daily with adversity in form of what the ailment is. So it's going to be very difficult if something happens. Family culture, you know, values, purpose. If it's clear for you where you're going, if you have a clear sense of purpose for yourself and, and for the family as well, and a crisis happens, you don't need to spend time to decide, where are we going to go? Because you already know where you're going to go. It's just figuring out how to get there. [00:50:24] Speaker B: Do you help families figure that out? [00:50:27] Speaker A: Yeah. So what, what where I come in is usually I, I'm, I'm more of, you know, bird's eye view. Look at what do we have today? Where are the weak spots? What are we good at? What are we bad at? What, you know, where do we need to improve a little bit? What can we double down on and get even better at? [00:50:47] Speaker B: Wow, I'm learning so much from you, Octavian. It's amazing. You give talks too. Where can we hear you speak? [00:50:52] Speaker A: I will be at a conference in Toronto in April. [00:50:56] Speaker B: Yeah, I could put it in the show notes afterwards. Yeah, where you're going to be. And I can put, you know, obviously I'll put all your website and your substack in the show notes as well. Well, and they can hire you as a consultant as well. [00:51:10] Speaker A: Yeah, I can be booked to speak. I can be booked to consult. You can read my substack. You can also there's a, there's a paid and a free version. So for the, for the paid substack, there's. I go a bit into more detail on certain things. There's more to come in the future, but I don't want to talk too much about it till I actually have it going. Thing with the ADHD is I always have these ideas and plans and I think, give me two months and they're going to be running and then it doesn't happen. So I have learned to talk about it once it's actually going well. [00:51:41] Speaker B: You have a very, very smart, fast brain. Thank you so, so much for coming on and it's been a pleasure. I mean, I could go on and on for more hours with you, but I want to honor your time and I want to say thank you. And I hope we could do this again. [00:51:53] Speaker A: Sure. Let me know. I'm happy to come again. [00:51:59] Speaker B: If this episode landed for you, share it with someone who might need to hear it. And if you haven't already, subscribe so you don't miss what's coming. But here's the real thing. I want you to know if you're carrying something you can't talk about, if you have every resource except someone who actually understands what wealth costs. I work one on one with people like you navigating exactly that. You can reach me at Diana O E H R L I dot com. Thanks for listening.

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