Ethan Starr: What 250 Billionaires Taught Him About Success and Failure, The Human Stories Behind America's Biggest Fortunes

My guest today is Octavian Graf Pilati — a member of an Austrian aristocratic family whose lineage traces back nearly a thousand years, and the founder of The Antifragile Family. At 25, he was handed responsibility for saving his family's centuries-old estate through a devastating financial crisis, a story so instructive that Harvard Business School turned it into a case study — Burning the Sails to Save the Ship. Since then, Octavian has built a body of work around what actually makes multigenerational families endure: governance, conflict, succession, and the human systems that either hold a legacy together or quietly tear it apart.

Chris Davis and Robert Hagstrom explore the tension between holding great businesses and keeping a winning stock from becoming too much of a portfolio risk. Why do two investors who believe in letting winners compound also use 10% position limits? On this episode of 100 Year Thinkers, Chris Davis of Davis Funds and Robert Hagstrom of EquityCompass join Matt Zeigler and Bogumil Baranowski to discuss position sizing, selling mistakes, index concentration and the cost of growth. From Chris Davis’s experience selling Costco to the debate over who will capture AI’s economic benefits, they examine what it takes to hold a business through uncertainty without ignoring risk. Stay for Matt and Bogumil’s closing discussion of the lessons for investors.

Find me on Substack! Today on Talking Billions, I'm joined by Michel Ingenbleek — an investor and writer whose career took an unusual road here: from leading teams in the Dutch Korps Commandotroepen and Royal Netherlands Marine Corps, to two decades running offshore energy projects and corporate strategy at companies like Subsea 7 and Technip. These days he writes Capital and Character, a weekly Substack on the psychology of long-term investing, and his debut book, Staying Intact, turns two decades of his own investment mistakes into a framework he calls the behavioral margin of safety. Episode Sponsor: Fiscal AI is a modern data terminal that gives investors instant access to twenty years of financials, earnings transcripts, and extensive segment and KPI data—use my link for a two-week free trial plus 15% off: https://fiscal.ai/talkingbillions/ Michel's path to investing began a hundred meters down, inside a pumped-dry habitat on the seabed, finishing a days-long weld on a 48-inch pipeline and asking himself, "is this it?" The former Dutch commando and Royal Netherlands Marine went on to project and strategy roles at Subsea 7 and Technip, and chose to invest his offshore bonuses himself rather than hand them to a wealth manager. The mistakes that followed became his book, Staying Intact. At its heart is the behavioral margin of safety. Graham's margin tells you the price at which an asset is worth buying; Michel's tells you the size you can hold without your judgment breaking if the position falls further before you're proven right. He shares the story of selling ASML and Nvidia in 2022, then realizing his follow-up research was really a search for reassurance: "I get fooled so easily basically by feelings." We trace the recurring ingredient of every bubble, from tulip mania to GameStop: not a lie but a truth, until rising prices get mistaken for evidence. Michel applies that lens to AI without pretending to forecast it. He separates loud, fast narrative risk from quiet, slow economic risk, explains why a deliberate pause can save a position better than more information, and revisits Long-Term Capital Management as a lesson in what models can't see. We also talk about red-teaming your own ideas, the strength in saying "I don't know," why "enough" is a horizon rather than a destination, the neglected years of simply owning, and his current work on what happens to investors when intelligence becomes commoditized. Podcast Program – Disclosure Statement Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and, unless otherwise stated, are not guaranteed.

Find me on Substack! My guest today is Neeraj Khemlani, the former president and co-head of CBS News and Stations, a veteran 60 Minutes producer and media executive, and the author of The Coffee Can Investor, A Stock Picker’s Journey to Build Generational Wealth, who uses the story of a Midwestern portfolio manager’s decades-long search for 100-bagger stocks to make the case that patient, concentrated ownership of exceptional businesses can build truly generational wealth.Episode Sponsor: Fiscal AI is a modern data terminal that gives investors instant access to twenty years of financials, earnings transcripts, and extensive segment and KPI data—use my link for a two-week free trial plus 15% off: https://fiscal.ai/talkingbillions/Neeraj Khemlani, former co-head of CBS News and Stations and longtime 60 Minutes producer, grew up in a lower-middle-class immigrant family in New York, where education was his path forward. He wrote The Coffee Can Investor "largely out of mission," wishing someone had taught him the basics of investing much earlier. The book began on an annual call with Matt, a portfolio manager he met in Denver in 1999 and his longtime "Marvin the Explainer." Matt had studied every hundred bagger since 1980. He planned to put $5 million of his own money into potential future ones, untouched for thirty years, as a gift to his three daughters. Neeraj's reaction: "Holy shit, that's a book." The idea traces back to Robert Kirby. One of Kirby's clients had a husband who quietly bought every stock Kirby recommended and never sold. After the husband died, he left behind a coffee can of stock certificates that beat the managed account, including a Xerox position that went to $800,000. Neeraj explains why holding is the hard part through Matt's early sale of Fastenal, which went on to grow roughly nineteenfold: "you don't learn to have patience until you learn what happens when you don't have patience." He shares the chessboard parable of doubling grains of rice. He also walks through Matt's findings: most hundred baggers were founder- or family-run, many grew through acquisitions, and 68% sold to other businesses. Neeraj saw the same pattern firsthand at Hearst, where Fitch became the biggest profit contributor. As he puts it, "the sexiest things are usually the least lucrative." The conversation closes at Thanksgiving, when Matt and his wife told their daughters about the coffee can. "The girls never once asked for anything," Neeraj recalls. The lesson for both fathers: "we already won. They already won." Podcast Program – Disclosure Statement Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and, unless otherwise stated, are not guaranteed.

In this Unfiltered Coffee episode, I share some thoughts that have stayed with me through recent conversations, listener emails, books, podcasts, and my own work with investors and families. I reflect on a different kind of urgency—not the manufactured urgency of expiring offers or opportunities that supposedly require an answer by Friday, but the urgency that comes from within. It’s the realization that something in your financial life may need attention today because being off by an inch now can mean being off by a mile five or ten years from now. I explore the difference between benign neglect and costly neglect, the extraordinary effects of compounding over time, and why what got us here may not always be the path forward. I also talk about consistency and what it means to be a constant in someone else’s life. Consistency isn’t perfection. It’s returning to a calm and thoughtful place after life tests us, showing up again, and remaining dependable through changing circumstances. Another recurring theme is family fortune and multigenerational wealth. I share why I increasingly think about family wealth through the lens of stewardship rather than ownership—and why what we inherit, care for, and pass along extends far beyond financial assets. Finally, I return to a deceptively simple question: what does it mean to invest sensibly? Capital can eventually begin doing some of the heavy lifting that once depended entirely on our own efforts. How we put that capital to work is deeply personal, but perhaps we make investing more complicated than it needs to be. Along the way, I revisit recent conversations with Paul Johnson, Lee Freeman-Shor, Alexander von der Vellen, Jan Petke, Jared Dillian, Peter Lazaroff, Ian Cassel, Owen Zidar, and Eric Zwick, and share a few things I’ve been reading and listening to lately. Some of the ideas in this episode: The difference between internal and manufactured urgency Benign neglect versus neglect that quietly costs us money Why small financial decisions can compound into enormous differences Luck, risk, and revisiting assumptions that have worked in the past Consistency as a practice in investing and in life What it means to be a constant for other people Family fortunes, stewardship, and multigenerational thinking The transition from earning money to letting capital do more of the work Why investing doesn’t have to be unnecessarily complicated