“Life is a big craps game. I've got to tell you, it's all been fun.” This is a companion piece to my writeups of Kerkorian's story (part I, part II). Kirk Kerkorian was a self-made billionaire, aviator, entrepreneur, casino developer, and investor. It's one of my favorite rags-to-riches stories.

I'm reading my latest piece, Gratitude, Desire, and a Money Paradox. “Desire is a contract that you make with yourself to be unhappy until you get what you want.” –Naval

I’m very excited to share my conversation with Sebastian Mallaby, the Paul A. Volcker senior fellow for international economics at the Council on Foreign Relations and author of several books including More Money Than Good, The Man Who Knew: The Life & Times of Alan Greenspan, as well as an upcoming book about the history of venture capital (The Power Law). I’m a big fan of More Money Than God and tweeted about the gems in its footnotes. This conversation was an absolute treat and I hope you will enjoy it as much as I did. Disclaimer: this podcast is for entertainment purposes only. It does not constitute an offer to sell or the solicitation of an offer to buy any securities mentioned or discussed. Seek your financial, tax, legal, accounting, or other advisor’s advice before making any investment decisions. Do you own work. I am are not your fiduciary or advisor. Conversation highlights: 2:00: Sebastian’s journey to the book and topic (hedge funds, also Alan Greenspan) 5:15: How to gain access and build trust. “The key was to do an unreasonable amount of preparation work.” “You win people's respect by doing a ton of homework. It shows that you're serious and you're not wasting people's time by asking the obvious questions.” 7:44: How to decide what questions to ask? “What you really want to know from them is specifically what their thought process was around a particular important or interesting trade. How did they make the call? How did they develop conviction? How did they hold onto the position during the inevitable hiccups and adversity? So it's that reconstruction of the case study.” 11:00: Where to look for information? “The answer is you've got to look everywhere.” 12:20: Finding memos in which Greenspan “described the creation of the Federal Reserve as one of the historic disasters in U.S. history.” 15:00: George Soros who joked "I can only remember the future." Learning the division of labor in the Soros team and the Thai Bhat trade. 20:00: “The culture within an investment company matters almost as much as the analysis that the company does of the market or of the trade.” 21:00: The Korean bank trade. 27:00: Different cultures and investment styles, contrasting Soros, Druckenmiller and Robertson. 31:30: Culture at Tiger and the Tiger cubs. 34:00: Julian Robertson outgrowing his original strategy and the loss of “supercharged incentives.” 39:30: Can investors evolve and adapt? 42:00: Mindset and personality. 47:45: Understanding Paul Tudor Jones. “Genius does not always understand itself.” Vic Braden 49:00: Jones tried to replicate his system with a quant. 52:00: The Lehman Brothers 2008 trade. 56:50: Jones’s process and his ‘market scripts.’ “Sometimes causation in human actions works in a weird way.” 59:45: Reflecting on the industry and book from today’s perspective, a decade later. 1:03: Rise of quantitative trading. 1:08: Sebastian's upcoming book, The Power Law.

Dominique Mielle was a partner and senior portfolio manager at Canyon Capital, a $25 billion fund, where she worked for twenty years. In this episode we discussed her career in the world of distressed investing, her book, and the hedge fund industry in general. 3:00: The WorldCom bond trade. 6:30: Dealing with a losing investment. 9:00: Importance of expertise and networks in distressed investing. Distressed investing as a game of chess. 11:40: Distressed investing as an apprenticeship business. 14:15: Generalist vs. sector specialist model. 17:30: Hertz bankruptcy. 20:40: Airline bankruptcy investing and Equipment Trust Certificates. 28:00: How distressed investing changed over the past decades. 32:00: Navigating the financial crisis in 2008 35:00: Mental resilience and losses. 38:00: Losses are unavoidable. 39:20: The business of investing: building a CLO business, raising capital. 40:59: Pitching, fundraising. 45:00: Women in hedge funds. “In 20 years, I only met one other female partner who was doing distressed. And she's a friend of mine.” 48:30: Implications of hedge funds as a mature industry. 51:25: Pitching and communicating ideas. 53:45: Managing a team of analysts.