Reasonably Happy with Paul Ollinger

Bill Cohan writes big, meaty books about the personalities and institutions that shape American finance. His latest, Money to Burn: The Unvarnished Truth About Leon Black, Apollo, and the Rise of a New Wall Street explores the complicated life of Apollo Global Management founder, Leon Black.With deep reporting and rich detail, Bill tells the story of Leon’s father’s leap to his death onto Park Avenue, his time working with junk bond king Michael Milken, Apollo’s astounding success, and how Leon made billions re-financing Twinkies.A man of considerable ambition and intellect, Leon’s professional instincts created an $18 billion fortune. His personal instincts, on the other hand, earned him a place on the Epstein list and an extortionate Russian girlfriend. (It happens!)Bill is a former investment banker who spent 17 years on Wall Street, co-founded news site Puck, and has written eight substantive books, six of which became New York Times bestsellers. Today, we discuss his career, his writing process, his book about the Duke Lacrosse fiasco, and how that relates to what’s happening today at Cornell.Learn more about Bill on his website and read his Puck column here.Follow Me on TwitterX and Instagram.Episode Notes:* Catholic Disclaimer: I mixed up Immaculate “Conception” with “Assumption.” I ask your forgiveness.* The other book I mentioned about the banana industry is called The Fish that Ate the Whale: The Life and Times of America’s Banana King. It’s a pretty fascinating story, actually.* In our discussion of the Duke Lacrosse case, Bill mentions Roy Cooper who was the state attorney who assumed the case after Mike Nifong recused himself. This week, Roy won the election to be the U.S. Senator from the North Carolina.Timestamps00:00:00 Trailer00:00:57 Intro00:02:01 Why my grandfather changed our name from Cohen to Cohan00:05:19 Andover and rooming near John F. Kennedy Jr.00:07:14 The teacher who said I’d never be a writer00:11:10 Hired on Wall Street a month before the 1987 crash00:15:19 Rosebud and the fall of Eli Black00:22:03 Who Leon Black is and what Apollo became00:25:16 Mike Milken and the invention of junk bonds00:28:34 How Leon Black bought Twinkies out of bankruptcy00:32:18 The Russian girlfriend and the $100 million extortion demand00:37:39 Why Leon Black paid Jeffrey Epstein $158 million00:43:10 $130 million for The Scream00:48:23 What everybody gets wrong about the Duke lacrosse case01:00:23 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Did you negotiate with terrorists this week? No, I’m not talking about a toddler who won’t eat his broccoli or a comedy club manager who “knows funny.” I mean real terrorists - the kind who kidnap children and plant bombs at marathons. Well, that’s what my most recent guest did for a living.Kyle Vowinkel is a West Point graduate and retired FBI executive who mediated the peaceful surrender of the Boston Marathon bomber, helped to save a 5-year-old boy who was abducted by a crazy man in an underground bunker in Alabama, and participated in over 100 high-risk missions in Iraq and Afghanistan. Share Kyle’s incredible story.One of only five agents ever to serve on both the Bureau’s Hostage Rescue Team and Crisis Negotiation Unit, Kyle received the FBI Director’s Medal of Excellence, FBI Director’s Award for Outstanding Counterintelligence Investigation, and the Attorney General’s Award for Exceptional Heroism, the Department of Justice’s highest award for valor. In other words, though he would never put it this way and he doesn’t come across with this energy at all, Kyle is a law enforcement badass who served his country in ways you and I will never fully appreciate.His new book, Shaping Chaos, is the story of his incredible career, the grueling training he endured to prepare for it, and the impact that service had on his family.It also reminds us of the sacred duty of law enforcement and the critical importance of the Department of Justice’s political independence.Get Kyle’s book here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

This week, I sat down with Caroline Shinkle, the Republican candidate for Congress in New York’s 12th District. Caroline studied economics at MIT and graduated from Harvard Law School before going on to work at the Federal Reserve Board of Governors, the European Central Bank, the Bank of Israel, and as a corporate lawyer in New York City. In this frank conversation, Caroline lays out why she believes the Democratic Socialists of America have hijacked the Democratic Party and why she thinks the chaos that is happening in France could soon find its way to America. We cover congestion pricing, sanctuary cities, the importance of supporting Israel, the rise of anti-Semitism in New York, the best gluten-free bagel in the city, and why she believes a Republican can finally win in Manhattan.Follow Caroline on her website and Instagram. Follow Me on Instagram and X (Twitter). Timestamps:* 00:00:00 Trailer* 00:01:01 Intro* 00:02:17 Mapping New York’s 12th District* 00:04:29 How the DSA hijacked the Democratic Party* 00:07:02 Congestion pricing, or how to tax the problem you created* 00:11:18 A second Cold War in our own backyard* 00:16:39 Running as a Republican in an 80% Democratic district* 00:19:04 No federal income tax up to $150,000* 00:21:37 Why supporting Israel matters to America* 00:24:19 Is Zohran Mamdani an anti-Semite* 00:28:43 Sanctuary cities and the Bronx ICE shooting* 00:32:22 The best gluten free bagel in Manhattan* 00:34:19 The biggest political realignment since FDR* 00:37:20 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe

My guest today is Jared Dillian, a former Wall Street trader, DJ, and the best-selling author of Street Freak, No Worries, and his new book, The Awesome Portfolio.Let me ask you a question: Can you let your investments ride without losing sleep or checking your portfolio every eleven minutes? I have trouble with this. Even though I feel really good about what I own, I still peek at my balances a couple of times a day—just to make sure the world isn’t exploding.In The Awesome Portfolio, Jared explains why owning one fund with 500 different stocks doesn’t necessarily make you diversified or safe from violent market fluctuations. He argues that a portfolio balanced across five different asset classes—equities, bonds, commodities (like gold), real estate, and cash—will produce very good returns and drastically reduce volatility.While nothing I say in this discussion should be considered professional financial advice, I think his idea is interesting and worth your consideration. We also talk about trouble in the bond market, political risk, financial advisor incentives, and investor psychology, including how our emotions can wreck even the smartest investment plan.Please check out my new article in The Hill: Nikole Hannah Jones Just Ran Head-first Into the Great Dumbing DownTo get invites to live streams with great guests like Jared, Dave Barry, and many more, subscribe to my Substack HERE.Follow Jared HERE and get the book HERE. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

If MLB first-ballot Hall-of-Famer Dave Winfield’s story tells us anything, it’s that you can’t judge a person by how things appear on the surface.What we saw from the outside: a formidable 6’6”, 220 lb athlete who had just signed a 10-year, $23 million contract. (about $85 million in today’s money)What was happening on the inside: self-doubt, anxiety, imposter syndrome, and the stress of a boss intentionally sabotaging him in the press and among his peers.In 1980, Dave signed the biggest contract in baseball history with the New York Yankees, who had won two of the previous four World Series. From the minute he arrived in the Bronx, Dave became an object of derision to George Steinbrenner, the Yankees’ mercurial owner.Seemingly for no reason, Steinbrenner insulted him in public, smeared him in private, and reneged on multiple contract obligations. He seemed to make the star player’s life miserable just because he could.It seems counter-intuitive that a rich and famous athlete at the height of his physical and commercial prowess—someone who appeared to have everything—would describe those years as “the worst period of my life.”And yet, that’s exactly the story Dave tells in his new memoir Touching All the Bases: A Story of Power, Purpose, and Surviving the Bronx and what he told me on this week’s episode of Reasonably Happy.The 12-time All-Star, seven-time Gold Glove winner, and World Series champion lays out his side of the decade-long feud with Steinbrenner, and how he kept making All-Star teams despite the toxic work environment. We cover his getting drafted by three professional sports leagues, Hank Aaron’s warning about playing in Atlanta, signing the first 10-year contract in sports, finally getting his World Series ring in 1992, and, of course, the Canadian seagull that got him arrested.Dave also shares what it was like to finally make peace with Steinbrenner before The Boss’s death in 2010.Follow Dave:Instagram: @davewinfieldhofX: @DaveWinfieldHOFFollow Me:Instagram: @Paul-OllingerX: @Paul-OllingerTimestamps00:00:00 Trailer00:00:50 Intro00:01:56 Pro baseball in 1973, when nobody played to get rich00:04:40 His first bank went bankrupt, his second bank burned down00:06:25 Growing up in Saint Paul00:07:40 Drafted by the NFL without playing a down of college football00:11:37 The yellow legal pad and studying the veterans00:14:51 50 years of the Winfield Foundation00:17:31 Free agency and the first 10-year contract in sports00:20:05 Dinner with Ted Turner and Hank Aaron’s warning00:23:13 Steinbrenner throws his lunch across the boardroom00:26:22 “If you don’t like it, sue me”00:29:58 How he kept performing through a toxic workplace00:31:46 “The worst 15 years of my life”00:33:19 Honorary doctorate in Syracuse, first pitch in the Bronx00:35:09 The seagull incident in Toronto00:37:39 Winning the 1992 World Series with the Blue Jays00:39:25 Lightning round: toughest pitcher, best teammate, worst fans00:42:53 Making peace with George Steinbrenner00:46:22 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Vitaliy Katsenelson grew up in the Soviet Union - in Murmansk, the largest city north of the Arctic Circle. Today, he is the CEO & Chief Investment Officer of IMA (Investment Management Associates).An award-winning writer, Vitaliy has authored two books on investing and the widely acclaimed Soul in the Game: The Art of a Meaningful Life, which has been translated into multiple languages. Forbes has called him “The New Benjamin Graham,” and his writing has appeared in the Financial Times, Barron’s, and The Wall Street Journal. His newsletter reaches a global audience of over 100k subscribers. In this Substack live-streamed conversation from last week, Vitaliy and I discuss:* Daily life up under a communist government* The rise in anti-Semitism from both the Right and the Left* Why he is so disturbed by President Trump’s profiting off of market-moving social media postsVitaliy lives in Denver with his wife and three children. In his free time, he enjoys reading, listening to classical music, playing chess, and writing about the intersections of investing and life.Subscribe to Vitaliy’s Substack here or his newsletter here.Subscribe to Paul’s Substack here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

This week, I sit down with Phil Gramm, economist, three-term United States Senator from Texas, former chairman of the Senate Banking Committee, and co-author of 'The Triumph of Economic Freedom: Debunking the Seven Great Myths of American Capitalism'. In the book, Senator Gramm argues that much of what Americans believe about capitalism, inequality, and poverty rests on incomplete data and a misunderstanding of history. We cover the true math behind income inequality and the war on poverty, the reason the Great Depression lasted so long, what really caused the 2008 financial crisis, and just how the heck America is going to reckon with its $40 trillion debt. (Spoiler Alert: it won't end well!)Get the book here.Follow Me on Instagram: hereAnd X / Twitter hereTimestamps:00:00:00 Trailer00:00:55 Intro00:02:08 From Oil Economist To U.S. Senator00:07:15 The Industrial Revolution Myth Debunked00:14:21 Did Free Trade Really Hollow Out Manufacturing00:20:25 JD Vance, The Dollar, And Reserve Currency Myths00:22:33 The Sugar Tariff Racket And The Cost Of Protectionism00:24:44 The Real Inequality Numbers Behind The Headlines00:31:01 The Truth About The War On Poverty00:34:32 Why Political Opponents Exaggerate Bad News00:41:26 Debunking The 2008 Financial Crisis Myth00:49:48 America’s $40 Trillion Debt And The Coming Reckoning00:53:45 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe

This week, I’m talking to Jack Raines, the guy behind the mega-popular Substack Young Money and author of a great new book called Young Money: A Field Guide to Wealth and Purpose in Your Twenties.After graduating from college and landing a finance job at UPS, Jack turned $6,000 in retirement funds into $400,000 trading SPACs in his spare time. Then, by continuing to trade SPACS, he turned that $400k into $200k! This experience was expensive but vital.Jack started publishing his thoughts about careers and finances on Young Money, and has built a following of over 60,000 “anxious but ambitious” readers. Morgan Housel, author of The Psychology of Money, called him “one of the best money writers around.”Perhaps that’s why he got a call from Penguin Random House and an eventual book deal. Like Jack himself, it’s a book of unbridled enthusiasm and optimism. It’s a trip to read about money through the eyes of a 29-year-old who’s had just enough interesting life experience but has lost zero of his youthful energy.If you have a young adult in your life who has found her way into adulthood, or one who is trying to figure himself out, Young Money might be the perfect read for them. In the meantime, check out my conversation with the pride of Tifton, GA, Jack Raines!We talk about travel, Macon, GA, billboards along I-75 (“Repent or die!”), working at UPS, the Allman Brothers Band, playing Call of Duty in his pajamas during COVID, Wall Street Bets, and the Wall Street Journal’s Spencer Jakab.Stay gold!Follow Paul on Instagram here and Twitter here.Get Jack’s book here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

What’s that you say – you want an interview with an economist who has both a great sense of humor and movie star good looks? Well look no further, friends. Matt Hill teaches economics at the University of Southern California, and is the creator and host of Econ Nerds, a project devoted to finding the economics hiding in everyday life. It’s like Freakonomics for the YouTube and Substack age.Matt has the rare ability to take economic ideas that normally require a textbook, a slide rule, and three hits of Adderall to get your head around and turns them into entertaining stories about things like Ozempic, the lottery, OnlyFans, gentrification, and why it took humanity so damn long to put wheels on suitcases.In other words, he can help you learn about economics without making you feel like you’re studying economics!More importantly, Matt uses story-telling techniques to shed light on important issues where the data and the prevailing public rhetoric diverge. Examples include the true nature of inequality, what’s really happening with climate change, and the actual number of alleged police violence incidents. (HINT: it’s much lower than you might think.)He’s using his great mind, a sense of humor and the power of economics to help spread understanding.Follow Paul on Instagram and Twitter here.Find Econ Nerds here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

“People do not decide their futures: they decide their habits and their habits decide their future.” – F.M. AlexanderIf you want to improve, be kind to yourself. That’s the message from this week’s guest, Dr. Beth Cabrera, a positive psychologist, professor, and author of the new book Being Well: A Positive Path to a Healthier, Happier You. Beth is also an old college friend who's now the first lady of Georgia Tech. In her new book, Beth argues that willpower and guilt are the wrong tools for lasting change (sorry, Catholic and Jewish moms). Because our brains are wired to survive, not thrive, and default to scanning for threats instead of good things, feeling good is actually the more effective fuel for building habits that stick. We cover the chicken-and-egg question of whether happiness causes success or success causes happiness, why optimistic salespeople at MetLife outsold others by 88%, how much of optimism is genetic versus learned, the brain's negativity bias and why social rejection registers like a broken arm. (So, please don’t reject me. Please!) Beth and I talk gratitude, hedonic adaptation, the basics of diet, sleep, exercise, and meditation, what it's actually like being the first lady of a major American university. And how the way to cheat death is to have a Purpose (capitalized intentionally).Get Beth’s book here. See her website here.Follow Me (Paul Ollinger) on Instagram here or on X (fka, Twitter) here. Timestamps00:00:00 Trailer00:00:35 Intro00:01:21 Beth Cabrera and her new book, Being Well00:04:53 How Beth got hooked on the happiness game at Arizona State00:07:07 The chicken and egg question: does happiness cause success, or the reverse00:08:31 Is optimism genetic, and how much of it we can actually change00:09:56 The brain's negativity bias, and why it kept us alive00:11:18 Gratitude assessments and noticing the good moments you'd otherwise miss00:14:06 Why social rejection registers in the brain like a broken arm00:19:04 Hedonic adaptation and why happiness set points reset00:21:07 The basics: diet, sleep, exercise, and meditation00:26:35 Life as the first lady of Georgia Tech, and putting on the game face00:30:45 Why want to beats have to as a driver of behavior00:35:03 Finding purpose, big P and little p00:36:47 A positive attitude about aging can add years to your life00:38:30 Why beating yourself up doesn't create positive change00:41:16 The three parts of self-compassion: mindfulness, common humanity, kindness00:42:35 The caddie metaphor: what would you say to a friend instead?00:43:46 Where to find Being Well and connect with Beth00:43:50 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe