Reasonably Happy with Paul Ollinger

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...

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...

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...

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 misun...

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 $...

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...

“People do not decide their futures: they decide their habits and their habits decide their future.” – F.M. Alexander If 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...

Last week, I received a bill from New York City for $71,1783.16. It was the balance due for my Non-primary residence surcharge, aka the pied-à-terre tax that is a premium on top of the $55k or so we pay in regular, old fashioned property tax. We got pinged because our home is owned by our trusts, which are not New York entities. The good news is that, since we are legit full-time residents, we wil...

This week, I sit down with Dr. Alvin Roth, Nobel Prize-winning economist, Stanford professor, and author of Moral Economics: From Prostitution to Organ Sales, What Controversial Transactions Reveal About How Markets Work . Al lays out why so-called repugnant markets like kidney sales, prostitution, horse meat aren't moral failures so much as trade-offs we refuse to name, and argues we should judge...

In this episode of Reasonably Happy, I sit down with Dr. Gad Saad, an evolutionary behavioral scientist, longtime professor, and author of the New York Times bestseller Suicidal Empathy: Dying to be Kind . Gad lays out why empathy, when it hyper-fires at the wrong targets, becomes a form of civilizational self-disembowelment. We cover open-border immigration, cultural relativism, the UK grooming g...

Investment management firm Fidelity is a private company that administers over $18 trillion in assets—that’s greater than the GDPs of Germany, Japan, the United Kingdom, and France combined . (Or, it’s18 Elon Musks.) Last year, the company earned almost $13 billion in profit , half of which goes to the family who started it. To be more precise, it goes to the founder's grandchildren, a few of whom...

Francis Foster is the co-host of the massively popular TRIGGERnometry podcast and author of the new book (Un)Educated: My Life as a Teacher, and Why You Should Never Become One (which you should buy here ). In this honest, fun, and sometimes stark conversation, Francis and I discuss: * Why teaching is a terrible job. * What he loves about TRIGGERnometry * His love for Buc-ees* (which are closer to...

I was most pleased to speak this afternoon with W. Kamau Bell, a Peabody Award and 4-time Emmy-winning comedian, filmmaker, and television host who is also a Celebrity Jeopardy champion! He is best known as the creator and host of CNN’s United Shades of America on which he spent seven seasons traveling the country exploring communities, subcultures, and perspectives that often go overlooked. The s...

Thanks very much to Bruce Feiler for joining me on the 5 Questions livestream to discuss his new book A Time to Gather: How Ritual Created the World—and How it Can Save Us . In this upbeat and positive conversation, Bruce and I discuss: • What came first, ritual or religion? • Why SEC football tailgating fits the definition of ritual • How Balinese tooth-filing ritual has much in common with moder...

On this third episode of 5 Questions, I speak with Andy Borowitz , whose massively popular newsletter The Borowitz Report tops out around 200 words per post. So this intro is going to be brief! Even if you belong to Andy’s army of loyal readers, you might not know that he is also the co-creator of The Fresh Prince of Bel-Air and wrote on classic 80’s TV shows, The Facts of Life and Square Pegs , w...

My guest today is Rosebud Baker. Rosebud is one of the sharpest and most honest voices in comedy today. She’s an Emmy-nominated and Writers Guild Award-winning writer whose credits include Saturday Night Live , Inside Amy Schumer , and That Damn Michael Che . In her new autobiography, Fully Baked: A Messy Memoir, Rosebud shares the story of being the grand-daughter of James Baker, the former Secre...

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ A.J. Jacobs is a journalist, bestselling author, self-described “human guinea pig,” and one of the most interesting people I know. He was a great choice to be my second guest on my 5 Questions series of Substack livestreams. Over the past two decades, A.J. has built a remarkable career by asking questions most of us would never think to ask—a...

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ Hello friends, this week's Reasonably Happy is me reading some of my favorite posts from my Substack over the past six months. They cover the Manosphere, schadenfreude, career trajectories, and more. I understand that you don’t always have time to read everything I crank out—you’re on the move, working out, or re-arranging your sock drawer. A...

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions , my bite-sized, live-streamed Substack interview show that I’ll be producing in addition to longer-form episodes of Reasonably Happy . Dave’s column was syndicated to hundreds of newspapers around the globe for several decades. He has published...

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ “Happiness is a choice that requires effort at times.” -Aeschylus Whenever I go back and re-listen to one of my podcast interviews, I always discover elements of the conversation I didn’t recall. Upon revisiting this 2025 conversation with best-selling author Gretchen Rubin, I of course remembered that she is a warrior for happiness and the p...

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can still hit hard. A native of Birmingham, AL, Roy has that rare ability to make you laugh while also making you think—whether he’s talking about race, class, media, relationships, or the strange little...

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ “Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the American Dream is dead. But my guest today calls this hogwash, baloney, and complete malarkey. Joseph Moore is a historian, entrepreneur, investor, and the author of a new book called  How to Get Rich In Ame...

If you’ve ever wondered if having everything you’ve ever wanted would make you feel like a complete human being, this episode is for you. My guest today is Dr. Paul Hokemeyer, a psychotherapist who works almost exclusively with ultra-high-net-worth individuals—the kind of people most of us assume have life completely figured out. Spoiler alert: they don’t. Dr. Hokemeyer is the author of Fragile Po...

“How am I ever going to be happy again?” That was the question the wife of this week’s guest asked him after the death of their one-month-old son, Fisher. Michael Cruz Kayne is a comedian, actor and a staff-writer on The Late Show with Stephen Colbert, where his work has earned him a Peabody Award, a WGA Award, and two Emmy nominations . He made his off-Broadway debut in Sorry For Your Loss , a ra...

Chris Pavone is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, The Doorman is set in a glamorous Manhattan apartment building where the lives of the ultra-wealthy residents intersect with the man who quietly watches it all—the doorman. Over the course of one explosive day, secrets, class tensions, and personal betrayals collide in a f...