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 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, an investment manager, writer, and author of Soul in the Game, recalls growing up in the Soviet Union’s Arctic north. He discusses shortages, state ownership, corruption, and the appeal of socialism. The conversation also explores antisemitism across political extremes, reserve-currency power, debt, inflation, private property, and concerns about political profiteering in financial markets.

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

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 will get out of this. Still, it’s pretty scary to get this kind of unexpected invoice. Suffice to say, it’s a wild time in New York city real estate. In addition to this new second—or third or fourth—home tax, there are a ton of policy changes in the works, including but not limited to:* The mayor and the Rent Guidelines Board just implemented a two-to-three year rent freeze for all the city’s rent stabilized units, comprising 41% of the supply of rental housing in the city.* Pending in the City Council is the Community Opportunity to Purchase Act (COPA) that, when it passes, will impose major restrictions on a multi-family unit owners’ freedom to sell their building.* Potential “Mansion” Tax reform could lower the threshold from $1 million to $500,000 transactions, increase rates by 40%, and switch the liability from the buyer to the seller.In short, there’s a massive amount of uncertainty about the future, but all trends point to an increasingly hostile and expensive environment for property owners. To try to make sense of how it works, I interviewed Paula Pant, founder and host of the Afford Anything podcast, a former newspaper reporter, and Knight-Bagehot Fellow at Columbia University. Paula is a NYC-based landlord who has developed an expertise on the city’s rent stabilization system, where it came from, and how it works.Most people assume that rent stabilization exists to help poor people, but that’s not the priority. It operates more like a lottery system where random, lucky “winners” lock in below-market prices regardless of how much money they make. In fact, a recent Wall Street Journal analysis indicated that more than 86,000 rent stabilized households earn over $200,000 a year!The system and its adjacent policies protect bad tenants, disincentivize capital investment and construction, and have led to 57,000 apartments being left vacant because it’s less expensive to leave them empty than to participate in the city’s rigged game.The whole thing is wacky and totally non-obvious. I learned a ton talking to Paula and I know you will too. Check it out.Follow Paula on Instagram here, or X (aka, Twitter) here. Get your free download: 7 Expensive Rental Property Mistakes to Avoid Follow Me (Paul) on Instagram here, or X (aka, Twitter) here.Get tickets to see me live in Sarasota 8/13-16 here.Timestamps:00:00:00 Trailer00:00:59 Intro 00:03:03 Hyper frugal in her twenties, for all the wrong reasons00:05:31 A $27,000 down payment on an Atlanta triplex00:08:21 Never be a landlord in New York City00:08:33 The price to rent ratio, and how to run it on any apartment00:14:10 Nobody has a right to 12% returns, and what a 9.9% cap would actually do00:16:24 Rent control versus rent stabilization: 16,000 units against a million00:20:16 If it were designed to help poor people, there would be means testing00:23:36 True working class people are subsidizing the rich00:24:23 How the units actually get handed out, and the friend earning over $300,00000:30:32 The Rent Guidelines Board, the 7 to 1 freeze, and the resignation in protest00:37:07 Check credit or verify income, but not both00:41:21 The 2019 law and the $100,000 turnover no bank will finance00:49:25 57,000 vacant units and the Community Opportunity to Purchase Act00:54:22 Austin as the model, and where Paula puts her own capital00:57:13 Analyst, not advocate. Data over dogma00:58:36 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 controversial markets by their real-world consequences instead of instinct alone. We cover why it's easier to buy heroin than hire a hitman, Iran's legal kidney market versus America's black market, the actual winners and losers of rent control in New York, why I can't buy a horse meat hamburger in California, and what a real accounting of scarcity and trade-offs actually looks like.Timestamps:* 00:00:00 Trailer* 00:01:07 Intro* 00:03:48 What market design actually means* 00:06:57 Markets are better at producing efficiency than equality* 00:10:08 What makes a transaction “repugnant”* 00:11:45 Same-sex marriage as the textbook repugnant transaction* 00:15:45 Why it’s easy to buy drugs but nearly impossible to hire a hitman* 00:17:32 Iran’s legal kidney market and America’s black-market problem* 00:22:10 The case against price-gouging bans, from Sydney to snow shovels* 00:27:07 The real winners and losers of rent control* 00:28:12 California’s ban on horse meat, and the loophole New York doesn’t have* 00:35:59 How a PhD in operations research became a career in game theory* 00:37:02 The 3 a.m. phone call that announced his Nobel Prize* 00:40:40 The kidney transplant shortage and what it will take to fix it* 00:41:51 OutroGet tickets to see Paul in Sarasota, Florida here.Follow Paul on Instagram here and on X (i.e. Twitter) here. Rate and Review Reasonably Happy here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 gang scandal, DEI and the anti-meritocracy push, his move to Ole Miss, and what a real prescription for the West actually looks like.Timestamps00:00:00 Trailer00:01:28 Intro00:01:40 From marketing professor to cultural critic00:03:20 Born Jewish in Lebanon during the civil war00:05:03 Defining suicidal empathy00:08:29 Civilizations die by suicide, not murder00:13:47 How open-border immigration became the flagship case00:14:29 Cultural relativism and the parasitic mind00:22:12 UK grooming gangs and the fear of Islamophobia00:28:13 One-way tolerance and the parasite analogy00:34:10 Anti-meritocracy, DEI and attribution bias00:40:16 The career cost of speaking honestly in academia00:43:34 Why he chose Ole Miss over the Ivy League00:49:09 Hope through the Southern freedom centers00:52:10 The prescription: an inverted U-curve for empathy00:57:36 OutroFollow GadInstagram: @doctorgadsaadX: @GadSaadFollow MeInstagram: @paul_ollingerX: @Paul_Ollinger Get full access to Reasonably Happy at words.paulollinger.com/subscribe