Paul Ollinger

Reasonably Happy with Paul Ollinger

Comedy EN ↓ 335 episodes

Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection. words.paulollinger.com

Author

Paul Ollinger

Category

Comedy

Podcast website

words.paulollinger.com

Latest episode

Jul 8, 2026

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Episodes

Claiming Confidence | Reasonably Happy with Paul Ollinger 23.10.2024

We are joined by Lydia Fenet, the founder and CEO of the Lydia Fenet Agency, a boutique agency representing best in class charity auctioneers. Lydia is a best selling author and ground breaking art auctioneer who sits with us to talk about art, confidence and how to decide what success means to you. Pick up a copy of "Claim Your Confidence" by Lydia Fenet: https://lydiafenet.com/the-book/ Follow R...

What Cocaine Taught Me | Reasonably Happy with Paul Ollinger 16.10.2024

We are joined by New York Times best selling author and former Wall Street wild man Turney Duff to discuss Hookers, Blow, Million-dollar bonuses on Wall Street and the journey through recovery and what lies the other side of the Wall Street hustle. Pick up a copy of "The Buy Side" by Turney Duff: https://www.amazon.com/Buy-Side-Street-Traders-Spectacular/dp/0770437176 Follow Reasonably Happy host...

The People Who Never Quit with Henry Oliver 27.08.2024

What did Ray Kroc, Maya Angelou, Margaret Thatcher, and Malcolm X all have in common? (Don’t worry - this isn’t a dirty joke!) They were all opsimaths, i.e. a person who blooms late in life. In his new book SECOND ACT: What Late Bloomers Can Tell You About Success and Reinventing Your Life, author Henry Oliver shares the stories of well-known people whose greatest accomplishments happened in or pa...

A Poet’s Life (with In-Q) 21.08.2024

Nobody gets into poetry for fame and fortune. And yet, there might be a tiny bit of each happening for In-Q, my guest this week who is a renowned poet and spoken word artist. When he started freestyling (aka, “rapping" for you old people) with his friends at age 13, In-Q felt an empowerment that didn’t exist in the rest of his life. The words inside him took on a life of their own and, after he st...

“Second Class” Americans with Batya Ungar-Sargon 14.08.2024

The spirit of the working class is crushed. So argues Batya Ungar-Sargon in her new book 'Second Class: How the Elites Betrayed America's Working Men and Women’. Batya says that working men and women in the United States have been abandoned by both political parties and left to fend for themselves all while unchecked immigration makes an already challenging job market untenable. As her title sugge...

Why the News is Bad with Angus Hervey 07.08.2024

**Hi friends - this is Paul writing to confess to an error in my introduction in this week's episode. The name of Angus Hervey's podcast is "Hope Is a Verb," not—as I called it—"Hope is NOT a Verb," which is kind of the opposite (insert winky emoticon). Unfortunately, I am unable to re-record the intro as we are traveling, but I can change these show notes, so that's what I'm doing. Sincere apolog...

Fighting for the Family Business with Stephanie Stuckey 04.08.2024

Stephanie Stuckey used her life’s savings to buy the company that is her family’s legacy. At it’s height in the1960’s and 70’s, there were hundreds of Stuckey’s stores selling gas, pecan candy, cold drinks, and quick meals near highway exits around the United States. But after her grandfather was bought out by a big corporation, the neglected enterprise and its stores fell into disrepair. Since bu...

Persevering Through Grief with Nicole Avant 24.07.2024

Nicole Avant is the former U.S. Ambassador to the Bahamas and author of a new memoir, 'Think You’ll Be Happy: Moving through Grief with Grit, Grace, and Gratitude’ which tells the story of her extraordinary family and her mother’s tragic death by murder. Her mom, Jacquie was a philanthropist and community activist whose example taught Nicole kindness, respect, and humility. Nicole’s father was Cla...

On The Move 03.07.2024

On this introspective episode of Crazy Money, Paul sits alone in his empty Atlanta house and talks openly about the thoughts and feelings that drew him back to Atlanta, and the head trauma that may or may not have initiated his desire to sell everything and move to New York City. Oh, by the way, my name is Mike Carano and I’m writing these surely-to-be-deleted episode notes. Paul is occupied with...

Who killed Rudolf Diesel? (with Doug Brunt) 12.06.2024

Yes, there was actually a guy named Rudolf Diesel who actually invented the diesel engine, which was incredibly revolutionary for its time. It earned Diesel a massive fortune and had huge implications for how war—especially maritime war in the early 1900’s—would be waged. As European countries scrambled for dominance just prior to WWI, Diesel disappeared, leading to speculation that he was murdere...

Restoring Politcal Sanity with Charlie Wheelan (Encore) 04.06.2024

Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Economics, (no nudity in either), and The Centrist Manifesto, all of which we discuss in this episode. The Chicago Sun-Times describes Charlie as someone who “combines a razor-sharp mind with a boatload of charm and impressive expertise in economics and f...

Mike Posner on Life Beyond Fame and Fortune 28.05.2024

Mike Posner is a Grammy-nominated rapper, singer, songwriter, and music producer from Detroit. His Spotify channel has generated over 3 billion plays and his song 'I Took a Pill in Ibiza' reached the top five on the Billboard Hot 100. Mike "had it all" at a young age and captured his lifestyle in the lyrics of his biggest hit: “A real big baller (who) made a million dollars and...spent it on girls...

Andrew Yang on Our Broken Political System (Encore) 21.05.2024

Andrew Yang is a former Presidential and NYC mayoral candidate and the founder of Venture for America. He's also the founder of the Forward Party where he advocates for structural reform to safeguard our democracy. He lays all this out in his new book, ‘Forward,' which we discussed today. We also discuss Andrew's life as a teenager, his obsession with post-punk bands like The Smiths, Depeche Mode,...

The Third Path with Jordan Harbinger 14.05.2024

Jordan Harbinger is one of the most popular podcasters in North America, but it all started by accident. As a young University of Michigan grad, Jordan decided to go to law school because it was something to do after college and eventually ended up at a Wall Street firm. A multi-linguist, Jordan traveled and met new people all over the world. He eventually started teaching networking to other youn...

Living The Constitution with AJ Jacobs 07.05.2024

Good morrow, chum! My guest this week is A.J. Jacobs, author of the new / amazing book 'The Year of Living Constitutionally: One Man’s Humble Quest to Follow the Constitution’s Original Meaning’, in which A.J. chronicles his year of living as an 18th Century citizen, including writing letters with quill and ink, carrying a musket around the Upper West Side of Manhattan while wearing colonial garb,...

Being Human at Work with Kim Scott, author of 'Radical Candor’ 30.04.2024

‘Radical Candor’ author Kim Scott once had to inform a colleague that they smelled bad….like, really bad. She was able to do so becuase she had created on her team a culture or radical candor. No, this doesn’t mean you can just walk up to colleagues and say, “you stink!” or “nice shirt, bozo!” On the contrary, radical candor is a culture where authentic personal caring co-exists with direct challe...

Power Couple: Debbi “Mrs.” Fields and Wade Shealy 24.04.2024

Debbi Fields founded Mrs. Fields cookies brand when she was in her early 20s and built the company into a well-known global brand. Wade Shealy got his start selling Bibles door-to-door then went on to develop and sell > $3 billion in resort real estate over the next few decades, including Hampton Island, GA whose residents include Ben Affleck / Jennifer Lopez and Robert / Lydia Monday. He is now C...

Death, Dying, and Israel with Rabbi Steve Leder 16.04.2024

Rabbi Steve Leder is the Senior Rabbi at Wilshire Boulevard Temple, a very large and influential congregation in Los Angeles. He is a New York Times best-selling author of several books, including 'For You When I Am Gone’ and 'The Beauty of What Remains,’ both of which pertain to death and dying. I had planned on speaking with Steve primarily about death for an hour, but our conversation covered e...

The Wealth Money Can’t Buy with Robin Sharma 09.04.2024

Robin Sharma is a leadership expert, coach and author whose books have sold tens of millions of copies around the world. The author of The 5AM Club, The Monk Who Sold His Ferrari, The Everyday Hero Manifesto, and Who Will Cry When You Die?, Robin has a new book out called The Wealth Money Can’t Buy in which he examines the ways we can all develop happiness with and beyond financial wealth. In this...

America’s Government Teacher, Sharon McMahon 04.04.2024

Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding her audience through “the fascinating world of democracy, politics, and history.” In the process, she is proving that Americans—and other good people around the globe—are hungry for unbiased political context and analysis. "With a heart for education an...

Poor Kid Makes Millions Trading, Fights Inequality with Gary Stevenson 29.03.2024

Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances), his gift for mathematics landed him a spot at London School of Economics (alma mater of Mick Jagger, Margaret Thatcher, and George Soros) where he attended with the sons and daughters of the global elite. His skill at a card game won him a job on C...

The Narcissist Next-door with Dr. Ramani Durvasula 20.03.2024

Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissistic People. In this insight-rich conversation, Dr. Ramani explains the traits and behaviors of narcissistic individuals, how they hijack our well-being, and the motivations behind their attention-seeking behavior. She also relieves Paul of the sneaking su...

TED's Chris Anderson on Infectious Generosity 14.03.2024

Chris Anderson is the Head Curator of TED and author of the new book, 'Infectious Generosity: The Ultimate Idea Worth Spreading' in which he argues that YOU and I can improve the world by embracing our natural inclination toward generosity. He speaks not just of financial generosity, though that’s certainly a huge part of it, but also of creative generosity and generosity of spirit. In this conver...

Mike and Paul’s Road Trip 05.03.2024

This episode is highlights of a conversation between Paul and Mike Carano, long-time friend and Crazy Money editor. It was recorded on a road trip between San Francisco where Paul had just performed at Cobb’s Comedy Club and San Luis Obispo where he was heading to perform in the SLO Fest Comedy Festival. Among other things, Paul and Mike discuss: Memories of commuting from SF to Yahoo! in Sunnyval...

On Fire for Life with John O’Leary 28.02.2024

When John O’Leary was 9 years old, he played with fire and got burned. Like really, really burned, over 99% of his body. Doctors gave him less than 1% chance to live and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, survive he did. His journey back took years, required dozens of surgeries, and cost him all of his...

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