Reasonably Happy with Paul Ollinger

Chanel Reynolds' journey to helping others began with a brutal accident that killed her husband, leaving her to not only grieve and raise their son alone, but to negotiate the bureaucratic thicket of living wills, life insurance, computer passwords and much more. She is the author of the What Matters Most: The Get You Sh*t Together Guide to Wills, Money, Insurance, and Life’s ‘What Ifs’. Listen an...

William Ollinger is a retired nuclear engineer, a genius of frugality, and my father. (Today, April 9, is his 92nd birthday!) Along with my late mother, Dad raised six children on a reliable but modest salary from the local utility. In an attempt to understand better where my attitudes toward money come from, I ask him to tell me about the financial goals and stresses when he was a younger father....

Brendan O’Connell is an American painter who chronicles our contemporary way of living. Called the “Warhol of Walmart” for his series capturing scenes within the retail giant’s stores, Brendan's work hangs in the homes of A-list celebrities, and has been reviewed in The New Yorker, The Atlantic, Cosmopolitan, Time and almost everywhere else art is discussed. Today we cover how he got his start on...

Mike Carano is a 52 year-old photographer, filmmaker, and podcaster. He has worked in comedy for 30 years and knows everyone in the business. He is also dead broke, thanks to years of compulsive spending, IRS debt and underlying mental health issues. He is working hard to get his financial act together, and is making a documentary about death and money, which I’m executive producing. He is my frie...

Ed Roland, lead singer and founder of deca-platinum+ rock band Collective Soul, joins us today to discuss how he got started in a music career and what has kept the band together for over 25 years. With seven #1 rock hits, over ten million albums sold, and a busy touring schedule, Collective Soul is not just a band, but a business that requires drive, grit, and a lot of work to maintain. Ed talks...

New York Times best-selling author, Anna David always wanted to be a writer and never worried about how she’d make a living. This may have been because her family had a lot of money… until they didn’t. But she survived… through the ups and downs of family fortunes. Through addiction and recovery. Through horrific publishing nightmares. And, most remarkably, through Jeff Bezos’ wedding. Today — a h...

Ron Lieber is the "Your Money" columnist for The New York Times and the author of The Opposite of Spoiled: Raising Kids Who Are Grounded, Generous and Smart About Money.  Find out more about Paul Ollinger on his website and/or follow him on the socials: • Twitter:  http://Twitter.com/Paul_Ollinger Instagram:  https://www.instagram.com/paul_ollinger/ Facebook:  https://www.facebook.com/PaulOllinger...

Turney Duff was making millions on Wall Street until cocaine addiction brought him to his knees. His book The Buy Side: A Wall Street Trader’s Tale of Spectacular Excess is a funny, horrifying, then hopeful read and a New York Times best-seller (you should buy it here).  Paul and the esteemed author share a lot of laughs as they discuss what money meant to Turney as he got rich, got lost, got sobe...

Dr. Drew offers candid insight into the ups and downs of a career in broadcasting and medicine. From Loveline to Celebrity Rehab, Dr. Drew has been a staple on radio and cable television for over 30 years, but that doesn’t mean he’s rich — he’s got triplets to get through graduate school, after all. But he is definitely conversant on almost any topic you throw at him, including opera, coffee and U...

Jessica Mah is a 28 year-old entrepreneur, hecto-millionaire, and CEO/Co-founder of Indinero ( https://www.indinero.com/ ), a tax software tool for businesses. In the very first episode of Crazy Money, Jessica tells Paul about life inside the rocket ship of a start-up and inside the jet she flies for fun on the weekends. Find out why this commercial-rated pilot and mega-successful internet executi...