Join legendary musician Paul Shaffer, famed as David Letterman’s long-time musical director, as he shares his extraordinary career journey—from his childhood in Thunder Bay to iconic roles on Saturday Night Live and The Blues Brothers. Shaffer sits with host Paul Ollinger and reflects on his early love for music, working alongside comedy greats like Martin Short and Bill Murray, and how rock and roll’s raw simplicity shaped his passion. Packed with nostalgic Hollywood and Broadway stories, this conversation is a must-watch for music and comedy fans alike. 🎵🎭

Get Paul Ollinger's book Here: "Reasonably Happy: Essays on Money, Work and Other Things that Piss Me Off" https://www.amazon.com/Reasonably-Hap...

Read Paul's Substack: https://words.paulollinger.com/

Paul sits down to talk happiness with Deepak Chopra who is a world-renowned pioneer in integrative medicine and personal transformation alongside award winning author, professor, writer and speaker Dr, John Kaag.

Visit Rebind at https://s.rebind.ai/0PmPOV and use the promo code reasonablyhappy to get 15% off your first Rebind book experience

Get Paul's book Here: "Reasonably Happy: Essays on Money, Work and Other Things that Piss Me Off" https://www.amazon.com/Reasonably-Happy-Essays-Money-Things/dp/0997270659

Read Paul's Substack: https://words.paulollinger.com/

Paul sits down with comedian and syndicated radio legend Rickey Smiley and talk about happiness in the face of grief after losing a son to opioid addiction, surviving being shot at point blank range and continuing a life in comedy in the face of tragedy.

Check out Rickeys book: "Sideshow: Living with Loss and Moving Forward with Faith"

https://www.amazon.com/Sideshow-Livin...

Paul is joined by SNL music director Eli Brueggemann to discuss everything from what landing a gig like Saturday Night Live does for a musician to how quickly a masters level university degree can become outdated because of simple technology.

Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

Paul sits down with the insanely funny comedian Mandal to discuss his rise, fall and rise again that lead him to be a go to opener for John Mulaney and performing at the world famous Hollywood Bowl. Paul and Mandel dive into the world of stand up comedy and how Mandel finds purpose and happiness and why it is the driving force in all of his artistic endeavors.

Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

Paul sits down with lawyer turned comedian Liz Glazer to discuss how a successful lawyer and law professor can find happiness by saying goodbye to a tenured career by pursuing a life in the arts.

Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

Paul sits down with comedian and actor Mehran Khaghani and gets deep into the psyche of a man who was brought to America from Iran as a 3 year old who discovered himself after years of addiction and psychedelics only to emerge on the other side as one of the funniest comedians working today and starring in the hit Off Broadway Steven Soderbergh show "The Fears".

Join us for an insightful conversation with Adrian Brambila and Brad Klontz, authors of "Start Thinking Rich," as we dive deep into the mindset strategies that lead to success. Discover how your background, no matter the challenges, should never hold you back from achieving your goals. Learn practical tips and valuable lessons on how to develop a wealth-focused mindset, overcome obstacles, and leverage the experiences of others to create the life you've always wanted. Whether you're aiming for personal or financial success, this episode is packed with actionable advice to help you think rich and succeed in any area of life.

Pick up a copy of "Start Thinking Rich: 21 Harsh Truths to Take You from Broke to Financial Freedom" by Adrian Brambila and Brad Klontz:

https://www.barnesandnoble.com/w/start-thinking-rich-brad-klontz/1146212034;jsessionid=9ADBFA21F7779A45F34745CE6E50B715.prodny_store01-atgap15?ean=2940191065052

Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

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 Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

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 Paul Ollinger: https://www.instagram.com/paul_ollinger

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 past middle age. In other words, there’s still hope for you! Maybe you’re 45 and haven’t written the great American Novel yet. There’s still time! You’re 55 and haven’t made your first million or billion? There’s still time! You’re 65 and havne’t gotten elected to political office? Well, let’s not push it, but you never know. If you are indeed an opsimath, you’ll keep working toward your goal for the sake of the thing and not in hope of any extrinsic rewards. In this informative and sometimes humorous conversation, Henry and I—two urbane gentleman that we are—discuss the following:

• Fluid intelligence v. concrete intelligence
• Why motivation is the closest thing we have to magic. 
• How and why to stay in the game as you get older
• The commonalities among late bloomers include hard work, intrinsic motivation and a willingness to keep trying and learning.
• The similarities between Ray Kroc’s relationship with the McDonald brothers and Mark Zuckerberg’s relationship with the Winklevoss twins.
• How Katharine Graham’s family’s suffocating wealth both helped and hindered her development

Pre-order Henry's book here. Subscribe to his Substack here. 

WAIT - don’t go until you’ve done 2 out of these 3 things:

💰Rate and review Crazy Money here. 💰

🔥 Register for Paul’s incredible newsletter here.🔥

🎤 See Paul LIVE for telling of comedy jokes here. 🎤

About Paul Ollinger and Crazy Money

After working as one of Facebook’s first 250 employees, Paul retired from the corporate world at 42, only to find himself bored, lonely, and driving his wife crazy. Today, he’s a standup comic, captivating audiences with his unique blend of humor and insight, performing alongside a diverse group of comedy powerhouses and iconic musicians, including Norm Macdonald, Dave Attell, Chelsea Handler, Styx, and Collective Soul. In 2019, Paul started this podcast, Crazy Money to explore the connection between money, happiness, work, and meaning. In one-on-one conversations with some of the world's most interesting people, he helps uncover the true sources of happiness in life and what wealth, success, and fame can (and can't) do for us. Previous guests include LL COOL J, Judd Apatow, Moby, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic gold medals. Paul is always on tour and coming to a comedy club near you. Check dates here.

This episodes Keywords:

late bloomers, success, age, intelligence, motivation, hard work, meandering path, passion, experience, network, late bloomers, success, reinventing life, Ray Kroc, McDonald's, Katharine Graham, Washington Post, David Duffield, Workday, internal motivation, careers, second careers, reinvention