The People Who Never Quit with Henry Oliver

Reasonably Happy with 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.

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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