Reasonably Happy with Paul Ollinger

How to Live a Stress-free Financial Life with Jared Dillian


Listen Later

Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks they’re wrong. Focusing on the little things, Jared argues, is pointless and unsustainable. But focusing on the big things, like your house, your car, and how much you pay for college, makes all the difference. A renowned investment strategist and author, Jared is widely recognized for his keen insights into market psychology and his ability to explain complex financial concepts in an accessible manner. He is also the author of the acclaimed book 'Street Freak: Money and Madness at Lehman Brothers' and the editor of the popular financial newsletter 'The Daily Dirtnap', where he shares his valuable perspective on the markets. Pre-order his new book, ’No Worries: How to Live a Stress-Free Financial Life’ here. On this week’s episode, we discuss:


  • Striking the balance between being a cheap f*ck and a high roller.
  • Why renting is often a much better idea than buying a home.
  • How much student debt is okay.
  • The five asset classes you should own in “The Awesome Portfolio"

  • Jared also graciously shares insights into his bipolar disorder and the side effects of the meds he takes. In so doing, he continues to help de-stigmatize mental illness. And for that, I thank him.


    See Paul live in comedy mode:

    • Austin, Jan 11 - Buy Tickets Here
    • San Francisco, Feb 22 -  Buy Tickets Here
    • Nashville, Feb 28 - Buy Tickets Here 

    • 🔥Learn and laugh by reading Paul’s Substack here. 🔥

      🚀 Follow Paul on Instagram here. 🚀


      DISCLAIMER: This episode contains a discussion of investment strategies and theories but in no way should be considered personal financial advice. Investing in any of the asset classes mentioned can result in material losses. 

      ...more
      View all episodesView all episodes
      Download on the App Store

      Reasonably Happy with Paul OllingerBy Paul Ollinger

      • 4.8
      • 4.8
      • 4.8
      • 4.8
      • 4.8

      4.8

      437 ratings


      More shows like Reasonably Happy with Paul Ollinger

      View all
      Afford Anything by Paula Pant | Cumulus Podcast Network

      Afford Anything

      3,549 Listeners

      Money Guy Show by Brian Preston and Bo Hanson

      Money Guy Show

      3,219 Listeners

      The Stacking Benjamins Show by StackingBenjamins.com | Cumulus Podcast Network

      The Stacking Benjamins Show

      1,978 Listeners

      Financial Independence Podcast by The Mad Fientist

      Financial Independence Podcast

      1,657 Listeners

      ChooseFI by ChooseFI

      ChooseFI

      5,138 Listeners

      BiggerPockets Money Podcast by BiggerPockets

      BiggerPockets Money Podcast

      3,082 Listeners

      How to Money by iHeartPodcasts

      How to Money

      3,164 Listeners

      Bogleheads On Investing Podcast by bogleheads

      Bogleheads On Investing Podcast

      625 Listeners

      Earn & Invest by Jordan Grumet (Doc G)

      Earn & Invest

      453 Listeners

      The Long View by Morningstar

      The Long View

      919 Listeners

      All the Hacks: Money, Points & Life by Chris Hutchins

      All the Hacks: Money, Points & Life

      1,611 Listeners

      Mile High FI Podcast by Doug Cunnington & Carl Jensen

      Mile High FI Podcast

      202 Listeners

      Money For Couples with Ramit Sethi by Ramit Sethi

      Money For Couples with Ramit Sethi

      3,430 Listeners

      Retire With Style by Wade Pfau & Alex Murguia

      Retire With Style

      184 Listeners

      Catching Up to FI by Bill Yount & Jackie Cummings Koski

      Catching Up to FI

      357 Listeners