Money and the Meaning of Life
Crazy Money with Paul Ollinger
How to Live a Stress-free Financial Life with Jared Dillian
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How to Live a Stress-free Financial Life with Jared Dillian

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:

🔥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. 

Discussion about this podcast

Money and the Meaning of Life
Crazy Money with Paul Ollinger
Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surrounding money, ultimately asking: what are the ways in which it can (and can’t) bring us happiness? Crazy Money won’t make you rich. But it will definitely make you think (and laugh).