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. 

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.