Are we actively watching the rise of the degenerate economy? What does it mean for our entrepreneurial behaviors? What does it mean for our portfolios? Does gambling your way to wealth make sense? And what types of trends will emerge and strengthen in 2026?

Smart things look stupid for a while until they look smart. Dan and Jeff share their thoughts on the recent viral X article “The Prison of Financial Mediocrity” and their views on the “socially acceptable” risk of entrepreneurship as an escape from the 9-5.

LINKS

Bento will beat your current email bill — up to 70% off or $300 in credits
“The Prison of Financial Mediocrity” Full Article
The End of Jobs by Taylor Pearson (Dynamite Circle member!)
The Psychology of Money by Morgan Housel
Same As Ever by Morgan Housel
The Courage to Be Disliked by Ichiro Kishimi et al
Meet lifestyle founders inside Dynamite Circle
Hang out exclusively with 7+ figure founders in DC BLACK

CHAPTERS

(00:00:52) The Traditional Path is Closed
(00:06:00) The Era of Long Degeneracy & Success Via Risk
(00:10:49) Opportunity When the Game is Rigged Against You
(00:20:27) The Socially Acceptable Lottery Ticket
(00:25:47) Financial Nihilism and Betting on Change

CONNECT:

Dan@tropicalmba.com
Ian@tropicalmba.com

Past guests on TMBA include Cal Newport, David Heinemeier Hannson, Seth Godin, Ricardo Semler, Noah Kagan, Rob Walling, Jay Clouse, Einar Vollset, Sam Dogan, Gino Wickam, James Clear, Jodie Cook, Mark Webster, Steph Smith, Taylor Pearson, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.

PLAYLIST:

How to Actually Build Systems in Your Small Business ft. Layla Pomper
“The World Is Ending.” These 5 Businesses Are Still Making Millions
Why $120K From Your Biz Beats $150K at a Job