You Can’t Beat ’Em

Don and Tom tackle the blurry line between free speech and market manipulation after the conviction of prominent short seller Andrew Left. They debate whether financial influencers should be allowed to profit from public stock recommendations, discuss why members of Congress continue trading individual stocks despite widespread public opposition, and explain why ordinary investors should avoid trying to outsmart people with superior information or influence.

The conversation then shifts into listener questions covering Roth employer matches, Roth IRA withdrawal rules, Roth conversion strategies for retirees, and whether paying taxes now simply to benefit heirs makes financial sense. Along the way, there’s plenty of lighthearted banter about soccer, politics, podcast reviews, and Don’s growing passion for his Litreading short story podcast.

00:05 – Introduction and Independence Day reflections
01:27 – Andrew Left convicted of stock market manipulation
03:24 – Is market manipulation protected free speech?
06:56 – Why Don opposes congressional stock trading
09:18 – Congress made over 13,000 stock trades in 2025
12:29 – Why public officials should be held to a higher standard
14:12 – The lesson for ordinary investors: you can’t beat insiders
15:27 – Podcast reviews, politics, and avoiding crypto
17:12 – Florida’s proposed property tax amendment
18:22 – Transition to listener questions
19:38 – Employer Roth 401(k) matching contributions
20:10 – Can you withdraw Roth IRA money before age 59½?
21:49 – Should retirees convert large IRAs to Roth accounts?
24:52 – Soccer, World Cup talk, and the “laws” of the game
26:44 – Don promotes Litreading and Short Storyverses

Questions? Comments? Click!