Should Have Yielded

Don and Tom revisit their long-standing skepticism of Yieldstreet after CNBC’s investigation reveals major investor losses. They highlight how promises of high returns and low risk almost always end in disaster, connecting this lesson back to their 2022 warnings. The episode underscores the dangers of “magical” investments, the myth of passive income, and why retirement accounts should avoid private assets. Listener questions focus on Roth vs. pre-tax strategy, bracket management, and conversion rules—showing the complexity of tax planning when wealth accumulates.

0:04 Why “too good to be true” investments always fail eventually

1:08 Yieldstreet problems exposed—CNBC investigation findings

2:26 Losses and watch-list numbers from their portfolio

3:48 Investors chasing 20% returns and Adam Neumann connection

5:01 Private investments pitched as “smoother sailing”

6:14 Throwback to 2022 TRM episode warning about Yieldstreet

7:38 False promises of 8% “distributions” and return of capital

9:10 FBI and SEC probes; fees, liquidity issues, and risks

10:33 Why magical investments work… until they don’t

12:22 Don’s “Financial Fysics” rule: only 3 ways to make money

14:24 Private credit in 401(k)s—why Don hates the idea

15:36 Listener Q: Roth conversion strategy before retirement

17:17 Five-year rule confusion and conversion clarifications

18:52 Why splitting Roth and pre-tax can make sense

20:09 Listener Q: Roth vs. pre-tax for high earners in California

22:08 The need for predictive tax planning with large balances

22:26 Wealth requires planning, not winging it

24:12 Wrapping up—Yieldstreet’s lesson and Roth themes
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