meta_pixel
Tapesearch Logo
Log in
Talking Real Money - Investing Talk

Should Have Yielded

Talking Real Money - Investing Talk

Don McDonald

Education, Investing, Business, How To

4.5 • 811 Ratings

🗓️ 25 August 2025

⏱️ 27 minutes

🧾️ Download transcript

Summary

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0

Reality Radio for a really great future.

0:08.0

We're talking real money.

0:10.2

Here's the problem with not being prescient, with not having any truly predictive powers,

0:19.4

not being able to tell you the future. Here's the problem. And we've mentioned

0:23.8

this over and over again, but it bears repeating, particularly given a recent story. And that is,

0:30.0

we can tell you that we believe there's something wrong with an investment that sounds too good to be true.

0:39.3

And yet, we can't tell you exactly what that bad thing will be, what that negative that

0:48.0

will impact these amazing investments in the future will be. But we're pretty sure that

0:54.1

whenever somebody promises you

0:55.9

high yields and low risk, that there will eventually be a catch. Well, I hate to say we told you

1:06.4

so, but we told you so, Yield Street, which was very popular.

1:13.2

A lot of you called about it.

1:15.3

They were promising high returns, low risk.

1:19.2

Well, they are having problems.

1:22.5

Yeah.

1:23.3

And to get to Yield Street, by the way,

1:25.7

I looked this up on Google Maps.

1:27.2

You start on Assets Avenue.

1:29.4

Uh-huh.

1:29.9

And then you make a left turn on BS Boulevard.

1:32.8

Ah.

1:33.7

And you end up right there at Yield Street.

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Don McDonald, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Don McDonald and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.