Mar 26, 2026
If you’re in or near retirement, one bad investment decision can have lasting consequences.
And new research shows just how risky stock picking can be:
Over the last 100 years, nearly 60% of all U.S. stocks underperformed Treasury bills—one of the safest investments you can own.
Even more surprising, fewer than 4%...
Mar 19, 2026
Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions.
But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes.
In this episode, I'm simplifying the Roth conversion...
Mar 12, 2026
📝 Note: The 6.5% withdrawal rate is based on an 80% stock portfolio, a 30-year time horizon, and a 90% "confidence score." Thanks for your patience while we update the episode to include that information. ~Taylor
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Most people spend far less in retirement than they likely could.
In fact, one study found married...
Mar 5, 2026
Health insurance is keeping millions of Americans stuck in jobs they’d otherwise leave.
In fact, 1 in 5 workers ages 50–64 say they’re staying put because of their employer health coverage.
And with recent changes to the ACA, that pressure is only growing.
In this episode, I cover:
→ Why healthcare before...