Why Is Paying Taxes So Complicated? Roth Conversions, Rollovers, & Expensive Mistakes (4/4/2026)

With tax deadlines approaching, we talk about the real-world complexity of Roth conversions—starting with a detailed caller scenario that highlights how confusing the rules can actually be. Brian and Jeremiah walk through how taxes are paid on conversions, when estimated payments are required, and unpack lesser-known strategies like the "withhold and replace" approach and the 60-day rollover rule.

The show also covers a second caller navigating a pension lump sum, breaking down rollover options, how to access funds without unnecessary penalties, and strategies like 72(t) distributions. Along the way, the hosts explain why even simple financial decisions can become complicated when taxes are involved, and why many advisors fall short when it comes to coordinating tax strategy with investment planning.

Financial planning isn't just about what you do—it's about how and when you do it, especially when taxes are involved.

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https://www.therealmoneypros.com

Hosts

Jeremiah Bates & Brian Wiley

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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