All Episodes

December 2, 2025 51 mins

McDreamy Dempsey wants to know if converting to Roth in the 37% tax bracket ever makes sense, and Gary in La Crosse warns Joe Anderson, CFP® and Big Al Clopine, CPA about Roth conversion "lag" and when it DOESN'T make sense to convert, today on Your Money, Your Wealth® podcast 558. Plus, Wine Guy and Gal in Northern California want a spitball on whether they should protect their ACA subsidies or keep converting to Roth before Medicare kicks in. Then it's the classic question for Robert in Napa, Luke and Lorelai in Indiana, and Phil and Claire in California: should they save for retirement in their traditional, pre-tax, tax-deferred accounts, or their post-tax, tax-free Roth accounts? Different needs and situations, same big question: which strategy gives you the smarter tax outcome?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-558 (full show notes & episode transcript)

Top 10 Tax Tips Guide - limited time special offer, download yours before Friday, Dec 5, 2025!

Ultimate Guide to Roth IRAs - free download

2025 Key Financial Data Guide - free download

10 Tax-Cutting Moves to Make Now - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

 

Connect With Us:

YouTube: Subscribe and join the conversation in the comments

Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

 

Chapters:

00:00 - Intro: This week on the YMYW Podcast

00:57 - Should High Earners Do Roth Conversions in the 37 Percent Bracket? (McDreamy Dempsey)

06:50 - The Hidden Roth Conversion Lag: When Conversions Don't Actually Pay Off (Gary, LaCrosse, WI)

18:03 - Should You Prioritize the ACA Subsidy Cliff or Roth Conversions Before Medicare? (Wine Guy & Gal, No CA)

26:27 - Traditional vs Roth Contributions:

Mark as Played

Advertise With Us

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

The Bobby Bones Show

The Bobby Bones Show

Listen to 'The Bobby Bones Show' by downloading the daily full replay.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.