Pay ZERO Capital Gains Tax vs Roth Conversions in Retirement: How to Determine Which is Best

Listener Drew asks about a tax strategy for juggling capital gains and Roth conversions. While it can be a complicated question – especially when large accounts are involved – James provides some general guidelines that can be helpful for anyone with similar gnarly tax strategy challenges in retirement. In this episode, we’ll cover the extent to which required distributions will be an issue, what you need to alleviate that issue, and the timeframe within which you have to do that. James explains how to work backward to project your various tax brackets and determine how to prioritize tax gain harvesting, Roth conversions, and other tax strategies. Questions Answered: What is tax gain harvesting? What is the tax planning window and how do I use it to my advantage? ======================= Learn the tips & strategies to get the most out of life with your money. Get started today → https://www.rootfinancialpartners.com/ Get access to the retirement software I use in this video and more → https://retirement-planning-academy.m... 🔔 Make sure to subscribe here to be notified for future videos!    / @rootfp   _ _ 👥 Make sure to connect with us on all socials below → https://beacons.ai/rootfinancialpartners ⏱Timestamps:⏱ 0:00 - Drew’s question 2:50 - Determine use for each asset 5:59 - Tax gain harvesting 11:10 - Back to Drew 15:30 - James’ priorities for Drew 18:41 - Usually not either/or 20:07 - Working backwards 24:50 - General principles 29:50 - Tax planning window 32:16 - Summary Other videos we think you'll like: About Root:    • Financial advisors with heart.   Worried about retirement? Start here:    • Worried About Retirement..Start With a Bla...   -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements. Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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What's the Right Roth Conversion Amount to Avoid a Tax Nightmare in the Future?

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Retirement Income Strategies: IRA vs. Brokerage Withdrawals (The Tax-Smart Choice for Retirees)

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$2M IRA—Why I'm NOT Converting to Roth (Even If You Were Told You Should)

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How to Avoid and Defer Capital Gains Tax

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I Have $4M in my 401(k). Here's My Tax Bill (and How I Avoid It)

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When a Roth Conversion Makes NO Sense (And Why It Depends)

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Why Converting Your Entire IRA to Roth Might be Genius

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How to Prepare for Retirement Within 5 Years: 401k, Savings & Investment Changes

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The 4% Rule Is Just a Worst-Case Scenario - Here’s a Smarter Way to Withdraw in Retirement

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Should You Do A Mega Roth Conversion? (FQF)

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IRA Tax Planning Strategies After OBBBA '25 and SECURE Acts with Ed Slott

If You Have $1M+ In Pre-Tax, Once You Retire, DO THIS…
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If You Have $1M+ In Pre-Tax, Once You Retire, DO THIS…

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RMDs Aren't as Scary as You Think — But Ignoring Them Will Cost You

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Fixing 10 Common Roth Conversion Misconceptions (Costly Errors)

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The Right Way To Do A Roth Conversion (Most Advice is Wrong)

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401k vs Roth IRA — THE REAL MATH (Which One Will Make You More Money?)