3-20-26 Tax Strategies That Actually Save You Money

Most people think about taxes once a year. Smart investors think about them every year. Richard Rosso & Sarah Buenger break down the critical difference between tax preparation and true tax planning, and why that distinction could be worth thousands of dollars to your portfolio over time. We'll walk through real-world anonymous case studies from our client work, including how we helped one client sell nearly half of a concentrated stock position while staying entirely within the 0% capital gains bracket. We also cover Roth conversion timing, IRMAA bracket management, tax-efficient withdrawal sequencing, portfolio migration strategies, and proactive planning for stock options and restricted stock. Whether you are accumulating wealth or drawing it down, understanding how these levers work together is what separates a good financial plan from a great one. Hosted by RIA Advisors Director of Financial Planning, Richard Rosso, CFP, w Senior Investment Advisor, Sarah Buenger, CFP Produced by Brent Clanton, Executive Producer 0:00 - INTRO 0:19 - Gilligan's Island & Taxes 2:27 - Market Commentary & Sentiment Survey 3:11 - The Fine Line Between Tax Prep vs Tax Planning 8:35 - Impact of OBBB & Rothification 10:17 - Avoid Tax Myopia 12:07 - Dealing with the Tax Torpedo 12:31 - Being Tax Flexible 14:11 - Your Tax Return is a Diagnostic Tool 17:16 - Widowed Survivors Paying Higher Taxes - Taxes are Barnacles 20:13 - The Tax System is Broken 23:07 - Stock Concentrations & Long Term Gains 25:13 - Trust Distributions & Capital Gains 26:40 Tax Brackets for Trusts 28:01 - Myriad Capital Gains Tax Rates 34:06 - Becoming IRMAA-centric 36:46 - Asset Location Strategies for Taxes 38:38 - The Mistake of "Silo-ing" Tax Advisors and Financial Advisors 41:15 - Why Avoid Gains to Avoid Taxes?? 42:58 - Why Not Take Losses Each Year? ------- Register for our next Candid Coffee, 3/21/26, and Ask Us Anything: https://realinvestmentadvice.com/resources/events/ask-us-anything/ ------- Do you enjoy our content? Rate us on Google: https://bit.ly/4b9JtEo ------- Watch Today's Full Video on our YouTube Channel: https://youtube.com/live/IvotNMC_fgk ------- Watch our previous show, "Will The Fed Backstop Exuberance Again?," https://youtube.com/live/IbKkqWayKu8 ------- Articles Mentioned in Today's Show: "Private Credit Stress: Will The Fed Backstop Exuberance Again?" https://realinvestmentadvice.com/resources/blog/private-credit-stress-will-the-fed-backstop-excuberance-again/ "USD Stable Coins And The Rebasement Of The US Dollar" https://realinvestmentadvice.com/resources/blog/usd-stable-coins-and-the-rebasement-of-the-us-dollar/ -------- The latest installment of our new feature, Before the Bell, "Markets Flail as Rate Cut Hopes Fail" is here: https://youtu.be/IOumOUnLKpM ------- Download Lance's Latest e-book, "Laws of Money & Wealth:"https://realinvestmentadvice.com/ria-e-guide-library/ -------- SUBSCRIBE to The Real Investment Show here: http://www.youtube.com/c/TheRealInvestmentShow -------- Visit our Site: https://www.realinvestmentadvice.com Contact Us: 1-855-RIA-PLAN -------- Subscribe to SimpleVisor: https://www.simplevisor.com/register-new -------- Connect with us on social: https://twitter.com/RealInvAdvice https://twitter.com/LanceRoberts https://www.facebook.com/RealInvestmentAdvice/ https://www.linkedin.com/in/realinvestmentadvice/ #TaxPlanning #WealthManagement #RetirementStrategy #CapitalGains #RothConversion