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What if you could turn those green numbers in your investment account into retirement income while paying as little in taxes as possible? That’s exactly what we’re covering today with Peter Lazaroff, Chief Investment Officer at PlanCorp. We’re tackling the challenge many of us face: managing deferred gains in our portfolios and figuring out the smartest ways to reduce the tax hit as we transition to retirement.

Peter and I talk through a range of strategies for handling concentrated stock positions, whether it’s selling off winners gradually, taking advantage of tax-loss harvesting, or exploring more advanced options like exchange funds or a 351 exchange. These aren’t just dry financial concepts—they’re real, actionable ideas that can help you simplify your portfolio and make the most of what you’ve saved. And trust me, simplifying your financial “closet” can feel like a huge weight lifted.

We also talk about the emotional side of investing. Why does it feel so hard to part with stocks that have been good to us? Whether it’s an attachment to the company or pride in your early picks, Peter shares why these feelings matter and how to move past them to make decisions that better serve your long-term goals. Stick around—you won’t want to miss the insights he has to share. 

Outline of This Episode

• (0:20) Peter Lazaroff’s Options for Reducing Taxes on Deferred Gains Pre-Retirement
• (01:46) Why retirees need to manage large brokerage gains.
• (03:10) The emotional challenge of selling winning stocks.
• (05:20) Risks of concentrated stock positions and diversification.
• (09:00) Tax-loss harvesting and direct indexing strategies.
• (14:30) Simplifying portfolios with the 351 exchange.
• (18:40) Portfolio simplicity and enjoying retirement income.

Resources & People Mentioned

• The Retirement Podcast Network
• Peter Lazaroff’s Book: "Making Money Simple" – www.peterlazaroff.com/freebook
• Peter Lazaroff’s Website – peterlazaroff.com
• The Long Term Investor Podcast – thelongterminvestor.com

Connect with Peter Lazaroff

• Peter's website

Connect with Benjamin Brandt

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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