Good morning, Retirement Starts Today Community. Welcome to "Every Day is Saturday," the newsletter reminding us that in retirement, every day is Saturday (including Thursday mornings).​​​

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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. Click here to listen​

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.

The Emotional Hurdle of Selling Winning Stocks

Selling a stock that has performed well can feel like giving up on a piece of your identity. Peter explains how our emotions, pride, and sense of loyalty to a company or a “winning pick” can prevent us from making sound financial decisions. Whether it’s being the first to buy a trendy stock or inheriting shares from a loved one, these attachments make letting go difficult.

He emphasizes the importance of reframing our perspective. Rather than seeing the sale as losing a part of ourselves, we should view it as a step toward achieving financial independence and securing a stable retirement. Breaking that emotional tie can unlock smarter decisions for the future.

Understanding the Risks of Concentrated Positions

Concentrating too much of your portfolio in one or a few stocks may feel comfortable, but it creates unnecessary risk. Peter highlights statistics showing that most individual stocks underperform the market, and nearly half experience catastrophic declines. Overconfidence in a few positions can expose you to avoidable financial pitfalls.

Diversifying isn’t just about managing risk—it’s about safeguarding your retirement. By spreading your investments across the market, you remove the outsized impact any single stock can have on your future plans. Peter stresses that if a stock’s decline would significantly hurt your financial plan, it’s time to diversify.

Tax-Smart Solutions for Managing Deferred Gains

Deferred gains can create significant tax burdens, but Peter offers solutions to help reduce the hit. From tax-loss harvesting to direct indexing, he explains how these strategies allow you to balance gains with losses, all while keeping your portfolio aligned with your goals.

For those with concentrated positions, more advanced options like exchange funds or a 351 exchange can create instant diversification while deferring taxes. Peter walks through how these approaches can transform a portfolio that feels stuck into one that’s primed for retirement success.

Simplifying Your Portfolio for Retirement Success

A cluttered portfolio can lead to stress and inefficiency as you approach retirement. Peter compares it to cleaning out your closet—letting go of what no longer fits to focus on what works best. Tools like the 351 exchange allow you to consolidate holdings and diversify risk without locking yourself into overly complex strategies.

By simplifying your portfolio, you can focus on what retirement is really about: enjoying your savings and achieving the financial freedom you’ve worked so hard to build. Sometimes, less truly is more.

Resources & People Mentioned

• ​The Retirement Podcast Network​
• Peter Lazaroff’s Book: peterlazaroff.com/freebook​
• Peter Lazaroff’s Website: peterlazaroff.com​
• The Long Term Investor Podcast: thelongterminvestor.com​

Retirement Starts Today (the book) is Available!

My new book, Retirement Starts Today: Your non-financial guide to an even better retirement, is available! To order Click here​

That's it for our three hundred and sixty-forth installment of "Every Day is Saturday." As always, reply to this email with your retirement questions and you might hear them featured on the show! I read and respond to (almost) every email.

Have a great "Saturday",
- Benjamin Brandt (your humble host)

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