Baobab Bulletin - Issue #12 - A late-June roundup on retirement transitions, stock-sale tax planning, a market chart, fresh reads, and a rental-property checklist.

Baobab Bulletin  •  Issue #12  •  June 2026
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Baobab Wealth

A twice‑monthly roundup from Baobab Wealth & Baobab Wealth Abroad

The Baobab Bulletin

Hi there,

In this episode of Baobab Bulletin, we remain focused on retirement timing, tax-aware income decisions, and the tradeoffs that show up once the planning shifts from saving money to using it well.

We’re also sharing Jimmy’s new video on stock sales and cost basis, a rental-property checklist, and fresh reads on retirement transitions, prediction markets, index mechanics, and legacy planning.

This week’s podcast lineup looks at a dividend detail many index investors miss, whether life insurance belongs in a retirement income plan, and what to think through before leaving money in America when moving back home.

As always, if you’d like to review how any of this applies to your situation, click below to schedule an appointment.

Have a question? Click HERE to schedule a screen share and we'll walk through it together.
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Featured Video
The Tax Mistake Investors Make When Selling Stocks

The Tax Mistake Investors Make When Selling Stocks

Jimmy breaks down one of the most overlooked tax planning opportunities investors have when selling stocks: cost basis management. The video explains why the shares you choose to sell can affect the tax bill and why a little planning before a sale can matter.

Prefer to listen? Explore related retirement tax episodes on the Divorce the IRS podcast.
WATCH THE VIDEO

Podcasts

Divorce the IRS Podcast

Divorce the IRS Podcast


Welcome to Divorce the IRS, the Retirement Income Planning Podcast, built for people who want to pay the least amount of taxes possible and create retirement income that actually lasts. Inspired by Jimmy Miller’s bestselling book Divorce the IRS, this show takes you behind the scenes of the tax rules, retirement strategies, and planning decisions that can quietly determine how much of your money you keep.

Abroad in America Podcast

As a non‑US citizen living and working in the United States, you face many new challenges when it comes to learning and understanding a completely new financial and tax system. The goal of this podcast is to help non‑US citizens and cross‑border families implement effective strategies to take full advantage of the opportunities to create wealth in the United States-both while you're here and even once you've left

Chart of the Week

There are always reasons not to invest

A pandemic, wars, inflation, tariffs, and other shocks can make sitting on the sidelines feel sensible in the moment. The chart above is a useful reminder that markets have faced plenty of frightening headlines before, yet the S&P 500 has historically pushed through turbulence and reached new highs over time.

Short-term risk doesn’t disappear. The bigger planning issue is that long-term decisions usually get harder when today’s uncertainty is allowed to steer every investment choice. Staying committed to a thoughtful plan can help keep temporary fear from becoming a permanent portfolio mistake.

Chart source: Capital Group, Standard & Poor’s. Data indexed to 100 as of January 1, 1987, based on cumulative total returns for the S&P 500 Index. Past results are not predictive of results in future periods.

What We're Reading / Thinking About

The Great Filter - Of Dollars And Data

Are Prediction Markets Good For Anything? - Asterisk

Useful Resources

What Issues Should I Consider When Owning a Rental Property?

Use this checklist to identify planning opportunities, avoid common tax pitfalls, and make sure your rental property supports your overall financial and retirement strategy.
DOWNLOAD THE GUIDE

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