Preparing to Sell | Your Zip Code & Legacy

ON SELLING YOUR BUSINESS: We often find that while business owners know that a large chunk will go to taxes when they sell their business, they don’t often have much clarity beyond that regarding what happens to those funds.

To help you visualize the transaction year, we put together this hypothetical sale.

• On the left is the structure of the incoming income.
• The green bar is the total inflows of the given year.
• From there, you’ll see a sample of the proportions of how the assets were allocated, including taxes, cost of living, savings, and more.

Every business owner’s chart will look different, but we want to highlight two things:

1. In our view, this type of framework may be more helpful for some owners—often those who begin planning several years before an exit—but appropriateness depends on individual facts and objectives.
2. We also believe this is why business owners who are more than 3-5 years away from selling should seriously consider thinking about their business as an asset, not just an income source.

We work with owners daily who undertake the prolonged, meaningful work of preparing their business for sale. We would encourage you to take a thoughtful, proactive approach that makes all the difference before and after signing the papers.

Disclaimer: Illustrative hypothetical example (not an actual client). Figures are estimates based on stated assumptions like sale price, cost basis, transaction structure, residence/state, filing status, applicable tax rates, and timing. Actual proceeds and taxes will vary materially. Not tax/legal/investment advice.

GOT STOCK COMPENSATION? We can help you evaluate planning considerations and coordinate with your tax professional as appropriate. Now that April 15th is behind us, we start planning for next year. A few landmines worth knowing:

• ISOs trigger AMT exposure the moment you exercise and hold—most employees discover this in April, not in time to act.
• The “escape hatch” is real: sell ISO shares in the same calendar year you exercise, and you can sidestep the AMT entirely. But trigger a wash sale? That exit closes.
• RSU and ESPP brokers often report $0 cost basis on 1099-Bs. If you don’t adjust for ordinary income already reported on your W-2, you’ll pay tax on it twice.
• ESPP qualifying dispositions still carry ordinary income on part of the gain—it’s not all long-term capital gain, despite what many assume.

The withholding your employer uses almost never covers your full liability. Tax projections before year-end aren’t optional for serious equity holders—they’re the difference between a plan and a shocking tax surprise.

Know what you hold. Know what it costs.

TODDLERS AND TOYS: The average American toddler has 100+ toys, but only plays with <10% of these toys (source: Epic Kidz, 2025). At the same time, only 15% of American families own a 529 (source: Investment News, 2026). What if every grandparent invested in 529s for their grandkids? Do your grandkids need more toys or a grandparent who models long-term impact and the value of education? If you’d like to discuss education planning and family gifting strategies, we’re happy to share general considerations and explain how we work with clients.

A HISTORIC LOW: The S&P 500 dividend yield hit an all-time low of 1.08% last week, going back to the 1800s.

Source: Multpl

TAXES CAN SHAPE LEGACY: Geography matters more than most families realize. As of October 2025, 17 states still impose an estate tax, an inheritance tax, or both, and the impact on your legacy can be significant. A thoughtful estate plan accounts for where you live, not just what you own. Let’s make sure your wealth reaches the people who matter most.

BEST OF THE INTERNET: Inspiration from a 93-year-old: watch here.

*The views expressed represent the opinions of Compass Ion Advisors, LLC, as of the date noted and are subject to change. These views are not intended as a forecast, a guarantee of future results, an investment recommendation, or an offer to buy or sell any securities. The information provided is of a general nature and should not be construed as investment advice or to provide any investment, tax, financial, or legal advice or service to any person. The information contained has been compiled from sources deemed reliable, yet accuracy is not guaranteed.

Additional information, including management fees and expenses, is provided on our Form ADV Part 2 available upon request or at the SEC’s Investment Adviser Public Disclosure website here. Past performance is not a guarantee of future results.