Should You Sell Your Business to Retire?

Published On: February 26, 2026

Selling a business is one of the biggest financial decisions you’ll ever make. It’s not just about finding a buyer, it’s about structuring the deal correctly, minimizing taxes, and making sure the sale supports your next chapter of life. John coaches us through major considerations business owners need to think about before signing anything. A business sale can create tremendous opportunity, but only if it’s handled with intention and strategy.

Here’s some of what we discuss in this episode:

📊 Installment Strategies — Spreading payments to manage tax impact

📈 Investing the Proceeds — Turning a payout into sustainable income

🏠 Income & Lifestyle Planning — Covering expenses and Social Security timing

🤝 Using a Broker — Fees, incentives, and when guidance makes sense

📚 Final Takeaways — Key reminders before signing the deal

Go Inside the Episode:

0:00 – Intro

1:29 – Listener Question: Selling a Business

3:18 – Asset vs. Stock Sale

5:01 – Installment Sales and Tax Planning

7:21 – Living Expenses and Social Security

10:58 – The #1 Piece of Advice / Start Slowly

15:22 – Benefits of a Business Broker

Resources:

Get in touch with us: https://mearsmoney.com/

Watch the Podcast on YouTube: https://bit.ly/3PmcOPM

Check out John’s FREE Books: https://je9gekmc.pages.infusionsoft.net/

Advisory services offered through Mears Money Management, Inc., an RIA registered in the states of California and Texas. CA Dept of Insurance License #0685203. Mears Money Mangement Inc is an investment advisory firm managing $27,809,479.00 (December 2023) for families nationwide. We provide prudent investment solutions firmly grounded in Nobel Prize-Winning academic principles, global diversification, and life-long investing. This is not an offer of sale of securities. All investing involves risk, and particular investment outcomes are not guaranteed. This website is for informational purposes only and does not constitute an offer to sell, a solicitation to buy, or a recommendation for any security, or an offer to provide advisory or other services by Mears Money Management Inc. in any jurisdiction in which such offer, solicitation, purchase or sale would be unlawful under the securities laws of such jurisdiction. The information contained on this website should not be construed as financial or investment advice on any subject matter.

Past performance is no guarantee of future results. All investing involves risks and costs and clients may experience a loss. Your advisor/coach can provide you with more information about the risks and costs associated with specific programs/investments. Information presented on this website is believed to be factual and up-to-date, but we do not guarantee its accuracy and it should not be regarded as a complete analysis of the subjects discussed. Discussions and answers to questions contained on the resources published do not involve the rendering of personalized investment advice, but are limited to the dissemination of general information and may not be suitable for members of the listening audience. These resources are based on the views of Mears Money Management, Inc. Other persons may analyze investments and approach investing from a different perspective from that reflected in this video. Nothing included herein is intended to infer that the approach to investing espoused in this video will assure any particular results. Actual results of accounts/assets under Mears Money Management Inc management may differ materially from results shown herein because of differences in the account inception dates, account restrictions and asset acquisition dates. Also, it is not possible for any account performance to precisely match an index since indexes are unmanaged and investors cannot invest directly in any index.

© 2026 Mears Money Management, Inc.