12 - Beyond the Sale Price: Tax Strategies, 1031 & Deal Value

When business owners think about a successful sale, many focus on the purchase price. But sophisticated dealmakers know the real question is what the seller actually retains after taxes, structure, and transition planning.  In this episode of the CVBBA Insights Podcast, host Heather Valeri, CBI, CEPA sits down with Richard B. “Rick” Chess, Counselor at Law, Past President of CVBBA, to discuss practical strategies for preserving wealth in business and real estate transactions. Together, they explore how 1031 exchanges, tax planning, and smart deal structuring can help business owners, brokers, and deal partners think beyond the headline number and focus on true net proceeds. Rick shares insights on when a 1031 exchange may be relevant, how it can create opportunities for reinvestment, and why early coordination between brokers, attorneys, tax professionals, and other advisors is essential. This conversation is especially valuable for business brokers, real estate professionals, deal teams, and business owners who want to better understand the intersection of transaction strategy, taxes, and long-term wealth preservation.  In This Episode, You’ll Learn: What a 1031 exchange is and why it matters in certain transactions How tax strategy can significantly affect a seller’s true net proceeds Why brokers and advisors should think beyond sale price alone Common planning considerations when real estate is involved in a deal The importance of assembling the right professional team early How business owners can make more informed decisions before going to market This episode offers a practical look at how thoughtful planning can help clients protect value, reduce surprises, and create more strategic outcomes at closing and beyond. Subscribe to the CVBBA Insights Podcast on your favorite streaming platform so you never miss an episode. Listen on Apple Listen on Spotify Listen on IHeart Radio If you found this episode helpful, please leave a positive review. It helps us grow the show and reach more professionals across the business brokerage and deal-making community. Interested in Being a Guest? If you are interested in being a guest on the CVBBA Insights Podcast, please contact: Heather Valeri Chair, CVBBA Podcast Committee Learn More About CVBBA Interested in learning more about the Carolinas Virginia Business Brokers Association? Visit: https://www.cvbba.com   Host & Guest Contact Information Heather Valeri, CBI, CEPA CEO, Meridian Business Advisors Vice President, CVBBA |  Board of Governors, IBBA [email protected] https://www.meridianbusinessbrokers.com LinkedIn: https://www.linkedin.com/heathervaleri Richard B. “Rick” Chess Counselor at Law Chess Law Firm, PLC 804-241-9999 [email protected] https://www.chesslawfirm.com