Making Cents

10. Tax Implications of Selling a Business with Nichol Chiarella

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In this episode, John Napolitano is joined by Nichol Chiarella, head of the Mergers & Acquisitions Tax Practice at Citrin Cooperman. With extensive experience advising lower middle market companies and their owners, Nichol helps us unpack what really matters when it comes to planning the tax side of a business sale. Spoiler alert: it starts much earlier than most sellers think.

Together, they explore:

  • Why waiting too long to engage the right advisors can cost millions, and how strategic tax planning can make or break your exit
  • Common mistakes business owners make, from misunderstanding qualified small business stock (QSBS) to forgetting how buyer preferences impact deal structure
  • What sellers can do in the year or two before a transaction to maximize after-tax proceeds and avoid IRS red flags

    • From state tax exposure to phantom stock plans gone wrong, this conversation is a must-listen for any entrepreneur considering a sale in the next few years. Learn what questions to ask now—before a letter of intent lands on your desk—and how a well-structured exit can preserve far more than just enterprise value.

    Tune in to sharpen your approach and walk away with clarity that could protect years of hard-earned equity.

    About Nichol – “I’m a self-proclaimed M&A tax nerd who could happily talk tax all day—just ask anyone who’s tried to leave a dinner party early.”

    Key Links
    • Napier Financial - https://napierfinancial.com
    • John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/ 
    • Citrin Cooperman - https://www.citrincooperman.com 
    • Nichol Chiarella’s LinkedIn - https://www.linkedin.com/in/nichol-chiarella-7898aa1a/ 

      • Podcast produced and distributed by Evergreen Financial Marketing https://www.evergreenfm.com/

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      Making CentsBy Napier Financial