Welcome back to Making Cents with John P. Napolitano. We’re here to break down the big questions high net worth families face–you know, the ones your “investment guy” never asks about. No Fluff. No finance 101. Just straight talk to help you make smarter decisions and keep your wealth working as hard as you do. Let’s get to it.
Created by the team at Napier Financial – home of the Fully Integrated Financial Planning approach. Napier Financial is a boutique fully integrated wealth manager and multi-family office.
Advisor Representatives at Napier Financial are either 1) Advisor representatives of U.S. Financial Advisors, a registered investment advisor, or 2) Advisor representatives dually registered through U.S. Financial Advisors and Great Valley Advisor Group, registered investment advisors. Financial planning and investment advice is offered through U.S. Financial Advisors and/or Great Valley Advisor Group accordingly.
Information about Great Valley Advisor Group can be found here: https://greatvalleyadvisors.com/whatwedo/
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Welcome back to Making Cents with John P. Napolitano. We’re here to break down the big questions high net worth families face–you know, the ones your “investment guy” never asks about. No Fluff. No finance 101. Just straight talk to help you make smarter decisions and keep your wealth working as hard as you do. Let’s get to it.
Created by the team at Napier Financial – home of the Fully Integrated Financial Planning approach. Napier Financial is a boutique fully integrated wealth manager and multi-family office.
Advisor Representatives at Napier Financial are either 1) Advisor representatives of U.S. Financial Advisors, a registered investment advisor, or 2) Advisor representatives dually registered through U.S. Financial Advisors and Great Valley Advisor Group, registered investment advisors. Financial planning and investment advice is offered through U.S. Financial Advisors and/or Great Valley Advisor Group accordingly.
Information about Great Valley Advisor Group can be found here: https://greatvalleyadvisors.com/whatwedo/
10. Tax Implications of Selling a Business with Nichol Chiarella
Making Cents
25 minutes 40 seconds
4 months ago
10. Tax Implications of Selling a Business with Nichol Chiarella
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/
Making Cents
Welcome back to Making Cents with John P. Napolitano. We’re here to break down the big questions high net worth families face–you know, the ones your “investment guy” never asks about. No Fluff. No finance 101. Just straight talk to help you make smarter decisions and keep your wealth working as hard as you do. Let’s get to it.
Created by the team at Napier Financial – home of the Fully Integrated Financial Planning approach. Napier Financial is a boutique fully integrated wealth manager and multi-family office.
Advisor Representatives at Napier Financial are either 1) Advisor representatives of U.S. Financial Advisors, a registered investment advisor, or 2) Advisor representatives dually registered through U.S. Financial Advisors and Great Valley Advisor Group, registered investment advisors. Financial planning and investment advice is offered through U.S. Financial Advisors and/or Great Valley Advisor Group accordingly.
Information about Great Valley Advisor Group can be found here: https://greatvalleyadvisors.com/whatwedo/
