The family business is often the crown jewel of a family’s wealth—but succession rarely happens on ideal terms. Whether due to emotional ties, unspoken expectations, or lack of planning, too many successful businesses fail to survive their founders.

In this episode of Making Cents, host John Napolitano sits down with Mark Henry, partner at Citrin Cooperman, one of the nation's top 20 accounting and advisory firms. Mark brings over 25 years of experience helping privately held and family-owned businesses navigate the challenges of leadership transition, succession planning, and long-term sustainability.

Together, they tackle the key issues that high net worth families face when integrating the future of a business into their broader financial lives:

• Why most family businesses don’t survive to the third generation—and what families can do to reverse that trend
• The hidden risks of defaulting to the oldest child or waiting too long to start transition conversations
• The role of communication, governance, and outside advisors in preserving not just enterprise value—but family harmony

You’ll also hear Mark and John discuss how a thoughtful buy-sell agreement, an updated estate plan, and well-defined roles for family members (and non-family executives) can be the difference between generational wealth and generational friction.

Whether you're thinking of passing the torch soon or just beginning to sketch your succession roadmap, this conversation will help you see the business through a longer lens—and prepare your family for the future with clarity and confidence.

Listen in to learn how the right planning today can secure your family’s business and legacy for tomorrow.

• Napier Financial –https://napierfinancial.com
• John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/
• Citrin Cooperman Website - https://www.citrincooperman.com/
• Mark Henry’s LinkedIn - https://www.linkedin.com/in/mark-henry-05759917/

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

“Cost segregation” is not a part of most people’s vocabulary, but if you own real estate, it should be.

In this episode, John Napolitano sits down with Ryan Foley of Cunningham & Associates, a national expert with more than 20 years of experience helping investors and business owners use cost segregation to reduce taxes and free up capital.

This conversation goes beyond accounting theory. It is a practical walkthrough of how to unlock powerful tax advantages inside your real estate holdings—especially when your assets are held in the right structures and backed by proactive planning.

During the conversation, John and Ryan explore:

• What cost segregation actually is, and how breaking down a building into its component parts opens the door to accelerated depreciation and major tax savings
• How your real estate fits into your overall financial plan, from passive activity rules to grouping elections that turn passive losses into powerful tax offsets
• Advanced planning strategies for owners and heirs, including the use of family limited partnerships, 1031 exchanges, and step-up-in-basis opportunities at death

If you’ve ever wondered whether you’re truly optimizing your real estate holdings—or missing out on tools your CPA hasn’t mentioned—this episode will change how you think about depreciation. You’ll come away with a sharper lens on how to use real estate not just to grow wealth, but to retain more of it.

Listen now to rethink how real estate fits into your tax and legacy strategy.

• Napier Financial - https://napierfinancial.com
• John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/
• Cunningham & Associates - https://www.jec-llc.com/
• Ryan Foley’s LinkedIn - https://www.linkedin.com/in/ryan-foley-tax-enthusiast-b33136aa/

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

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.”

• 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/