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:

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.

“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:

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.

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:

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.”

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

Lots of wealthy people own Bitcoin, but very few understand it. What is it? How does it work?

In a world where digital transformation touches every part of our lives, the evolution of money may be the most significant—and the most misunderstood. For families with complex financial lives, the conversation around Bitcoin often begins with skepticism and ends with confusion. But what if it’s time for a different perspective?

In this episode, John Napolitano sits down with Bob Burnett, CEO and Founder of Barefoot Mining, and a leading voice in the Bitcoin space. With a rich background in technology, economics, and a deep respect for the principles of sound money, Bob helps demystify Bitcoin for high-net-worth families who want to understand—not just speculate on—this powerful digital asset.

Together, John and Bob explore:

Listeners will also hear practical guidance on whether to buy Bitcoin directly, use ETFs, or explore custody solutions, as well as a clear explanation of why Bitcoin's value is rooted in more than just hype.

Listen in and come away with a new framework for thinking about Bitcoin—one that could reshape how you view wealth, sovereignty, and security in the digital age.

Bob Burnett is CEO and founder of Barefoot Mining, a Bitcoin Mining company and he is also the founder of Barefoot Bitcoin Fund, a fund focused on Bitcoin and Bitcoin related companies. Bob also serves on the Board of Directors for Ocean, the world’s most decentralized Bitcoin mining pool, and also serves on the Board of Advisors for several Bitcoin organizations including the Satoshi Action Fund, The Epoch Bitcoin Fund, Saz Mining, Resolvr, and Blockspaces. 

Bob is a frequent speaker at Bitcoin events around the world and is the author of a monthly newsletter for Financial Advisor magazine called The Bitcoin Advisor. Bob has spent over 40 years as a technologist including 13 years at Gateway, Inc., a Fortune 200 personal computer company, where he led the company’s product development efforts as Chief Technical Officer and Executive Vice President of Products. He has eight US patents and a BS in Computer Engineering from the University of Wisconsin at Milwaukee.

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

What if the biggest transaction of your life was the one you were least prepared for? For many business owners, the idea of selling their company sits quietly in the background—until it’s suddenly urgent. But the best exits don’t happen by accident. They’re built intentionally, years in advance.

In this episode, John Napolitano sits down with longtime collaborator and financial advisor Alex Weiss to explore how business owners can prepare for an eventual sale—not just financially, but personally and strategically. With over 15 years of shared experience guiding clients through these transitions, John and Alex unpack the often overlooked details that make or break a business exit.

What You’ll Learn in This Episode:

Whether you're thinking about selling a business next year or in the next decade, this conversation will shift how you think about integration, preparation, and what it means to exit on your own terms.

Tune in and discover what it means to approach your business transition with clarity, confidence, and intention.

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.

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

Sometimes, success speaks for itself. You're booked out months in advance, your community can't get enough of what you offer—and then, someone says: “Can I open one of these in my town?” What if that question is more than a compliment? What if it's your next business model?

In this episode of Making Cents, host John Napolitano welcomes Rick Morgin, a seasoned expert from The Franchise Consulting Company, to unpack the powerful potential of franchising as a growth strategy for high-performing small businesses. Whether you’re an entrepreneur exhausted by the day-to-day or a business owner seeking smart scalability, this episode explores how franchising can shift your business from a local passion project to a nationwide presence.

If you've ever felt like your business could be bigger—but you’re not sure how to make that leap—this episode might just be your turning point. Tune in to reimagine what scaling can really look like and walk away with a clearer path to building a legacy beyond your zip code.

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

Confidence is the baseline for any advisor-client relationship, but what most people don’t think about is what happens when the person you’ve trusted for decades steps away.

In this special episode, we’re sharing an interview John Napolitano did with Michael Gordon, founder of Inside Advisor Transitions. Michael asks questions geared at John’s experience as longtime advisor, former CPA, and founder of a multi-generational RIA.

The topic: what it really takes to build a business that doesn’t just serve one generation, but many.

Whether you’re a client wondering how your advisor’s retirement might impact your financial life—or an advisor thinking about how to secure the future of your firm—this conversation offers a rare, behind-the-scenes look at succession done right.

John shares:

It’s a thoughtful conversation about legacy–not just personal legacy, but business legacy. It’s about the vision to build a firm that lasts long after the founder has stepped away.

Listen in to see what a well-planned transition really looks like—for both clients and advisors.

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

Is your business worth what you think it is—or what someone tells you it is?

Whether you're considering a future sale, bringing in a partner, or simply building long-term wealth, understanding the true value of your business is a must—not a maybe.

In this episode of Making Sense, John Napolitano welcomes Bill Clement, Managing Partner at South Coast Financial Partners, for a candid, in-depth conversation on business valuations. 

Together, they unpack why every high-net-worth business owner needs to think beyond the day-to-day and start viewing valuation as a strategic tool—not just a number on paper.

You’ll learn:

Whether you're planning ahead or just getting curious, this episode will help you see your business through a new lens—and make smarter decisions because of it.

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

What is more valuable than money–and easier to steal?

In today’s episode of Making Cents, John Napolitano sits down with cybersecurity expert Mark Hurley to expose the invisible risks lurking in your digital life. A West Point graduate and founder of Digital Privacy and Protection, Mark shares why cybercrime has become a bigger business than the global drug trade—and how high net worth families are increasingly in the crosshairs.

You’ll learn:

Digital threats aren’t going away—but with the right steps, you can stay ahead of them.

Listen in and learn how to lock the front door to your digital life.

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

Are you treating tax planning as a once-a-year headache instead of a year-round wealth-building strategy?

In this episode of Making Cents, host John Napolitano sits down with Bill Clement, Managing Partner of South Coast Financial Partners, to discuss why high net worth families need to integrate tax planning into every aspect of their financial planning. Forget the stereotypical approach of scrambling in April—this conversation dives into the proactive strategies that help you maximize opportunities and minimize surprises.

As you listen, you’ll discover:

This episode will change the way you think about tax planning and how it fits into your long-term financial strategy. Tune in now and start making smarter decisions that keep your wealth working as hard as you do.

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