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.
Key Links
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.
Key Links
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.”
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/

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:
Why Bitcoin isn’t just a volatile asset class but a redefinition of money itself
How Bitcoin acts as a store of value and a borderless, bearer-based system outside of traditional banks
What it means to separate money from state control, and why that matters more today than ever
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.
About Bob Burnett
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.
Key Links
Making Cents Podcast - https://www.makingcentspod.com/ 
Napier Financial - https://napierfinancial.com/
John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/
Barefoot Mining - https://www.barefootmining.com/our-team
Bob Burnett’s LinkedIn - https://www.linkedin.com/in/bob-burnett-995960108/ 
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:
When the clock really starts: Why planning your exit should begin 3–5 years before a sale, and how to use that time to clean up financials, set post-sale goals, and align your team.
The power of forecasting and valuation: How to model your life after the sale, determine what you need from your business, and identify the gaps between where you are and where you need to be.
Building the right transaction team: From accountants and attorneys to brokers and bankers, discover how to evaluate your current advisors and assemble a team that’s capable of executing a high-stakes transition.
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.
Key Links
Making Cents Podcast - https://www.makingcentspod.com/ 
Napier Financial - https://napierfinancial.com/
John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/ 
Alex Weiss’ LinkedIn - https://www.linkedin.com/in/alexanderweiss/ 
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.
What You’ll Hear in This Episode:
The Franchise Roadmap: Rick breaks down the entire franchising journey—from building legal infrastructure and training systems to national marketing and support networks. Hear how Franchise Genesis, a sister company of The Franchise Consulting Company, equips founders to franchise efficiently and effectively.
From Surprising to Successful: You'll hear about remarkable franchise stories like an art studio born in a garage in Hawaii and a pet crematorium with 500 walk-ins a week. These examples will open your eyes to what’s possible—even if your business doesn’t seem like the “typical” franchise.
What Makes a Business Franchisable: Not every owner is ready to scale—and that’s okay. Rick shares the mindset, structure, and operational indicators that separate businesses that are ripe for replication from those that need more time in the oven.
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.
Key Links
Napier Financial - https://napierfinancial.com
John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/ 
Rick Morgin’s LinkedIn - https://www.linkedin.com/in/richardmorgin/ 
The Franchise Consulting Company - www.thefranchiseconsultingcompany.com
Franchise Genesis - www.franchisegenesis.com
The Great American Franchise Expo - www.franexpousa.com
Franchise Journal Magazine - www.franchisejournal.com
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:
Why great succession planning starts years before an advisor retires
How he developed a team of next-generation advisors who carry on his values and client relationships
The decision-making process behind keeping the business independent vs. selling to a larger firm
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.
Key Links
Napier Financial – https://napierfinancial.com/
John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/ 
Michael Gordon’s LinkedIn - https://www.linkedin.com/in/knowyourfirm/ 
Michael Gordon’s Website - https://www.themichaelgordon.com/ 
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:
Why knowing your business’s value matters well before you’re ready to sell—or even think about it
How equity compensation plans work, and why they’re a powerful lever for attracting talent when cash is tight
The difference between strategic and financial buyers—and how that difference can significantly impact your sale price
How to align your valuation with your long-term goals and avoid common mistakes that could cost you down the line
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.
Key Links
Napier Financial – https://napierfinancial.com
John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/ 
Bill Clement’s LinkedIn - https://www.linkedin.com/in/billclementcpa/ 
South Coast Financial Partners - https://southcoastfp.com/about-us/ 
Podcast produced and distributed by Evergreen Financial Marketing https://www.evergreenfm.com/