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/

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: The surprising ways cybercriminals gain access to your wealth and identity—from your home network to that “harmless” email link Why your password habits and Wi-Fi choices may be leaving the door wide open Three essential steps every family should take to protect their digital footprint 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. Key Links Special Session: https://www.dpripro.com/napier  Napier Financial - https://napierfinancial.com John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/  Digital Privacy Protection - https://www.dpripro.com/home 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: Key items to focus on throughout the year How strategic Roth conversions look different for wealth preservation The key considerations when gifting business shares, discounting valuations, and planning for the next generation The real facts about changing your state domicile to reduce tax burdens 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. Key Soundbites Highlight 1 Highlight 2 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/

When it comes to buying property, most people think it’s as simple as securing a mortgage, signing paperwork, and getting the keys. But high-net-worth families need a more strategic approach—one that integrates real estate into their overall financial plan. Are your advisors making sure you're covered or are they asleep at the switch? In this episode of Making Cents, host John Napolitano CFP®, CPA, PFS, MST sits down with Alex Weiss CFP®, President of Napier Financial, to uncover the crucial but often overlooked aspects of real estate planning. From how you title a property to creating alignment between your financial, tax, and legal considerations, they break down what it means to actually looks like to integrate real estate into your wealth strategy. Here’s what you’ll take away from this episode: Why proper ownership matters and how placing a property in the right trust or entity can protect you and your family. How to help a child buy a home without unintended consequences and why co-signing a loan might not be the best move. The hidden risks of vacation homes and investment properties and how to structure ownership to avoid financial and legal pitfalls. For high-net-worth families, the stakes are higher for real estate. Too often, real estate transactions happen without a second thought to the long-term impact on wealth preservation. This episode will help you rethink your approach and make smarter, more strategic decisions for your financial future. Listen now to make sure every real estate move you make is working as hard as you do. Key Links Making Cents Podcast – https://www.makingcentspod.com/  Napier Financial –https://napierfinancial.com/ John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/  Thomas Schulte’s LinkedIn - https://www.linkedin.com/in/twschulte/ 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/

Are you really getting the financial advice you need—or just what your advisor is “allowed” to talk about? In this episode of Making Cents, host John Napolitano sits down with Thomas Schulte CFP®, Director of Financial Planning at Napier Financial, to uncover the awkward truth behind what most financial advisors won’t tell you. Let’s dive deep into fully integrated financial planning—what it really means, why most advisors don’t do it, and how high-net-worth families can ensure every facet of their wealth is working in sync. Here’s what you’ll take away from this episode: The myth of “We do better when you do better” – Why most advisors focus only on managing assets and ignore the bigger financial picture. Why business owners need integrated planning – A real-world example of a 40-year-old entrepreneur looking to buy her company’s building and the key financial decisions that come with it. The missing piece in your financial team – How accountants, attorneys, and investment advisors fail to communicate, leaving major gaps in your wealth strategy. If you think your financial team is handling everything, this episode might make you think twice. Tune in to learn how to take control of your financial future with a truly integrated approach. Key Links Making Cents Podcast – https://www.makingcentspod.com/  Napier Financial – https://napierfinancial.com/  John Napolitano’s LinkedIn - https://www.linkedin.com/in/johnpnapolitano/  Thomas Schulte’s LinkedIn - https://www.linkedin.com/in/twschulte/ 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/

Welcome back to Making Cents with me, 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.