Buyouts, Business and Bourbon

Selling Your Business Is Like Becoming an Empty Nester with Matt Meline

What happens after you sell your business? For many founders and business owners, the financial side of an exit gets most of the attention. But the emotional side can be just as important. In this episode of Business, Buyouts and Bourbon, Gerry Spitzer sits down with financial advisor Matt Moline to discuss the surprising parallels between becoming an empty nester and transitioning out of a business you’ve spent years building. Matt shares his own journey from banking to financial advising, launching his independent firm, and creating a show focused on the empty nest transition. Together, Gerry and Matt explore why business owners often struggle with identity, purpose, succession, and meaning after a sale. They also discuss how ESOP transactions can give owners more runway, why succession planning matters, how to think about life after liquidity, and why giving back can become a meaningful next chapter. If you’re a business owner thinking about selling, transitioning, or stepping back from the company you built, this conversation will help you think beyond the numbers. In This Episode 00:00 Introduction to Matt Moline 01:13 Matt’s journey from banking to financial advising 03:39 Why Matt focuses on the empty nest transition 05:35 The emotional shift of becoming an empty nester 07:45 Paying for college and teaching kids financial lessons 10:02 Reimagining life after the kids leave home 12:15 Housing, lifestyle, and community decisions after transition 14:16 Why selling a business can feel like “selling your baby” 15:35 Finding meaning after a business exit 17:56 ESOPs, succession planning, and staying involved after a sale 20:32 Why life after a transaction needs to be planned, not assumed 22:11 Giving back after retirement or a business exit 25:50 Teaching personal finance in a county jail 30:31 Bourbon, wine, golf, tennis, and pickleball injuries What do you think is harder for a business owner: deciding when to sell, or figuring out what comes next after the sale? Let us know in the comments. #BusinessExitPlanning #ESOP #BusinessOwners #SuccessionPlanning #ExitPlanning #BusinessBuyoutsAndBourbon #RetirementPlanning #FinancialAdvisor #BusinessTransition #BourbonPodcast --- Connect with Us: If you enjoyed this episode, please like, comment, and subscribe for more inspiring stories from business leaders and entrepreneurs. Have questions or want to suggest a guest? Drop a comment below! About Gerry Spitzer: Gerry Spitzer is an expert in ESOPS and exit planning for business owners. As co-founder of Questar Capital Partners, he helps founders design tax-efficient exit strategies that preserve legacy, reward employees, and maximize value. With 30+ years in wealth management, Gerry works with companies generating $20M–$300M in revenue, guiding them through complex succession and liquidity events. 📞 Connect with Gerry ✉ gerry@questarcap.com [gerry@questarcap.com]  📱 850-655-6500  🌐 https://www.questarcap.com/ [https://www.questarcap.com/]  🔗 LinkedIn: https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895/ [https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895/]

NFL Records, Leadership, Business Ventures, and Life in the NFL with Zaire Franklin

In this episode of Buyouts Business and Bourbon, All-Pro linebacker Zaire Franklin of the Indianapolis Colts shares his journey from Philadelphia to the NFL, breaking down what it takes to lead at the highest level while building businesses and preparing for life after football. From record-setting performances to entrepreneurship and philanthropy, this conversation dives into the mindset behind sustained success on and off the field. In this episode: • Zaire Franklin’s NFL career, including his All-Pro recognition, leading the league in tackles in 2024, and climbing the record books with the Indianapolis Colts. • His football journey from Philadelphia to La Salle College High School and becoming the youngest captain in Syracuse history at Syracuse University. • What it felt like to be drafted in the seventh round and the mindset shift required to prove himself in the NFL. • Leadership inside the locker room, embracing the role of a servant leader, and mentoring teammates. • Building businesses beyond football, including rental properties and a Rita’s franchise. • The mission behind Shelice’s Angels, his foundation honoring his late mother and grandmother, supporting young women, scholarships, and Girls Flag Football initiatives. • Preparing for life after football by diversifying identity, building financial awareness, and keeping options open. • Why current pro athletes need media platforms and how podcasting plays a role in shaping their narrative. • A lighter conversation on bourbon, whiskey, and his upcoming trip to the Kentucky Derby. This episode goes beyond football stats and highlights. It is a conversation about leadership, legacy, financial growth, and building purpose beyond the game. Zaire Franklin’s story offers insight into what it means to succeed in the NFL while intentionally preparing for business, philanthropy, and life after the final whistle. #ZaireFranklin #NFL #IndianapolisColts #leadership #entrepreneurship #lifeafterfootball #personaldevelopment #businessgrowth Make sure to connect with Zaire and Shelice’s Angels:  LinkedIn: https://www.linkedin.com/in/zaire-franklin-6170431aa [https://www.linkedin.com/in/zaire-franklin-6170431aa] Website: https://www.shelicesangels.org [https://www.shelicesangels.org] --- Connect with Us: If you enjoyed this episode, please like, comment, and subscribe for more inspiring stories from business leaders and entrepreneurs. Have questions or want to suggest a guest? Drop a comment below! About Gerry Spitzer: Gerry Spitzer is a nationally recognized expert in ESOPs and exit planning for business owners. As co-founder of Questar Capital Partners, he helps founders design tax-efficient exit strategies that preserve legacy, reward employees, and maximize value. With 30+ years in wealth management, Gerry works with companies generating $20M–$300M in revenue, guiding them through complex succession and liquidity events. 📞 Connect with Gerry ✉ gerry@questarcap.com [gerry@questarcap.com]  📱 850-655-6500 🌐 https://www.questarcap.com [https://www.questarcap.com]    🔗 LinkedIn: https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895 [https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895]

ESOP Exit Planning with Josh Freeman & Richard Reyle

Exit planning for middle market companies is becoming urgent, especially for Baby Boomer owners between ages 55 and 70 who have not yet structured their transition. In this episode, Josh Freeman and Richard Reyle break down mergers and acquisitions strategies, tax-free transaction structures, and why Employee Stock Ownership Plans are increasingly used as a powerful exit tool. Business owners will gain insight into how ESOPs and Qualified Replacement Property can potentially defer capital gains, preserve legacy, and create long-term financial efficiency. In this episode: • Exit planning strategies for middle market business owners preparing for a liquidity event. • Different ways owners can sell their businesses, including strategic buyers, private equity, ESOPs, and family transfers. • Why Employee Stock Ownership Plans offer significant tax advantages for both owners and employees. • How Section 1042 of the IRS tax code allows sellers to exchange privately held stock for Qualified Replacement Property on a tax-deferred basis. • What Qualified Replacement Property includes, such as floating rate notes, real estate, and equities. • Why floating rate notes are commonly used due to lower interest rate risk and higher borrowing capacity. • How the ESOP and QRP strategy is executed, including the 12-month reinvestment window and the use of margin loans. • The concept of negative cost of carry and why tax savings may outweigh borrowing costs. • How independent advisory firms compete with major institutions by offering open architecture and flexible lending solutions. • The additional benefits of ESOPs, including employee ownership, community goodwill, and long-term wealth creation. • A lighter discussion on bourbon favorites including Buffalo Trace, Pappy 23-year-old, Old Fitzgerald, and Eagle Rare. For business owners evaluating succession options, this conversation provides a detailed look at how ESOP structures and Qualified Replacement Property strategies can align tax efficiency, employee ownership, and legacy preservation. With the right preparation and advisory team, owners can approach their exit with clarity, control, and a long-term wealth management plan in place. #ESOP #exitplanning #sellingabusiness #middlemarket #taxstrategy #qualifiedreplacementproperty #MergersAndAcquisitions #businessowners Make sure to connect with Josh:  Website: https://sanctuarywealth.com/people/josh-freeman/ [https://sanctuarywealth.com/people/josh-freeman/]  LinkedIn: https://www.linkedin.com/in/josh-freeman-26ab80163 [https://www.linkedin.com/in/josh-freeman-26ab80163]  Connect with Richard: Website: https://www.questarcap.com/bio?BIO_ID=4313 [https://www.questarcap.com/bio?BIO_ID=4313]  Email: richard@questarcap.com [richard@questarcap.com]  --- Connect with Us: If you enjoyed this episode, please like, comment, and subscribe for more inspiring stories from business leaders and entrepreneurs. Have questions or want to suggest a guest? Drop a comment below! About Gerry Spitzer: Gerry Spitzer is a nationally recognized expert in ESOPs and exit planning for business owners. As co-founder of Questar Capital Partners, he helps founders design tax-efficient exit strategies that preserve legacy, reward employees, and maximize value. With 30+ years in wealth management, Gerry works with companies generating $20M–$300M in revenue, guiding them through complex succession and liquidity events. 📞 Connect with Gerry ✉ gerry@questarcap.com 📱 850-655-6500 🌐 https://www.questarcap.com/  🔗 LinkedIn: https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895/

Exit Planning, Selling Your Business, and Family Offices with Josh Pearce

Selling a business is one of the most complex decisions an entrepreneur will face, yet many founders wait too long to prepare. In this episode, Jerry Spitzer and M&A corporate lawyer Josh Pearce break down the full exit planning process, from early preparation to post-sale asset management through family offices. Learn how strategic planning, diligence, and the right mindset can maximize value and minimize risk. In this episode: • The importance of starting exit planning early, as most founders never truly prepare. • How an exit readiness audit can guide the best path forward, whether selling, transitioning to family, or exploring private equity. • The common misconception that selling a business is simple and why buyers scrutinize every detail. • How diligence and risk affect pricing and deal terms, requiring a shift from building a business to selling one. • Prediligence steps 12 to 24 months out, including corporate hygiene, commercial foundations, financial credibility, people and IP matters, and regulatory cleanup. • The high cost of delaying fixes and how last-minute issues can reduce deal value. • Qualified Small Business Stock (QSBS) opportunities, including eligibility, tax-free benefits, stacking strategies, and holding period considerations. • Fractional family offices and how they support ongoing asset management, tax planning, and operations for families with $20 million or more in assets. Selling a business is not just a transaction. It is a transformation that requires preparation, diligence, and strategic thinking. By understanding exit readiness, leveraging tax opportunities like QSBS, and planning for ongoing wealth management through family offices, entrepreneurs can secure their legacy, optimize deal value, and create long-term financial security. #exitplanning #sellingabusiness #familyoffices #QSBS #entrepreneurship #businessgrowth #wealthmanagement Make sure to connect with Josh:  Website: https://www.bressler.com/people-joshua-pearce [https://www.bressler.com/people-joshua-pearce]  LinkedIn: https://www.linkedin.com/in/japearce [https://www.linkedin.com/in/japearce]  --- Connect with Us: If you enjoyed this episode, please like, comment, and subscribe for more inspiring stories from business leaders and entrepreneurs. Have questions or want to suggest a guest? Drop a comment below! About Gerry Spitzer: Gerry Spitzer is a nationally recognized expert in ESOPs and exit planning for business owners. As co-founder of Questar Capital Partners, he helps founders design tax-efficient exit strategies that preserve legacy, reward employees, and maximize value. With 30+ years in wealth management, Gerry works with companies generating $20M–$300M in revenue, guiding them through complex succession and liquidity events. 📞 Connect with Gerry ✉ gerry@questarcap.com 📱 850-655-6500 🌐 https://www.questarcap.com/  🔗 LinkedIn: https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895/

Unlocking The Power of Self-Insurance with Daniel Campbell

In this episode, Dan Campbell of Campbell Petrie discusses his journey in the benefits consulting world, focusing on self-insurance and captive insurance. He shares insights on the evolution of health insurance, the importance of understanding different insurance models, and how businesses can benefit from innovative strategies to manage healthcare costs. The conversation also touches on real-world examples of companies that have successfully transitioned to captive insurance, emphasizing the long-term financial advantages and the need for a mindset shift among business owners. In this episode: 00:00 Introduction to Benefits Consulting and Personal Journey 12:11 Understanding Self-Insurance and Captive Insurance 24:40 Navigating the Risks and Benefits of Captives 26:31 Navigating Competition in Health Insurance 27:01 Understanding Health Insurance Costs 28:51 The Benefits of Self-Funding 30:36 Long-Term Financial Planning for Health Insurance 31:57 Shifting Mindsets in Health Insurance 32:54 Client Education and Scenarios 35:03 Cash Flow Benefits of Self-Insurance 36:38 Captives and Business Valuation 37:56 Long-Term Investment Strategies in Health Insurance 39:45 Trends in Captives and Nonprofits 40:40 Questions for Business Owners Considering Captives 41:49 Community and Collaboration in Captives 43:24 Challenges in Healthcare for Retirees 44:55 Personal Insights and Closing Thoughts Make sure to connect with Dan:  Website: https://campbellpetrie.com/about-us/team/dan-campbell/ [https://campbellpetrie.com/about-us/team/dan-campbell/] LinkedIn: https://www.linkedin.com/in/daniel-j-campbell-bb61246/ [https://www.linkedin.com/in/daniel-j-campbell-bb61246/] #BusinessExits #ESOP #BourbonTalk #Questar Tune in to discover how ESOPs can transform business exits and why they might be the best-kept secret in the industry. Subscribe now to not miss an episode! --- Connect with Us: If you enjoyed this episode, please like, comment, and subscribe for more inspiring stories from business leaders and entrepreneurs. Have questions or want to suggest a guest? Drop a comment below! About Gerry Spitzer: Gerry Spitzer is a nationally recognized expert in ESOPs and exit planning for business owners. As co-founder of Questar Capital Partners, he helps founders design tax-efficient exit strategies that preserve legacy, reward employees, and maximize value. With 30+ years in wealth management, Gerry works with companies generating $20M–$300M in revenue, guiding them through complex succession and liquidity events. 📞 Connect with Gerry ✉ gerry@questarcap.com 📱 850-655-6500 🌐 https://www.questarcap.com/  🔗 LinkedIn: https://www.linkedin.com/in/gerry-spitzer-cpwa%C2%AE-cepa%C2%AE-2472895/