Navigating Family Business Succession and Sale: Insights from Rick Calabrese and Joe Bergin, Commonwealth M&A, and Lyle Newkirk, SeatonHill Partners (Family Business Radio, Episode 64)
In this episode of Family Business Radio, host Anthony Chen welcomes three experienced advisors to discuss the intricacies of planning for family business succession and sale. Rick Calabrese and Joe Bergin from Commonwealth M&A share their personal journeys and expertise in assisting small businesses with transitions, covering topics such as business valuation, the emotional aspects of selling, and the importance of having a professional advisor. Lyle Newkirk from Seton Hill Partners brings a different perspective, discussing his experience in corporate M&A and the importance of preparation and strategic advisory for small and mid-sized businesses. The discussion includes practical advice on preparing for an exit, the role of private equity, and addressing common misconceptions and pitfalls. The episode aims to provide family business owners with valuable insights to ensure a seamless transition and maximize their business’s value.
Anthony concludes the show by underlining the need for thoughtful retirement planning.
Family Business Radio is underwritten and brought to you by Anthony Chen with Lighthouse Financial Network. The show is produced by John Ray and the North Fulton affiliate of Business RadioX®.
Key Takeaways from This Episode:
Rick Calabrese, Commonwealth M&A
- “There’s no perfect time to sell—only the right time, when your goals and your business are aligned.”
- Rolling equity (a partial sale with continued involvement) allows owners to take chips off the table now and participate in a second payday later.
- Emotional readiness is just as important as financial readiness in family business succession.
Joe Bergin, Commonwealth M&A
- “Your business is worth what someone is willing to pay. That’s why process and positioning matter.”
- Valuation isn’t just math. It’s about risk, recurring revenue, and how the buyer sees your future cash flow.
- M&A advisors aren’t just negotiators. They’re emotional buffers and translators between the parties.
Lyle Newkirk, SeatonHill Partners
- “Don’t wait to clean up your books. Due diligence is like a 90-day colonoscopy.”
- Many deals fall apart not on price, but on poor preparation, such as missing contracts, inadequate reporting, or emotional resistance.
- Fractional executives can professionalize operations, prepare for exit, and give owners a trusted outside perspective.
Anthony Chen, Lighthouse Financial
- Retirement planning isn’t just about the numbers; it’s about the lifestyle. Financial success is meaningless without a clear vision of what fulfillment looks like post-exit.
- Think beyond the golf course. True retirement satisfaction requires more than vague hobbies. Entrepreneurs must get specific about how they want to spend their time and structure their lives once the business chapter closes.
- Plan for retirement well in advance of the proposed deal. Planning for retirement should begin long before a business is sold. Knowing what comes next adds clarity and confidence to the decision to exit.
Topics Discussed in this Episode
00:00 Introduction to Family Business Radio
00:48 Meet the Guests: Rick Calabrese and Joe Bergin
01:01 Background Stories: Rick and Joe’s Family Business Roots
05:31 Understanding Business Valuation
07:41 Timing the Sale of Your Family Business and Family Business Succession
10:17 Options for Partial Liquidity Events
13:45 Misconceptions About Private Equity
17:16 The Importance of M&A Advisors
19:02 Emotional Aspects of Selling a Family Business
23:25 Recognizing When to Step Aside
24:19 Resources for Business Owners
24:37 The Importance of Early Planning
25:46 Introducing Lyle Newkirk
28:01 Common Mistakes in Business Transactions
30:22 Preparing for a Successful Exit
35:05 The Role of Fractional Executives
38:29 Final Thoughts and Key Takeaways
Rick Calabrese, Esq., CPA, LL.M., Co-Founder, Commonwealth M&A
Rick Calabrese is a licensed attorney and certified public accountant in the Commonwealth of Pennsylvania and also has a Masters of Law in Taxation from Villanova University School of Law. Prior to attending law school, Rick obtained a Bachelor of Science in Business Administration (accounting) from the University of Pittsburgh. After law school, Rick worked at “Big 4” accounting firm PricewaterhouseCoopers LLP in Center City, Philadelphia, prior to engaging in the active practice of law primarily in the fields of tax, corporate business, M&A and commercial real estate at suburban Philadelphia-based law firms.
During his time practicing law (which he still does part-time), Rick handled multi-million-dollar transactions for small to medium-sized businesses. While many other clients may have to use multiple advisors on a given transaction, Rick used his unique and specialized tax, business, M&A, and CPA background to assist clients through the entire process of family business succession, from initial planning and structuring to drafting purchase agreements and closing.
Rick now lives with his wife, Lindsey; their son, Luca; and their dog, Maverick, in Chester County, PA. In his free time, you can find Rick out on the links or passionately cheering on the Big 4 Philadelphia sports teams, Villanova basketball, and Pitt Panthers football.
Joe Bergin, Co-Founder, Commonwealth M&A
Joe Bergin graduated from Penn State University (University Park) with Bachelor’s Degrees in Finance and Economics. Joe is also a Certified Management Accountant and worked at Johnson & Johnson for over a decade spanning multiple roles & responsibilities culminating in a series of roles spent analyzing, structuring, and executing M&A and venture capital transactions.
During his time in Corporate Finance, Joe developed experience and skills ranging from strategic planning to complex financial modeling and business valuation. Joe passionately believes that Commonwealth M&A clients deserve to be represented with the same level of sophistication that Fortune 100 companies receive, regardless of deal size.
Born and raised in West Chester, PA, Joe is a passionate fan of all Philadelphia and Penn State sports. In his free time you can find him spending time with his wife and daughter or attending Penn State football games in the Fall.
Lyle Newkirk, CFO Partner, SeatonHill Partners
Lyle Newkirk is a CFO partner with SeatonHill Partners. He has over 35 years of experience in CFO and executive finance roles. He has worked with public and private companies based both in the US and internationally, where he developed the strategies to achieve significant top-line revenue growth and helped to facilitate various successful acquisitions and strategic exits, including three exits to Fortune 500 companies. Lyle has extensive experience in technology companies in general and SaaS companies specifically. Lyle’s expertise also includes FP&A, growth planning and tactics, cash management, HR, sales operations, and regulatory compliance
SeatonHill provides organizations financial leadership with a strategic and operational focus by placing elite CFO talent to challenge the business and contribute to operational decisions to achieve results. With their curated talent, their financial leaders guide small and medium-sized businesses through complex financial problems to mitigate risk and achieve organizational goals.
SeatonHill is the fastest-growing CFO services firm in the nation, offering the power of combined thought leadership and the support of the country’s top financial talent to the benefit of all our clients. SeatonHill has offices in Boston, Dallas, Fort Worth, Los Angeles, Austin, Houston, New York, Atlanta, Chicago, Philadelphia, Phoenix, San Diego, and Washington, D.C.
Anthony Chen, Host of Family Business Radio
Family Business Radio is sponsored and brought to you by Anthony Chen with Lighthouse Financial Network. Securities and advisory services are offered through OSAIC, member FINRA/SIPC. RAA is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of OSAIC. The main office address is 575 Broadhollow Rd., Melville, NY 11747. You can reach Anthony at 631-465-9090, ext. 5075, or by email at anthonychen@lfnllc.com.
Anthony Chen started his career in financial services with MetLife in Buffalo, NY, in 2008. Born and raised in Elmhurst, Queens, he considers himself a full-blooded New Yorker while now enjoying his Atlanta, GA, home. Specializing in family businesses and their owners, Anthony works to protect what is most important to them. From preserving to creating wealth, Anthony partners with CPAs and attorneys to help address all of the concerns and help clients achieve their goals. By using a combination of financial products ranging from life, disability, and long-term care insurance to many investment options through Royal Alliance, Anthony looks to be the eyes and ears for his client’s financial foundation. In his spare time, Anthony is an avid long-distance runner.
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