Smart Business Dealmakers: The Middle-Market M&A Podcast

Dr. Brian Dooreck is a board-certified physician specializing in gastroenterology and hepatology who leads Executive Health Navigation. The firm helps high-net-worth individuals and those in the c-suite ensure they and their family have unmatched accessibility, support and navigation to the best doctors — in the U.S. and around the world. In this conversation, Dr. Doorick talks about what it is that he saw throughout his career that led him to launch the business, why integrated health planning is a must for family offices and wealth managers, and what CEOs tend to ignore about their health and what should they do about it.

Bill McComas, co-founder of Jensen & McComas and seasoned M&A lawyer, highlights common negotiating pitfalls in middle-market deals. He talks about timing advisors early, choosing the right buyer, valuation and deal-structure traps, diligence disorganization, protecting key people and culture, and how leverage and fatigue can sway outcomes.

For most business owners, the first time they sell their company is often the last. With only one chance to maximize the value that will be leveraged during life after business, it's important to get it right. Mark Jensen, a member at Jensen & McComas, offers an overview of the arc of an M&A deal — from assembling the deal team to the day of close. He offers tips on what to do and what not to do, and how to deal with the emotional issues that come with selling what is often a life's work.

Join Andy Rudolph, a partner at Royer Cooper Cohen Braunfeld with a knack for ESOP transactions, Marc Hirschfield, an advisor skilled in financing ESOPs, and David D'Alessandro, an expert in transaction mechanics, as they explore the often-overlooked Employee Stock Ownership Plans. They discuss the compelling tax benefits, the integral roles of key parties in a deal, and what steps founders should take for a smooth transition. Discover how ESOPs not only secure legacies but also foster a thriving ownership culture within companies.

Regardless of what uncertainty exists in the market or from where it originates, deals continue to get done. However, doing deals during more turbulent times takes some strategic maneuvering. Riveron's Alex Shahidi, Transaction Services Leader, Jeff Bernstein, Equity Capital Markets Leader, and Ryan Gamble, Tax Advisory Leader, explore the current deal environment, and the factors affecting public and private dealmaking. They talk tariffs, capital and debt markets, legislative changes affecting tax, IPO, SPACs and other factors that affect the execution of M&A deals in uncertain times.

Wright Lewis, a Partner at Dunlap Bennett & Ludwig, specializes in advising government contractors on M&A. He discusses the evolving landscape in the government contracting sector, particularly the impact of new SBA rules and budget cuts threatening company valuations. Wright highlights strategic differences between government and commercial M&A, the importance of due diligence, and identifying red flags in contractor evaluations. He also emphasizes the urgency for small businesses to sell before rule changes take effect in 2026.

At this year's Baltimore Smart Business Dealmakers Conference, an expert panel provided actionable insights to mitigate risks and maximize opportunities for both growth and divestiture in an increasingly complex time of tax policies and tariffs. Paragon Biosciences' Peter Buzy, Evergreen Advisors Capital's Stephen Prichett and First National Bank's David Valentiner and Mac Tisdale headlined the panel, moderated by First National Bank's Mac Tisdale.

Perhaps the worst thing a business owner can do ahead of the sale of their company is not be prepared. Not only could that crater the returns the owner was hoping to get for what is often their life's work, it could nuke a sale entirely. Fortunately, attorney James Hipolit has advice for those who've never sold before. In this podcast, the M&A partner with Troutman Pepper Locke covers the basics, from first steps to pre-diligence to common pitfalls, offering advice to get first-time sellers off to a strong start.

One area of complexity in a buy-side M&A transaction is commercial insurance. Given all the potential liabilities, hidden risks, industry-specific needs and coverage gaps, knowing what to look for during due diligence is critical to maximizing post-deal value. On this episode, Brian Stovsky, senior vice president and practice leader for the Oswald Companies and Unison Risk Advisors Mergers & Acquisitions Practice, and Joe Curtis, vice president and director of benefits for Michigan at Oswald Companies, talk about buyer pre-and post-close M&A due diligence considerations of commercial insurance for risk management.

At the 2025 Dallas Smart Business Dealmakers Conference, Zenwork Founder & CEO Sanjeev Singh shared the entrepreneurial journey that led to a nine-figure private equity minority investment. From launching Zenwork with his wife to scaling the business and bringing on a PE partner, Sanjeev discusses the challenges, pivotal moments and strategies that fueled Zenwork's growth.