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

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.

For business owners thinking about their exit, the choice often seems limited to selling to a competitor or to a private equity firm. But there's a third option, ESOPs, that secures their legacy and rewards the very people who helped build the company. Royer Cooper Cohen Braunfeld's Andy Rudolph, Marc Hirschfield and David Dalesandro take a deep dive into Employee Stock Ownership Plans to break down how this unique succession path works — from the powerful tax advantages to the mechanics of financing the deal. They also explore the founder's role after the sale and the keys to building a thriving ownership culture long after a transition.

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.

It was supposed to be a great year for M&A in the government contracting sector. New SBA rules were expected to drive GovCon sellers to market as they raced to beat the rules' implementation. But then the Department of Government Efficiency happened, which sought to cut government budgets, something that threatened to negatively affected many GovCon businesses since, as the name implies, government contracts are key to their value. Helping to identify the trends that are pulling GovCon businesses in two extreme directions, Wright Lewis, a Partner at Dunlap Bennett & Ludwig, stops by the Smart Business Dealmakers Podcast to talk about the factors weighing most heavily on M&A in the sector.

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.  

There are many myths about ESOPs — that they're complicated or that once within its structure a company owner loses control, or that banks won't lend to them. David Solomon, a member at Levenfeld Pearlstein and head of the firm's Employee Stock Ownership Plan practice, is here to bust those myths. In this episode, David sets the record straight on what an ESOP is — and what it isn't.

What happens when a publicly traded company transitions to become privately owned? During the midday Fireside Chat at the Boston Smart Business Dealmakers Conference, two CFOs share firsthand insights on the realities of life as a public company, the strategic considerations behind their respective sales to private equity firms, and what the transition process entailed. Cassandra Hudson, CFO of StackAdapt and former CFO of EngageSmart, and John Wagner, former CFO of Brightcove, sat down with Bank of America Managing Director Phil Ianniello to discuss what changed post-transaction and how the shift has impacted operations and financial strategy, and offer key lessons from navigating this major transformation.

A letter of intent, often referred to as an LOI, is essentially the first formal document in a sale process between a buyer and a seller. It not only establishes the intent of two companies to move forward into a sale process, but it sets some terms for the process that sellers should carefully consider. Tony Montanaro, transaction advisory partner with Louis Plung & Company, talks about LOIs and what sellers need to know about the terms within them before moving forward with a deal.

Kicking off this year's Boston Smart Business Dealmakers Conference, we explore innovative strategies, regional growth and the transformative power of public-private collaboration in shaping the future of Massachusetts and the Boston region. In this panel, moderated by Smart Business Chief Content Officer Dustin Klein, Timberline Construction CEO Steven Kelly and Commonwealth of Massachusetts Chief Digital Officer Janak Joshi explore the dynamic landscape of economic development in the state.

Things seem to be looking up for the St. Louis economy. And with positive national economic trends expected to continue, the city seems poised to build on its momentum. At the 2025 St. Louis Smart Business Dealmakers Conference, Dustin Allison of Greater St. Louis Inc., Rhonda Hamm-Niebruegge of St. Louis Lambert International Airport and John Manetta of Bank of America joined Bank of America St. Louis President Marilyn Bush to analyze the economic indicators, infrastructure developments and investment strategies shaping the city's future. 

What really makes a company tick? And more importantly, what makes it worth more? At the 2025 Pittsburgh Smart Business Dealmakers Conference, a group of regional executives and investors dissected the art — and science — of creating serious company value. From scaling strategies that turn small wins into big exits to the nuanced dance of acquisitions and sales, panelists John Lewis and Christopher Brodman of Metz Lewis Brodman Must O'Keefe, Rob Carskadden of 3 Rivers Capital, George Pilafas of Continuim Equity Partners and Patrick Patterson of Level Agency pulled back the curtain on what drives growth in today's deal-driven market.

Self-funding health insurance through a group medical captive can be a way for businesses of any size to better manage what is often their second greatest expense. And, according to Roundstone Founder and President Mike Schroeder, it may also be a way for business owners to increase the company's value ahead of a sale. On this episode of the Smart Business Dealmakers Podcast, Schroeder talks about the self-funding model as well as its impact on an M&A transaction.