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.

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.