In this episode of Branching Out, Elizabeth Shea sits down with Andrew Sherman, senior partner at Brown Rudnick, for a candid look at how deals really get priced, structured, and won. Andrew explains why M&A is cyclical, the differences between strategic and financial buyers, why sellers must perform reverse due diligence on buyers, and how to surface the “gold bars in the attic” — the intangible value drivers that buyers won’t pay for unless you point them out. He also unpacks common gotchas like PPP/EIDL distortions, rollover equity, earnouts, and under-capitalized “buyers” who look legit until it’s time to close. The bottom line: don’t just prepare your business — prepare your story, your expectations, and your deal team.

In this episode of Branching Out, Elizabeth sits down with Bess Winston, the founder of The Winston agency. She talks about how one modest media relations project-turned-campaign laid the foundation for her to meticulously build a nationally respected boutique firm with a powerhouse team before ultimately selling her agency in 2022. Bess shares her journey with the humor and unfiltered honesty only an experienced founder can bring. She sheds light on the emotional jolt of parting with a company, the importance of protecting your people, navigating post-acquisition culture shifts, the advice she wishes she hadn’t ignored, and the moment she learned the hard truth: “When you sign your name, you’re done.” This episode is for anyone weighing a major inflection point — whether you’re debating when to slow down, when to scale up, or who really deserves a seat at your deal table.

In this episode of Branching Out, Allan Klassen, former CEO and managing partner of Albi Homes, shares how he helped turn a Calgary-based luxury home builder into a “niche of one” and a strategic acquisition target which was acquired by Brookfield Residential in 2015. Allan walks through the realities of negotiating with a globally recognized asset management company, keeping a deal alive when it nearly collapsed, and the lessons he learned about non-negotiables, timing, and values alignment. He also opens up about the deeply emotional transition from entrepreneurial leader to an executive inside a finance-driven organization, and how that journey led him to a new role as Chief Experience Officer and ultimately to launching his own advisory practice, Clarity Quest. This conversation is a must-listen for founders and leaders who want to prepare not just their business — but themselves — for a future transaction.