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.

In this episode of Branching Out, Ethan McAfee shares how he built Amify from a one-man operation in his Arlington townhouse into one of the largest Amazon agencies in the country, helping major consumer brands with their strategy content, advertising, and supply chain before selling to Cart.com in 2024. Drawing on his earlier career as an internet stock investment analyst, Ethan explains how venture capital, market cycles, and founder energy can all factor into the timing and structure of an exit. He offers practical advice on preparing your company years ahead of a sale, reducing founder dependence, and balancing growth against burn to maintain control over your options. Now a senior advisor at a private equity fund, Ethan reflects on what it’s like to move from operator to investor-mentor — and why closing one chapter can be the best way to open the next.

In this episode of Branching Out, Susan Apgood, the former CEO of News Generation, shares candid insights about her journey selling her company in April 2020 in the midst of the COVID lockdown. She opens up about navigating a challenging broker relationship, unexpected cultural clashes between merging teams after the acquisition, and the emotional reality of watching a company you built change in ways you didn’t foresee. Susan also reflects on why due diligence, communication, and support networks—especially for women founders—are essential during an exit. Now a full-time professor at American University, she brings those lessons forward to empower the next generation of women business leaders.

In this episode of Branching Out, Jake Bittner, former CEO of Qlarion, recounts his path from co-founding a government data analytics firm to leading it through a successful acquisition by GCOM in 2021. He offers a transparent look at what it’s like to navigate the sale process with private equity buyers, from managing due diligence to balancing emotion with strategy. Jake also reflects on how selling a business changes your perspective on leadership, purpose, and personal identity. His story reveals the often-overlooked realities of exiting a company—and finding clarity on what comes next.

In this episode of Branching Out, Cary Hatch, former CEO of MDB Communications, opens up about the deals she walked away from, the one that finally felt right, and what it takes to step away from the CEO seat after decades at the helm. She shares how timing, values alignment, and a deep sense of purpose shaped her journey — and offers honest insights into the realities of selling an agency after years of leadership. Cary discusses the critical factors that influenced her decision, the importance of understanding market dynamics, and the challenges of transitioning to a new role post-sale. She also highlights the need for introspection and the emotional aspects of letting go. Her story is a powerful reminder that success in an exit isn’t just about valuation—it’s about vision, integrity, and fulfillment beyond the deal.

In the inaugural episode of Branching Out, Elizabeth Shea interviews Viraj Gandhi– former CEO and founder of Paradyme Inc. – about his 21-year journey from building a local and state contracting business to leading a major federal contractor acquired in 2024. Viraj shares how an unexpected AI partnership propelled the company toward acquisition and reflects on the complexities of cultural fit, emotional readiness, and life after selling a business. Their conversation offers candid insights for founders preparing to navigate both the practical and deeply personal sides of an exit.