Most business owners can name the exit they think they want, but far fewer can clearly explain the problem they are trying to solve. Jason Miller and Makenzie Wirth dig into the 10 powerful questions every owner should ask themselves before choosing an ESOP, a management buyout, or a third-party sale, because transition problems usually start with incomplete questions, not bad intentions.

From uncovering hidden risks and leadership gaps to evaluating succession readiness, personal goals, and the true value of the business beyond the owner, these questions reveal what’s really happening beneath the surface. This conversation will help you gain clarity, preserve your options, and build a stronger foundation for a successful transition.

If you want a clearer path through exit planning, business succession, and ESOP readiness, hit play and bring these questions to your next advisor meeting.

In this Journey to an ESOP and Beyond podcast episode, Jason and Makenzie continue the Foundations of Transition series by exploring the sixth foundation: capacity building. Framed through the lens of leadership transfer, this conversation examines why a business is only truly transferable when leadership, decision-making, and organizational judgment can transfer as well. As owners prepare for succession, an ESOP transaction, or any future transition, developing leadership depth becomes a critical part of preserving and growing enterprise value.

Throughout this episode, Jason and Makenzie introduce the concept of “leadership debt,” describing how organizations accumulate risk when founders and owners remain the primary source of decisions, relationships, and problem-solving. They discuss the importance of transferring not only tasks, but also the context, authority, and judgment behind those tasks. Through practical examples and actionable takeaways, listeners are encouraged to identify opportunities to build leadership capacity, strengthen management depth, and create a company that can continue to thrive beyond the daily presence of its founder.

In this podcast episode, Jason and Makenzie interview Art Smith, President of DB Engineering, about the company’s transition to 100% employee ownership. The conversation explores the decision-making process between a strategic sale, management buyout, and ESOP, along with the challenges of leadership transition, communication, and building an employee-owned culture. Drawing from firsthand experience, Art shares valuable insights and lessons learned throughout the ESOP transition process, offering an honest look at the complexities, challenges, and rewards of navigating ownership transition in a growing professional services business.