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.

In this episode of Journey to an ESOP and Beyond podcast, Jason and Mackenzie discuss the full lifecycle of an ESOP company. The conversation covers what changes in the first 90 days after an ESOP transaction, including new debt obligations, administrative responsibilities, and the importance of employee communication and engagement. The podcast also discusses how boards and leadership teams evolve over time, why committee structure matters, and how companies can successfully navigate the growing complexities of mature ESOPs. From early-stage growing pains to long-term planning challenges like diversification, repurchase obligation, and balancing opportunities between long-tenured employees and newer participants, this episode provides a practical and candid look at what it truly means to operate as an ESOP company for the long haul.

In this episode of Journey to an ESOP and Beyond, Makenzie breaks down the negotiation process behind an ESOP transaction. From purchase price and seller note terms to governance, SARs, board composition, and fiduciary requirements, this episode explores the key terms that are typically negotiated between the seller and the ESOP trustee. If you’re considering an ESOP or preparing for a transaction, this episode offers a practical overview of what to expect during negotiations and how the process compares to a traditional M&A deal.

In this episode of the Journey to an ESOP podcast, Jason and Makenzie interview brothers Marc and John Farrell of to discuss their company’s transition to employee ownership and the multi-generational legacy behind it. The Farrell brothers share the history of their 80-year family business, why they chose an ESOP over other transition options, and what they’ve learned in the early stages of becoming employee owned. From succession planning and leadership transitions to culture and communication, this conversation offers practical insight for business owners thinking intentionally about the future of their company.

In this Journey to an ESOP podcast episode, Jason and Makenzie continue the Foundations of Transition series, focusing on the theme of turning strategy into execution, exploring how these elements play a critical role in preparing for a successful ESOP transaction. Each workshop-style conversation in this series is designed to help business owners think more intentionally about the future of their company and the role they play in shaping it.

This episode encourages owners to look beyond strategy alone and consider how effectively their plans are being carried out. Jason and Makenzie introduce the concept of “mini” strategic planning: breaking down not just what needs to be done, but how to implement it and how often to revisit progress. Through practical insights, they highlight why building strong accountability and execution habits early can reduce friction during a transaction and better equip your team for the work ahead.

In this episode, Jason Miller speaks with Steve Baker of The Great Game of Business about the critical role of financial literacy in building successful employee ownership and ESOP cultures. They explore why ownership alone does not automatically create an ownership mindset and why education is essential for helping employees understand how businesses actually work. Steve shares practical insights on how organizations can strengthen engagement, accountability, and performance by teaching teams to think and act like owners through a deeper understanding of financials and business performance. The conversation highlights a key takeaway for ESOP companies and leadership teams: financial literacy is the foundation that connects employee ownership to real behavioral change and long-term business success.