In this episode of the Journey to an ESOP podcast, Jason and Makenzie kick off a new series that will continue throughout 2026: The Foundations of Transition, a workshop-style series focused on owner readiness. Each episode builds on the last, creating a practical framework for navigating ownership transition. The first foundation explores owner readiness and identity, helping owners define their vision for ownership and the future of their business. The conversation centers on identity: how your values and beliefs shape who you are as an owner, guide your decisions, and influence the life of your company. Understanding identity is critical, as it affects not only who your business is today, but also what it becomes after transition.

Season 7 begins with a simple truth: change is inevitable, but being unprepared is optional. In this opening monologue, Jason introduces Continuity Through Change and outlines what this season will explore: leadership under motion, foundations that hold through transition, and the often-ignored emotional mechanics behind ownership decisions.

In this episode of the Journey to an ESOP podcast, Jason sits down with Danny Massey, Head of Strategy and Communications for Expanding ESOPs--a national coalition working to dramatically broaden employee ownership across the United States. Danny shares how he became involved in the ESOP world, and the conversation dives into the powerful benefits of employee ownership, why it matters now more than ever, and how expanding access can create lasting impact for workers and businesses alike.

In this holiday episode, Jason and Makenzie explore the ESOP as a meaningful gift to a company’s employees. They break down how ESOP benefits work for both owners and employees and unpack the mechanics behind inside notes versus outside notes. This episode is a helpful resource in understanding ESOP verbiage and the real benefits that employees receive through a company transitioning to an ESOP.

In this episode, Jason and Makenzie let three “ESOP ghosts” guide us through the employee-ownership journey. They revisit the origins of your ESOP, take a candid look at how things stand today, and discuss how to intentionally choose its future. They highlight how the decisions, habits, and culture shape long-term ESOP success.

In this episode, the Journey to an ESOP podcast speaks directly to founders who feel the weight of leadership and wonder how their team will successfully shift into an ESOP model. Through a blend of personal story and practical insight, Jason explores how identity, encouragement, and intentional leadership can help bridge that gap and prepare both leaders and teams for a confident, sustainable ESOP transition.

In this episode, Jason and Makenzie dive into the real purpose of ESOP feasibility and why it’s far more than just another spreadsheet. They break down what “feasibility” truly means in an ESOP transaction and walk through the key factors companies should evaluate, from existing debt to entity structure (S-corp vs. C-corp) to long-term sustainability. They also dig into how feasibility helps determine whether an ESOP will genuinely benefit the company, the owners, and the employees.

In this 15-minute episode, Jason and Makenzie take on some of the biggest misconceptions that keep companies from exploring an ESOP. They break down why ESOPs aren’t the overly complicated, out-of-reach structures many assume they are and why owners don’t suddenly lose control the moment they sell. They also dig into the fear that employees won’t understand the benefits of an ESOPs hurt bonding capacity or borrowing power, and the belief that only large companies can afford them.