Journey to an ESOP & Beyond

The fastest way to ruin an ESOP is to focus on the tax benefits and ignore the rules—and the people—who will live with the plan afterward. In this episode, Jason Miller interviews Joshua Sutton, an employee benefits attorney, about why Employee Stock Ownership Plans (ESOPs) are complex yet rewarding when approached with the right mindset and team. Jason and Josh discuss what sets an ESOP apart fro...

Employee stock ownership plan (ESOP) transitions can look complete on paper yet the company often remains psychologically and operationally centered on the founder. In this episode, Jason Miller unpacks why this disconnect happens and why it often goes unnoticed until the first tough quarter. He explains that transferring shares is not the same as transferring leadership, authority, identity and k...

How do you protect a legacy without selling out the people who built it? In this episode, Jason Miller interviews Spike Lord, President of Lord and Son Construction, Inc. and Ryan Chavers, Director of Operations, about a Fort Walton Beach, Florida construction company built on decades of steady work, long careers and loyalty. They explore the family business’s history, the culture that has kept pe...

Your business might be profitable and still be worth less than you think. In this episode, Jason Miller and Makenzie Ragland continue their Foundations of Transition series by discussing value creation, protection and risk awareness. They explore how business owners can begin viewing their company through the eyes of an outside buyer or Employee Stock Ownership Plan (ESOP) trustee, focusing on wha...

What can happen in one year when you stop waiting for the perfect moment and start taking action? In this episode, Jason Miller looks back at a year of personal and professional progress—not as a victory lap, but as evidence of what happens when you turn decisions into action and create tangible proof of progress. This episode is about more than Employee Stock Ownership Plans (ESOPs). It's ab...

Determining if an employee stock ownership plan, or ESOP, is right for your company starts with a straightforward but sometimes challenging question: Where do you see your business heading, and why? In this episode, Jason Miller and Makenzie Ragland explore how ESOP planning and forecasting empower owners to prepare for a transaction and make informed decisions throughout the process. They break d...

Washington is sending new signals about employee ownership, but the headlines don’t help much if you’re a business owner trying to decide whether an Employee Stock Ownership Plan (ESOP) is actually feasible. In this episode, Jason Miller and Makenzie Ragland welcome back Corey Rosen from the National Center for Employee Ownership to discuss the latest developments shaping the future of employee ow...

Your processes may be well documented, but your operations can still be fragile. In this episode of the Foundations of Transition series, Jason Miller and Makenzie Ragland explore process maturity and operational strength. They discuss why strong operations involve more than documented procedures and how building a culture of continuous improvement can help owners prepare for an Employee Stock Own...

The most common question we hear may seem simple, but it can significantly change the outcome of an Employee Stock Ownership Plan (ESOP) transaction: Should you remain an S corporation or convert to a C corporation? In this episode, Jason Miller and Makenzie Wirth break down the key differences between the two structures and how each one affects the company and its selling shareholders. They also...

In this episode, Makenzie Wirth delves into the Mandela Effect and how memory can shape the stories we tell ourselves. Many business owners explore an employee stock ownership plan, or ESOP, with fragmented information gathered from other owners’ experiences—some accurate, some not. These stories can shape important decisions about ESOP planning, the benefits of an ESOP and the perceived advantage...

Your feed feels personal for a reason, and it’s not magic. Jason Miller and Makenzie Wirth dig into the idea that the “algorithm” isn’t a villain with a secret agenda. It’s an objective system built on subjective inputs, and the input it cares about most is your attention. We share real snapshots from our own algorithms and what they might mean beneath the surface: curiosity, problem-solving, prep...

In this episode, Jason Miller and Makenzie Wirth continue the Foundations of Transition series by exploring the importance of financial fluency and clarity. This workshop-style conversation aims to help business owners better understand the numbers behind their operations and why financial confidence is essential for making informed decisions throughout the ESOP journey. This episode encourages ow...

In this episode, Jason Miller explores how advisors can recognize when an Employee Stock Ownership Plan (ESOP) deserves a place in a client’s transition planning conversation. Rather than positioning ESOPs as a one-size-fits-all solution for business owners, this 14-minute field guide offers practical advice for professionals aiming to engage in meaningful discussions with clients whose objectives...

In this episode, Makenzie Wirth sits down with David Thrush, Principal in Doeren Mayhew’s Audit Department and National ESOP Practice Leader, to break down why employee benefit plan (EBP) audits are essential for ESOP companies. With extensive experience in ERISA compliance, employee benefit plan audits, and ESOP administration, David explains how EBP audits support accurate Form 5500 reporting an...

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 un...

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 suc...

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 experien...

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 evo...

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...

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 becomi...

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...

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...

In recognition of April as Financial Literacy Month, this episode explores a critical question in employee ownership—why financial literacy matters when employees are given ownership but do not fully understand its value. Jason Miller and Makenzie Wirth discuss the role of financial literacy in employee ownership and Employee Stock Ownership Plan environments, and why understanding concepts like e...

What’s the right first question when an owner starts exploring an ESOP? It may not be “Can my company do one?” In this episode, we unpack why technical possibility and strategic fit are not the same thing. Using the metaphor of the kitchen in a family home, we explore what owners are really trying to preserve, strengthen, and pass on through transition — and why an ESOP works best when it supports...

In this episode of the Foundations of Transition series, Jason and Makenzie focus on the theme of Communication, Culture & Trust, exploring how these elements shape the success of an 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...