The most common question we hear may seem simple, but it can significantly change the outcome of a deal. 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 discuss the unique tax advantages associated with each approach.

From S corporation tax exemptions to Section 1042 capital gains deferral, this conversation highlights the various factors that influence your decision, including ownership goals, liquidity needs, future growth plans, financing strategy, and long-term succession objectives. Whether you are just starting to explore an Employee Stock Ownership Plan (ESOP) or evaluating transaction structures, this episode provides a practical framework for understanding why there is no one-size-fits-all answer. The right structure depends on your specific goals and circumstances.

In this episode, Makenzie Wirth delves into the Mandela Effect and how our memories influence the stories we tell ourselves. Many business owners begin their exploration of Employee Stock Ownership Plans (ESOPs) with fragmented information they have gathered from the experiences of others—some of which may be accurate and some not. These stories can subtly influence significant decisions. Makenzie discusses the common misconceptions surrounding ESOPs, clarifies which elements are unique to each transaction, and highlights insights revealed during the ESOP process that can drastically alter how owners perceive employee ownership.

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, preparation, anxiety, and the very human need to reduce uncertainty. Then we connect it directly with business owners, founders, and leaders considering exit planning, including ESOP conversations. Our takeaway is that the algorithm is a dashboard, not a destiny, and attention becomes intention, intention becomes habit, and habit becomes character.

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 owners to move beyond simply reviewing financial reports. It focuses on interpreting what these numbers truly convey. Jason and Makenzie discuss how clear reporting, visibility into key performance drivers, and a deeper understanding of financial metrics can reduce uncertainty, strengthen decision-making, and prepare business owners for a smoother, more successful ownership transition.

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 may align with employee ownership. From addressing common assumptions around complexity, costs, strategic buyers, seller financing, management depth, company size, and control, this episode empowers advisors with the tools to ask the right questions and identify when an ESOP deserves a closer look. Don’t miss the opportunity to enhance your advisory practice and offer your clients informed and effective solutions!

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 and what companies should be doing now to prepare for upcoming deadlines. From building an annual ESOP calendar to coordinating with service providers, reviewing census data, participant statements, valuations, and distributions, this conversation highlights the year‑round planning and compliance practices every ESOP company must embrace to stay compliant and avoid surprises.

If you’re looking to strengthen your ESOP processes, improve audit readiness, and stay ahead of regulatory requirements, this episode is a must‑listen.

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.