The Owner's Playbook

In this episode of The Owner’s Playbook , Carol Dewey discusses one of the most overlooked threats to a business owner’s long-term wealth: unnecessary taxes. While many owners focus heavily on revenue, growth, and profit, fewer pay attention to how much of that success actually reaches their personal balance sheet. Carol explains the “success trap,” where a business may grow larger and more profit...

In this episode of The Owner’s Playbook , Carol Dewey breaks down an important distinction every business owner needs to understand: tax preparation and tax strategy are not the same thing. Many business owners rely on their CPA to prepare returns, file forms, meet deadlines, and keep them compliant. Those responsibilities are important, but they do not always reduce future tax burdens or help own...

Building a successful business is one thing. Building a business that supports your life—and eventually gives you the freedom to exit on your terms—is something entirely different. In this episode of The Owner’s Playbook , Carol Dewey brings together the key themes from this series and introduces the framework she uses to help business owners move from feeling stuck inside their businesses to crea...

Many business owners build successful companies but still feel trapped inside the very thing they created. Revenue grows, responsibilities increase, and over time success can begin to feel less like freedom and more like pressure. In this episode of The Owner’s Playbook , Carol Dewey explores the critical shift from building income to building true wealth. Through the story of “Lisa,” a successful...

Many business owners assume that years of hard work, steady revenue, and business growth will naturally translate into long-term wealth and freedom. But beneath the surface, hidden risks often exist—risks that slowly erode business value over time without being immediately visible. In this episode of The Owner’s Playbook , Carol Dewey explores the unseen gaps that prevent many businesses from beco...

Many business owners spend years—sometimes decades—building successful companies, generating income, and creating value. Yet despite outward success, many have never built a clear strategy for how they will eventually step away from the business on their own terms. In this episode of The Owner’s Playbook , Carol Dewey explains why most owners do not have a strategy problem—they have a coordination...

In this episode of The Owner’s Playbook , Carol Dewey breaks down one of the most powerful drivers of business valuation: recurring revenue . While many business owners focus on growing revenue, buyers focus on predictability . Recurring revenue reduces risk, increases visibility, and ultimately drives higher valuation multiples. Carol explains why restructuring revenue not just growing it—is the...

In this episode of The Owner’s Playbook , Carol breaks down one of the most misunderstood concepts in business: revenue does not equal value . While many entrepreneurs focus on top-line growth, buyers focus on predictable, transferable cash flow . Carol explains why margin, discipline, and financial structure—not revenue alone—determine your company’s true worth and exit potential. Key Takeaways R...

In this episode of The Owner’s Playbook , Carol Dewey tackles one of the most common barriers to business growth and valuation: owner dependence. When everything flows through the owner—sales, decisions, relationships, and strategy—the business becomes a hub-and-spoke model , where the owner is the center. While this structure may work in the early stages, it ultimately limits scalability and lowe...

In this episode of The Owner’s Playbook , Carol Dewey delivers a powerful leadership message: the greatest threat to your company’s valuation may not be the economy, competitors, or regulation — it may be unexamined leadership. Many entrepreneurs build profitable businesses, but not transferable assets. When everything depends on the owner, valuation drops, scalability stalls, and exit potential s...

In this episode of The Owner’s Playbook , Carol Dewey breaks down one of the most powerful drivers of company value: Monopoly Control — your competitive moat. Monopoly Control is your pricing power. It’s what protects your profits, strengthens your valuation, and makes your business the first, best, or only choice in your market. Carol explains why specialization beats generalization, how buyers e...

In Part 2 of the Hub and Spoke series, Carol Dewey focuses on how business owners break free from owner dependence by evolving their leadership. This episode shifts from diagnosis to solution—showing why scaling a business requires scaling the owner first. Carol explains how moving from operator to architect unlocks growth, enterprise value, and personal freedom, and why leadership capacity—not ef...

In this episode, Carol Dewey breaks down one of the most common—and costly—business owner traps: the hub and spoke model , where the owner becomes the center of every decision, relationship, and operation. While this structure may work early on, it eventually limits growth, reduces enterprise value, and traps owners inside their own businesses. Carol explains why owner dependence kills scalability...

In this episode of The Owner’s Playbook , Carol Dewey explains why preparation—not reaction—is the key to business freedom and successful transitions . As 2026 approaches, she outlines how business owners can move from intention to execution by preparing financially, operationally, strategically, and personally. This episode reframes traditional financial planning through an entrepreneurial lens,...

In this launch episode of The Owner’s Playbook , host Carol Dewey sets the foundation for what this podcast is all about: understanding the end game of business ownership. Drawing from nearly two decades of working with business owners, Carol introduces the core themes that will shape the entire show. She explains the universal truth that every owner will eventually exit their business and highlig...

In this episode of The Owner’s Playbook , Carol Dewey breaks down two of the most critical drivers of business value: financial performance and growth potential . She explains why many owners operate without clear financial visibility and how that lack of insight affects value, scalability, and long-term freedom. Carol explores how financial statements reveal the true story of a business and why p...

In this episode of The Owner’s Playbook , Carol Dewey explores one of the most important drivers of company value—the Switzerland Structure , a measure of how independent and diversified a business truly is. Carol breaks down why overdependence on a single customer, vendor, key employee, or even the owner is one of the biggest hidden risks in business ownership. She discusses how dependence erodes...

In this episode of The Owner’s Playbook , Carol Dewey explores one of the strongest drivers of business value: recurring revenue . She breaks down why predictable income improves stability, strengthens decision-making, and dramatically increases valuation—often doubling multiples compared to businesses built purely on one-time transactions. Carol explains the true meaning of recurring revenue beyo...

The Owner’s Playbook is a podcast for business owners who want to think differently about the future of their company. Hosted by Carol Dewey, founder of Claris Advisory Partners, the show opens the conversation most owners delay for far too long—the end game. It’s not about the end of the business, but the beginning of freedom. Every episode explores how to build a company that can thrive without...