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, helping owners understand how to convert business value into personal freedom, reduce owner dependence, and create real optionality for the future.

The Power of Preparation- Your …

1. Preparation is a strategy, not a response to crisis
2. Traditional financial planning is not built for business owners
3. True readiness requires financial, operational, strategic, and personal preparation
4. Leadership capacity—not the market—is often the biggest bottleneck
5. 2026 will reward owners who are prepared, flexible, and intentional
6. The Power of Preparation- Your …

1. Get your numbers truth-ready
2. Build optionality into your business
3. Strengthen leadership and reduce owner dependence
4. Convert enterprise value into personal, tax-efficient wealth
5. Align your transition plan with purpose and next-chapter goals
6. The Power of Preparation- Your …

"If 2026 arrived tomorrow, would you be prepared—or reactive?"

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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 beyond subscription models and highlights how any business, in any industry, can identify and build predictable revenue streams. She walks through the six types of recurring revenue, ranked from weakest to strongest, and illustrates why predictability matters both operationally and emotionally for owners.

This episode also uncovers the mindset shift from chasing sales to building systems—turning consistency into freedom, stability, and long-term value.

• Why recurring revenue is one of the most powerful drivers of company value
• The difference between unpredictable sales and predictable income
• How recurring revenue impacts confidence, cash flow, and valuation
• Six categories of recurring revenue, from weakest to strongest
• Questions to help owners identify recurring revenue opportunities within their current model
• The strategic advantages of predictable income for hiring, planning, and long-term stability
• Why recurring revenue increases freedom by reducing the stress of starting each month from zero
• How predictable revenue signals loyalty, repeatability, and lower risk for buyers

• 21-Point Business Readiness Assessment
• Book: How to Beat the IRS Legally
• Value Builder Assessment

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 value, increases vulnerability, and limits the future options available to the owner. Through examples and practical breakdowns, Carol outlines the three major forms of dependence that quietly weaken a company’s stability and salability. She also highlights the indicators that reveal whether a business can run without its founder and what makes a company truly durable.

The episode then shifts to building independence through diversification, stronger systems, and leadership depth. Carol walks through the components that help a company operate “like Switzerland”—stable, neutral, and able to function regardless of changes in relationships or personnel.

• What the Switzerland Structure means and why it matters
• How dependence quietly reduces business value
• The three most common dependence traps
• Questions that reveal how independent your business really is
• Strategies for building diversification and reducing risk
• How systems, automation, and cross-training strengthen business stability
• Why independence increases freedom, resilience, and long-term value

• 21-Point Business Readiness Assessment
• Book: How to Beat the IRS Legally
• Value Builder Assessment

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 profitability alone doesn’t determine health. She also discusses the difference between being busy and performing, introducing the five financial levers that influence both value and sustainability.

The conversation then shifts to growth potential—how it’s measured, what impacts it, and why it determines the future options available to an owner. Carol highlights the elements that shape a company’s ability to scale, innovate, and operate without constant owner involvement.

• Why many business owners operate without a clear financial dashboard
• The difference between revenue, profit, and cash flow
• How to distinguish profitability from performance
• The five financial levers that drive value: revenue growth, margins, cash flow, reinvestment, and owner independence
• The “treadmill trap” of being busy but not building
• What defines true growth potential
• Four areas that reveal whether a business can scale: market opportunity, scalability, innovation, and talent depth
• The shift from operator to architect mindset

• 21-Point Business Readiness Assessment
• Value Builder Assessment
• Book: How to Beat the IRS Legally

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 highlights the reality behind why so many planned exits fall short. The episode breaks down the difference between income and transferable value, the importance of preparing early, and the common traps owners fall into when their business depends too heavily on them.

Carol also introduces key concepts that will recur throughout future episodes, including the wealth gap, the value gap, and the Eight Key Drivers of Company Value—focusing today on four foundational drivers:

• Financial Performance

• Growth Potential

• Monopoly Control

• Hub & Spoke

The launch episode frames exit planning not just as a business strategy, but as life planning. Carol shares how clarity, structure, and vision shape a business that can thrive beyond the owner and support the life they want after the exit.

• The purpose and vision behind The Owner’s Playbook
• Why every business has an end game
• National research on business sales and success rates
• The difference between income and transferable value
• The common “fatal trap” many owners fall into
• Introduction to the wealth gap and value gap
• Four key drivers that influence business value
• How alignment between business goals and life goals sets the stage for a successful transition

• Eight Key Drivers of Company Value
• Value Builder Score Assessment

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 you, grow with intention, and eventually be transitioned on your terms. Whether you’re planning to exit soon or simply want more clarity and control, The Owner’s Playbook helps you understand the strategies, structures, and mindset that shape a stronger, more valuable business.