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#441: What Happens After You Sell the Business? with John Rood
What really happens when an entrepreneur sells their business? For John Rood, it was the start of a deeply personal reckoning with identity, purpose, risk, and time. In this episode, we go beyond the typical exit story and talk about what it actually feels like to step away from the company you built—and what comes next when you’re no longer busy, no longer needed, and no longer sure what’s next.
Watch on YouTube
John is the author of Beyond the Exit, a book that captures the stories and lessons of dozens of founders who’ve exited their companies and found themselves struggling to rebuild meaning and structure in their lives. In this conversation, we talk about the psychology of letting go, why retirement is a myth, and how most owners get trapped by the very businesses they created—even long after a liquidity event.
We also dig into the false choices entrepreneurs are sold (retire or keep grinding, sell or stay), and how to reclaim your time and purpose without blowing up your identity. If you’ve ever wondered what the other side of a successful exit really looks like, this conversation will change how you think about freedom.
Key Takeaways for Owners
- Exit isn’t about the check—it’s about who you’ll be when the job title is gone.
- You can’t plan your next chapter after the LOI. You have to start before you even think about selling.
- Most owners underestimate how much identity, relevance, and momentum come from their business.
- Purpose after the exit won’t show up on its own—you have to design it.
- Time is your most valuable asset—but only if you know how you want to spend it.
John Rood is the author of Beyond the Exit, a book that explores what really happens to founders after they sell their companies. Drawing from interviews with over 200 post-exit entrepreneurs, John dives deep into the emotional, strategic, and philosophical side of life after business ownership. He previously built and sold a successful marketing company and now coaches a select group of founders on how to navigate the messy middle between liquidity and meaning. His perspective is rooted in experience and research—and he's one of the clearest voices on what freedom, relevance, and contribution look like after the deal closes.
Chapters:
Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by Design™, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals.
With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by Design™ to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast.
Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around.
Resources:
John Rood LinkedIn: https://www.linkedin.com/in/johnrood1/
Beyond the Exit
IBD Owner’s Scorecard: Time, Cash Flow, Equity trade-offs https://ryantansom.com/clarify-goals
Independence by Design™ Workshop: https://ryantansom.com/independence-by-design-workshop
Independence by Design™ Ownership Coaching: Ryan Tansom’s Ownership Accelerator programs and coaching https://ryantansom.com/coaching
Ryan Tansom Website https://ryantansom.com/
Ryan Tansom LinkedIn https://www.linkedin.com/in/ryantansom/
Ryan Tansom Twitter https://twitter.com/RyanTansom
Ryan Tansom YouTube https://www.youtube.com/@ryantansom
Ryan Tansom 30-Minute Ownership Strategy Call https://calendar.app.google/tsKk7z6ohugDchWq8
Sound Bites
- "Entrepreneurs are really good at doing hard things—yet they trap themselves in businesses they’ve outgrown."
- "Freedom doesn’t mean doing nothing. It means choosing how to spend your time—and knowing what makes that time meaningful."
- "You don’t need another business. You need to figure out why you feel like you do."
- "Most exits solve for money—but leave owners with unanswered questions about identity, relevance, and contribution."
View all episodes
What really happens when an entrepreneur sells their business? For John Rood, it was the start of a deeply personal reckoning with identity, purpose, risk, and time. In this episode, we go beyond the typical exit story and talk about what it actually feels like to step away from the company you built—and what comes next when you’re no longer busy, no longer needed, and no longer sure what’s next.
Watch on YouTube
John is the author of Beyond the Exit, a book that captures the stories and lessons of dozens of founders who’ve exited their companies and found themselves struggling to rebuild meaning and structure in their lives. In this conversation, we talk about the psychology of letting go, why retirement is a myth, and how most owners get trapped by the very businesses they created—even long after a liquidity event.
We also dig into the false choices entrepreneurs are sold (retire or keep grinding, sell or stay), and how to reclaim your time and purpose without blowing up your identity. If you’ve ever wondered what the other side of a successful exit really looks like, this conversation will change how you think about freedom.
Key Takeaways for Owners
- Exit isn’t about the check—it’s about who you’ll be when the job title is gone.
- You can’t plan your next chapter after the LOI. You have to start before you even think about selling.
- Most owners underestimate how much identity, relevance, and momentum come from their business.
- Purpose after the exit won’t show up on its own—you have to design it.
- Time is your most valuable asset—but only if you know how you want to spend it.
John Rood is the author of Beyond the Exit, a book that explores what really happens to founders after they sell their companies. Drawing from interviews with over 200 post-exit entrepreneurs, John dives deep into the emotional, strategic, and philosophical side of life after business ownership. He previously built and sold a successful marketing company and now coaches a select group of founders on how to navigate the messy middle between liquidity and meaning. His perspective is rooted in experience and research—and he's one of the clearest voices on what freedom, relevance, and contribution look like after the deal closes.
Chapters:
Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by Design™, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals.
With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by Design™ to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast.
Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around.
Resources:
John Rood LinkedIn: https://www.linkedin.com/in/johnrood1/
Beyond the Exit
IBD Owner’s Scorecard: Time, Cash Flow, Equity trade-offs https://ryantansom.com/clarify-goals
Independence by Design™ Workshop: https://ryantansom.com/independence-by-design-workshop
Independence by Design™ Ownership Coaching: Ryan Tansom’s Ownership Accelerator programs and coaching https://ryantansom.com/coaching
Ryan Tansom Website https://ryantansom.com/
Ryan Tansom LinkedIn https://www.linkedin.com/in/ryantansom/
Ryan Tansom Twitter https://twitter.com/RyanTansom
Ryan Tansom YouTube https://www.youtube.com/@ryantansom
Ryan Tansom 30-Minute Ownership Strategy Call https://calendar.app.google/tsKk7z6ohugDchWq8
Sound Bites
- "Entrepreneurs are really good at doing hard things—yet they trap themselves in businesses they’ve outgrown."
- "Freedom doesn’t mean doing nothing. It means choosing how to spend your time—and knowing what makes that time meaningful."
- "You don’t need another business. You need to figure out why you feel like you do."
- "Most exits solve for money—but leave owners with unanswered questions about identity, relevance, and contribution."