#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.

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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: 

• (00:00) Reconnecting with John: Life and identity 4 years post-exit
• (07:00) The identity crisis and status shift entrepreneurs face after selling
• (14:00) Why planning your post-exit life must happen before the LOI
• (21:00) Liquidity concerns and risk assessment: Why timing matters for exits
• (28:00) Time, cash flow, and wealth: The three constraints of business ownership
• (35:00) Find