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Exit, Rest, Restart: Rob Walling on Navigating the Entrepreneurial Lifecycle

Rob Walling

At the age of 41, Rob Walling sold Drip, an email marketing software, for enough money that he “would never have to work again.”

His only problem? Figuring out what to do next.

In this special edition of Built to Sell Radio, we explore how to redefine your purpose and find happiness and fulfillment after you exit your business.

You’ll discover how to:

  • Decide when to sell your business.

  • Calculate your minimum number.

  • Manage your mental health during an earn-out.

  • Leverage “The 6th Month Rule.”

  • Spot the early warning signs of entrepreneurial burnout.

  • Talk to your kids about being rich.

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More About Rob Walling

Rob Walling is an accomplished entrepreneur with a focus on bootstrapping Software as a Service (SaaS) ventures. He is the mastermind behind TinySeed, the premier startup accelerator specifically tailored for SaaS bootstrappers. As an investor, Rob has backed over 35 startups and is the author of the seminal book on bootstrapping, “Start Small, Stay Small.”

Beyond that, he hosts the long-running podcast “Startups for the Rest of Us,” which boasts a decade of episodes, exceeding 500 in number and garnering over 10 million downloads. His insights and expertise have been featured in leading media outlets such as The Wall Street Journal, Forbes, Entrepreneur, and Inc. Magazine.


18 questions to ask yourself on a founder’s retreat.

  1. What is my ultimate vision for the business?

  2. Do I still feel passionate about what I’m doing?

  3. What are my core values and how well does the business align with them?

  4. Am I growing for ego or opportunity?

  5. What would make me consider selling the business?

  6. What’s my “Minimum Number” for financial freedom?

  7. How sustainable is my current work pace?

  8. Am I leading or just managing?

  9. What are my top three priorities for the next quarter?

  10. How would the business run if I stepped away for two months?

  11. Do I have the right team to reach my goals?

  12. What are the weak links in the business?

  13. What am I avoiding or procrastinating on?

  14. What can be automated or delegated?

  15. What are the biggest threats to the business?

  16. Is my product or service a vitamin or a painkiller?

  17. How do I define success personally and professionally?

  18. What will I do if the business achieves all its goals?

Do You Know What the Value of Your Business is?

Take our Value Builder Assessment to get a free estimate of business value and see how your company stacks up against the 8 Key Drivers of Business Value.


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