The $100 MBA Show

MBA2626 Extended Interview: Rob Walling - How to Build and Sell Your Business without Regret

May 19, 2025
In this enlightening conversation, Rob Walling, founder of Drip and TinySeed, shares his insights on building and selling businesses without regrets. He discusses the essential elements of creating a sellable company, emphasizing sustainability and reducing founder dependency. Rob also addresses the emotional complexities of selling, including loyalty and the psychological journey that comes with letting go. Drawing from his new book, he offers practical strategies for entrepreneurs to prepare for an exit and highlights the importance of personal growth in this process.
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Building Sellable Business Keeps Options

  • Building for a sellable business keeps your options open and prevents burnout.
  • Entrepreneurs rarely want to grind the same business for decades in today's internet age.
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Make Business Independent for Sale

  • Build your business to not rely on you directly for sales, marketing, or fulfillment.
  • Create processes so others can run it if you're unavailable or unable to work.

Freedom Motivated Drip Sale

  • Rob Walling sold Drip to secure financial freedom rather than lifestyle luxuries.
  • He valued the freedom the sale offered over maintaining the business's current state.
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