Rob Walling’s 20 Year Master Plan
Cash Machines
Rob Walling’s 20 Year Master Plan
May 15, 2025
In this episode of Confessions of a B2B Entrepreneur, host Tom Hunt chats with the legendary Rob Walling. A true veteran of the SaaS bootstrapping world, Rob shares insights from his two decades in the game, from building and selling Drip, starting the influential MicroConf community and the TinySeed accelerator, to hosting the 'Startup for the Rest of Us' podcast. They discuss the power of compounding effort, the crucial lesson of following market feedback, iterating your approach based on what the market wants, and the journey of building multiple successful ventures without relying on traditional VC. Rob reflects on the lessons learned over twenty years, offering invaluable perspective for any entrepreneur looking to build sustainable, long-term growth.



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