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Founder Mode – Episode 13 – Building AI Before It Was Cool with Dennis Mortensen

by Jason Shafton

Episode 13: Kevin Henrikson and Jason Shafton sit down with serial entrepreneur Dennis Mortensen (IndexTools, Visual Revenue, x.ai, and now LaunchBrightly) to unpack what it was really like to build an AI company years before large-language models existed. Dennis recounts owning the x.ai domain before Elon, hand-labeling 32 million emails to train an early scheduling agent, and the costly product-design decisions that followed. He shares hard-won lessons on focusing on pain over technology, reverse-engineering post-acquisition goals, and why parenting teenagers is the ultimate sales boot camp. Dennis then introduces LaunchBrightly, his new platform that automates every product screenshot in your help center—and he caps the chat with an exclusive free setup offer for Founder Mode listeners.

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