The Underdog: From His Parent’s Basement to $25M | Starter Story

David Park spent nearly a decade failing before he built Jenny AI, a content-writing tool that reached a $25 million valuation in two years. The turning point came not from a brilliant product insight, but from a series of hard, unglamorous decisions: cold-calling for eight hours a day, moving to Malaysia to stretch a $100,000 investment, and choosing to double down on a shaky business rather than sell it after a cancer diagnosis. Park’s story is less about a single breakthrough and more about the grinding, iterative work of finding product-market fit and scaling content.

The Long Runway of Failure

Park started his first company at 16—a clothing brand that failed. Over the next nine years, he and his co-founder Henry tried roughly ten different startup ideas, all of which flopped. “The sum total of failed startups that we did together was probably nine or ten,” Park says. The idea for Jenny came from a silly experiment with GPT-2, which generated the line “nothing is darker than a butthole.” That absurd sentence convinced them to build an AI writing assistant for agencies.