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    Home»Entrepreneurship»From Failure to Failure to a $25 Million AI Startup: The Incredible Journey of the Creator of Jenny AI
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    From Failure to Failure to a $25 Million AI Startup: The Incredible Journey of the Creator of Jenny AI

    Afonso NevesBy Afonso NevesJune 12, 2025Updated:June 17, 2025No Comments4 Mins Read4 Views
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    In the fast-paced world of tech startups, few stories are as inspiring and full of twists and turns as that of David Park. In just two years, David transformed an AI app idea, Jenny, into a company valued at $25 million. But the road to success was far from easy, marked by rejections, financial hardships, and a personal challenge that almost made him give up on everything.

    This is a story of resilience, vision, and the power of perseverance that every geek and entrepreneur needs to know. You can follow the full story, told by David himself, in the video below.

    Watch the full story on YouTube here

    Coming from a family of entrepreneurs, David Park felt the call of the business world from an early age. His first venture, a clothing brand at 16, “failed spectacularly,” in his own words. Feeling like a fish out of water in college, he dropped out to pursue his startup dreams.

    The turning point came when he met his co-founder, Henry, an AI enthusiast. Together, they explored the potential of the then-emerging GPT-2. The “eureka” moment came in an unexpected way: a hilarious and nonsensical phrase generated by the AI about a “butthole” convinced them of the technology’s potential. Thus, Jenny was born, an AI tool designed to help agencies create high-quality content.

    The Desert of Rejection and Unconditional Support

    The early days of Jenny were “a terribly painful time.” Working from his parents’ bedroom, without a penny to his name, David spent his days and nights making cold calls, facing a constant wave of rejection. In those moments of despair, when he felt like a “real loser,” it was the unwavering support of his parents, especially his mother, that kept him afloat, ensuring he never lacked food or faith in his project.

    The Plateau and the Most Valuable Lesson: Listening to Users

    Despite a promising start with the advent of GPT-3, Jenny stagnated, hitting a ceiling of $2,000 in monthly revenue. It was then that David learned one of the most crucial lessons for any entrepreneur: the importance of talking to users. By asking the tough questions about what his customers disliked about his product and what they loved about competitors, he discovered a new direction. Users didn’t just want a tool; they wanted “a friendly AI-assisted writing journey.” This new vision allowed them to refine the product and attract a new audience.

    With finances at zero, a stroke of luck changed Jenny’s course. David’s appearance on a random podcast reached the ears of a scout for Jason Calacanis, who invested a miraculous $100,000 in the company. To stretch the investment, David and Henry moved to Malaysia, drastically reducing costs. Shortly after, a viral Twitter thread created by Zay Khan triggered an avalanche of new users, catapulting the monthly revenue from $2,000 to $10,000 in a single month.

    Leveraging the power of social media, they brought in a college friend to manage TikTok and Instagram Reels, which generated a second wave of virality. However, at the height of success, when the company was reaching between $50,000 and $80,000 in monthly recurring revenue, David received devastating news: a cancer diagnosis. He felt that his dreams and nightmares were happening simultaneously.

    The Decision to Double Down and the Climb to $25 Million

    The cancer diagnosis led David to consider selling Jenny, fearing the company’s instability in his absence. However, after deep reflection, he decided not to give up. Instead, he doubled down, focusing on hiring talent for marketing and growth and implementing strategies to scale content creation on platforms like TikTok.

    The decision could not have been more right. After a decade of attempts and failures, David achieved resounding success in just 18 months, a testament to the discipline and sacrifice that the entrepreneurial life demands. Looking back, he recognizes that not selling Jenny at that critical moment was a crucial decision, as the company’s value has increased exponentially since then.

    The journey of David Park and Jenny AI is a powerful lesson on the importance of resilience, adaptability, and never underestimating the power of a good idea, even if it starts with a joke about “buttholes.” It is proof that, even in the darkest moments, perseverance can lead to results that exceed all expectations.

    AI startup angel investment bootstrapping David Park founder story Jenny AI monthly recurring revenue (MRR) product-market fit startup growth viral marketing
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