How David Park Built Jenny AI Into a $25M Success Story

How David turned a decade of failures into Jenny AI, a $3M-a-year content-writing tool.

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Welcome to Money Making Story,

Today, we’re thrilled to share the story of David, who turned a decade of failures into Jenny AI, a $25 million SaaS business.

In this discussion, we’ll discuss his:

  • Top Advice from David

  • Early Ambitions and Struggles

  • A Decade of Failure and Finding a Co-Founder

  • Building Jenny AI

  • 9 Free LinkedIn Courses

  • The First Breakthrough

  • A Miracle Podcast

  • Scaling Jenny AI

  • A Life-Changing Diagnosis

  • The Future of Jenny AI

  • Lessons for Aspiring Entrepreneurs

  • A Story Worth Reading

Top Advice from David:

“You can’t give your dream a one-week or one-year shot. You have to sacrifice everything for many years, knowing there’s still a chance you might fail. But if you truly care about what you’re building, it’s worth it.”

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David Park’s journey is a testament to resilience, creativity, and the relentless pursuit of a dream. From working long hours in cold-calling in his childhood parents’ bedroom to leading a multimillion-dollar AI company, his story is a remarkable illustration of turning failures into stepping stones.

Early Ambitions and Struggles

David’s entrepreneurial journey began when he was just 16. Growing up in a family of entrepreneurs, he was inspired by the idea of creating something impactful. His first venture—a clothing brand—ended in failure, but it was just the beginning of a decade-long journey marked by setbacks and learning experiences.

Despite his parents’ sacrifices to send him to college, David felt out of place. His entrepreneurial spirit clashed with the traditional paths expected of him. Ultimately, he made the bold decision to drop out and dedicate himself to building a startup.

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A Decade of Failure and Finding a Co-Founder

David spent years hustling and failing, but he wasn’t alone. Along the way, he met Henry, a like-minded and equally passionate tech enthusiast. Together, they started over 10 failed startups, exploring ideas that ranged from AI tools to apps. Their turning point came with GPT-2.

“We asked GPT-2 to tell us a story, and it spat out, ‘Nothing is darker than a butthole.’ We couldn’t stop laughing—it was funny but also profound. That sentence convinced us to create Jenny.”

Building Jenny AI: The Turning Point

After several failed ventures, the duo stumbled upon OpenAI’s GPT-2, which they initially explored out of curiosity. A quirky line generated by the AI—“nothing is darker than a butthole”—sparked the idea that would eventually evolve into Jenny AI, a tool designed to help agencies create better content with AI assistance.

The early days of Jenny AI were grueling. David cold-called agencies for hours daily, faced constant rejection, and struggled to make ends meet.

“I called agencies for 8 hours a day for weeks. 99% of the time, they rejected me or hung up. I had no money and even had to borrow my mom’s card to buy Chipotle.”

Yet, he was sustained by the unwavering support of his family, friends, and co-founder.

9 Free LinkedIn Courses

The First Breakthrough: Learning from Users

In 2020, OpenAI’s GPT-3 was released, providing Jenny AI with a new level of sophistication. Despite initial traction, growth stagnated at $2,000 monthly revenue. The breakthrough came when David began actively engaging with users, asking hard questions about their needs and refining the product based on their feedback.

This user-centric approach paid off. By focusing on creating a friendly and practical AI writing tool, the team unlocked new growth opportunities.

A Miracle Podcast and a $100K Check

At his lowest point, David agreed to be interviewed on a small podcast. Unbeknownst to him, one listener was a scout for investor Jason Calacanis.

“Jason wrote us a $100,000 check. It was surreal—I’d been living off instant ramen and my parents’ cooking, and suddenly I had six figures to work with.”

David and Henry used the money wisely, moving to Malaysia to extend their runway and doubling down on refining Jenny.

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Scaling Jenny AI

With funding in hand, David and Henry relocated to Malaysia to stretch their runway. The real work began as they iterated on the product, eventually experiencing a surge of users following a viral Twitter thread that included Jenny AI. Revenue jumped from $2,000 to $10,000 monthly, a pivotal moment for the fledgling startup.

Recognizing the power of social media, they doubled down on viral marketing, leveraging platforms like TikTok and Instagram. This strategy propelled their growth, eventually surpassing $1 million in annual recurring revenue (ARR) and later reaching $3 million ARR.

A Life-Changing Diagnosis

As Jenny AI gained momentum, David was diagnosed with thyroid cancer. The news was devastating, as it threatened both his health and his ability to lead the company.

“The most worrying part was that my voice might be damaged. I thought about bolting out of surgery, but a Bible verse on the ceiling reminded me to leave everything to God.”

The diagnosis forced him to reflect on his life and the immense sacrifices he had made for his startup. Despite the emotional and physical toll, he chose not to sell the business. Instead, he doubled down, hiring talent and scaling the company further.

David’s resilience paid off. By focusing on effective strategies and scaling content production, the company’s valuation skyrocketed from a potential $3 million sale offer to over $25 million.

The Future of Jenny AI

Today, Jenny AI stands as a testament to what passion, grit, and adaptability can achieve. With millions in ARR and a growing user base, David’s dream of building something impactful has come true. Yet, his story isn’t just about business success—it’s about the human spirit’s ability to overcome adversity and thrive.

Lessons for Aspiring Entrepreneurs

David’s journey offers several key takeaways for aspiring entrepreneurs:

  1. Persistence is Key: Success often comes after years of perseverance and learning from failures.

  2. Talk to Your Users: Understanding customer pain points and workflows is crucial to building a product they love.

  3. Leverage Social Media: Viral marketing can be a powerful growth engine when done strategically.

  4. Trust Your Gut: Sometimes, the hardest decisions, like not selling early, turn out to be the most rewarding.

  5. Balance is Important: David’s story highlights the importance of finding time for loved ones and personal health.

David Park’s story is a powerful reminder that success doesn’t happen overnight. It’s the result of relentless effort, learning from failure, and staying committed to your vision. From $2,000/month to $3 million in ARR, David proved that persistence and adaptability can turn any dream into reality.

A Story Worth Reading

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