The Story
David Park built Jenny AI to a $25 million valuation in just 2 years - after a decade of failing. He started his first company at 16, and at 27, that's 11 years of gut punches before finding success in the last 18 months.
David grew up in a family of entrepreneurs. In seventh grade, he dreamed of being a founder. His parents gave him $20,000 for college, hoping he'd become a lawyer or doctor. But he didn't fit in anywhere - not in his fraternity, not with people in his major. He dropped out to chase his startup dreams.
He met his co-founder Henry, who loved AI while David loved writing. Together they failed at 9-10 startups. Then they stumbled upon GPT-2, asked it to tell a story, and it spit out: "Nothing is darker than a butthole." That profound/hilarious line convinced them to create Jenny AI - a tool to help agencies write better content with AI.
Key Insights
The Painful Beginning
- •Cold called agencies 8 hours a day for weeks
- •99% rejection rate
- •Worked from parents' bedroom day and night
- •Had to ask mom for her card to buy Chipotle
- •"I was a real loser" - but parents never made him feel that way
The $100K Miracle
- •Went on a random podcast with few listeners
- •A scout for Jason Calacanis happened to listen
- •Got a $100,000 check
- •First thing: Booked flight to Malaysia to cut burn rate by 75%
- •"I didn't feel successful - now the real dirty work was getting started"
The Viral Breakthrough
- •Stuck at $2,000/month for a while
- •Key learning: Talk to users, ask difficult questions
- •"Why do you dislike my product? What do you love about OTHER products?"
- •Zay Khan posted a viral Twitter thread featuring Jenny AI
- •Went from $2K to $10K MRR in one month
Scaling with Social Media
- •Brought on college buddy for TikTok/Instagram Reels
- •Experienced second wave of virality
- •Strategy: Start TikTok account → Try different formats → Find one that works → Turn into series → Multiply accounts with multiple creators
- •Pay creators baseline + incentives for views/conversions
The Cancer Diagnosis
- •At $50-80K MRR, got thyroid cancer diagnosis
- •"Dreams and nightmares happening at the same time"
- •Surgery complications, fever, rescheduled
- •Saw Bible verse on ceiling: "Leave everything to God" - same verse his mom wanted to tell him
- •Voice recovered after surgery
The Decision Not to Sell
- •Shopped Jenny for acquisition after cancer
- •Could have cashed out for a few million
- •"It didn't feel right to throw my cards in early"
- •Within 6 months: More than doubled the business
- •Would have sold for $3M → Now worth $10-30M
Growth Timeline
- •$2K → $10K MRR (viral Twitter thread)
- •$10K → $50-80K MRR (social media scaling)
- •$80K → $250K+ MRR (post-cancer doubling)
- •Current: $3M+ ARR, $25M valuation
Key Advice
"I started my first company at 16, I'm 27 now - that's a decade of failing. I only got any semblance of success in the last 18 months. You can't give it a one-week shot. You can't even give it a year shot. You have to put your all into it, sacrifice everything for many years, and then you have a shot - maybe a chance at success. Even if you put your all into it, there's a chance you will fail. If you still try despite knowing you could lose everything, that must mean you really care about what you're building."