Non-tech college dropout builds $30M AI startup

The struggles and lessons from the journey of Jenni AI’s founder

David Park was an average teen.

But unlike most of his friends, at 16, he was more into starting businesses than high school things.

His first business was a cool clothing brand that he ran from his bedroom.

You can say it was a bedroom-based startup.

Spoiler alert: It failed spectacularly, and he lost all his money.

But it was just the beginning.

David was on his way to build Jenni AI, a $30M AI startup that’s growing fast.

The birth of Jenni AI

Each setback taught him something new.

He wanted to build something big.

Between college, side gigs, and a lot of rejections, he started to question if he was just dreaming too big.

Like trying to build a spaceship kind of big.

But then came along Henry, his perfect co-founder who could code.

Illustrated portrait of David Park and his co-founder Henry.

Despite his past failures, David didn’t give up.

He saw each setback as a stepping stone to greatness.

College felt like a pair of too-tight jeans to him—restrictive and kinda unnecessary.

It felt like it was holding him back from his real goals.

The real tug-of-war?

Degree vs. dreams.

He couldn’t ignore his gut feeling any longer.

He packed his dreams (and probably some socks) and dove head-first into the startup world, with Henry as his partner in not-crime.

They were young, eager, and ready to make a splash.

The future was theirs to shape, and they couldn’t wait to start painting it with their ambitions.

David and Henry knew that AI was getting big and started looking for ideas.

Illustrated portrait of David Park and his co-founder Henry brainstorming.
Illustration of David Park playing around with ChatGPT 2.
Illustrated portrait of David Park and his co-founder Henry getting excited to find out what ChatGPT 2 can do.

They built Jenni AI, an academic AI assistant that helps users with research and, writing and everything in between.

Then reality smacked them hard.

They were struggling to get enough users.

Cold calls weren’t working, investors weren’t buying in, and ramen became their staple food.

Their apartment turned into a live-work-noodle space.

Every rejection made them doubt, but they didn’t let it kill their spirit.

Every “No” just made them more determined, every setback was a hard-earned lesson.

David even pitched to a random person on an airplane just because they looked like a successful, wealthy person.

Illustration of airplane where David Park approaching to a stranger in it.
Illustration of David Park pitching his startup idea to a stranger in it.
Illustration of stranger replying to David Park's pitch in the airplane.

David and Henry poured their hearts and souls into Jenny AI.

At first, it seemed like they were onto something big.

Then, growth hit a snooze button.

Turns out, users were giving Jenni a “meh” rating, not the love letter they hoped for.

The real issue?

The duo realized they needed to really get what users/writers love, not just add more bells and whistles.

Putting egos aside, they got down to the nitty-gritty with users’ feedback.

They made more calls than a telemarketer and sent out surveys like it was going out of style, discovering that Jenni needed to be less of a tool and more of a writing buddy.

Armed with these insights, they transformed Jenni.

They cut the unnecessary fluffs and kept only the features their users really needed.

And just like that, user engagement started growing.

This was more than an update; it was Jenni’s rebirth, proof that listening to users and evolving was the key to moving forward.

The first 100 users

Jenni AI’s journey to its first 100 users involved a focused and manual effort by leveraging influencers within niche communities.

They identified key influencers and engaged with them directly, ensuring these early adopters were genuinely interested in and saw value in the product.

This strategy of “influencing the influencers” allowed for a grassroots growth approach, where genuine endorsements and word-of-mouth played a crucial role.

Their luck turned significantly when a tweet highlighting useful websites, including Jenni AI, went viral, attracting a massive influx of users.

This unexpected exposure was a game-changer, significantly boosting their user base and visibility.

For TikTok advertising, Jenni AI adopted a creative and relatable strategy by crafting ads that didn’t immediately appear as promotions.

They focused on common struggles, like last-minute essay writing, making their ads highly engaging and relatable.

This approach ensured viewers were invested in the content before even realizing it was an ad, leading to a successful marketing campaign on the platform.

Here’s an example of the video they used:

The luck

The road was still rough for David and Henry.

Money was tight, competitors were popping up left and right, and burnout was sneaking around the corner.

But they kept at it.

Then, out of nowhere, a podcast chat about Jenni with a small podcaster who had a tiny number of listeners caught the attention of Jason Calacanis, a well-known investor and co-host of All-in-Podcast.

Jason became the first investor of Jenni AI.

He decided to put $100,000 into David’s venture.

Illustrated portrait of Jason Calacanis.

Then, they immediately moved to Malaysia because the duo didn’t want to run out of money fast.

Everything in Malaysia is one-fourth of the price in the US.

They could survive for a little longer there.

The cancer

Because of a viral tweet tweeted by content creator Zain Khan, Jenni AI had a crazy influx of users.

After that, the growth didn’t stop.

They were able to figure out some growth tactics every month.

Just as they were doing super well and everything was up in the air, life threw a curveball—David got diagnosed with thyroid cancer.

David’s spirit was about to be tested like never before.

Illustrated portrait of David Park at a hospital when he was diagnosed with cancer.

When David faced his health battle, it didn’t slow them down.

Instead, the Jenni AI team pulled even closer, turning their challenge into a source of strength.

Together, they kept building and growing, showing that even the toughest times could bring out their best.

Wrapping up

Fast forward, and Jenny AI has now become a $30 million giant. 

It was a wild ride, full of ups and downs, but David and Henry’s never-quit attitude, their knack for bouncing back, and their drive to keep evolving pushed them to the top. 

David’s journey from his bedroom to the big leagues wasn’t smooth. 

Every no, every stumble, made him stronger. 

Cancer didn’t beat him; it just made him fight harder, both for his life and his dreams. 

Jenny AI’s success was more than just numbers; it was a symbol of hope, showing that relentless belief and adaptability can turn even the boldest dreams into reality.

Illustration of David Park looking out to the city and thinking about his dream and goals.

David’s tale isn’t just about Jenni AI’s rise; it’s a shout-out to anyone ready to chase their dreams. 

Got an idea? Eager to solve a problem? Don’t let fear stop you. 

The road’s rough but rewarding. 

Fail, learn, bounce back. 

Most importantly, believe—in yourself, your vision, and that no dreams are out of reach. 

Illustrated portrait of David Park saying inspiring words to people who are failing.

That’s a wrap.

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