How a college dropout built an AI edtech with $6.5 million ARR in two years

David Park started with a high school clothing brand. Now he's got a $30 million AI startup. He's 27. Four failed startups in eight years. Dropped out of college. Got cancer while building Jenni AI. His AI assistant is now used worldwide. Here's what happened.

From t-shirts to tech

David got started early. His first business was a clothing brand he launched in high school. It failed and he lost all his money. But seeing people he didn't know wearing his products gave him a passion for building valuable products.

He dropped out of college to go full-time on his first tech startup after raising money from someone he met on a plane. This business also failed.

Next, he tried building a dating app and an app that allowed users to add people to different social media platforms. Sadly, these startups failed as well.

David's college friends got jobs at big tech companies. He was still living with his parents, working on ideas that weren't taking off.

The failures hurt but he kept going.

"You can always fail. You can fail at something you don't love, so you might as well fail at doing what you love."

From MVP to billion-dollar idea

David's failures taught him about products, users, and startups. The Jenni AI idea came from his literature background and his co-founder's engineering skills.

The two were interested in building something in natural language processing.

Jenni AI’s MVP was built on top of GPT-2 and helped writers write 10-20 percent faster. That’s all it did. They built an agency around it and the product was used as an internal tool by writers working for this agency that offered content services.

Then GPT-3 came out. It could write useful stuff. They switched from agency to SaaS, making a product for everyone.

Finding their Ideal Customer Profile was a struggle. But they were able to do it and it helped them land on a billion-dollar idea.

Stripping features to build a better Jenni AI

Jenni got better by removing features. Cutting stuff made the product and vision clearer.

David cold called to get customers. He talked to users to understand their needs. They found students were using it a lot. So they focused on building for academics and researchers.

"Prioritize talking to users more than anything else. More than money. Don't ask them questions to fluff yourself up. Ask them about their pain points, current flow, and the bad things about your product."

Almost dying before growing to $6 million ARR

Jason Calacanis, an early Uber investor, put $100,000 into Jenni AI after a tip from one of his scouts.

At the time, Jenni was making $2,000 a month and wasn't growing. The founders moved to Malaysia to save money.

For almost eighteen months, Jenni's revenue stayed flat at $2,000 a month. They were nearly out of funds when David almost lost a $250,000 deal with a Korean VC due to a simple oversight.

He managed to save the day by raising money from another US investor to extend their runway.

Jenni's big break came from a viral X thread by Zain Kahn, the founder of Superhuman. This led to a huge influx of users, with the website getting 10 users every second.

After that, Jenni AI grew 15-20 percent month-over-month using various distribution tactics. Today, they have an annual recurring revenue of $6.4 million and a monthly EBITDA of $150,000.

“Being a founder, you have to be more disciplined than the person waking up every day, showing up to every meeting because there's an insane amount of responsibility.”

Free tier, big annual discount, and an influencer program

Jenni has a simple freemium model. The free tier offers 200 words per day. The paid plan is $30 per month for unlimited words. The annual plan gives a 60 percent discount, much higher than the usual 10-20 percent.

Jenni AI runs an influencer program for TikTok, Instagram, and Twitter creators, paying them $15 for each subscriber they refer to them, and $5 per month for every retained user. 

Growing 27,000% in 2 years with 3 team members

Jenni AI's marketing team is three people, including David. They grew from $2,000 to $533,000 monthly revenue in under two years following their fortunate breakthrough. 

They focused on four key channels for marketing: organic short-form content, influencer marketing, SEO, and paid ads. Their "POV: You have an essay due" series alone got over 300 million views and more than half a million dollars in revenue.

For influencers, they made lots of small bets instead of relying on large influencers. They aligned incentives, used performance-based pay, and tailored content for the audience of every influencer.

SEO efforts ran parallel to other growth channels, targeting featured snippets, increasing brand name searches, and optimizing site structure for search engines.

They did some paid ads at first. Scaled up after product-market fit, ensuring that they make $3 for every ad dollar spent.

"A young marketer with TikTok brain rot who has a great work ethic will often times outperform the "established" digital marketing agency with a ton of fake Google reviews."

The road to $10 million ARR

Jenni AI is aiming for $10 million annual revenue this year. David's not worried about big tech yet. Schools still have AI doubts. That's their chance.

"A small tool that is specialized is often more valuable than a larger tool that's broad but doesn't solve the deep pain points for the target users."

The Cancer diagnosis

David's biggest challenge came in the form of a health scare: a cancer diagnosis. He got it right when Jenni AI started taking off. But after receiving surgery a few months later, he became cancer-free.

"Three month difference between possible death and fulfilling a lifelong dream. The startup life is truly a roller coaster."

Go big on short-form

Jenni AI's short videos went big. Nearly 250 million views. They made $1-2 per thousand views.

David says going viral with AI on short-form platforms is “ridiculously easy”. His advice: use these platforms for distribution of AI products as their demos are generally flashy and impressive, making them perfect for these channels.