How a Chipotle burrito 🌯 led me to co-found a $6M ARR AI startup

I started my freshman year and met David Park because we were both looking for roommates. We met up at a Chipotle near campus.

We made our order (no guac), sat down, and talked about our interests. David told me about the T-shirt brand he built during high school. I shared about the computer games and Minecraft mods I built.

As we ate our burritos, an idea struck us: wouldn't it be cool if I built an app, and David marketed it?

Imagine how many $10 Chipotle burritos 🌯 we could earn!

So we started building.

2015: Social sharing app 👬

We spent our first year in college building a digital business card that shared your contacts with a single swipe. Like most naive founders, we didn't talk to users and built in stealth. We made an app nobody wanted and failed after launch.

We made 0 Chipotles 🌯

2016: Dating app ❤️

Our second product was a dating app that leveraged AI. At that time, I was taking machine learning classes and became interested in neural networks.

We thought: let's optimize finding long-term relationships using AI.

This time we finally got some users! But we just couldn’t figure out a monetization strategy. A profitable dating app is one that needs high retention and shouldn’t actually solve long-term relationships.

We still made 0 Chipotles 🌯

2017: Crypto trading 📈

Bitcoin was starting to become mainstream, and we had to jump into this hype.

I thought we could leverage AI to trade crypto and profit. David raised a $10K angel check for this idea by pitching to a stranger over a 3-hour flight. He framed the check on the wall in our living room.

We raised 1000 Chipotles 🌯

I bought NVIDIA Titan V GPUs and had it running in my closet while trying to train a model that could trade cryptos, but I couldn't get the trading algorithm to profit.

We lost 500 Chipotles 🌯

2018: AI Platform 🤖

I joined the PhD program at UCSD and researched music generation and language models with neural networks.

We thought: what if we could create an AI platform to let people upload their data, and we'll automatically train a deep learning model for them? AutoML was all the rage back then.

We spoke to some startups and even got an LOI. But those startups shut down a few months later and we lost all our customers.

We made 0 Chipotles 🌯

2019: Jenni AI 🖊️

When GPT-2 was released, we were excited about shipping something with language models. I dropped out of the PhD program and we both committed to our startup full-time. We started from our college basement with ~$5K starting capital.

Jenni started as a writing assistant for SEO content writing. We wanted to help SEO content marketers produce content faster using GPT-2.

To learn how SEO worked, we initially ran Jenni as a content mill and dogfooded our product. After a year, we scrapped the agency and launched our product as a SaaS.

We hovered at 100 Chipotles/mo 🌯

By then, COVID was at its peak, and marketing agencies were cutting back their spend, so it was hard to acquire new customers to fund ourselves. We applied to YC21 and got rejected. To extend our runway, we booked a one-way ticket to Malaysia to reduce our burn.

We built many iterations of Jenni but struggled with product market fit. One of our big SEO customers emailed us saying they wanted to churn from Jenni and use our competitor instead. We were losing in both distribution and product quality.

At that point, we were close to throwing down the towel. But there was one thing we noticed during these months that kept us going.

There was a group of users using Jenni actively despite us not marketing to them: college students 🎓. After interviewing these students, we discovered that they had pain points that nobody catered to, so we decided to pivot from SEO to academic writing.

With this pivot in mind, I aggressively pruned features in our product and optimized a single killer feature that delighted students. David experimented with many distribution strategies and cracked a formula for going viral on TikTok.

One morning, I was woken up at 5 AM by my co-founder calling me on the phone and telling me Jenni had gone down. Turns out we hit our OpenAI API limit because there were too many students signing up.

After 2 years of struggle, we finally had our first sign of PMF.

From that moment, we focused on scaling and strengthening our PMF. We continued to optimize the product, add features, and tune Jenni to solve more problems within an academic's research workflow.

Over the last 2 years, Jenni has grown 15% month-over-month to 250K monthly active users.

Now we make 60,000 Chipotles/mo 🌯

With guac 😎