Eight Years of Failure, Then Cancer, Then $30M Growth

Eight years of startup failures. Cancer diagnosis at 27. And still building a $30 million AI company that's growing 20% month over month.

David Park dropped out of college, burned through his life savings multiple times, and watched his friends graduate into six-figure Microsoft jobs while he lived with his parents, grinding on startups that weren't working. Most would have given up. He kept going.

Then, just as Jenni AI finally broke through with 2.5 million users and viral growth, he got the call that changed everything. In this raw conversation, David reveals how he built a thriving business while battling thyroid cancer, why boring days are harder than crisis days, and the counterintuitive truth about startup "failure."

David: My family wasn't rich, but my parents really gave me a lot of love, a lot of confidence. In a lot of ways that helped because I was able to believe in myself and do crazy things like start a company.

My first business was a clothing brand where I would just sell to people in my high school, sell to people in neighboring high schools. Obviously it was my first business - I failed pretty spectacularly, lost all my money. I was 16 years old. I was just naive. I didn't know the basics of business. I thought if you build something cool that's the most important thing. It's not enough to just make a t-shirt and then just give up and say now I'm gonna be a millionaire.

I remember the coolest moment of my life was when I sold clothes. I didn't sell that much, but I was at the mall one time and I saw this really tall athletic jock kind of guy, someone who would never really be my friend, and he was wearing one of the sweaters that I made. It was a really cool feeling because what I built was so valuable, what I built was so cool that he was willing to wear it. I think ever since then I've always been kind of interested in making products that provide value to people.

David: I went to UC San Diego. I was on a plane from Seattle to San Diego, and there's a guy sitting next to me. I saw he had Coinbase open - Coinbase is like how you trade crypto in America - and I realized he was probably pretty rich. So he was my captive prisoner for 3 hours. He couldn't leave. We were on a plane, so I could just continually pitch him my startup idea.

I think he was annoyed, but I think he recognized that I really cared about what I was building. Less than 3 days after the plane landed, we met up. He gave me a cashier's check - my first investment ever - and then I dropped out of college and immediately went full time.

David: My first business after was a social media app. I was in college and would meet so many people and they'd say 'add me on Snapchat' or 'add me on Instagram' or 'here's my LinkedIn.' So we made an app where you click one button and then you get added on Instagram, Facebook, Snapchat, LinkedIn all at once. It didn't do well. I didn't know how to get customers at the time. I didn't know network effects. We also weren't building for our users. We made a lot of poor product decisions.

Then I made a dating app startup which also failed. The dating app was actually pretty cool. It was like an AI dating app where you don't swipe at all. We use machine learning to look at your face and your previous partners to see who you might be physically attracted to, then look at your Facebook to see your interests, then try to find people. We partnered with restaurants in the city and set up your first date for you at a restaurant you both liked with a coupon. So it was like a concierge service, and the local businesses loved it because they got free customers.

But when I went to raise money, the VC said, 'I'm not gonna invest in your startup because we actually want them to stay on your dating app as long as possible. If they find a boyfriend or girlfriend and they get happy, they're gonna delete the app, not renew their subscription, and you're not gonna have a billion dollar business.'

Honestly, that was really sobering for me. I was still 19 or 20 at the time. When I heard that, I felt like I had just crossed the chasm into the adult world of venture capital. I was pretty disillusioned and we actually stopped working on that because that was such a crazy sobering moment.

David: When I failed my first startup it didn't feel good but it didn't feel that bad because I was still a student in college. It was only when I started failing after I dropped out of college that I really felt a lot of pressure, felt pretty bad.

I would see on Instagram my friends would be graduating - they'd have those pictures with the graduate gowns and the hats - and then I would be at home either living with my parents or working on some startup that wasn't really doing that well. Then fast forward a year and they'd have high paying jobs at Microsoft and I would still be the same thing - still be at home, still not doing well. I think those failures really hurt a lot more because even though I wanna say 'oh I don't compare myself to people, I try to be the best version of myself,' you can't have full control over your mind so it was a little hard.

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

David: I was a literature major so I really loved poetry in college, so I loved writing. My co-founder was a computer science engineer. He eventually did his PhD in natural language processing. So writing and AI - we always wanted to find some way that we could connect those two.

We started Jenni when there was only GPT-2, and I remember we were just playing with it and there was one crazy generation that we got. The AI spit back: 'Nothing is darker than a butthole.' That's what the AI told me and I thought that was so funny. I thought that was the funniest thing I've ever read that no human has ever said to me before. At the time for some reason I thought it was kind of profound as well. I'd be like 'this is so crazy, the fact that an AI wrote this. We have to find some way to make a business out of this.'

I really don't recommend anybody do this. We just got really lucky. In the beginning, Jenni AI could just make human writers 10% faster with GPT-2, and that was the first Jenny. We'd bring writers to our office and time them with AI, without AI, and we'd be like 'OK, we're aiming for 10% faster, 15% faster, 20% faster.'

Then GPT-3 came out and we realized, holy guacamole, GPT-3 is actually insane. It could actually give you text that's useful. That's when we transitioned from an agency more to a SaaS and we said 'OK, we don't actually need human writers because GPT-3 is so good.' Then we became more of a general tool so anybody could use it. It was just like Microsoft Word but AI first.

David: We started removing features. It's a weird thing - as we've removed features, Jenni continually got better. As we kept ripping things out, our vision just got more clear. This is the thing that people come for - how can we make this our time to value? Can we make it so a user comes and gets their first autocomplete within the first 5 minutes?

The way we got our first few customers, I would literally just cold call businesses. I would literally just talk to them, become their friends, and try to figure out how could I deliver the best product for them. Then the few users that came to us, we would talk to them and then we would tweak our tool a little bit and then we'd launch again and we'd tweak it and launch again.

Eventually we realized we had a huge wave of users and they were all students. We just made the decision - it seems like these researchers, these people in the academic field like Jenni, we might as well keep building for these people that actually get value from our tool.

In the beginning you care a lot about money because obviously you're a struggling founder, but really in the early stages money doesn't matter at all, especially if you're trying to build a big company. If you can convince someone to talk to you about your product and try your product and you give them a month free or 2 months free, that's no problem at all.

David: When you're an early stage startup you have nothing going for you. You will take any call. I remember when I was really struggling I would even respond to those spammy LinkedIn messages where they're clearly just messaging 1000 people, but I would even respond to them because I just needed anything. We were struggling so much.

I remember one time I got invited to a podcast. Very, very few people listened to this podcast, and I think out of the listeners, one out of the very small pool of listeners happened to be a scout for Jason Calacanis. Then the even crazier luck was they sent me an email saying 'hey, we wanna meet with you, possible investment.' I didn't see the first email. I ignored the first email, so that was really unlucky. Then they actually decided to send another email. I responded to the second email. They decided to put in $100K.

I remember when I first got it, I went to my grandpa's house and we were just swearing in Korean - $100K! I remember I took a screenshot. I've never seen that much money in my life. I took a screenshot of it and I just stared at it all the time. It was so crazy.

David: Immediately after the $100K when he invested in me, my startup was not doing super well. We kind of had a little bit of growth, but it was like we made $2,000 month 1, $2,200 month 2, $2,300, $2,005 - very small growth. Almost negligible. I almost didn't trust myself with the money because I was a young founder, I was kind of unsure of my own decisions.

So immediately my co-founder and I, we booked a flight to Malaysia, Southeast Asia, because everything in Malaysia is 1/4 of the price. Just like we predicted, we were still young founders making amateur decisions. It took us another 1.5 to 2 years to finally grow - we were stuck at $2,000-ish MRR for 1.5, 2 years. If I didn't go to Malaysia, we would've died.

It was 1.5, 2 years of just continual failure, and I remember the craziest story ever. I got invited to something called KSGC - K Startup Grand Challenge - and if you get top 10, you win some money. So I went to Korea. We were really low on money and I was able to get a VC to invest $250,000. It was pretty much a done deal.

But then there was this girl I really liked. I had a meeting the next day with this VC that was gonna invest in us, and just because I was dumb I was like 'it's OK I can just stay out late.' I stayed up really late with her. I came back and realized there was some document I needed to fill out. I opened it and realized it's fully in Korean and my Korean's OK, but I can't do a legal document in Korean.

So I'm doing the ugliest Google Translate trying to fill out this document before my meeting at 9 AM. I finish at 3 AM. I barely sleep. I wake up at 8. I get there. I'm late to the meeting. That night he sends me an email saying 'actually, we're not gonna invest. We don't think that this is the right fit.'

That night, because we were 2 months away from dying - we were 2 months away from dying and I had a team. I had one software engineer whose wife was pregnant at the time or they just had a baby. I realized I had a lot of responsibility and I really messed it up. I cried pretty hard that day. That was one of the worst days of my life.

David: I remember I was sitting at home. It was late. I'm kind of a night owl, so my co-founder was asleep. It was around 11 PM. Suddenly our site starts going crazy. I see every time I refresh the page, every 2 seconds 10 users would come to Jenni.

Jenni is actually included in one of the most viral Twitter threads in history. I think it's actually the most viral Twitter thread in history that has to do with AI or startups. We had OpenAI credits at the time and we had a limit of I think $1,000, $5,000 OpenAI credits, which at the time was a lot. I think within one hour we lost all the credits. The users used all the credits because we had such a crazy influx.

I'm calling my co-founder. He's not waking up. I remember I was just swearing at him on Slack. I was like 'wake up, this is our big break. We have to capitalize on this.' I was just handling Intercom, messaging every single person trying to save every single person. 'Hey, we're not available right now, but can you give me your email? We'll let you know when we're available' because I didn't know if this was a one time thing or this was gonna be a sustained thing.

That was the first time we ever had the feeling of some semblance of success because raising money doesn't feel like success - it feels like 'OK now the job really starts, now we can really get our hands dirty.' After that first initial growth I was preparing my heart. I was like 'OK, there's no way that we can continue growing like this. That was the most viral Twitter thread ever - there's no way we can continue this growth, but we'll continue our best and we'll continue slowly.'

But it didn't stop. Every month we were able to figure out some new distribution or growth tactic and the growth has been super awesome.

David: That month was 2 months after the most viral tweet. I was in Korea. I always had this growth on my jaw. I get it checked out every once in a while. It's like 'OK, it's been a few years. I'll check it again.' So I went to go get checked and then she was like 'Since you're here, do you wanna check your neck too, since you're here?' I was like 'OK, sure.'

You know things are not good when this nurse is suddenly quiet and then she says '50% chance that you have thyroid cancer because they see some tumors in my thyroid.' I didn't know what to say at that point. I still didn't think I had cancer because my entire life all I've known is a life without cancer so it's hard to imagine.

Then I remember I got an email from the doctor saying that I had thyroid cancer. I remember this quote: 'a tree can't reach heaven unless its roots reach hell' and that's how I really felt. I worked my whole life, 8 years of my life, startups, 8 years, $100,000, just failing, failing, failing. Finally I'm finally able to peek a little bit above the clouds and I feel like we're finally growing. And then I get a cancer diagnosis.

David: Before my surgery, I was like 'I don't want my startup to die if I die,' so I wanted to raise a little bit of money. But unfortunately I think that the VCs could smell the desperation and I was like 'not only am I raising money, I need the money within this month. You need to wire it within this month.' It was a weird situation.

I remember the day of the surgery was really crazy. I was really nervous for the surgery and then the doctor comes in and says 'you have a fever. We don't know if we can do the surgery today. Would you like to reschedule it?' And I said 'there'll always be probably some reason,' so I said 'let's just do it.' My body temperature kept going up before the day of the surgery, so they start bringing ice packs. I'm just laying in bed, ice packs all over my body.

I remember my mom, she saw that I was really stressed. She sat next to me and she said 'don't worry, don't worry, things will be OK. Before your surgery I'll tell you something and it's gonna give you all the strength you need and everything will be OK.' My mom leaves a little bit, I think to go to the bathroom or something, and then suddenly all the nurses run in. They're like 'we just have the operation table, someone pulled out, we need to do surgery now.'

I was about to go in surgery. My mom wasn't there. They weren't gonna... I was afraid I wouldn't understand the instructions. I had a fever. The risk of my surgery was higher. All these things, so I wanna leave. But for some reason the waiting room there was a Bible verse on the ceiling and it said something about 'don't be afraid, leave it all up to God.'

They took me to the surgery room, they did the surgery. I woke up, surgery went well. After a few days I was able to speak and I remember I asked my mom 'hey, what was that thing you wanted to tell me before the surgery?' And she was like 'oh, I wish I could've told you - it was this Bible verse that I found online' and it was the same Bible verse that was on the ceiling.

I'm not a very religious person, but for some reason I was like 'OK.' So much of my life has been these miraculous things - sitting next to my first investor on a plane, having Jason Calacanis invest in me from a random podcast, having a crazy viral tweet from someone I've never met, getting cancer. I guess to sum it up, I've just been so grateful for my little miracles every day. I'm just really grateful all the time.

David: Lately I don't know why, but startups have been romanticized with all these Netflix series of Theranos or Uber, and a lot of startups really is just - it's not very sexy, it's just putting in the work day after day, finding out what's the most important thing to do. Sometimes the most important thing to do is just get out a spreadsheet, look at these numbers, find out a relationship, and then the next day through that relationship, how can you make a product decision based on that. These things are never shown in these Netflix series or these movies because they've been kind of fetishized.

The sad truth isn't that you'll fail. I think that if you build a startup and you really work towards it on a long enough time horizon, you'll probably be able to make something and make somewhat of a living. But the sad truth is it just won't be super eventful many days. Many days will just be really boring.

The dread of staring to the void, not knowing what's gonna happen is so much more painful than now. Every day there's probably some fire I have to put out. I have to make huge decisions every single day in terms of how to spend money, who to hire, who to partner with, whether to take a check from this person. It's not nearly as painful as when I was in my room alone and it was just super boring and I had to do these boring things. I had no idea what to do and it was just not even eventful.

My advice is just be ready. Just be ready for the many years of putting in the hours, putting in the reps. I wish you the best of luck.