Cailyn Yong

I went on a business trip to New York for ten days.

It was my first time back in four years, since 2021.

This trip felt different because New York is where I started my very first startup.

Back when I was at NYU Stern, I took a startup class and started a company called Eddie.

I actually began writing on Brunch after admitting to myself that Eddie had failed.

Now, four years later, I’m already on my third startup.

If anything, college Cailyn probably saw this coming.

I still remember a day when my professor looked over students’ resumes. When she saw mine, she said I was too independent, and that companies probably wouldn’t like my characteristics.

At the time, I was already in the middle of running a startup, so it didn’t really matter to me anyways. I already felt like I was on the right path.

That professor was the first person who really taught me about startups, and I got a lot of help from her. I reached out this time when I was in New York, but unfortunately we couldn’t meet.

When I was building my first startup, I didn’t even know what PMF meant. I thought doing a hundred user interviews meant I’d found it, and spent eight months building the product. Looking back, I realize I was just building without ever finding PMF.

After finishing that semester in New York and going back to Abu Dhabi, I spent a long time thinking about what to do with Eddie. One day I was on a Zoom call with my only startup friend back then, Minjoon, and that’s when I finally accepted that Eddie had failed.

Letting go of something that felt like my own child hurt way more than I expected.

A lot of time has passed since then, but going back to where everything began made me realize how much I’ve grown in the past four years. That made me happy.

These days I often think my first two startups weren’t really startups.

I didn’t have a company. I didn’t have investors or customers. They were more like small projects that I called “startups.” So when I tell people, especially investors, that I’ve done two startups before, it sometimes backfires. Investors still don’t really like hearing about failure.

I’ve heard things like, “You couldn’t find PMF before, what makes this one different?” or “Do you even have what it takes to be a founder?” or “What makes you so sure this will work?”

That’s why I think this third one, Momo, is finally my first real startup.

This time my mindset feels solid. I’m actually learning how to do sales, I have real customers, and revenue is coming in.

It’s been five months since Momo started. The product has gone through several versions, and I’m finally starting to see some hypotheses being proven. Honestly I’m really excited. Everything I do these days feels fun. I want to remember this feeling.

I still get rejected by investors, still get criticized, and still hear people tell me to build the product differently. But I’ve realized it’s better to half-ignore investors and fully trust users.

Now I finally have confidence in sales, and I know the exact moment customers decide to buy.

I know what the biggest and clearest problem is.

From here, I just need to narrow it down, sharply and relentlessly.