Instead of a Third Startup, I Chose DelightRoom

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It took me 12 years from the time I entered college to finally get my bachelor's degree. That's twice, or maybe even four times, as long as it takes most people. Perhaps because I was the oldest graduate, I was graciously asked to give the commencement speech. I haven't done anything extraordinarily special, but thinking of my younger cousin who was just entering college, I shared a few words of advice from the perspective of someone who's lived just a bit longer. To sum it up: "It's not the ability to quickly find the answer, but the ability to properly define the problem that moves us forward." And today, I work at a company that puts those very words into practice better than anyone else.

Two Student Startups

"Because I want to make 100 billion won by the time I turn thirty."

That was always my go-to answer whenever someone I just met asked why I started a business. "Think about it. If you graduate at 26 and immediately land an executive role at Samsung Electronics, your salary might be 10 billion won. That's a lot of money, but even if you save every penny for four years, it's still not enough. So I figured it was a goal I couldn't achieve just by working a regular job."

I don't remember exactly, but it's a goal I probably came up with back in high school. This was long before the term "financial freedom" became a buzzword. We weren't particularly poor, and I never had to give up on something I desperately wanted to do because of money. Still, I wanted to enjoy life without any worries from the age of thirty onward.

College was an incredibly free place. There were no school-wide rankings, and unless you were aiming for a scholarship, there was no real reason to obsess over good grades. Naturally, my studies took a back seat, and I was able to focus entirely on the startup life I had dreamed of. I built a tutoring brokerage service called "Pedaling" with some upperclassmen, and later joined the writing app "Sseum." Within a year of its launch, Sseum was selected as "App of the Year" on both the App Store and Google Play Store, and its user base surpassed 1 million. We even raised Series A funding from a well-known VC.

Two Reasons Startups Fail

It was a year mixed with surprise and anticipation. But monetization was the issue. We gathered a lot of users, but we just couldn't seem to make money. We tried publishing and selling books from the texts our users wrote, partnering with publishers to sell books, and even selling cheaper short stories, but the results were negligible. Ultimately, less than two years after receiving our last round of funding, we had to shut down the company.

A few years later, I rejoined the old Pedaling team, which had pivoted into an online class platform called "Class101." This was during the COVID-19 pandemic, a time when remote and contactless services were experiencing explosive growth. Riding that wave, we also secured tens of billions of won in investment, and our annual revenue nearly hit 100 billion won. Surrounded by an overflow of users and capital, I had the confidence that we could achieve anything. My head was completely filled with thoughts of work and the company.

Unfortunately, that growth didn't last forever. The sheer size of the company—which we had grown without truly understanding why we were succeeding—eventually held us back. We were forced to start restructuring, and our team of over 300 eventually shrank to just 40. There were times when we lacked the funds for tomorrow's payroll, forcing the co-founders to take out personal credit loans just to lend money to the company. Fortunately, we managed to turn our operating profit positive, and using our past failures as a lesson, we created a new business model. Investors responded positively, and we successfully raised 18.5 billion won in funding.

Through these two startup experiences, I learned the hard way about the two main reasons startups fail. First, the company doesn't know why it's doing well. When users flood in and revenue spikes, you get the illusion that you're doing something right. But when asked, "What specific value of our product is retaining users?", you can't give a clear answer. Second, even if you know why you're doing well, making money off of it is a completely different story. Most startups fail at one of these, and even if they get lucky and pull one off, the trap is that you need to be good at both to achieve sustained growth.

Preparing for a Third Startup

After leaving Class101, I was preparing for my third startup. Over the past few years, our goals had always been bigger growth, the next round of funding, and higher revenue. The countless decisions we made to scale the company ultimately led to three rounds of layoffs.

Business is often compared to war. Companies conquer markets and crush their competitors. You have to do that to secure the next investment. But war drains people. This time, I wanted to build a company that solved people's problems, received fair compensation for it, and could stand on its own without outside investment—even if it didn't grow explosively.

A company that makes its own money is free. There's no need to inflate revenue while taking on massive losses, nor is there any reason to feel anxious while being chased by competitors. Instead of worrying about how outsiders view you, you can just focus on understanding and satisfying your customers better. If you spend less than you earn, everyone can work sustainably for a long time without burning out.

Meeting DelightRoom

DelightRoom, the makers of the alarm app "Alarmy," was a company of 34 people generating 33.7 billion won in annual revenue and 19 billion won in operating profit, all without taking a single dime of outside investment. That's 1 billion won in revenue per person. They had maintained an operating margin of over 50% for more than three years. (For the record, their projected 2025 revenue is 46 billion won, with 20 billion won in operating profit.)

The numbers alone are incredible, but that wasn't what truly drew me in. DelightRoom was a rare breed of company that was simultaneously nailing the exact two things I had failed at in my previous startups.

This company knew exactly why they were succeeding. One of DelightRoom's core principles is a "problem-definition-centric planning culture that obsesses over the Why rather than the How." Product specs are written in a WWH (What/Why/How) format, and when adding items to the product backlog, they debate fiercely over the problem definition.

While other alarm apps approached their product as a "feature that tells the time," DelightRoom focused on the fundamental problem of "waking the user up completely." And they didn't stop there. They dug into the issue of users simply turning off their phones, tackling it platform by platform, and persistently looked for ways to solve customer problems across each operating system. They rigorously addressed seemingly impossible customer needs through various creative solutions. Every week at the company-wide town hall, they debate based on data across all departments, and even engineers personally analyze product metrics to propose areas for improvement. It's not just about looking at numbers; the process of finding the "real problem to solve" in the data is internalized as a basic reflex of the organization.

They were also exceptional at converting that understanding into revenue. By building deep expertise in ad monetization, they maintained an average annual ad revenue growth rate of 80%, and successfully landed a paid subscription model as well. You might wonder who would pay for a subscription to an alarm app, but tens of thousands of people gladly pay for it, saying the alarm saves them an hour every morning. Later on, they even packaged their ad monetization know-how into a B2B product called "DARO," creating a structure where a byproduct becomes a completely new business. That's something only an organization that knows exactly what it's good at can pull off.

A Company That Defines Problems

Honestly, I was curious. I wanted to see exactly how they worked. I figured if I started a company and it did well, I'd want it to be like DelightRoom, so there was no reason not to experience it firsthand. On top of that, DelightRoom was expanding its team and envisioning even bigger growth. The timing was perfect on multiple fronts.

Over the past 10 years, I've painfully learned the importance of problem definition. The place I'm in now is an organization where "thinking one step further" is just part of everyday life. If the Why isn't clear, we don't move on to the How. We never skip problem definition just for the sake of execution speed. That habit, built up over more than a decade, has led to tens of billions in revenue and an operating margin over 50% without any outside investment.

If there's one thing I've learned from repeated failures, it's that you can't buy a good team and a good culture with money. No matter how much funding you have, an organization that doesn't ask "Why" will eventually collapse. Conversely, an organization that has a habit of properly defining problems will find a way even when resources are scarce. DelightRoom is currently looking for people to help build their next 10 years together.