Building things is exciting. It is also easy to romanticize the grind.
Ambition can quietly turn into obsession. Obsession can become burnout. The difficult part is knowing where that line is.
I still don’t know.
Back in April, I went for a run with a close friend. She was training for the London Marathon. My running has been limited because of a knee injury, so I mostly join for an easy run once a week.
For months, she had been telling me the same thing:
“You should scale datespots.nyc to more cities.”
The problem was the domains.
Owning a separate domain for every city wasn’t practical. Many city-specific domains have residency or registration restrictions, and even where they don’t, managing dozens of domains quickly becomes expensive and messy.
Somewhere between that run and brunch afterward, it clicked.
Instead of buying a domain for every city, why not buy a single top-level domain and make every city a subdomain?
nyc.datespots.city
paris.datespots.city
tokyo.datespots.city
Simple.
That weekend I bought datespots.city.
Then the real work began.
Scaling from a hobby website to a global platform meant I couldn’t keep building the way I had before. WordPress had served its purpose, but this needed to be something entirely different. It had to be fast, scalable, SEO-friendly, and inexpensive to operate across dozens of cities.
For the next three months, I became every department.
Software engineer. Systems engineer. Infrastructure engineer. UI/UX designer. SEO specialist. Product manager. QA tester. Technical writer. Customer support. Everything.
I even started reading Thinking, Fast and Slow by Daniel Kahneman, partly because I wanted to think more deliberately about how people navigate interfaces and make decisions. Good UI is as much about psychology as it is about pixels.
The schedule was… unhealthy.
Most nights I slept four or five hours.
I’d finish work around 6 p.m., be at my desk by 7, and often work until 2 or 3 in the morning before repeating the cycle. Some days I skipped cooking and ordered food. Some days I forgot to eat entirely. Occasionally training disappeared. Sometimes the side project had to wait because work demanded everything.
The one thing I refused to compromise completely was my health. Somehow I still managed to fit in six or seven hours of training every week between running, swimming, and strength training. It wasn’t perfect, but it kept me sane.
Could I have built this in a healthier way?
Probably.
Would it have taken longer?
Definitely.
Today, on June 30, 2026, I’m finally launching datespots.city.
The platform launches with 24 cities, with another 24 planned by the end of this year or early next year.
The goal is simple: make it easier for people to discover genuinely good places to go on dates, wherever they are.
One unexpected highlight came a few weeks ago.
Mostly for fun, I applied to the Cloudflare for Startups program. Technically, this isn’t a startup. It’s a bootstrapped side project with no funding and no company behind it.
To my surprise, Cloudflare accepted the application anyway, granting the project an Enterprise plan along with $10,000 in cloud credits for the year. That was an encouraging vote of confidence, and one I’m genuinely grateful for.
I’m proud of what this has become.
More than anything, I hope someone discovers a café, a bookstore, a museum, or a quiet little spot through this project and ends up having a memorable date because of it.
If that happens even a handful of times, the late nights were probably worth it.
Not everyone understood why I was doing this.
Some people were incredibly supportive. Others were skeptical.
A few mocked the amount of time I was putting into it. Some joked that I was psychopathic for treating a side project like a second full-time job. Others couldn’t resist pointing out the irony of building a dating platform while being single myself.
None of it really bothered me.
If anything, criticism has always been useful fuel. Building something worthwhile almost always looks irrational before it looks obvious. People rarely see the months of uncertainty, failed ideas, and late nights. They only see the finished product.
There’s a saying I like:
“First they ask why you’re working so hard. Then they ask how you got so lucky.”
Luck certainly plays a role in anything worth doing. But showing up, day after day, long after the novelty has worn off, matters too.
Whether datespots.city succeeds or fails, I’m proud that I built it, learned an incredible amount along the way, and shipped something into the world that didn’t exist three months ago.
That’s enough reason to keep building.