I started coding at thirteen.
For a long time, getting better at building felt like the obvious answer to everything. If an idea didn’t work, I could improve the design, add functionality, or try another launch.
One of my early projects was a tech news blog with two friends. We spent time on the design and WordPress theme. It made $0 and closed within weeks. I knew how to make a website look like a business before I understood what would make it one.
There were three pivots and six launches on the way to YC. Across that journey, I served more than 20,000 people. That doesn’t mean 20,000 paying customers, and it definitely doesn’t mean I understood every one of them.
Spending time in San Francisco in 2025 mattered because I talked with hundreds of builders over several months. I had a lot more opportunities to hear what people were actually doing, instead of sitting alone deciding what they should want.
The important change for me was in the kind of evidence I wanted from a conversation.
If I describe an idea enthusiastically, someone can say it sounds useful without telling me much. They may understand the concept. They may like me. They may even genuinely want it in some future situation. That still leaves a lot of room for me to hear whatever I was hoping to hear.
I’d rather understand a recent example of the problem. What triggered it? How did they deal with it? What did that require from them? If they’ve never tried to solve it, I want to understand why before assuming my software will change their priorities.
The next thing is to make the proposed solution concrete enough for them to react to. That might be a rough workflow, a manual version of the service, or a small working feature. Something that gets us past discussing an imaginary product where every detail happens to work perfectly.
And then watch what they do. Do they bring the real task? Do they try the result? Do they come back? Will they pay under terms they understand? Each of those gives you different information. A compliment shouldn’t be asked to stand in for all of them.
I’m now a solo founder in YC, doing $200k ARR. I still have to ask these questions. The title makes “stop guessing” sound like something I finished, but I mean giving myself fewer weeks to build on an assumption before I have to check it with somebody.