Rejection, outreach, and why I didn't quit

It was the end of May. I was doing what I usually do most evenings, scrolling through job listings on Wellfound, YC not expecting much, just keeping the habit alive. I had a filter in my head by then. Series A or B, building something real, not another agency or a company running on PHP and prayers. That evening I came across a startup building AI search tools. Great funding, fast growth, the kind of profile that makes you sit up a little straighter while reading.

I sent an email. Nothing fancy, just casual, the way I usually reach out. I didn't think much of it after that. You send these things and most of the time they disappear into nothing.

But that noon, I got a reply. The founder wrote back saying something like, you are exactly the kind of person we are looking for.

I read that line a few times. Not because it was some grand promise, but because it's rare. Most replies, if they come at all, are polite and vague. This one felt different. It felt like someone actually looked at what I sent and meant it.

The screening call

A few days later we got on a screening call. It went well. We talked about what I'd built, how I think about problems, the usual back and forth. Near the end they told me the process would have five rounds, and the first ones would be focused on React, front end heavy, not just backend logic.

I started preparing immediately. I went deep into the usual suspects. useEffect, useState, custom hooks, render cycles, all the things that trip people up in live coding rounds. I used Claude Code, ChatGPT to throw curveballs at myself, simulate weird edge cases, anything I could think of that an interviewer might ask. I wanted to walk in feeling like nothing could surprise me.

What I was picturing

Somewhere in those weeks between the screening call and round one, I let myself imagine it properly. Moving to Europe. Actually getting on a flight for something real instead of just talking about it. Working alongside people who were genuinely good at what they did, the kind of engineers you learn from just by reading their pull requests. I pictured the whole thing in a way I don't usually let myself do, because usually I try to stay grounded and not get ahead of where I actually am.

But this one felt close enough to touch. Five rounds in, a founder who replied like he meant it, a real product with real revenue. I wasn't being delusional about it. It felt like a door that was actually opening, not one I was imagining open.

All of that, the flights, the team, the version of my life where I'm sitting in some office in Europe figuring out hard problems with smart people, came down to one email in the end. That's the part that's hard to write about honestly. Not the rejection itself, but how much I had let myself build around the idea of it happening.

Round one

The day came. And what they actually asked me to build was a whack a mole game. I was not ready for that. Not even close. All my prep was algorithmic, state management heavy, the kind of stuff you'd expect from a serious frontend round. Instead I was sitting there building a literal game, timers, random positions, click detection, all of it live, all of it in 60 minutes.

I genuinely don't know how I pulled it off. I remember being in that strange state where you're panicking on the inside but your hands are still typing, still making decisions, still somehow moving forward. I submitted it without much confidence that it was good enough.

A few days later I got an email. I was selected for round two.

Round two

For round two I prepared completely differently. They told me this one would be backend focused, so I went deep into API design, database structure, caching strategies, all the system level stuff you'd expect from a real backend round.

What actually showed up was a TypeScript test. Not system design. Not databases. A set of failing conditions I had to fix until everything turned green.

I sat with it, fixed the type errors one by one, got every condition passing. It wasn't the round I prepared for, but it was the round I could still solve. I submitted it and felt cautiously good about it.

Then I waited.

The wait

Four or five days passed with nothing. No update, no email, nothing. That kind of silence has its own weight. You start running the round back in your head, wondering if a particular fix was clean enough, if there was a better way to structure something, if silence this long is a good sign or a bad one.

On the evening of June 15th, around 7 or 8 PM, the email finally came.

I had been rejected. The feedback was short. I needed to work on my JavaScript fundamentals.

I read it more than ten times. Not because the words were confusing. Because I had just spent a week solving a TypeScript challenge they gave me, fixing every condition, getting it all green, and somehow that wasn't enough proof of the fundamentals they were asking about.

That night

I sat with it the whole night. I'm not going to dress this up. I felt genuinely sad. Not the kind of sadness you can shake off by telling yourself it's fine, it happens, there are other companies. I knew all of that logically and it still didn't help.

The next morning the feeling hadn't moved much. I was still sad. I actually came close to crying, sitting there with my laptop open, not doing anything, just feeling the weight of five rounds of effort landing on one rejection email.

I want to be honest about that part because I think people skip it when they tell these stories later. They jump straight from rejection to comeback, like the sadness was just a quick pit stop. It wasn't. It sat there with me that whole morning.

What I did anyway

At some point that same morning, still sad, still not feeling okay, I opened my laptop and started writing emails again.

I didn't do it because I suddenly felt motivated or because some switch flipped inside me. I did it because there was nothing else to do that actually mattered. Sitting there feeling bad wasn't going to change the outcome. It wasn't going to make that company reconsider. The only thing left in my control was whether I kept reaching out to other people or not.

So I went back to the same kind of search I'd done at the end of May. Founders, early stage companies, the kind of teams where a direct message might actually get read by the person who can say yes. I sent sixteen emails that day.

I'm not going to walk through the exact format of those emails or the precise way I find these companies. Some of that is still something I'm refining for myself, and some of it I'd rather not hand over completely right now. What I will say is that it wasn't random. There was a system behind it, the same kind of thinking that got me that first reply back in May.

What came back

Two founders replied. One had an open role they thought I might be a fit for. The other was open to freelance work, with the possibility of something more if it went well.

That's where things stand right now. I don't have a new offer to show you. I don't have a clean ending where the sixteen emails turned into a job and everything wrapped up neatly. I'm still in the middle of whatever this turns into.

But something did change the moment those replies came in. Not because two replies out of sixteen is some huge number. It's not. It's that they proved the door that closed on June 15th wasn't the only door that existed. There were other ones, and I just hadn't knocked on them yet.

Why this matters

I keep going back and forth on what the actual point of this story is, since I don't have a job offer to wrap it up with. But I think that's exactly why it might matter to someone.

If you're in the middle of a process like this right now, five rounds deep, prepping for things that might not even show up, getting curveballs you didn't see coming, and then still getting told no at the end, I don't think you need someone promising you it'll work out. I can't promise that for myself either.

What I can tell you is that I was still sad the next morning. I almost cried. I didn't fake my way into feeling strong or motivated. I just didn't have any other real option except to keep moving, so I did. Not because I felt ready. Because the alternative was just sitting there with a feeling that wasn't going to change on its own.

That's really the only thing I'd want someone to take from this. You don't need to feel okay before you start again. You just have to start, even while you still feel exactly the way I did that morning.

I'll write the next part of this once there's an actual ending to share. For now, this is where it stands.