People love overnight success stories. You know the ones - two brilliant founders in a garage, one perfect YC application, and boom - instant startup glory. Our story... isn't that. We were rejected so many times that the rejection emails started to feel like old friends.

Those rejection emails hit different. But here's the thing about rejection emails - they get easier to handle around the fourth or fifth time. This is the story of how we got into YC on our fifth try, and what we learned along the way

We applied five times over three years. Five. Times. Our first rejection came in 2018 - that standard "thanks but no thanks" email that thousands of founders know too well. The one that makes your heart sink a little, no matter how much you tell yourself it's just part of the journey.

Two more rejections followed. Each one stung, but we kept building. That's the thing about building startups - the world keeps spinning whether you get into YC or not. Users still need their problems solved.

Then came April 2021. I still remember exactly where I was when that interview invite hit my inbox. I literally couldn't believe my eyes. Called John and Hakeem immediately - pretty sure Hakeem screamed (sorry for outing you here, bro). We did everything "right" - prepped like crazy, even got an Airbnb with my last card so we could all be in the same room for the interview.

And then... rejection. That night was brutal. Just laying there, waiting for a call that never came. You know that feeling when your brain just won't shut off? Yeah, that. I swore I was done with YC applications. Completely done.

The next few months were rough. Investors weren't interested, business was challenging, I was broke and honestly? We were tired. Really tired.

Then one day in August later that year, YC sent an email saying we were among the best startups they'd interviewed. It was like someone cracked open a window in a stuffy room. Maybe we weren't crazy after all?

The wild part? When we applied again, we barely stressed about it. No Airbnb this time. No obsessive preparation. Just... here's what we're building, here's why we care, take it or leave it.

Our interview with Harj, Tom, and Dalton was quick - just 10 minutes of straight questions from Harj. When his call came later to say we were in, it felt surreal. The same team that had been rejected four times before was now "YC material."

Here's what I learned: YC rejections aren't about you, they're about timing. Sometimes the market's not ready. Sometimes you're not ready. Sometimes YC's not ready. We got in when we stopped performing "what we thought YC wanted to see" and just focused on building something users needed.

For those keeping count - that's three rejections without interview, one rejection after interview, and finally an acceptance. Each rejection made our skin a little thicker, our vision a little clearer, and honestly? Made the eventual acceptance that much sweeter.

So if you're sitting there with a YC rejection in your inbox, remember this: 40% of YC companies got in after multiple attempts. The program runs twice a year (Now 4 times a year as of 2024). Their rejection email isn't saying "you're bad" - it's saying "not yet."

Keep building. Keep learning. Keep applying. Not because YC is the only path to success, but because persistence is the common thread in pretty much every meaningful startup story out there.

And hey, maybe I'll see you at the next YC Reunion ;)

I have to shout out Michael, Olumide and Yele here - they helped us review our applications and running us through mock interviews. Michael especially holds a special place in our journey - he was the first investor who ever truly believed in us, back when most people couldn't see what we were building. When everyone else was giving us the standard "come back when you have more traction" line, Michael saw the potential and backed us. That kind of early belief in founders is rare and precious.