YC's Four Rejection Journey

A story about how Amjad Masad's company Replit finally got into Y Combinator after multiple rejections, thanks to Paul Graham's interest in their work.

"We kept applying to YC every season and getting rejected. VCs wouldn't talk to us - some would even yawn in meetings, and I think one of them actually fell asleep during our pitch.

The breakthrough came when I started writing articles about the hard problems we were solving. These articles kept getting attention on Hacker News. Paul Graham, who reads Hacker News a lot, noticed us. One day in December 2017, I wake up to a DM from Sam Altman saying 'Hey, I run YC and we're interested in what you're doing.'

I met Sam at the OpenAI office in the Mission. He turned his computer around and showed me Paul's email, saying 'this company is very important, you should reach out to them.' Sam gave me Paul's email, and I started this fascinating email relationship with Paul Graham where he wrote me essays about the problems we were solving.

When Sam finally invited us to apply, I was frustrated about filling out the application again after doing it 4 times before. I did a bare-bones application and for the required video, I actually rickrolled them - I just pasted a YouTube link to the Rick Astley song. This backfired in the interview when Michael, the CEO at the time, was very angry and said 'That's not how you get into YC.' They gave us a very tough interview after that, and I immediately regretted my decision."