I got rejected from YC twice. Now it’s two months after Demo Day.

Over the course of the last year and a half I’ve gone through three YC interviews, been rejected twice and finally accepted the third time. I wanted to document my story because it has some humorous aspects and encourage people to apply, even if they don’t feel ready or have been rejected before. There are still 4 hours left to apply: ycombinator.com/apply

The first time I had ever heard of YCombinator was about halfway through my freshman year at MIT through this email to a list I was a part of:

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For reference, at MIT Course 6 is Computer Science, Course 15 is Business and Management, and Course 17 is Political Science. In this the second email is sarcastically pointing out how obvious of an assertion the first email is. Reading that I felt silly since I was a Course 6 major and had never heard of this site!

4 months after that email, one of my close friends, Brett Van Zuiden, got into YC with his startup, Filepicker.IO. I spent that summer at Square and got to hear some fantastic stories from Brett about what YC was like. I quickly decided it was a program I wanted to have the privilege to participate in later in life.

Fast forward about a year later and I had applied to YC for the first time and had made it to the interview process. About a week before I was supposed to fly out for interviews, my cofounder and I decided to part ways.

I went into the interview really unprepared and got torn apart for losing my cofounder the week before interviews. We got this fateful email shortly afterwards:

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At the time receiving this news was pretty devastating because I wasn’t sure how me and my other cofounder, Eric, would be able to continue working on Nightingale. Luckily enough we got a little bit of funding from RoughDraft VC and I was awarded the Thiel Fellowship.

Jump ahead another 6 months of hard work and our product had evolved a decent amount, had about 1000 patients using it, so we applied to YC yet again with our lessons learned.

This time around Eric and I practiced our pitch with almost twenty different alumni, and had nailed our answers to almost every possible PG question.

We went into our interview and it was clear that PG’s biggest concern with us was how we would scale our sales side of the business to get lots of clinics onboard. One of the pivotal moments in this interview was the following exchange between PG and I:

PG: “So how are you going to learn to manage a sales process?”

Me: “Well so far I’ve been learning through reading lots of books, my favorite being ‘How To Win Friends And…”

PG: sighs and facepalms

Me: “Influence People’ by Dale Carnegie. I’ve learned..”

PG: interrupts “Putting that book in the hands of a Thiel Fellow is like giving North Korea a nuclear weapon.”

After those comments PG completely checked out of the interview, only giving us a small piece of feedback at the end that we sounded too rehearsed. Shortly afterwards we received an email from PG, though we were more accustomed to rejection at this point:

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Though I felt far more prepared, after that experience with PG I knew there was no chance we made it in. However, the application and interview process made my cofounder and I realize we had some fundamental issues with our current product and business model.

We ended up participating in StartX Med and pivoting into a completely different vertical in healthcare, focusing all of our efforts onto tools for behavioral therapists for autism.

We stuck with it, found some initial customers, iterated on our product, and even raised a little bit of funding after StartX. Not much, but enough to last me and my cofounder plus an employee.

Applications for the summer class started to roll around and this time we spent only half an hour on our application and threw it in the day of the deadline.

As it turns out it’s a lot easier to write an application when you know exactly what you’re building and have actual users.

When the interview came around this time, we were too busy working on our product to prepare. Unlike other times where we neurotically showed up two hours beforehand, this time we accidentally cut it too close and walked straight from our car into the interview.

We had the exact same partners as the previous interview, however this time around the answers to all of their questions rolled off the tongue because of extensive knowledge of our market and users rather than spending weeks with alumni carefully crafting our answers to every question.

As soon as we finished we walked right back to our car and drove up to SF, spending a total of 13 minutes on YC’s campus.

Having been rejected twice already I had set my hopes incredibly low and actually went to go hang out with some friends and quickly forgot about the 13-minute interview.

All of a sudden around 8 PM that night I got the fateful phone call from PB, which went something like this:

Me: “Hello?”

PB: “Hi this is Paul Bucheit from YCombinator. I’m happy to let you know we’ve decided to offer you funding.”

Me: “Great!”

pause

PB: “So… do you want to do it?”

Me: “Oh woops, yes, of course! We accept.”

I quickly hung up so I could go tell Eric and get back to hanging out with my friends.

Two weeks later we had our first office hours scheduled. With Paul Graham, our fateful North Korean analogy-maker.

I’d probably thought about this moment ever since I had heard about YC, the day that Paul Graham would use his incredible intellect to think about my puny problems, and it was everything I expected it to be.

We walked into one of the rooms at YC, the one with the soft, oddly green carpet. There wasn’t any furniture in the room and PG immediately walked over to the window and stared out.

I remember thinking ‘Huh, I guess he likes to stare out the window when he does office hours.’

PG: ‘See all those cars parked backwards in their spots. Those are all the secret service agents.’

Me: ‘Why are they here?’

PG: ‘Obama is coming by later for dinner and they have this place on lockdown. Anyways, so what are you working on again?’

First, Obama was coming for dinner, wowzers. Second, I’d heard about how PG would go off on random tangents during his office hours and was glad I finally experienced firsthand.

He folded his legs and sat down on the carpet, gesturing to Eric and me to join him on the floor. He then unloaded incredible directional advice with exactly everything we needed to do between then and Demo Day.

On the outside I was expecting YC to be a formal institution with procedures and traditions that helped impart startup knowledge onto all of its participants. As it turns out, 95% percent of the value comes from experiences like we had above with PG. Basically the incredibly diverse and extraordinarily intelligent YC partners sit you down and think through the problems your startup is facing to solve them. Not only that but you get to listen in on how they help all the other startups in your batch. In the process their decision making framework is imprinted upon you via osmosis so that no matter what startup you’re working on you can imagine how the YC partners would think through it.

It’s been a month since we graduated from YC and it’s been incredible to reflect on our time over the summer and YC’s continued influence on the trajectory of our company. In all reality, nothing has really changed since we graduated. We continue to focus on the same things that we did during YC, and continue to have office hours with the partners during major inflection points for the company, though they happen less often now.

So to sum it all up, if you’ve been rejected from YC before, keep your head up, keep chugging along, and in the end maybe it’ll all work out for the best.

Also YC was the fastest I’ve ever learned and learned how to keep learning. Can’t imagine a better group of people to be a part of in the world.

 
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