Gaming my way into Y Combinator

High School

In high school, my friend showed me these essays by someone named Paul Graham. He wrote a bunch of essays on how you can do your own job with a startup and with a lot of hard work “compress your working years” into a shorter amount of time.

It was very appealing to me. The more I looked into this Paul guy, the more I liked him. He didn’t seem to be selling self help or anything really. There was no online school or mentorship program or book he was shilling. The only business he ran was offering to give you $120,000 (previously $20,000) in exchange for a 6-7% of your company.

To top it off their program avoided all the things I considered bullshit work like 5 year business plans or even how you make money (that’s pretty easy to change).

It seemed pretty reasonable to me.


In college I kept track of companies coming out of this program. It was hit after hit. Reddit, Airbnb, Stripe, Justin TV (later Twitch). I realized every major website I used had been funded by them. I wanted to be part of it.

One company from their demo day at the time had been getting a fair amount of press called Tutorspree. It was a website to find or offer tutors in pretty much anything.

I had recently made a slightly viral project that was hacked and it was very stressful. I spent that year studying cybersecurity and even joined a team my school had to compete in it. I wasn’t particularly good at it but I had a few basic tools I learned that most websites seem to get wrong.

So one day while bored and using Tutorspree I decided to see if I could find any SQL injections. I did not, but I did find you could upload files other than images for their user profiles. I showed another friend who was more into security and pondered whether someone could put a reverse shell into that pic and control their whole website. Much to my dismay, he actually did that instead of pondering and had control over everything. Realizing what I did, I contacted the CTO of Tutorspree and showed him what was possible and how to fix it.

He offered me a job on the spot.

I declined stating I am trying to start my own startup and to say hi to Paul for me. (Note: I later found out they did not say hi to Paul for me.)

I didn’t try a startup for another 3 years. Probably would have been wise to take that job.

Finally I had the interview.

Post College

In my mind I had played every move right. I had gotten several other YC alumni to recommend us ahead of time by reaching out, the biggest of which was Sam Altman. I read online about how they had an internal mailing list for founders to suggest and deals and advice to each other.

Sam had just become the president of Y Combinator that year. I met him after he gave a talk at Stanford about Y Combinator. After the talk he just stood there awkwardly and the room cleared out. No one knew who he was or wanted to talk to him. I didn’t either.

I was leaving the room when my friend literally pushed me at him and said “James is working on a startup.” I awkwardly jumped into action with what I knew.

“Y Combinator has been funding more hardware companies, right?”


“We are trying to handle the logistics side for those companies. Picking, packing, delivery, etc.”

“Cool. Send me an email and apply to Y Combinator.”

That was the whole conversation.

When I applied, I sent him an email. The president of Y Combinator was now recommending my company.

The Interview

We had prepped through all the questions we heard they might ask online over and over. We practiced our succinct answers down to who would answer it between my cofounder and I.

We had gotten the interview the very last day before the new batch was starting. Everything about our process felt like the start of an amazing success story.

We did our interview with Kat Manalac, Garry Tan, and Michael Seibel. It went smooth and we nailed every answer. It was over.

We thought.

Nope! We asked to do a second interview. This was not something I had prepped for.

The Second Interview

I walked in the room and immediately noticed a camera there. I may have even winked at it.

Our interviewers were more intimidating this time: Jessica Livingston, Kevin Hale, Qasar Youni, and Geoff Ralston.

Jessica didn’t say a word the whole time but was watching us a little more intently like Kat did. I have heard some of the partners are trying to decide if you’re a bullshitter or asshole during the interview.

The table was too small so Geoff was off to one side and ended up not saying anything or even being in the conversation. We weren’t sure why he was there, but he did a good job opening and closing the door for us.

Kevin and Qasar did all the talking, mostly at the same time.

We sat down and my cofounder quickly mentioned our team change for the second time (third cofounder was let go) before they could begin

Kevin aggressively jumped in, “Hey Yeah, someones missing here. Who is here and who isn’t?”

My cofounder repeated the information again in different words.

Kevin and Qasar ask some more questions aggressively and wanted to know why he was gone. We mentioned he wasn’t fully committed and Kevin looked annoyed. “Not committed, What does that mean anyway?”

We go back and forth and quickly say he wasn’t getting things done on time. One minute out 10 already wasted but they moved on.

Rapid fire questions.

Several questions we had no idea what was said because Kevin and Qaasar were talking over eachother to the same person. They didn’t seem to notice they were doing this.

This was much closer to the interview stories I had read about online.

They didn’t like how little work we were offloading to 3rd parties.

We don’t own the warehouses. We didn’t have an idea of what type of hardware companies needed our service most. In retrospect thee are indeed red flags. I had talked to about 300 potential hardware companies, but we only had one paying customer.

“How would this scale?”

“We are automating every interaction between the warehouse and e-commerce store”

One of them thought we were competing with FedEx, “I once saw a commercial for FedEx saying they do this. How do you compete with them?”

I don’t believe FedEx really had a service as none of the customers in our pipeline mentioned it.

Not a convincing answer. They stuck onto that and argued with us until the time was up. cutting me off mid-sentence.

Unlike my first interview, I had no more CoffeeBars to hand out.

Post Interview

I found out before leaving that multiple interviews is not a good things. It means they aren’t sure. They were on the fence with us.

All in all, we were interviewed by over one-third of the partners at the time.

And they rejected us.

Whoops. I would get in another time. And I did eventually.

There is no way to game success. Even if you have success on your own terms, you can’t control other people.

We did get a nice picture with the sign though.