Meeting Heroes: My Y Combinator Interview Experience

Benjamin Southworth (left), me and Sanderson Jones at the Y Combinator Offices

Growing up in the seaside town of Brighton, I never thought I would meet and mingle with “famous” people (famous in the form of well respected icons – not the here today, gone tomorrow celebrity variety).

When I was small, just going to the local park or the walk to school seemed like a big trip. When I was a bit older, my life was lived inside the Brighton bubble. Without the modern day internet as we know it at home, it was hard to leave it.

It wasn’t until I got to university that people that I had read about – the famous people in question here – started to appear on campus and in my life. The authors of some of the textbooks I referred to in my essays were professors still teaching at the university and people I could talk to, interact with, question. I attended a guest lecture from Jung Chang, author of Wild Swans. The double Nobel Prize for Literature winning author J. M. Coetzee gave a guest lecture at exactly the same time as I was writing my dissertation on perhaps his most famous work, Disgrace.

These people – built up so much in my mind and put on pedestals so much as to become the status of other worldly heroes – weren’t scary or too smart too approach, as I thought they might be. They were normal people, with lives to live, livings to make, desires, dreams and ambitions. I could meet them at their level (or at least have a decent conversation with them and even buy them a drink in the pub).

I never did the exercise at school where a teacher made you write to a famous person and ask them a question. If I had, I’m sure I would have learned this lesson earlier.

To show the disconnect I still experience in this area, last week I flew to San Francisco together with Sanderson and Benjamin to pitch Sunday Assembly to Y Combinator, arguably the most “famous” accelerator programme in the world. If you’re a tech startup, this is the equivalent of meeting your heroes.

I’ve read Paul Graham’s essays, regularly read Hacker News and am well aware of the many successful startups (and, to be fair, the failures) that have gone through the Y Combinator programme. And, I’m sure like many people have, I’d built them up and put them on pedestals through respect of their work.

Before the interview, we prepared comprehensively through research of questions we were likely to be asked (try out iPaulGraham if you’re interested to see what kind of questions are asked). We ran through the questions with each other and got the answers down to concise, tangible answers. We felt prepared.

We turned up about an hour early for the interview at the Y Combinator offices. There were other applicants and alumni from the programme there, so we could chat to people about their startups and get advice from the alumni. We relaxed in the atmosphere and imagined this is what it would be like to be part of the programme.

One of the alumni we got talking to was Gautam Sivakumar, who runs Medisas and was part of a YC cohort last year. We ran through a few practise questions with him so he could find out more about our plans, but it became immediately clear to him that we were too polished and had resorted to marketing speak. His advice was to give honest, human answers to the questions we were asked.

When we sat down for the first interview (we were called back for a second interview later on), his advice became even clearer to me. The people we were being interviewed by – 5 of the Y Combinator partners – were normal people, not the otherworldly heroes built up in my mind. They were friendly, warm and welcoming. They weren’t out to trick us with hard questions. They just wanted to understand the business (or non-profit in this case) and if we would be a good fit for the programme.

In the end, we weren’t the right fit. But we gave a good showing for what we have planned for Sunday Assembly.

Overall, the Y Combinator interview was a fantastic experience. There’s a post by Rob Fitzpatrick on called “to the teams currently being rejected by YC”, which is worth a read and sets the context for the process well. Thanks to Sanderson for giving me the opportunity to fly out to San Fran with him – he really is a great founder. And it was great to get to know Benjamin better – look out for what he’s up to with the Ada Lovelace Academy.

If I did apply to Y Combinator again, or find myself in a similar situation of meeting people whose work I respect so much as to put them on a pedestal, I’ll have more confidence to be honest, human and meet people at their level.

People are just people, no matter how much you build them up. I’ll try to remember that whenever I meet my heroes from now on.

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