“These words will rarely tell tales of wild adventures or exotic travels”

I remember starting this blog back in July last year, and my inaugural post was focused on my intentions of writing more often. In fact, I actually included a disclaimer that went something like this:

“These words will rarely tell tales of wild adventures or exotic travels”

As it happens, I’m now writing these words on a plane to San Francisco, and I’d be lying if I said I wasn’t expecting to wake up from a crazy week-long dream any minute now! After having just watched The Secret Life of Walter Mitty, an uplifting film about throwing caution to the wind and living life to the full, and with 7 hours of the flight remaining, I decided there was no better time to take stock of the adventure so far and to get these chaotic thoughts out of my head and onto (digital) paper.

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To explain why I’m currently 34,000ft above sea level, we need to go back about two years in time to a conversation had with a good friend of mine, Neil. Back in first year, I remember discussing future career options with Neil during one of our practical sessions at the Computer Lab, and I was surprised to hear that he wanted to form a startup straight out of University. The idea of running my own business had appealed to me for a long time, but I had always been under the impression it was something that was done with a lot of real-world experience under one’s belt, and I certainly hadn’t planned on doing my own thing before I’d even turned 21. I admired his ambition, though, and he certainly got me a lot more interested in the startup scene. (Not least by introducing me to Hacker News!)

In second year, as most of my Cambridge friends will know, I came across a problem that required solving related to May Week, a week of decadent festivities in June (ha) after our exams have finished that seem to keep the Daily Mail in business. Over the course of one glorious week, the majority of Colleges will put on a May Ball or June Event, which is typically a black- or white-tie event lasting from around 9pm until 5am. Tickets range anywhere from £50 to £200, depending on how much you care about champagne and expensive dinners, and a ticket guarantees the bearer to unlimited food and drink throughout the evening, plus the chance to see both famous and local student acts perform all evening. With tickets being as expensive as they are, students put a lot of careful thought and consideration into which event they want to go to, and much to my surprise, no single source of information existed upon which these decisions could be based.

I woke up one morning in December 2012 to find a lengthy message thread between friends about which Ball to go to, and I became frustrated by how much of our information was based on rumours and here-say, so decided to hack together a simple single-page website containing all of the information for May Week 2013 in one place. I barely moved from my desk for about six hours straight, and when WhichMayBall was released to the world, the reception was far better than I had expected. I had been genuinely shocked that no such website existed already, and this was echoed in the feedback of both friends and people I’d never met before.

The satisfaction I gained from seeing an idea through from inception to execution was extraordinary, and, more importantly, I was proud to think I was providing a service to ease the decisions of others. I definitely wasn’t “enhancing people’s lives” or any corporate bullshit like that, but I was saving people time, and that felt good.

I’ll write a more in-depth post about the story of WhichMayBall later on, but in a nutshell, the experience, although small-scale, was enough to get me seriously considering a career either at a startup, or as the founder of my own, and it led me to successfully apply to Entrepreneur First, which you can read more about here. Around a month after the whirlwind which was the EF application process, a transatlantic storm arrived in the form of Neil and his crazy idea to apply to YCombinator, the most prolific tech accelerator in the world.

I’ll be honest, I was initially hesitant. Having just been accepted onto EF, and having been offered an internship at Decoded for the Summer, I was extremely content with the London-based future I had crafted for myself, and uprooting all of that felt uncomfortable and reckless. However, very few great stories begin with a refusal to get onboard, and much like Bilbo at the beginning of the Hobbit, I woke up the next day and went running back to a bearded man to tell him I didn’t want to turn down such an exciting invitation.

After getting in touch with our friend Amar, who’s currently studying for a PhD in Machine Learning, we began to draft up our application. However, one thing led to another, and before we knew it, the deadline day had arrived, and things kicked into overdrive as we frantically answered a slew of tricky questions and filmed our 60-second pitch to YC. Four minutes before the deadline, Neil pressed Submit…and the system crashed. We had no idea whether our application had gone through properly, but the clocks had just turned 3am GMT time and the deadline had passed, so I headed to bed.

We had treated the whole process as a learning experience, as Neil and I knew it was extremely likely we’d be applying to YC eventually, either shortly after EF, or further down the line, and so none of us ever expected to receive an email with the following line on the 16th of April:

“Your application looks promising and we’d like to meet you in person.”

As you can expect, I got absolutely no work done that day, and the afternoon and evening just blurred into a series of bewildered conversations with Neil and Amar as well as excitable Skype calls with contacts in the Valley.

The next week involved a lot of refinement of our idea, a lot of useful conversations with Cambridge grads, supervisors, and lecturers with relevant experience and wisdom, and a lot of practice interview questions, which leads us to here. Sadly, Amar is presenting at an AI conference in Iceland this week, so isn’t joining us, but he’ll be Skyping in at the same time as we step into the interview room at 2.30pm PST tomorrow. This whole story is made even more mad when you consider that we’re flying 5,300 miles for a 10-minute interview! Oh, and Neil and I are landing in the UK at 7am on Monday and popping into 10 Downing Street with EF on Monday. Yeah, really.

So that’s the story so far. I’ve never been to America before, let alone outside of Europe, which means free in-flight food, movies, and seemingly unlimited complementary soft drinks are completely new to me, and massively exciting. Landing in the States is going to be nothing short of surreal.

Actually, the drinks trolley is just coming down the aisle now – I’ll keep you posted.

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