Our Y Combinator interview experience

In November 2008, Fenn and I had one of the more momentous experiences of our lives. After six years working together on various startup ideas from in our home town of Melbourne, Australia, we were selected for an interview with Y Combinator in Mountain View, California. Here’s how we got through it.

The Preparation

After allowing ourselves a couple of days to come to terms with the surprise of our interview invitation, we set about preparing. As we already had a working product, we didn’t need to spend much time on our demo. From YC’s interview preparation guide, the most important points seemed to be that we should have a good idea of how we’d make money, and find someone to help us practice our interview skills.

As complete outsiders to Y Combinator and Silicon Valley, practicing with YC alumni or experienced operators in the Valley didn’t seem to be an option. We didn’t even really have any friends or associates we felt would be capable of asking the right questions in the right way. But we did know of a prominent Melbourne-based web startup founder and blogger called Steve Sammartino. We’d never met Steve, but he seemed like the sort of guy who’d be willing to help, so I dropped him an email and he was good enough to reply quickly and make himself available to help us out at only a few days’ notice.

In the days leading up to our meeting, we thought and talked through our product, market, and business model enough to be confident in our ideas, but the task of being able to convey it convincingly to potential investors still lay before us. Steve turned out to be the perfect person to help. Being more of a business guy than a hacker, and being oblivious to Y Combinator and Paul Graham’s essays, it took a thorough explanation of our business approach and concept for him to be convinced, particularly with respect to our revenue model. But after a three-hour discussion that started as simulated interview/interrogation and ended in relaxed camaraderie, he commented that he was particularly impressed with our passion and determination. The comment I most remember from Steve that evening was “You guys sound great when you’re not trying to pitch”. This gave us a huge confidence boost.

Three days later, Fenn and I set off on our 18-hour journey to California feeling as though we were as well prepared as we could be. We arrived in San Francisco about 48 hours before the interview, and spent most of the remaining time trying to rest and relax, with a few sessions grilling each other with whatever questions we could imagine might be asked.

The Interview

We’d chosen a late-afternooon interview slot, selected to allow ample time to get there and minimal time sweating over the outcome. Arriving at the YC office over two hours before our appointed time, we were greeted by Loopt-founder Sam Altman and directed to the big orange room where we joined several other nervous aspirants. We chatted a little with candidates and alumni, then Fenn and I took a wander around the surrounding streets to give each other a few more final practice questions before returning to the office to await our appointment. I was nervous as hell but I knew we’d done all we could to prepare.

Jessica emerged to welcome us with her effervescent charm, expressing amazement that we’d flown half way around the world for a 10-minute interview and promising to try to give us an extra couple of minutes for our trouble, before introducing us to the rest of the crew: Paul, Trevor and Robert.

Paul opened proceedings and cut to the chase: our market is already very crowded, although most of the players suck; how are we different from the many established competitors? Suddenly, finally, our show was on the road. This was a pleasing, if slightly unexpected opening; we didn’t even need to explain what we were doing or why, just how we’re better than the incumbents. I opened up with a response and was going quite well until things hit a snag. Mid-explanation, Paul pulled me up with his first challenge, saying “surely your competitors can do that”. I replied that they couldn’t but he refused to believe it, and with Robert now furiously typing away at his laptop to check out my story, my confidence started to waver; I was convinced of our superiority over our competitors on several fronts, but I hadn’t checked them all for this specific feature. Just as I started to panic, Fenn came to the rescue, pointing out that although it may seem as though our competitors have this functionality, for some crucial technical and implementation reasons where our product excels, the others are all abysmally deficient. Our story checked out, and the panel was satisfied.

As we proceeded to explain how our site worked, we suggested turning to the demo and the YC team agreed. So far I’d thought I was the nervous one of the two of us, but as Fenn drove the demo I could see he was shaking enough to make it a little hard to control the mouse. But he kept it together and got through the demo in style. The team seemed satisfied.

To be honest I can’t recall many details of what happened next. What I do remember is that it never felt like the intense grilling I’d been expecting from reading other founders’ stories. That’s not to say it was ever cordial or casual, but I never felt like we were under a blowtorch. The question of how we’d make money was never explicitly asked, but discussions inevitably led to our ideas of the business model. I’d barely begun to exalt my grandiose plans when Trevor said “OK so you’d be building a more efficient market for flights”. Um, yeah, that’s it. They got it. From that moment I relaxed and was able to enjoy the remaining few minutes chatting about everything from our insights into the industry to the immigration minefield that lay ahead should we be successful.

After what seemed like about 3 minutes, Jessica announced we’d been going for 17, so the interview was wrapped up and we made our exit.

The Aftermath

We walked back towards downtown Mountain View, talking a little but mainly just thinking to ourselves, trying to make sense of the whole experience. As my composure returned, I stopped, looked at Fenn and said “You know what? I think we went really well”. He replied “I think we did too” and we gave each other a brief manly hug. We weren’t confident of getting funded; we’ve learned from many setbacks never to be overconfident. But I felt as though we’d done everything in our power, and that if we were unsuccessful, it wouldn’t have been because we were badly prepared or because we’d sucked in the interview. Whatever happened, we could feel proud of how far we’d come and be optimistic for the future.

We headed for St Stephen’s Green Irish Pub in Castro Street, and ordered what has become our requisite opening combo for momentous occasions: a single-malt Scotch, neat, and a pint of beer. We’d barely got through the Scotch when Fenn’s phone rang. Thanks to shoddily implemented international roaming, Paul Graham’s call from the YC office less than 2 miles away was being routed to Australia and back, so the words “We’d like to fund you” were difficult to decipher, but audible nonetheless.

Another manly hug and a few drinks later, we were back on the Caltrain to San Francisco for a quiet dinner and our most relaxing night’s sleep in a couple of weeks.

The Lesson

Given this experience, I’d advise candidates that more than anything else, you must (a) intimately know your market and competitors and (b) convey your determination.

I went into the interview confident I knew exactly how and why we could beat our competitors, but in the heat of the moment I wasn’t able to articulate it convincingly. Given my time over, that’s the main thing I’d work on.

As for determination, that’s harder. On this point Fenn and I possibly had a natural advantage. Our long-time friendship and persistence in business, along with the effort and expense of travelling across the Pacific Ocean for a 10-minute hearing probably gave us a head start. I’d think hard about how dedicated you are to your business and how you’re going to make that evident to your interviewers.

Make sure you think and talk about your idea so much that you understand it so intimately and can visualise it so vividly that you get really excited at the thought of it succeeding. Talk to as many people as you can, and learn what you have to say and how you have to say it to get people excited at the thought of how much better the world will be once your product exists.

Once you’re in that zone, it won’t matter whether YC funds you, you’ll set about working on your startup anyway, and with enough determination and persistence, you’ll be sure to build a great company.

By Tom Howard