Trapeze gets an interview with Y Combinator (W2019)

Welcome to our first blog post! For those of you who don’t know, Trapeze is a new mobile app thats helps you find exciting date spots in New York City. New York is filled with amazing restaurants and great things to do, but with so many options, it can often be hard to find the right idea for you. We took it upon ourselves to make this app and help people explore everything the city has to offer. We’re also trying to keep the discovery process simple and fun, so planning a date doesn’t seem like tedious work.

Last Tuesday the Trapeze team was lucky enough to interview with Y Combinator for a spot in their Winter 2019 startup batch. If you don’t know what Y Combinator is, you can check it out on Wikipedia. Y Combinator is extremely well known as one of the top seed accelerators in the world, having helped start companies such as Airbnb, Dropbox, Reddit, and Twitch, just to name a few.

At this point, YC is so well known that getting into their program basically guarantees a large round of funding on their Demo Day (which is now actually 3 days long and has roughly 500 investors attending). For small companies, the connections, advice, and brand status you gain from YC is easily worth the 7% equity they ask for (they also throw $150k your way).

For an early stage start-up, Y Combinator is essentially the holy grail. So, as a fledgling company, we were ecstatic when we found out we had gotten an interview. At the time of our application, Trapeze was only about 4 months old and we had not even launched to the public yet. Getting into YC would have jump us straight into the fast track. Unfortunately, our interview fell short and we missed the cut-off, but we still learned a lot from the process and thought we’d share our experience here.

The Application

At over 50 questions long, the YC application can be a daunting task. If you’re looking for tips on how to fill out the application, you should probably start here. It gives you a good idea what they’re looking for and even gives you a sample application (from Dropbox). Here’s another useful sample application.

The way we personally handled the application was by putting all the questions in a giant spreadsheet and then having each of the four of us put down our thoughts on each one. Our CEO then wrote out a first draft of the answers, we reviewed the answers together, revised them, then repeated this revision process until we were satisfied with the application (which took about three revision cycles).

The main focus of our attention in the application went to the idea section. Most of our answers in this section were several paragraphs long. For a start-up that is doing a B2C company in a very competitive space (dating) we thought this was where we had to show we were special. Also, we thought for this section it was important to not only show you had a strong idea, but also to show you could talk intelligently about your idea. YC cares more about the team than the product so showing you have the brains to navigate your idea and execute it can be just as important, if not more important, as showing you have a strong idea to start with. We made sure to do a bit of research on our competitors and on the dating and discovery markets to back up our answers and show our expertise in the area.

The other sections we focused on were the individual sections. Our strengths in this section were probably the reason we got an interview. Each of us has a strong educational and professional background. It also probably helped that all four of us were technical founders and had previous experience coding.

The two essay questions in this section were:

  1. Please tell us about the time you most successfully hacked some (non-computer) system to your advantage.
  2. Please tell us in one or two sentences about the most impressive thing other than this startup that you have built or achieved.

For these questions each of us listed a few things we thought might fit the prompt, then the other three members of the team evaluated those options and select what they thought was the strongest answer. In the end, we mostly went with the more long-term, professional accomplishment. For example, I won a few Hearthstone Tournaments back in 2015, but also have a screenplay that is probably going into production with an independent company next year. We went with the latter anecdote because, let’s face it, no one really cares if you can win at a children’s card game (I was literally just virtually beating up teenagers online).

Interview Prep

We got notified about a week before our scheduled interview, which didn’t give us a lot of time to practice. On top of this, I was sick at the time and our CEO was at a wedding in Korea, so our preparation was scattered at best. Luckily there are a lot of resources for this online. We mostly referred to this article, but if you’re more interested in reading a personal experience, you can check out this blog post or, better yet, keep reading.

To prepare, we scoured the internet for potential interview questions, came up with a few of our own, put them in another spreadsheet, then wrote up bullet points we wanted to hit if any of those questions came up. Again, we made sure to have data at hand to back up our points (both general market data and user feedback). We also assigned each person to a different type of question. I was in charge of questions relating to our product and about our competitors. Our CEO was in charge of any questions relating to our vision and overall mission as well as questions about our team.

For early practice we used this website. The questions on that site were mostly generic, but it did give us a good sense of the pace of the interview. Speed is a big factor in the interview, so it’s important to keep your answers concise and have them ready to go. This early practice helped a lot with that. At the beginning, we found ourselves using up most of our time just figuring out what our answers were going to be, but towards the end, we were just rattling them off like a bunch of uh… rattlesnakes, I guess?

Off to California!

We flew into SFO the day before the interview. I watched The Devil Wears Prada on the flight because when else am I going to have an excuse to watch such a girly movie? We ate lunch at a small Ethiopian restaurant and then met up with a friend who gave us a mock interview. Our first mock interview went pretty well. We answered all the questions in an appropriate amount of time and touched on all our core strengths (very important). There were a few mistakes, but hey, nobody’s perfect (except maybe Anne Hathaway, damn).

Then we visited another friend, Curtis, who happens to be a previous YC alum and the cofounder of a multi-million dollar company. We went to his office, did a quick mock interview, and that’s when we started realizing there were major problems with our application.

Curtis picked up on it right away. Firstly, he noted that we had just launched and had no traction. Unavoidable, but true. Secondly, he noted that we would probably have to pivot at some point because the market we were moving into (dating) was highly competitive; it’s very common for B2C companies to pivot at some point. It seemed like he wasn’t enormously impressed with our idea and that for a company with no traction moving into a competitive market, he really had to be wowed.

We spent the rest of that night talking about Curtis’s notes and trying to come up with a way to maneuver around the issues that we had, but ultimately we didn’t have a strong answer to either point. We didn’t have traction since we just launched, and we were set on moving into the dating market. We settled on playing up our strong user feedback as evidence that we could probably get traction fairly soon, and downplaying our involvement in the dating market by focusing more on the discovery aspects of our app.

The Interview

Halloween. The day of our interview. We woke up early and had breakfast (free Nutrigrain bars at our Airbnb!), then took an Uber to the Y Combinator headquarters. We got there about an hour early. We spent most of that hour just pacing around, trying to relax, but we did manage to talk to two other interviewing companies and compare notes. One of those companies was actually from Brooklyn so we got two of the founders to download our app and check it out. Sweet. Gotta get user growth whereever you can find it right?

Onto the actual interview. There were 4 interviewers. Three were YC Partners and then there was Qi Lu who’s the head of YC China and former COO of Baidu. We’re not sure if he was supposed to be the silent guy who was only there to take notes, but actually all four interviewers asked questions, so maybe the “one silent guy” rumor is just a myth.

The interview started out pretty normal. They asked us what our company did. We gave a quick answer – we provide recommendations for personalized date spots. They asked what problems users had that we were solving. They asked how we came up with the idea. They asked why users would use our app over Yelp. We explained how Yelp was better for searching for specific things whereas our app was more useful for people who had no idea what they wanted to do. All of these were questions we were prepared for.

Then they started to get specific. Qi Lu asked us if we had heard about Toutiao, a Beijing-based news platform that has a discovery engine similar to ours (using machine learning). We had no idea what he was talking about. We diverted to Dianping, a Chinese company we were familiar with. They started grilling us on how we were going to take on the dating market. Apparently one of them was in a YC group that had three companies in the dating market and they all had to pivot. They asked if we had thoughts on pivoting and moving away from the date market. We said we did (and listed a few examples), but they didn’t seem convinced.

Despite that, we did manage to close the interview pretty strong, citing that our insights were mostly on how discovery should work and that we were not attached to the dating market. They also asked how committed we were to the project and if we already had funding, allowing us to point out we were all highly committed to the project, having known each other for 20+ years, and with very little day to day costs could easily continue working on the project for years with little funding.

Still, it wasn’t enough. The rejection letter we received later that day was as expected: We think the team is strong, but dating is very crowded and more traction is needed. We are not moving forward with Trapeze. Please consider reapplying in the future.

Disappointing, but it was a result that we were were prepared for, given that we felt fortunate to get an interview in the first place. Maybe if our ideas were stronger or our team more impressive we could have squeezed our way in, but at the end of the day, having no traction in a competitive industry is having no traction in a competitive industry. Because of YC’s great track record, there are tons of great companies applying, many of which already have proven traction and steady revenue. There was little reason for them to accept us until we showed them something solid.

Still, despite our failure, it definitely wasn’t waste of time. We learned a lot during the process. We learned more about what seed accelerators like YC are looking for, we learned how to sell ourselves and our company, we aligned more on what our company’s mission is, and we found out that we’re moving into dangerous territory with our app, one that is difficult to conquer. Hopefully we’re up to the task!

Also, I got to watch Crazy, Stupid, Love on the flight back, so that was a plus. Mmm… that Ryan Gosling… I mean uh… Emma Stone.

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