Lessons from our Y Combinator interview

Frank Lagendijk
Dec 21, 2018 · 6 min read

What it was like & lessons learned (so you can do better).

The valuable talks, interviews, and all of the other great stuff that is published online for startup folks to consume, that’s how I got to learn about Y Combinator and their accelerator program years ago.

When we started building Shipright (a tool to help companies understand their customer feedback at scale, so they can build products people love) and got our first customers early 2018, we’d always had it in the back of our minds: getting the opportunity to join a YC batch would be amazing. Experienced advisors to learn from, a network of people that think alike, awareness for your company, a platform to raise funds, and many other advantages that would allow to propel a startup forward.

After applying late for the 2019 Winter batch, we were surprised and delighted to hear that we were invited to come over for the YC interview on December 5th!👌

Spoiler alert: we didn’t get accepted but it has been a great (learning) experience nevertheless. Writing these experiences down seems like useful reflection, and maybe even something anyone can benefit from for their own interview.

Prepping the interview

We had ~2 weeks left before hopping onto the plane when we heard the news. We read a few articles, and watched quite a few YouTube videos of other founders that documented some of their experiences. It gave us some more context on what to expect…

Prepping for such a fast and furious 10-minute interview is a great exercise. You don’t only need to carefully think about every angle of your business but you also need to be able to articulate things in a very clear & concise manner. Hopefully you try and do that already as a founder but it might not happen often enough, since you are in the trenches all the time and things change constantly. Hence, most founders struggle to even concisely explain what they do in layman’s terms (as you can see in live office hours as well).

The experience itself is a great way to find out if you have any blind spots and practice solid articulation of describing important parts of your business.

We’d created a list of common YC interview questions (based on a bunch of articles we’d found) and documented how we could answer them concisely. Find our shortlist of questions here, if you’re interviewing yourself. I’d definitely recommend anyone to go through a similar exercise. Even in case you won’t get these questions during your interview or in case you won’t be accepted: it’s a great way to uncover potential blind spots on different levels and practice solid articulation when answering important business questions.

Our prepping continued during our 15-hour flight, and so did some ‘ingenious’ marketing efforts ;)

If you ever encounter a weird ‘Trivia’ leaderboard on an Aer Lingus flight…

Additionally, Alex, a great YC alumnus that mentored us during YC Startup School, invited us over to help out on practicing the interview. We received some solid feedback. It was clear that we needed to put in some work to improve. And so we did, continuing during our commute time.

Try this tool to practice answering the most common questions in 15 seconds 👌

Tip: in case you ever plan to do something like a YC interview, try to get YC alumni (or anyone else with a bunch of experience) to interview you in a similar fashion.

Game time

Fast and furious it was. Time literally flies by during such an intense 10-minute chat. Afterwards, we figured we’d done quite an ok job.

We had Geoff Ralston (former vp of product at Yahoo), Gustaf Alströmer (former lead product growth at Airbnb), and Stephanie Simon (Former founder & engineer at Earnest) as our interviewers. They seemed to get what we were doing today and seemed genuinely interested. One of the biggest issues: we failed to communicate the potential of what Shipright could grow into. That’s what we learned from a big part of the e-mail that stated they weren’t going to fund us as well:

“…The software you’ve built looks great and, without doubt, adds value to your customers. However, at the current price point, this is a very small market. And it is not obvious that you will be able to charge too much more since you are (currently) operating like a feature of Intercom…”

The fact that we didn’t take the opportunity in the first 30 seconds of our conversation to convince them of the huge opportunity ahead, made the conversation go more into where we are today. Had we better emphasized the bigger potential, we could have steered the conversation a bit more in that direction. At least we would shown them more prominently what that bigger picture could look like.

Obviously, we then got follow-up questions on: how many customers we currently serve, how Shipright was used by our customers, what our current pricing looked like, how the product exactly worked (demo) etc.

A few key take-aways

By no means can I give advice on things that work (we weren’t accepted, after all) but if we would interview again, there are a few take-aways on how we would prepare differently:

  • Take the first 20/30 seconds to not only state what you do, but also give a teaser on the huge potential more prominently
    Remember, they are looking for companies that could get to billion dollar valuations and can’t read your thoughts on how you might get there. The opening would be different if you already have enormous traction and growth. You should address it either way, but when in an earlier stage, I’d say it’s even more important to clarify the potential right away.
  • Prepare even better for the ‘obvious’ follow-up questions, not only for the popular questions listed by others
    Example: we were asked to give a very explicit example of how one of the insights from Shipright affected a specific product decision for one of our customers. If you don’t prepare for such questions (which seems quite an obvious follow-up question to gauge real-life customer value), you either take too long to answer, or you fail to answer with a proper example at all.
  • Practice. Not only with your team or by yourself but with others that don’t shy away from poking holes in your answers (and force yourself to simulate the conversation over and over again)
    People outside your team aren’t framed by a similar experience and will ask different (follow-up) questions. Obviously, practice with people that are relevant to your field, and are further along in terms of experience (preferably). You want to try to simulate the interview as realistically as possible. I think we ourselves managed to do this pretty well but could have taken a bit more time upfront. Flying in a few days before to see if we could meet up with other interviewees to challenge each other. Which seems like a great way to connect with like-minded people anyway.

It’s been a great experience we enjoyed and learned from. I’d highly recommend any startup founder that finds itself in an early stage to apply. Worst case, you learn a bunch and have a great trip.

Founding team Shipright

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