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So you have a YCombinator interview coming up?  Congratulations.

You’d like some advice from a YC alum (S ’11) about how to prepare?  Happy to help.

If your startup is interviewing with YC, you’re probably all set on the product side and you probably have a great team.  That’s the foundation for a good interview.  You need to make sure you can explain what your product does in plain, clear, concise language and explain the value and expertise that your team brings to the table in the same way.  The YCombinator partners may have questions for you about either of those topics, but if you’ve been offered an interview, you’re probably capable of discussing those. You don’t need my help there.

Where you might struggle is when they start asking about your users.  My advice to every startup preparing for a YC interview is to know your user and to be prepared for a user-oriented line of questioning.  You might know your product inside and out and you certainly know why your team is awesome, but do you know your user?  Really?

Here’s an example of the sort of user-oriented questions that I see trip up many of the startups that ask me for YC interview advice.  You need to have answers for these.  You might not get asked them (I was asked them during my interview), but if you do, be prepared.

  • Who is your user?
  • What problem are you helping them with?
  • Why is this a problem for them?
  • What do they use to solve that problem right now?
  • No, what do they really use to solve that problem right now?
  • What do they like about this solution?
  • What do they not like about this solution?
  • What do they wish that solution could do for them?
  • How is your solution better?
  • How much better is your solution?
  • Why would they switch to your solution?
  • What do you know about these users that no one else knows?
  • How many of these users are there?
  • How many do you have now?
  • How did you get them?
  • How will you get more?
  • How many more will you have in 3 months?
  • What do these users currently pay to have this problem solved?
  • Would they be willing to pay more for something better?
  • Why are these users good users to try to solve problems for?
  • What other kinds of users could you go after once you get all these users using your software?

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This sort of customer drilldown can be disorienting at first if you’re not ready for it.  Most of the startups that ask me for YCombinator interview advice can’t answer more than a few of these when put on the spot.  This is understandable.  As an early stage startup founder, you have a lot of code to write.  As you write that code, it is very easy to get bogged down in the details, focusing on what your app can DO rather than the needs of the person that’s going to USE it.

But if you want your startup to be great, you need to know your users.  You need to be relentlessly empathetic.

Paul Graham has written that good startup founders are relentlessly resourceful.  This is true.  The best companies from my YC batch are run by founders who could find their way home in a few months if you airdropped them into a foreign country unexpectedly.  They can find a solution, even a crappy one, to any problem you put in front of them.

But another quality that the best startup founders have is that they tend to be relentlessly empathetic as well.  Oftentimes, this comes down to a single founder being the “user guy/gal” who makes it his or her job to talk to users all day, and in an empathetic way.

It’s very easy to talk to users without empathy.  I do this often and have to catch myself.  When you talk to a user without empathy, you’re looking for confirmation of your own beliefs and assumptions rather than actually listening for what their problems are and what kind of help they’re looking for.  Just listening isn’t enough.  You have to listen empathetically to learn things that will help your company take over the world (Peter Thiel refers to these sorts of strategic insights as “secrets” in a lecture he gave last year).

When talking to YC companies during office hours, PG often references how Airbnb CEO Brian Chesky flew back to New York City every week during his YC session so he could talk to users and stay at apartments listed on Airbnb in NYC.  Airbnb had a critical mass of listings in NYC at the time, so it meant he needed to be there, not in San Francisco, even though it required a lot of obnoxious travel during YCombinator.  The reason this was so impressive and memorable is because it was a display of relentless empathy, the kind of empathy that eventually helped Airbnb build a great product that million of people love.  By spending time in New York, dogfooding his own product and talking to users, he was able to learn things that made their business better.  (Did you know Airbnb thought the “breakfast” in Airbed & Breakfast was a crucial part of their product experience at one time?  A lesser startup would have persisted in this assumption for too long.  By talking to their users relentlessly, Airbnb was able to learn that no one cared about the breakfast, ditch it, simplify their product and make it better for it.)

So as you prepare for your YCombinator interview, ask yourself, do you know your user?  Are you able to drill down into the minutiae of their pains and the tools they currently use to ease them?  How deep can you get into the questions I posted above before you hit your first “I don’t know?”

Are you bringing relentless empathy alongside your relentless resourcefulness?

If so, you’re in good shape!  Good luck!  If not, it’s time to start sending more e-mails, setting up more customer phone calls, and having coffee with A LOT of potential customers.  If you can’t get inside your user’s heads, your software is never going to get inside their hearts.

Brad Flora

Brad Flora is co-founder and President of Perfect Audience. A former journalist, he started Perfect Audience to help make retargeting something that companies of all shapes and sizes can benefit from. He likes dill pickles and recently took first place in the Star Cup at 150cc in Mario Kart 64.

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