My experience interviewing for Y Combinator W2019 and what I would have done differently

Last week my friend Mike and I had the awesome opportunity to interview at Y Combinator for their Winter 2019 class. Spoiler Alert: We didn’t get accepted. Nevertheless, it was a great experience and I wanted to share how it went for us and how we might have approached it if we were able to hit rewind and do it again.

I’m going to go through all of the events leading up to the interview in some detail but if you want the TLDR version, go ahead and skip down to the section titled The Do-Over.

The YC application asks you some standard questions about your product, the market, the competition, how far along you are, how the founders know each other etc. It also asks some fun questions like:

The trickiest/most fun part of the application is the 1 minute video. The instructions are, “In the video please introduce yourselves, explain what you’re doing and why, and tell us anything else you want to about the founders or the project.” That’s a lot to cover in under 60 seconds! They also specify that they want you to keep it unscripted. Babblers, you’ll have to really reign it in!

We submitted our application in October (a week late) and expected to hear back later that month or in November (as the application suggested).

Early one morning in mid-December I was surprised to see two emails from Y Combinator in my inbox. The first was letting me know that we had made it to the final step in the application process, the in-person interview. The second was an email confirming our interview time, just over 3 weeks away on January 2nd. This is the part where you freak out! My wife and I talked in more detail about what this could actually mean. It sunk in now more than it had before because getting in was a real possibility.

Being accepted to YC means moving to the Bay area for at least 3 months. We would find out whether we were accepted into the program the day of our interview and the kick off for the program was the very next day. We would then be expected to move there as quickly as possible. YC gives you a $150K investment for a 7% stake in your company. Getting in is the closest thing to a startup rocket ship there is. This is a life-changing event. It’s an awesome and scary feeling.

We flew out to SFO the night before and stayed up late practicing the questions and going through the demo.

We woke up the next morning and walked to the nearby CVS to grab some breakfast (microwave oatmeal — tasty!). After eating, we took one more run through the iPG tool and then headed out for the YC office. It was about 20 minutes walking distance from the apartment we had rented on AirBnB (YC class of Winter 2009 by the way). We got to walk through the beautiful neighborhoods of Mountain View and wax poetic about what we were about to do. The weather was perfect. We felt good.

We arrived at the YC office 90 minutes early. The office on both the outside and inside is unassuming, especially compared to the spiffy Silicon Valley offices of the companies that have graduated from the program. The office space is primarily made up of numerous small interview rooms and the large hall where the famous dinners, alum key notes, and Demo Day take place. I’m embarrassed that I didn’t think to take a picture of the hall but I had the interview on my mind.

There are sofas in the waiting area and lots of founders practicing their pitches, pacing back and forth and trying to keep their minds off the fact that a 10 minute interview stands between them and being part of the most prestigious startup club in existence. Oh yeah, did I mention that? The YC interview is only 10 minutes long! Founders from at least 500 companies fly to Mountain View from all over the world for the chance to get grilled for just 10 minutes. This isn’t your standard startup pitch either. You know the fun part where you get to show off a pretty slide deck with informative charts, screen shots of your product and customer testimonials. Nope. At YC you skip over all that fluff and jump straight into the part where the VCs grill you on why they think your idea won’t work and see how you stand up to the pressure. Needless to say, there is a lot of nervous energy in that room!

Our interview slot was at 11:45am and so at 11:47 I walked up to gentleman running the schedule to make sure we hadn’t missed our name being called. He explained that they were running a few minutes behind and let me know that we were up next in room 2. Wait … room 2? When we checked in he had told us room 3. Right about that time the door opened and we were up. We had no idea who we were interviewing with. We walked in with big smiles on our faces and got started!

We were ready for the first question which is pretty consistent no matter who is interviewing you, “Tell us what you’re working on.” We had practiced the answer over and over so we’d get it concise and crisp. “We’re building an app that uses data to help workers in the gig economy make more money.”

After what felt like 2 or 3 minutes of intense questions there was a knock at the door. “Ok — well thank you for coming!” It was the fastest 10 minutes I’d ever experienced. We thanked them for their time and walked out of the room a little bewildered. “That was fast.” I said. “How do you think it went?” Mike asked. “I have no idea.” I replied. Having read a ton of other accounts of interviewees both successful and not, we knew it was pretty common to leave the interview without a clue as to whether it went well.

We sat down for a second and I played the interview back in my head. They had pushed us really hard on the concept, the specifics of how we’d increase our users’ income, and whether people would pay for our product. We knew our numbers and our audience and I felt we answered many of the questions well. We had remained upbeat and hadn’t let the pressure push us into a defensive stance. There was one question though that kept replaying in my head. “So how much more money do your customers earn on average during the 30 day free trial?” We had already told them we didn’t have customers. We were pre-launch. There was only one way to honestly answer this question, and they knew it. We simply said, “This is something we’ll have to learn.” While I tried to stay optimistic, that question would continue to haunt me throughout the day.

We got back to the apartment and looked up who we’d interviewed with. It was an influential crew:

Despite the impressive resumes, I couldn’t help but feel like the conversation might have gone differently if we had indeed interviewed with Kevin, Steph and Gustaf. I tried not to let “what if” scenarios run wild in my head.

After interviewing, you will hear back from YC that evening in one of two ways:

We rested at the apartment for a bit, then grabbed the Caltrain to San Francisco. We ran into multiple other founders we had seen at YC and commiserated a bit on the interview process.

As we walked up the Embarcadero I felt my phone vibrating. I pulled the phone out of my pocket and saw a number I didn’t recognize. We stopped dead in our tracks. I answered, “Hello?” “Hello, is this Jesse Harding?” I swallowed … “Yes, it is.” there was a pause. And then a phone salesman launched into his pitch. Once I realized what was happening I politely told him I wasn’t interested and ended the call. Mike and I exhaled and then chuckled.

Geoff said the decision came down to two things:

Bullet one: The question that had been haunting me all day. The question we were just too early stage to answer. Bullet two was something I felt we had addressed rather well, but combined with the first bullet it created too much doubt for the team to place their bet on us.

Though it felt like a long trip, the overwhelming feeling we had as we returned home was very positive. The basic concept had been at least broadly validated by the application committee. And although we didn’t get in, all we need is a little more time and data to prove we can do what we think we can do.

So what would I do differently if I could go back? I can boil it down to 3 things:

1- Be certain about our room assignment: This might seem like a small thing but in a situation where many aspects are out of your control, it’s always best to fully manage those you can. There was no excuse for us not knowing who we were interviewing with. The room assignments were on a screen by the front door, and I could have easily double checked. Instead we spent unnecessary time looking into YC partners that ultimately weren’t going to interview us and conversely didn’t know anything about the people who did interview us. Worse than that we were caught off guard by the mix-up seconds before entering the room which, however small, was a zap to our confidence.

2- Treat it like a pitch: This is the most important thing I would share with future YC applicants. Everything we read said this is not a pitch. It’s chaotic. It’s unorganized. Disorienting. Random questions being thrown at you. Sometimes 2 or 3 conversations going on at once. While it is definitely different than a standard pitch, it was far less chaotic than we thought it would be. And the problem is, we had prepared for that chaos. We hadn’t prepared for a pitch. The list of potential questions you’ll read online or practice in the iPG tool are great to know, but I would worry less about answering them rapidly in random order, and worry more about having concise answers to them in case they are asked.

I would instead create a simple outline and do my best to steer the conversation through each item (even if it is out of order). I would also prepare answers for when the partners contradict or disagree with each item. It would be something like this:

For us, the conversation went off course and into the weeds a couple times. There was no way to steer it back on course because we hadn’t prepared a course to begin with. We were at the mercy of whatever course the partners decided to take us on.

This will be one of the fastest conversations you’ve ever had. Know the bullet points you need to hit and make sure you hit them. Also, remember, the partners aren’t being mean or pessimistic. They don’t hate your idea. They don’t hate you. They are pushing you to see if you’ve done your homework. DON’T get defensive. Smile!

3- Try to “encourage” a demo: We had a pretty powerful demo that we never got a chance to show. If I had a second chance I would have answered that first “So what are you working on?” question by handing the partners a phone with our demo on it while reciting our elevator pitch. It’s unlikely they’d go through the whole demo, but the hope would be to peak enough interest that we’d land the mythical 2nd interview. If the partners feel like they didn’t have enough time with you, they can ask you to stick around so they can dig in a little more. YC is very clear that is not an indication that you made it. But in my opinion, more time with the partners can only help your chances.

We learned so much and were extremely impressed with how organized the process was and especially the ability of the partners to make life-altering decisions based on 10 minutes and their gut.

40% of companies in the Summer 2018 class were started by founders who had previously been rejected by YC. I can see why. It’s a unique experience. I definitely feel like with the knowledge I have now, I could return better prepared. Will I ever do it again? Yeah, I am pretty certain I will.

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