January 15, 2020

Interviewed with Y Combinator

David Small @mrdazm

Last October Passbox managed to achieve the holy grail of getting to the front page on Hacker News - peaking at number 7 over the course of a day. What I did not mention in my post about the experience is that I was motivated to “launch” on Hacker News as a result of having my first ever Y Combinator (YC) interview roughly a week following the post! Here’s a recap of my interview experience and spoiler: I was not invited to be part of the Winter 2020 cohort where I would’ve exchanged 7% equity for $150,000 in funding plus mentorship from some of the best in Silicon Valley to further develop and grow Passbox.

The Backstory

I built Passbox out in parallel with and during YC’s open, online 2019 Startup School program. Startup School featured a $15,000 equity-free grant. The possibility of receiving the grant is what primarily moved me to apply to YC’s accelerator program - a requirement for the grant - as a first-time founder in Miami, Florida. Startup School participants were eligible to be selected for the grant if:

  • they met certain criteria throughout the course; and
  • also applied to be part of the following YC Winter batch but were not selected for it.

Applying to YC

In my opinion, the application form is straightforward - asking questions about what you’re building, why, what business opportunities exist for it, your team (ie, founder) composition and other related questions. In reading application preparation resources online (and YC’s own recommendations) it is stressed to be clear in your application. Avoid jargon, be expressive and concise. Do the same in the minute-long video clip of your team that you’re asked to include with your application. In it you’re asked to introduce your team and what you’re building. About three weeks after submitting my application for the late September deadline I got unexpected news: I was invited to interview to be part of the Winter 2020 accelerator batch!

With being invited to interview I was given a fixed date and the option to select the time slot in which I’d be interviewed. Funny enough by the time I read the invitation email - around 3 AM EST - and logged in to select a time slot there was only one remaining! Clearly I was late to this party.

The Interview

My interview preparation primarily consisted of reaching out to those in my social network who had been part of YC previously and graciously willing to offer advice that included: looking up YC interview resources online, reviewing and condensing my user interview notes, Hacker News, Product Hunt and Reddit comments in addition to research into competitors in the space. I also spent some time looking into my app’s user behavior analytics.

In my opinion, one thing to note about a YC interview is that there’s no magic behind it. It’s quite simply a conversation about your startup and its users/customers. It’s a 10-minute panel conversation with around 4-5 notable names/faces that you may recognize from the tech world who are genuinely curious about what you’ve built (if applicable), what you plan to build and whether it aligns with the profile of companies that YC funds. From my blurry recollection of the interview it started out simply with what I was building with Passbox and progressed to conversation about incumbent solutions, competitors, my Hackers News feature and challenges with Passbox truly dominating its market and succeeding. Again, this is a natural and thoughtful conversation. I chose to prepare printed charts of some of my user analysis - in hindsight they weren’t needed but are good reference notes for my own ability to talk about how Passbox has done so far.

As you know from the intro above Passbox was not selected. The thoughtful feedback I received on their decision against funding Passbox centered around building a service that needs to outlast its users/customers and needing to compete with existing password management tools for ultimate relevancy - after all, it wouldn't be useful for the app to contain outdated credentials.

My Recommendations

With the understanding that this opinion is coming from someone who was not selected to be part of a YC batch I’d summarize my preparation tips as follows:

  • Relax, it’s only a short conversation introducing smart people to what you’ve been working on.
  • Be able to clearly explain/pitch what you’re building and why without jargon.
  • Have an understanding of your users’ needs (ie, talk with them).
  • Know your market: competitors, business opportunity for your startup, ways you stand out.
  • Review other, more in-depth accounts and preparation tips for interviewing with Y Combinator.

In retrospect I’m in awe and appreciative of having such an epic opportunity to chat with members of the Y Combinator team about my humble project that I started coding a few months prior to the interview. In particular I’m in awe of being a Silicon Valley outsider given the chance to be propelled forward in startup land in a huge way!

Though I wasn't invited to be part of the current cohort of startups in YC, I'm happy to write that Passbox was selected to receive the $15,000 grant! Feel free to join the mailing list for updates as I continue on seeing how best to create value!

Happy to answer questions on the experience as best as I can.


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