“So it’s like a wiki?” he says, moving his fingers in circles against his temples. His eyes are closed. He’s concentrating. He has 10 minutes to understand me.

This is the story of how we interviewed at, and were turned down by, Y Combinator. I decided to write about the experience because storytelling is one function where we startups tend to shit the bed. Hopefully this post helps kick that ball forward a bit.


This past May, it cost $2,428.13 to have three of us spend 10 minutes with Paul Graham. Being from out of town (Toronto) this included flights, taxis, and accommodation for 3 nights. In hindsight, spending three nights in sleepy Mountain View was a great decision. There’s nothing to do but talk about your business from morning to night. The extra time also meant we were extremely well prepared for the interview. Or so I had myself believe.

Only now, having been tested by the pressures of a ticking clock and the questions of an impatient (and widely respected) mind, do I have the courage to say that the reason we didn’t get into YC was because I didn’t know my business well enough.

Sounds crazy, right? I mean, as far as titles go, I’m the guy who’s primary role is to know what the hell business we’re in. I’m not asked to write the code that brings it to life, or define the user experience that sets the tone – I’m asked to tell our story clearly, effectively, and when needed, very f*cking quickly. So maybe this post should have been titled, ‘What I should have said to PG’ – because this one was on me.

The following is a rough outline of my conversation with PG.

“So what is Rocketr?” he opened. To which I replied…

“Rocketr is a bottom-up approach to knowledge management. We connect people through their notepads. Basically, people take notes and decide how to share them. The primary mechanism by which they share them is through co-authored notebooks.”

“So people can all write to the same place. So it’s like a wiki?” he asked.

“Not really, no. A wiki is more like a google doc – it has one true version at any given time. Sure, there’s a revision history, but nobody lives in the revision history. Rocketr is about having one author for a given note, and a threaded conversation around it.”

It may not be immediately obvious what’s wrong with this picture, but if you picked up on it, kudos to you. There are 2 things wrong with how the interview opened:

  1. PG drove and I quickly found myself back on my heels.
  2. I stripped out so much of the marketing jargon (a YC rule), that I skipped right over the customer’s pain and the value of solving it. I gave the “features” pitch, not the “benefits” pitch.

I came into the interview ready to react. I had an answer for everything, but no real story that I was going to tell. In hindsight, I should have opened like this:

“Rocketr bridges two worlds that could not be further apart right now – how we capture information (using personal tools), and how we get work done (using team-based tools). We’re betting that these worlds will converge, because if they don’t, it will get harder and harder for teams if they can’t collaborate at the speed that information is changing around them. Oh… and the medium we use to facilitate all this, is note-taking – something we all know how to do.”

Yes – it’s a little longer, but that shouldn’t matter if I’m the one driving for those 10 minutes. Even if I was interrupted, I could pick the story up where it left off. In this version, I’m illustrating the pain, the trends, and only at the end do I mention the vehicle by which we go about it.

The missteps continued when he asked, “Who needs what you’re making?” I reacted with something like the following:

“There are two sides to the market. Organizations need this to drive innovation and individuals needs this to satisfy both use cases – personal note-taking and sharing those notes for the purpose of getting feedback. Currently, they’re resorting to email for the latter which is a terrible environment for notes to grow up in.”

Just reading that now makes me shudder. So far I’ve communicated that we are “another note-taking app”  with some social features AND that every entity on Earth needs us. Kill me.

What I should have said was:

“Paul, we think Y Combinator needs this in a big way. You’re managing 460+ companies. I’m guessing you send them articles, competitive intel, potential customer leads, and a wealth of other ideas. You’re probably using email to do it. And while you might use labels or folders to keep all this information organized on your end, your startups don’t have access to that. You’re effectively relying on them to either a) action every idea immediately, or b) do multiple queries of their inbox every time they want to revisit an idea you guys discussed.”

Not perfect, but much better. It becomes obvious that the pain increases the more “teams” or “topics” you’re managing. Furthermore, by putting YC in the middle of the story, I am making it easy for him to stand in the customer’s shoes. This all but guarantees his next question will move the conversation forward – not sideways.

And if you don’t have the lucky fortune of being able to use YC as an example customer, then use someone close to them – like one of their companies. And be sure to use peoples’ names. It will make it easier for them to empathize with the plight.

No matter which way you look at it, 10 minutes goes fast. It’s incredibly easy to get flustered and not have enough time left on the clock to recover. And despite all the wonderful resources that point to the questions you’ll be asked, I promise you, you will be asked many more that aren’t listed.

My recommendation for any startup reading this, is to shift your mindset ever so slightly. Prepare like you would, but when you walk in that door, have a 4 or 5 minute story to tell, instead of 25 answers to 25 commonly asked questions. In fact, take this approach on every occasion where you get to pitch your business.

The next time someone asks you, “So what does your startup do?”, lay it on thick. Tell a story. Get them to empathize.

And most importantly, drive.

Andrew Peek
Written by

Co-Founder of Pilot.