Turning a maybe into a yes after the YC interview

By Kam Leung

Introduction

We applied to YC back in February under a different idea than Papercups (an open core Intercom alternative). It was supposed to be expedia but for booking ocean freight. Currently to make a freight booking you have to call multiple procurement teams at a shipping company. We were trying to make freight pricing more transparent by letting people book and compare prices on a website. We had worked on the project for a few months and thought it was worth a shot to apply. We filled out the application, recorded our video, sent it out, and didn’t think much of it.
A few weeks later, COVID hit the US in full force. California and NY were locking down, the stock market had crashed, and I had fled to a cabin upstate in an attempt to avoid the pandemic. So when the email came in letting us know we had gotten an interview, YC was the last thing on our minds

Getting Freight Traction

Things had slowed down quite a bit with China and Europe being shut down. All of freight entered panic mode with shipments being canceled or delayed by days and weeks. Regardless of that, we figured the best way to prepare for the interview was to get more traction. We started out by sending several hundred cold emails and emailing every connection within our network. At the same time we started building out features that would help companies price freight over email. We made some progress and had a few conversations started but was hoping for some LOIs or some deeper conversations with decision makers.
We decided to spend the weekend before our interview preparing by having friends run mock interviews and ask us tough questions. We thought this helped expose a number of weaknesses and it forced us to be concise in explaining our business and our ideas.

YC Interview

I’d read a study once that said that judges are more likely to give prisoners parole after lunch. Thinking that maybe a full belly would similarly put our interviewers in a good mood, I made sure to book the interview after lunch. The call was scheduled for 1:00 pm and it went by in a flash. The partners asked us about the progress of the company and business model. Then they asked about how we were going to be a billion dollar company. At this point we got a little loss in the numbers. We were describing how much money these logistics companies had sunk into their software but the partners were really skeptical.
At the end of the interview we were just glad it was over and could take a breather. But within 30 minutes of our interview they sent us an email telling us to do a second interview with partners that were more knowledgeable about the freight industry.
For the second interview, Dalton Caldwell and Aaron Harris were on the call. Aaron had worked closely with a company in the past that worked on a similar idea. He was very comfortable with the industry jargon and was very knowledgeable but it became clear that he didn’t think we should be working on this idea.
Aaron asked us why - if this is an important problem - hadn’t Flexport built an internal version of our product. We didn’t have a good answer. Dalton then started asking us about what we would do if we had to pick a different idea. It became pretty obvious that they were not fans of the idea. Before we knew it, the interview wrapped up as I spat out some other ideas we had worked on in the past. Even though the interviews didn’t go great we were kind of relieved that the process was over.

Post YC Interview

You normally hear back on the same day and they send the rejections by email and acceptances by phone call. So for the next few hours we sat there waiting. Until finally at 8:19pm we got an email from Aaron.

Email 1
Well that wasn’t what we were expecting. We had never heard of getting follow up questions as a part of the YC interview process. But at that moment when I saw that email I jumped into action. I thought we should get back to Aaron as fast as possible. I responded with the following email at 8:30 PM
May 4, 2020, 8:30 PM
Email 1
Then I hopped on facebook and frantically messaged everyone that might have a connection to someone that worked at Flexport. As a Hail Mary plan I even messaged Ryan Petersen (CEO of Flexport) on Linkedin asking for help. Within 15 minutes someone got back to us with an introduction to an engineer at Flexport. Within 30 minutes we got on the phone with an engineer and got our answer. We quickly sent the email below:
May 4, 2020, 9:59 PM
Email 3
Next afternoon Aaron shot back the following:
May 5, 2020, 2:43 PM
Email 4
From our frantic messaging the night before we got a few more people from flexport on the phone that afternoon and got a better understanding.
May 5, 2020, 4:00 PM
Email 5
Then we waited for a response. I thought we were going to get an answer that night but we didn’t hear anything. For the next two days we were glued to our email and phone waiting for a response.
Finally on May 7, 2020, 8:32 PM we received an email:
Email 6
Turns out my spam blocker had redirected his number. I called Aaron back within 5 minutes and that's when he told us we had gotten into YC and asked if we would accept. Which I promptly said yes even though we were a bit nervous about the remote batch. What followed after was a phone call with Alex and a very loud celebration with my cabinmates.
Recently as I was writing this article I was asking for his permission to use his name in the article and had asked for the reason we got in. This was his answer:

Reflection

In the end we did pivot away from freight. From the interview process and conversations we got a better sense of what founder market fit meant. Originally we thought that we should pick an industry where there isn’t too much competition and that other developers would shy away from. We later realized that we should stick to our strengths and industries where we are familiar with. We chose Papercups partly because Alex had worked on customer messaging tools at Stripe and I had worked on open source projects at Pivotal. This worked much better to our strengths and we were able to make way more progress in 2 months than we did in 6 months of working on freight.

To learn more checkout our github repo: https://github.com/papercups-io/papercups
Special Thanks to:
Aaron Harris, Alex Reichert, Stepan Parunashvili, Joe Averbukh for reading and helping me edit the post