YC has been a ton of fun and work, and things seem all rosy from the outside, but launching your company at Y Combinator is no joke. There is a certain rite of passage that every YC company must take, and it’s called “The Whiteboard Conversation." It’s one of the most exciting times in a soon-to-be-hatched company’s life, but you must pass the gatekeeper to get there, and his name is Paul Graham. This is the tale of our journey to The Whiteboard. Read on if you dare. It all started back in November when Grubwithus got an interview spot in YC’s Winter 2011 class. As cocky as it sounds, we honestly thought that if we got the chance to interview, we wouldn’t have a problem sweet talking our way in. To guarantee we got in, however, we knew we had to do something to ‘wow’ the judges before our interview. Since Grubwithus brings people together over food, we hatched an ingenious plan (or so we thought). Most interviewees would no doubt contact a bunch of YC alumni for interview questions and tips, so why don’t we reduce their burden by hosting a series of dinners where a consolidated group of YC hopefuls can speak to a few YC founders over a great meal? Brilliant! We went to work right away. Daishin set up all the San Francisco restaurants and I contacted the YC founders. Y Combinator has a ‘pay-it-forward’ mantra and it really showed. A bunch of YC alumni got back to me instantly, saying they’d love to come and help out. They were probably also really excited that we were offering them free dinners… After we set everything up, I posted on Hacker News with a title similar to “Grub with YC Alumni during interview week” and linked to our site. Immediately the post was getting upvotes and we were hitting the front page. It was probably my second post to HN ever, and it was feeling real good. A few people instantly reserved seats and we thought we were golden. How could YC reject us if we were clearly showing that we built something people wanted? And then my biggest fear happened. 43 minutes after I posted, my post got killed. I didn’t think I was doing anything harmful, but I didn’t want to anger the HN Gods by posting again before our interview, so I asked some of the YC alumni for advice. The general consensus was to email pg and ask him about it. That was something I really, really didn’t want to do. I imagined pg doing something very important while seeing my pesky email and getting annoyed that this wannabe YC guy is bothering him with a tiny HN matter. We definitely weren’t so cocky about getting into YC anymore… A little while later, pg thankfully responds with “It sounded like it was somehow sponsored by YC.” Okay, no problem. I’ll just post again and make sure people know it’s not YC sponsored. So I quickly repost, only to see my link gain no traction and slowly disappear into the abyss. Not one upvote. Not to be dismayed, I didn’t want to spam HN by posting the same exact link again, so I wrote a blog post with a juicy title and linked to Grubwithus from the blog post. Surely I could get people to click into the blog entry and check out the meals from there! Still no action. I was still reminiscing about the early success of that first blog post, but there was no giving up at this point. We thought of other crafty means of getting the word out, and we remembered that a bunch of the interviewees had put their twitter handles in a private YC spreadsheet (NOTE: DO NOT DO WHAT WE ARE ABOUT TO TELL YOU! BAD BAD BAD!). So naturally we thought, hey, we have everyone’s twitter handles, let’s tweet them and tell them we’re setting up meals for the interviewees! I mass tweeted a bunch of people, and while most of them were pretty receptive, I totally forgot that other candidates still had jobs and didn’t want employers/friends to know they were interviewing. Bad! A few unhappy emails later, we deleted all the tweets and were back at square one. Sometimes being too scrappy has its downside… We resorted to tweeting random people who were talking about YC and trying out the Diggs and Reddits of the world with limited success. Our first dinner was coming up and we knew we didn’t have too many more chances to post on HN before being the first invited company in history that pg refuses to interview. I posted to Hacker News one more time, and it still didn’t make a dent. The one thing I was learning, however, was that there are certain times of the day that HN gets a ton of new links posted onto the site, so unless you’re posting a super compelling story, definitely avoid those times or else your story will be wiped off the front page of the ‘new’ section super quickly. Little did I know, that behind the scenes, Paul and Jessica were already a little unhappy with “The Grubs”, as pg now calls us. Jessica wasn’t too happy that we were pimping out these YC dinners and we weren’t even part of the organization, while pg thought the dinners might be fake. We found out from a YC alum at one of our dinners, that pg actually emailed everyone in YC and asked if we were for real and if the YC alumni actually agreed to go to these dinners. Another note to future applications, definitely do something before the interview to wow people and show that you can execute, but maybe don’t do anything to irk the partners deciding your fate. At least one thing was for sure: they would definitely remember us when we actually interviewed. Finally, it was our time to interview. We were a little nervous, but we had comfort in knowing that at least they knew what our company did by now! We actually had a really fun interview and one of the people in the room actually went to one of our pre-interview dinners. Of course, the topic of our YC-dinners came up and we apologized for causing problems. They were still smiling though, and pg said, “It’s okay, you’re not the first company to overstep their bounds." We finished our interview, chest bumped a few times, and got our acceptance call that night. People frequently ask us about our pre-interview tactics and our journey to the White Board. The problem is, while pg outwardly disapproved of our actions, we know he secretly loves founders that push the limits. So our advice is: be naughty enough to get your goal accomplished, but retreat if necessary and make sure you apologize! This story was originally posted on Grubwithus' blog (now Superb).
