YC Applicants: Q&A with Abby and Ivan Kirigin of Tipjoy
I have recently exchanged Q&A emails with Ivan Kirigin, the founder of tipjoy.com, about his experiences being in the Y Combinator. I want to really thank Ivan and Abby for replying all these questions with depth. I've promised I would share these Q&A with the community so all YC applicants can have a taste and feel of what's to come and more importantly what the application process is like.

I also want to thank Andrew Warner from mixergy.com for helping me and inspiring me to apply for Y Combinator. If you ever need to learn entrepreneurship, his interviews is a great way to learn it from.

Here's the Q&A:

Q: Did you have to assist the financial risks that were involved with both of you in the same business? Isn't it like putting all your eggs in one basket?

The worst case scenario was that we would have to go back to 'regular' jobs. Leaving a job at a big company to start your own company is probably the best reason to leave, and it is important to keep ties with that world so that you can rejoin it if need be. We figured out how much time we had before needing to move forward with this "nuclear option". We just keep aware of our runway so we don't get surprised. Between our savings and our investors, we've been able to be secure.

Q: What was your overall Y Combinator application experience like?

I told Abby about it in summer 2007, saying it might be for college students. She looked it over and thought it was good for any company. We'd been reading lots of Paul Graham's essays and thought YC's approach was exceptionally creative. We edited our application over time, crafting the message and wording a lot. Working through the application like this really helped us refine our idea, our goals, and our vision. It was very valuable. Once we were accepted to the interview, we practiced pitching to a few friends and colleagues. It was amazing how much our approach to talking about and presenting Tipjoy evolved during those sessions.

The interview was definitely not what we expected. We butted heads with Paul quite a bit. There were some user experience approaches
which Abby felt were key to what we were doing. Although the UX approaches don't add up to the entire product, YC's main concern was that we were so passionate about our idea that we might not be willing to alter it if the market demanded. Abby thought we didn't get in. I wasn't sure. Ultimately they must have enjoyed the debate because we were accepted! Working with YC has been an amazing experience.

Q: Besides submitting an application, did you do anything extra to help you get into the interview round with Y Combinator?

We had a demo system live that I'm pretty sure they didn't look at. Making it was a good exercise for us though.

Q: What was your interview experience like? Do you have any advice for the new applicants this year?

Lots of people make the mistake of assuming the interview is a presentation. That's not the format. It's a conversation with maybe a 3-second demo component. They asked a lot of questions right away and that guided the conversation. I'd recommend practicing by pitching to people that understand your market.

Q: When you got funding by Y Combinator, did you have to give up a lot to move to California? How did you feel right before you moved?

We had to move from Arlington, Massachusetts. We had a house, which we kept and eventually moved back into after moving back to
Massachusetts. We had a spot in a nursery school for our son, which we also managed to keep. Really we didn't have to 'give up' anything. Everything that mattered was coming with us.

Once we knew we were moving (of course we accepted YC's offer right away), Abby spent a lot of time getting all the logistics worked out. She found a temporary place for us to live in Mountain View which would work for our family. In addition to our son Luka, we brought our dog and also my mom who came to live with us and take care of our son Luka full-time. When it came time for the move, my brother helped me drive a carful of stuff across the country. We owe a lot to our family who are always there to help.

We were very excited to move. It felt a bit crazy like a fox, but the opportunity was too big to pass up.

In fact it was great that we were taken out of our normal routine and life in MA. That way we were able to completely focus on building
Tipjoy. It was also great to spend several months entrenched in the Valley network.

Taking this leap together has been pretty amazing. Our company and our family are stronger and richer from the experience.