Y Combinator
Lauren Kay
Founder of Dating Ring (YC W14)

Dating Ring

Dating Ring is an online dating service that combines matchmaking and technology. When members sign up, they are assigned a personal matchmaker. Each week, matchmakers send their members a curated match. To help their matchmakers improve future matches, members give feedback after each match and again if they meet the match in person.

Q: Tell us about your experience at Y Combinator.

It was intense! I spent most of YC in the house I shared with my cofounders and working 12-14 hour days, 7 days a week. The exciting part of each day was generally walking around the corner to Safeway and grabbing Starbucks. Weeks were broken up by Tuesdays, when we spent most of our time at the YC office, catching up with other founders, attending group office hours and Tuesday night dinners.

Q: What is the atmosphere like at YC during those 3 months with Demo Day approaching?

It feels like finals period during college, except for 3 months straight. But it never felt competitive. YC has a "no assholes" rule and it really shows through the founders they choose. Most people are working in such different industries, and startups are at all different stages, so really, it would be hard to compete if you tried.

The other founders are extremely helpful. Even though everyone is under the same pressure to get as much done as possible on their startup, most founders would drop everything to sit with you for a few hours if you needed help on something.

Q: Was being female either an advantage or disadvantage in working on your startup?

Hard to say. Dating is of course a space that has a pretty even split of male and female consumers. I think it was easier at times for us to connect with people who felt that our service had a more trustworthy and human approach to the problem, but I don’t think this was necessarily because our founders are female. I definitely experienced a good amount of sexism during fundraising, but that didn’t stop us from continuing to grow and improve our company.

Q: What do you wish someone had told you when you were 15?

So much. As it relates to the startup world, I wish I was told to spend a lot less time trying to maintain a perfect GPA, and a lot more time making friends and working on extracurricular projects, without worrying about the outcome. I was always so concerned about what people thought of me, which stopped me from pursuing a lot of the crazy ideas I had as a teenager. I would have been way too scared of failure to start a matchmaking service in high school. I would have worried that I wasn’t popular enough, and that no one would join.

I also wish I was told to not stress myself out over the littlest things. In a college psych class, I learned something about how most things that seem super important have little to no impact on us a week, or a month later. So now when I'm stressed– over bad feedback a client gave, or the website being down for a few hours– I ask myself if it's something that I'll care about in a week. Almost always the answer is no, which allows me to focus on more important things.