Female Founder Stories: Katelyn Gleason, Founder of Eligible (YC S12)

by Y Combinator2/8/2015

Eligible offers healthcare eligibility, payment, and reimbursement APIS.

Q: What did you do before starting your startup?
I was a professional stage actor in New York City focusing on Shakespeare. I was also a 20-year-old sales manager of 40+ person sales team.

Q: How did Eligible get started?
I was living in NYC and was really frustrated with the acting/stage scene. I wasn’t able to get any work and the theatre culture seemed stuck in the past. I went through a sort of semi-existential crisis at 23 which led me to start reading a lot of different autobiographies and learning about philosophy. I quickly became obsessed with the idea of finding the “movers of my generation”.

I wanted to find the artists that could actually use their art and creations to change the world. I found Drchrono shortly after on craigslist and got a job with them. I immediately fell in love with building a product and company and, before I knew it, was working 90-hour weeks to help them bring their product to market. I then moved to a small, one-room apartment on Castro Street in Mountain View and started my own company, Eligible, with $5,000 in the bank and no idea how I would make the idea work. (I was repeatedly told I was insane to do this– even by my boyfriend of over 12 years!)

Q: How did you meet your cofounders?
As a non-technical founder, I felt a ton of pressure to go out and either become an engineer or find a technical cofounder. I made a lot of progress teaching myself the basics of engineering, but I felt insecure without a technical partner. At the time, I was bootstrapping and had no money to pay anyone and was pretty desperate (which inevitably leads to bad decisions!).

I ended up recruiting two cofounders I should have known would not be able to dedicate their lives to the company as much as would be needed for it to succeed. One was a teenager just graduating high school (a friend of the family) and the other was a 40+ year-old I met via Stack Overflow who had a full time job at ING Bank plus a family with four children. Both of them had huge hearts, but neither of them had enough time to devote to what needs to be a 24 hour / 7 day a week commitment. Eligible lost each of them in less than one year of each other and I ended up without any technical cofounder.

All of our investors and advisors freaked out and tried to talk me into finding new cofounders immediately, but this time I was smart enough to wait.

I hired, on-boarded, and trained the entire Eligible engineering team myself. Two of the earliest engineers I recruited (one from AngelList and the other from Elance) earned the cofounder title one year after starting to work for Eligible. They are now the Chief Technology Officer and the Director of Engineering and have been with the company for over two years.

Q: What was your experience with YC like?
Not to sound extreme, but Eligible would not exist without YC. Office hours with PG are beyond something you can explain. He has the ability to (within three minutes) pinpoint the exact source of the most important problem you are facing. He doesn’t offer you a solution, per se, but he digs into the problem with you at lightning speed usually leading you to your own solution. I remember there was about a one-month period during summer 2012 where we wanted to pivot from the Eligible system we had built and one office hour meeting with PG was the sole reason we didn’t.

He said something to the effect of, “You’ve built something, people want it, they are willing to pay for it, and the market is really big. Why give up now?” It sounds corny, but I think his belief in the company helped me believe in it again. Doing a startup can get really depressing and isolating, and I remember that particular day being one of the darkest for me. I think just hearing positive reinforcement that Eligible had the potential to be really big was enough to make me continue to go for it.

Q: What is the atmosphere like at YC during those 3 months with Demo Day approaching?
Exciting, intimidating, widely educational. The Tuesday dinner speakers are the best investors and founders in the world. Some of the most important lessons I needed to learn were absorbed by simply listening at those dinners. One example is that when you are creating a company it is better to slide your way into an existing massive market that is being pushed into a new generation of technology rather than trying to build a brand new market from nothing.

Q: Was being female either an advantage or disadvantage in working on your startup?
I have a tendency to see everything through an optimistic lens, so I like to believe that being a young driven woman may have actually helped me in the YC interview process. It certainly helped me stand out. It continues to help me stand out when hiring, closing deals, and fundraising.

Q: What do you wish someone had told you when you were 15?
That I was a nerd. All throughout college and high school I was a straight A student in all honors and “gifted and talented” classes. But all my best best friends were the jocks and cool kids and they were never in any of my classes. I think I always knew I was different in that I excelled in learning and they excelled in sports. But instead of embracing that, I spent an awful lot of time trying to cover it up.


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