Innovating Into the Future

How Lydia Winkler ’13 is using technology to change property management and renting.


From dreaming about going into government to expecting to move to Silicon Valley after graduation, saying that my interests have changed over the course of a year is an understatement. Over the past year I have shifted my career from International Studies, my major, to tech, business, and entrepreneurship. 

Since I left Venezuela in 2016, the conditions of the country have worsened significantly. Humanitarian aid delivery was either constrained or nonexistent. A year and a half ago, I got together with a few friends and founded Yakera, a crowdfunding platform that revolutionizes how humanitarian aid is delivered around the world. I realized the capability technology has to transform lives. I began to take programming and statistics classes, and the work I did outside of the classroom started to go into becoming a business and tech-savvy individual. When I started Yakera, I began to rely more on the Kenyon network to find alumni who had gone the same route. That’s how I met Lydia Winkler '13.

Lydia is the co-founder of RentCheck, an application that allows renters and property managers to conduct property inspections and ensure that there is a mutual understanding over the property’s actual condition. Lydia’s solution to property management and arbitration of security deposits are poised to generate greater trust between individuals. Although Kenyon does not offer business as a major, we are both examples of how the Liberal Arts mindset and the Kenyon experience can prepare us to use our imagination and critical thinking to provide solutions to major problems that affect our lives and millions of others. 

You have been able to found and lead a very successful startup. How do you end up there?

I majored in African American Studies at Kenyon. My senior comps was really special. I studied the Tuskegee Airmen, and realized that a lot of them were still alive and living in Ohio, and the Tuskegee Airmen were the first black military aviators in the US Army. I realized that this is a part of history that a lot of people don't know about. It's not in textbooks. It's not something you learn in school. So I Interviewed every living Tuskegee airmen in the state of Ohio my senior year. And then I invited several of them to campus and interviewed them in Rosse Hall. We had a packed house.

I've always been aware that I've had many opportunities that are awarded to me, and have always come at it from a place of not taking anything for granted. That's similar to education. I didn't want to take my Kenyon education for granted. 

What was the transition from a liberal arts campus to business school like?

I loved business school. The student body is diverse, not just in ethnicity, but in backgrounds. You have people that are coming from finance, coming from startups, coming from NGOs, etc. That was really exciting to me, because you get to learn from each other. 

While I was in business school, I always knew that I wasn't going to be someone that went to a big four consulting company that didn't interest me. I think that I caught the startup bug when I was living in the Bay, which is very easy to do, because you're surrounded by it. Then, when my landlord unjustly kept my security deposit and I went through the whole ordeal with taking them to court and winning, co-founding RentCheck was a no-brainer. I think I've always been someone that likes to take risks. Granted, they're calculated risks, but all entrepreneurs have to be a little bit crazy. What we do is a roller coaster. But without risk, there's no reward. And for me, it's really gratifying to be able to build a product out of nothing.

RentCheck came from a very personal experience that I had. After my first year of Law School, I had to move from the place that I had rented. 30 days came and went and I never got my security deposit back. 30% of all renters lose some or all their security deposit each year, which then creates this $6 billion tug-of-war over security deposit deductions. When I experience a problem, I try to ask, why did I experience this problem? How can it be fixed? What can I do to prevent this from happening to not only myself, but others in the future? And that's really snowballed and grown. Now RentCheck is used in all 50 states, every single day.

Has there been a point where you've been able to connect your Kenyon experience with what you are doing? 

I think the beauty of Kenyon is the people you surround yourself with, being able to choose your friends and have them choose you back. You’re constantly surrounded with people that inspire you to be better. Gambier is, as you know, a town with a population of 2000 people. There's not a lot of distractions. So, what do you do? You sit in a room and talk to each other. Having intimate conversations with smart people, I think, is the most valuable education possible. 

It's hard for me to pinpoint a particular class that really propelled me, but if I had to think of one it would be Greg Spaid’s photography class. I never saw myself as an artist, but that was one of my favorite classes. I would take two rolls of film to get one photo. That type of work ethic and precision prepares you for the real world.

I also played tennis at Kenyon all four years, and I think being an athlete has been one of the best experiences that prepared me to become an entrepreneur. As an athlete, you get a lot of chances to compete. When you lose, you're going to have another chance to compete again, so you don't dwell on it. The same thing happens running a business. Things are going to hit the fan at some point. It's how you handle those situations that defines your success. Having a mindset where you are resilient and you can work well with other people is so valuable. 

Going to Kenyon exposes you to so many different cultures and options in terms of learning. I took tap dancing, a biology class on animal behavior, and a music theory class my senior year. You have an instant connection with someone that went to Kenyon. That's how I feel. I was excited when you reached out because I'll talk to anyone that went to Kenyon, and we're stronger together. I want to see you succeed, and I am invested in your success because I know we both have this shared experience.

That’s amazing. What do you miss the most about Kenyon?

Living within a half mile of all your friends is something you'll never replicate again. Soak every minute of that up. I also miss the chocolate milk from Peirce.

It’s so good!

I miss Peirce. Peirce is great. I think everyone talked a lot of crap about Peirce, but after Kenyon everyone misses it.