50 Years of Kenyon Women: Lydia Winkler ’13

Lydia WinklerTo celebrate 50 years of coeducation at Kenyon, we profiled Kenyon alumnae during the 2019-20 academic year. Lydia Winkler ’13 was an American studies major and accomplished tennis player at Kenyon who went on to earn business and law degrees from Tulane University in New Orleans. Winkler is an entrepreneur who co-founded RentCheck, an app that aims to increase transparency and reduce disputes between tenants and landlords, and launched REEP Now (Relief Effort for Earning Parole), a non-profit that assists inmates appearing before Louisiana’s parole board.

How do you prioritize your life and get things done? 

The key to getting things done is having a good routine, which takes discipline. I’m my best self when I exercise regularly, eat well and spend time with my friends and my dog, Tyson Chandler. When you’re in a rhythm of getting things done, it’s a lot easier to continue and make progress. 

At the same time, it’s important to be flexible and adaptable when you’re starting a company. One thing that helps is to consistently ask “What is the problem I’m trying to solve?” When I do that, it’s easier to prioritize tasks and make a game plan. 

Where did you first discover your power? 

Right now, living in the South, I’ve never been more aware of my privilege and how the opportunities I’ve been presented with have propelled me in my career. Education transforms lives, and I’m grateful for what I learned at Kenyon and at Tulane.

During my first year of law school, I successfully advocated for and represented someone who was up for parole. It was then that I realized how education is a powerful tool that can be utilized to help those who haven’t had the same access.

Who at Kenyon inspired you? 

[Professor of Art] Gregory Spaid. I took film photography second semester of my senior year, and while it was the hardest class I took at Kenyon, I loved every minute of the struggle. This was the first art class I took, and it did not come naturally. I would take entire rolls of film of the same shot just to make sure I got it right. It taught me to be patient. 

Art takes time, and like most things, when you get it right it’s worth the wait. It’s very indicative of my journey as an entrepreneur — I learned to welcome failure, act on it and try again. 

What’s the best advice you’ve ever received? 

“Every problem is an opportunity.” My dad, a member of the Kenyon Class of ’77, always said that to me when I was growing up. For example, RentCheck is a direct result of a personal problem I faced: when I was a law student, I had to sue my former landlord over a security deposit that was wrongly withheld. I was successful, but realized my problem could be eliminated through the use of technology, and RentCheck was born.

How has your worldview evolved since leaving Kenyon?

We’re living in a politically divisive time — far more divisive than when I graduated. I’m a firm believer that empathy is one of the biggest drivers of innovation. It’s vital to surround yourself with people who don’t look like you and think like you. Otherwise, we will fail to create and build products and communities that are radically inclusive. 

This interview has been edited for length and clarity.