The View from the Office
I met Lydia Winkler, a founder, investor and advisor, at Slate Cafe in NoMad. She had black coffee; I had a latte.
Lydia co-founded RentCheck, a New Orleans startup whose software lets property managers have residents document a home’s condition on their phones at move-in and move-out. The record helps residents and property managers agree on whether repairs are needed.
The idea came from her own experience. Her landlord refused to return her deposit, so she sued. She hired two private investigators and rehearsed with a retired judge in his 80s who lived across the street. After 18 months, she won, recovered her legal fees and used the money for a trip to Southeast Asia.
RentCheck raised a $1 million pre-seed round, with Jim Coulter, founder of TPG Capital, among its first investors. The company went through Techstars. When the pandemic hit, property managers needed to inspect units but couldn’t send people inside. RentCheck let tenants do the inspections themselves. The number of properties on the platform grew 1,000%, according to the company.
We hadn’t seen each other in perhaps 25 years. I first met Lydia at Bloomberg’s annual company picnics. She is the daughter of my former boss, Matt Winkler, Bloomberg’s original editor-in-chief.
There’s something extraordinary about seeing someone you knew as a child and learning what she has accomplished as an adult.
Lydia told me three stories that shaped her life.
In August 2020, she crashed a paraplane into a tree in Chesapeake City, Maryland. She was left hanging 110 feet in the air for eight hours as gasoline from the aircraft caused severe burns. A fire truck couldn’t reach her, so a state trooper called an arborist, Rick, who climbed a nearby tree and brought her down. She was airlifted to Johns Hopkins and made a remarkable recovery. She tries to visit the tree each year and calls Rick on the anniversary.
In law school at Tulane, she joined a program that sent students to Louisiana State Penitentiary to represent older prisoners at parole hearings. She later started a program matching law firms’ pro bono work with parole cases.
Her first job took persistence. In 2011, during the NBA lockout, she decided she wanted to work for the Golden State Warriors. She moved to the Bay Area in 2013 and called human resources every two days until they agreed to meet. That led to a job in corporate partnerships.
Last year, Lydia left her full-time role at RentCheck and moved to New York. She now mentors startups at Oneday, an MBA program built around starting a revenue-generating business. She also builds apps and works as a performance artist.
If you are building something you should reach out to her as she can probably help.
Connect with Lydia on LinkedIn or DM me for a warm introduction.
