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Gary Lerhaupt is a tech entrepreneur from Cincinnati who earned his master’s degree in computer science at Stanford University, where he fell in love with the Bay Area and the idea of building products and launching startups. He has worked at Dell and Salesforce and been active as a founder or early employee at six startups, as well as engaged in some notable side projects, such as HackerTable.

In 2016, he co-founded Clockwise, an intelligent calendar assistant that uses AI to help users track, manage and even free up time to think, write and innovate. With an infusion of $31.6 million in funding, Clockwise has grown from three to 30 employees. It has over 100,000 users, most of them from big companies such as Twitter and Slack.

Lerhaupt, 41, lives in San Francisco with his wife, Sarah, an analyst at the California Public Utilities Commission, whom he met on JDate, and their two children, 5 years and 18 months old. They belong to Congregation Emanu-El and The Kitchen.

J.: Clockwise, the software company you co-founded, helps in scheduling and syncs a person’s calendar to Slack and Google. While you were VP of engineering at RelateIQ, how did the idea for Clockwise sprout?

Gary Lerhaupt: People on my engineering team often told me they have so many meetings, they don’t have time to focus on projects. Sometime I’d spot them working in a coffee shop or unmarked conference room. It seemed so wrong. I thought about building a system that understands preferences of people you work with. I wanted a product that supports flexibility, so people can move meetings around to open up time. Instead of having a half-hour here and there, what we call “Swiss cheese” on your calendar, you’d have a block of time. An optional function lets you sync your personal calendar into Clockwise. It blocks off time without divulging the details of your private obligations to your work colleagues.

Has it become more popular during Covid?

It’s particularly useful for parents working at home with kids. Clockwise is the engine powering sanity for my wife and me. Clockwise “sees” if my meetings overlap with my wife’s and rearranges them so one parent is always available to watch the kids. Our slogan is: “Make time for what matters.”

HackerTable, another of your projects, was once voted one of the coolest websites by 7×7. It let people make last-minute reservations at top restaurants — from French Laundry to Chez Panisse.

A colleague and I thought it would be a cool project to find all the last-minute open reservations for the top 50 hard-to-reserve restaurants. I built it for fun in a week, never meant it to become a business. But HackerTable lasted over five years. I’m a bad planner, so HackerTable also was useful for me. I’d go onto my own website and grab a last-minute reservation. I called it an “antiviral experience” because users wanted to keep it secret.

What was the funniest or quirkiest moment for you as an entrepreneur?

We were very busy getting RelateIQ ready to launch publicly in 2013 when two co-workers surprised us. They brought Stanford football coach Jim Harbaugh to our office. He gave us a sort of pre-launch rally talk. I learned everything you need to know to be successful in life is in the lyrics of “Row, Row, Row Your Boat.” But instead of “gently” down the stream, Harbaugh prefers the word “relentlessly.”

Your parents are both post-World War II Polish Jewish immigrants. Your late father was born in Uzbekistan, raised in Poland and then moved to Israel, where he served in the Six-Day War and learned diamond cutting. He immigrated to Cincinnati and ran a company that made jewelry. What’s the story of the ketubah your family donated to Yad Vashem in Jerusalem? 

My grandfather and grandmother fled from Poland to Russia. One day, while he was working in a cafeteria, he noticed a woman crying because her father needed medicine. My grandfather managed to give her enough sugar [and] she traded it for medicine to save her father.

Fast-forward to my grandparents’ arrest for lack of papers. In the Siberian workcamp, the woman and her elderly father recognized my grandfather and wanted to repay him. It turns out the old man was a rabbi. He performed my grandparents’ Jewish wedding — illegal in Stalinist Russia. The rabbi hand-wrote their ketubah in Aramaic. When my grandparents died, my family gave that ketubah to Yad Vashem.

What are some of your hobbies?

Bike riding with my daughter, going to Ocean Beach and hiking. And pre-kids, we even hiked up Half Dome. I used to go to a Jewish overnight camp in Indiana. Last summer, we hoped to go to Camp Tawonga as a family. Then Covid hit.