Legends Baseball Founder David Klein ‘05 Talks Entrepreneurship, Baseball, and Disconnecting From Technology

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This is the 55th article in Bears Doing Big Things, a weekly column celebrating the stories of notable M-A alumni.

David Klein ‘05, Founder and Executive Director of Legends Baseball, moved to Menlo Park when he was ten. He lived by Bob’s Country Corner, where he would later get his first job. With video games that “weren’t as good as they are now” and no phones, Klein recalled, “I spent a lot of my time in the streets playing roller hockey, biking around, and sneaking on the baseball field playing Home Run Derby.”

At M-A, Klein played baseball and football and played guitar in his band. 

Some of his favorite memories came from math teacher Bobby Wong, or “Wong” to him and his friends. He remembered, “He was always me and my buddies’ favorite teacher. We would go out and get Korean barbecue together, and he would help us after school with whatever we needed.”

On football, Klein said, “It was one of the greatest experiences I’ve ever had because I got to build relationships. I was also exposed to people from all different backgrounds and walks of life, instead of just the West Menlo Park kids, which was eye-opening for me. I think it helped me build relationships later on with all different types of people.”

Klein (left) with four other alumni playing for the Legends

Going into sophomore year, Klein wanted to make the varsity baseball team, but the only position open on the senior-heavy team was catcher. So, Klein spent his summer learning the catcher position and played it for the rest of his baseball career. 

Klein continued to play baseball at the University of California, Santa Barbara (UCSB). He entered as a Psychology and Music major but switched to Communications during his sophomore year. He graduated with a degree in Communications and a double minor in Technology Entrepreneurship and Sports Management. 

“I thought Communications was more applicable to what I thought I would eventually get into. Little did I know that most of the stuff that I learned in class in college didn’t apply to what I’m doing now. I learned more in college by way of playing intramural sports, relationship building, time management, being a fraternity president, and all those other things that weren’t necessarily academic curriculum,” he said.

Modeled after the Santa Barbara Foresters summer team, Klein founded the Legends collegiate team at the end of his senior year, initially as a passion project. Klein remembered, “The jerseys didn’t come in in time for our first game. My parents and I were up until four in the morning ironing on Michaels patches on the back of shirts.”

Upon graduation, Klein became a sales representative for medical devices. At the same time, he worked to expand the Legends program. “Every summer, I would go back and coach my baseball team and kind of quit my job,” he said.

Klein returned to M-A as a varsity baseball coach from 2016 to 2019. There, he would start a new project: America Offline, a program where teenagers would spend 48 hours at an offline retreat to learn how to develop a healthy relationship with technology and, in turn, the world. He said, “One of the first things I realized when I was coaching at M-A was that kids weren’t getting their driver’s licenses despite being old enough. I was like, ‘Whoa, why is that?’ and I couldn’t figure it out.”

Klein said, “I started to pay more attention to what was going on with kids at the time, and I realized that my athletes carried a lot of anxiety with them. They were very school-obsessed and grades were everything. I saw way less camaraderie within the team, and a lot of it pointed back to technology, where kids were spending more time studying behind a screen or on their phones and less time interacting with people in person.”

“If you drive around the streets nowadays in Menlo Park, they’re quite empty compared to how they used to be. There’s just so many things going on. Kids are so overbooked,” he noticed.

If you drive around the streets nowadays in Menlo Park, they’re quite empty compared to how they used to be. There’s just so many things going on. Kids are so overbooked.

When COVID hit, America Offline dissolved. Klein said, “Everything went online. That’s when I went back into the baseball world where I am today. I still incorporate a lot of the holistic development practices such as time management, technology, awareness, mindfulness, meditation, and all the things that I learned through that into my baseball experiences.”

Klein started taking the next steps for the Legends program by expanding to an elite collegiate summer team which also included youth summer baseball camps. In this process, Klein learned, “There’s going to be a moment where you may have to go outside of your comfort zone and push the boundaries. You have to just will yourself to be successful.” 

For Klein, that moment was driving to M-A from UCSB and back one day his senior year—a ten-hour round trip—to book the baseball field for his summer program. He remembered, “The lady that was booking the fields was ignoring all my emails and phone calls. I finally just thought, ‘I am not going to let this stand in the way of me having my summer team.’”

Legends now has 2 summer collegiate teams and is the only registered franchise in the country to specialize in baseball and softball. Legends has 10 locations across Northern California, Southern Calfornia, and Arizona. Klein said, “We like to say we specialize in fun. A lot of programs out there are all about development and getting kids to play at the next level with nonstop drilling. We like to work hard, but at the end of the day, my goal is to put kids through an experience that’s ultimately super meaningful, memorable, and transformational.”

Today, Klein lives in Redwood City with his wife and two kids as he continues to build the Legends program.

Klein’s advice to current M-A students:

The idea that schooling is your ticket to the future is very prevalent at M-A. But, I think that getting great work experience as early as possible is the best thing to do—not just to put it on your resume, but to genuinely figure out what you like, what you’re good at, and to develop some legitimate skills.

Klein’s advice to students looking to go into sports management: “Again, I would say intern early. It’s a competitive field because everybody wants to work in sports and, because of that, it’s very competitive and you need to stand out. Read a lot about what’s the latest and greatest and stay up on things so you’re at the cutting edge. Get your hands dirty early.”

Celeste is a junior in her second year of journalism. She is the co-writer of the weekly column Bears Doing Big Things, featuring alumni. She also is a copy-editor and manages the publication's Spanish translations and social media. She enjoys covering issues affecting the M-A community through features and writing Bear Bites about local restaurants. Her story on La Biscotteria was recognized as a top-10 NSPA Blog Post of the Year.

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