ometimes a childhood hobby can grow into a lifelong career. For Josh Bowman, that hobby was chess. From a young age, he not only loved the game but excelled at it—eventually ranking among the top 1,000 chess players in the U.S.
Over the years, Josh gave private lessons, but it was during Covid that the idea for Chess Chevra was born. A friend asked him to run a Zoom class for his son and a few classmates, and the response was so positive that Josh realized he was onto something bigger. Once in-person learning resumed, he developed the concept into a thriving, sustainable business.
Today, Chess Chevra clubs are running as after-school programs in schools across the country, with some schools even incorporating Chess Chevra directly into the curriculum as a class or enrichment activity. Beyond that, Josh now works with dozens of certified Chess Chevra coaches who tutor both children and adults eager to sharpen their skills.
Josh and I spoke about his personal journey, how he keeps his own game sharp, and the advice he offers to anyone looking to become a stronger chess player. Enjoy!
—Nesanel
I was born in the Valley outside Los Angeles, and I moved to Philadelphia when I was nine. I really consider myself a Philly guy, and we settled there after I got married.
“I’m the oldest of four. My father was a researcher in the pharmaceutical industry, though he didn’t talk about his work very much. My mother is a social worker and still works in that field, helping connect people with the services they need. Earlier in her career she worked in adoption and social care, but she also took off 13 years to be a stay-at-home mother.
“I went to public school in Philadelphia. I actually started playing chess later than most. I didn’t even know the rules until I was almost ten. Today, I’d say most kids in the frum community already know the basics by the time they’re seven. Once I learned, I jumped right in. At ten, I asked my parents to hire a chess coach for me, and they agreed. From there I got into tournaments and began improving quickly.
“I ended up winning the Philadelphia elementary school championship, the Pennsylvania middle school championship, and later the high school championship for the entire state. A big highlight was when I got to represent Pennsylvania in the national tournament of high school chess champions (I placed 15th out of 50 states).
“I dove deep into the game. Over the years, I played in about 250 official US Chess Federation tournaments and studied dozens of chess books cover to cover. I would spend hours each day immersed in chess strategy and practice. Looking back, I think that was extreme, and today I discourage kids from devoting so much of their time to the game, but then, it was my passion.
“Outside of chess, I was active in a Jewish Boy Scout troop and eventually earned the rank of Eagle Scout. I also joined the wrestling team, though I can’t say I was particularly good at it. I was always much stronger at chess than at wrestling.
“I wouldn’t have called myself entrepreneurial as a kid, or even as an adult. The only entrepreneurial venture I was involved in before Chess Chevra was that after I got a high score on my SATs, I started tutoring other students in my high school. I had a long lineup of students waiting for help, though it never turned into an organized business. It was just something I did on the side.
“I went to Stanford University in Palo Alto, California, where I majored in public policy. At the time, I didn’t really know what I wanted to do. It was more of a ‘help the world’ type of major, something broad and idealistic. Even after I graduated in 2014, when I was 22, I still wasn’t very career directed.
“I grew up with a strong Jewish identity. We belonged to a Conservative synagogue, and I stayed in Hebrew school all the way through 12th grade, which was rare. The all-Jewish Boy Scout troop also helped reinforce my identity. When I got to college, I signed up for every Jewish group I could find: Chabad, Hillel, Israel groups. I ended up clicking most with the Meor kiruv organization. I connected with the rabbi there, Rabbi Ephraim Kamin, who had a Chofetz Chaim background. I came in with a very typical liberal college mindset, but I had already started questioning the standard positions on issues like Israel and social justice. Rabbi Kamin and I would constantly discuss all these topics, and those conversations opened up my eyes and pushed me to think more seriously about what is really true.
“I decided to do some soul searching, so I started booking meetings with all different types of Jewish leaders—Reconstructionist, Reform, Conservative and non-religious—as well as people from other faiths like Bahai, Muslim, Sikh and Buddhist. I wasn’t interested in joining their religions, but I wanted to use those conversations to crystallize my own beliefs.
“Coming out of that process, I felt strongly that Rabbi Kamin’s mehalech was correct, and I wanted to become frum. I went to Machon Shlomo in Har Nof, and I had a great experience there. Rabbi Beryl Gershenfeld is the rosh yeshivah, and I really connected with him as well as with Rabbi Yehoshua Styne.
“I learned a tremendous amount during that time. I gained the skills to learn Gemara and Chumash with Rashi, and I also learned about hashkafah. It was a full immersion. The chevrah there was incredible. Most were baalei teshuvah in their 20s and 30s, and there was a real sense of friendship, camaraderie and shared growth.
“I decided to stay in Israel, so I joined ‘the Chabura’—Rabbi Barry Klein’s yeshivah. I lived in a dirah off of Meah Shearim Street with a few guys packed into each room. The yeshivah itself was a unique mix: part baalei teshuvah and about three-quarters guys who had grown up frum but were looking for more personal mentorship in life and learning skills. Rabbi Klein himself grew up Modern Orthodox. He’s a fascinating person. He used to be a basketball coach, and he incorporates that coaching style into his learning and guidance. Rabbi Klein’s mentorship helped me so much, not just with Gemara skills but also with integrating with frum culture. His entrepreneurial approach to creating and running the Chabura also personally resonated with me. He was actually one of the first people to encourage me to start an education company.
“While in yeshivah, I decided I wanted to go into the field of education. By my mid 20s, I had been tutoring chess and SATs for years, but I didn’t see myself as a classic classroom teacher or school administrator. What I really wanted was to build my own company, do things my own way and create my own schedule. After spending four years in Israel, I went on to grad school with that vision in mind.
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