Business of the Month: S3 Leagues

s3 Leagues chitribe business of the month ben shimon

Meet Ben Shimon – Founder of S3 Leagues

Meet Ben Shimon, founder of S3 Leagues, originally from Mequon, Wisconsin, and a tenured Birthright Israel staff member. Ben is the mastermind behind S3 Leagues in Chicago, providing co-ed recreational opportunities all year round. From softball to bowling, S3 Leagues offers programming for all different skill levels. ChiTribe was excited to learn more about Ben and S3 Leagues.

My leagues welcome all skill levels, are only coed social leagues and half the fun is that ALL teams walk to the same bar together for drinks after playing!

Ben Shimon, s3 Leagues Founder

Where are you from? 

I’m from a small city just outside of Milwaukee, Wisconsin called Mequon. Unofficially known as “The Quon”

What did you do Jewish growing up? 

What didn’t I do!? I sacrificed my childhood to attend Sunday school as well as Hebrew school 2 additional days a week. This led me to my Bar Mitzvah, where I nailed my haftorah portion and then celebrated by embarrassing my 13-year-old self on the dance floor in front of all my friends and girls I had a crush on that I invited to my welcome-to manhood party. I was a member of the temple youth group, the best part being that we got to go out of town 4 times a year to weekend retreats. In college, I visited Israel with Birthright and realized that Israel was amazing! Being a kid in college on a scholarship, I became a Birthright trip leader and got to go back 6 more times to help other people have an amazing experience like I had. After college, I volunteered in Israel for 5 months. After that, I settled down into life and have been your regular Reform Jew ever since.

s3 Leagues chitribe business of the month ben shimon
Photo of Ben from 5-month volunteer program called Isreal Service Corps, 2007

What do you do for fun? 

I love to hang out with my wife and 2 little girls the most. It brings out the child in you! We also really enjoy taking vacations to places most people don’t go to. We also go to Disney and the like. I enjoy going to concerts, not even the huge ones but the local ones where you can set up a blanket and half the time you don’t even know who you’re watching. Just being outside is the best. Come winter, I like to distract myself from the cold by hanging out with friends, watching movies, and relaxing after a super busy summer of leagues. But I also enjoy my work as well, so that’s a hobby right?

When did you start your business?

It all started in the spring of 2009. If you’d like the full story, head here. The short version is that I was selling ads in the actual phone book, in a cubicle with a headset on, and realized I wasn’t happy. I decided to travel the world and be happy. Before I left, I started one 16″ softball league just to make some money for the trip. My leagues all started as leagues for SINGLES! Everyone was single, and it was a blast. I decided to grow and I changed it from Singles Social Sports (S3) to Simply Social Sports (S3) to allow anyone to join. We still get tons of singles but you can also bring your spoken-for friends.

My leagues welcome all skill levels, are only coed social leagues and half the fun is that ALL teams walk to the same bar together for drinks after playing! Plus you can join as a team or individual or small group and are guaranteed to be placed on a team. If you’re new to the city or just looking to make new friends on top of being active playing, this is a great opportunity for you.

Where is your business located? 

We play at lots of locations all across Chicago! All-year-round. Fun fact: We also have leagues in Boston that an amazing girl named Jess runs!

What products/services does your business offer? 

Fantastic Coed Recreational Sports & Social Leagues. Also, some pretty fun events during the year like First Friday Stand-Up shows at the Laugh Factory, River Tubing BYOB Float Trips, Parties for the Super Bowl, NYE & More!

s3 Leagues chitribe business of the month ben shimon

How have you stayed motivated during the Pandemic?

The business went right to zero overnight and it was tough, but I created S3 from scratch and I wasn’t going to let it cease to exist. We ran some virtual trivia leagues during the pandemic, when we had windows to run leagues we ran what we could, and stayed positive. It was a challenging time because the income from the leagues supports me and my family. Thankfully things have improved and demand for the leagues is higher than ever! It’s been a blessing and I’m incredibly grateful for the support I’ve had from all my past teams and players, and lots of new ones too.

What are your goals for your business? 

I believe the idea of a more welcoming, social, organized, and unique sports league could thrive in any city in the world. Honestly, I just want to keep running my leagues the way they are for as long as possible. I truly love what I do and care a lot about making my leagues great. It’s hard to grow as well because all locations where we could play are already booked and have been for years. I guess running 80 leagues a year by myself will have to be enough haha.

How do we get involved in the leagues?

I hope you do! You simply go to and register! It really is that easy. Sign up a full team to put together your own roster and make it cheaper per person, or register by yourself or with a friend or a few! Once signed up you’re guaranteed to play and before we start you get a super long but highly informative email with everything to know for the season.

When the Tribe Gathers… laughing and kvetching ensues

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Rebecca Schwab

Rebecca Schwab

Rebecca creates best practices and executes marketing campaigns for Jewish organizations who are trying to reach the next generation of the Jewish community - specifically Millennials and Gen Z - through digital marketing, social media, online and in-person events.