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Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 1)

Posted on Tuesday, May 4th 2021
Profile photo of Kristi Herold

If you haven’t already, please study our free Bootstrapping course and the Investor Introductions page.

Kristi built a thriving bootstrapped business over twenty years until Covid hit. Read how she is surviving Covid.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

Kristi Herold: I grew up in a small city called Sudbury, Ontario. It is about four hours north of Toronto. I have two older brothers and a very supportive mother and father who encouraged us to get involved in sports. They taught us to do what we wanted in our life. My father is an entrepreneur. My grandfather was an entrepreneur as well. I followed the footsteps of both my brothers to be entrepreneurial going through high school and university.

In high school, I didn’t want to work for anyone else, so started my own lawn cutting business. Before I had a driver’s license, I was walking through the neighborhood cutting grass for anyone who was within walking distance. I went to Queens University in Kingston where I studied commerce. I didn’t do well in my commerce degree. I passed, but my marks were never great because I was running two businesses while in the university.

I ran a franchise of college for three years. I also ran a custom clothing business. After university, I moved to the big city of Toronto. I didn’t know all the people in Toronto, but I decided at that time that I wanted to run my own business. I didn’t know what the business would be. I had heard about a sports social club that I believed was called Golden Gate Sports Social Club. I thought that this would be something that I could try.

I loved sports and I loved connecting with people. I thought that this was something that I could try in Toronto because it would help me connect and meet with more people. It was like looking for an opportunity within my own problem.

In 1996, I started the Toronto Sports Social Club. Over the last 25 years, we grew the social club to be one of the largest adult recreation league sports providers in the world. We get over 150,000 people playing on an annual basis across nine different cities in Canada and the United States.

We were looking to grow a lot bigger and then the pandemic hit, which forced us to stop our operations. We have not been able to operate for the last 13 months. That was when we pivoted to a whole new organization called JAM. 

Sramana Mitra: Let’s go back to 1996. Remember that we are doing an Entrepreneur Journey story. Let’s try to understand what you did with the sports league and then we will come back to the pandemic time and how you pivoted. Go back to 2006 and tell me what you did to launch your sports league.

Kristi Herold: In 1996, I had moved to Toronto and didn’t know a lot of people. I didn’t even have an email address. This was before the internet was popular. I remember in January of 1996, I had picked up my address book and started calling people saying, “This is my idea. I’m thinking of running a sports league for adults which includes soccer, basketball, flag football, ultimate Frisbee, and volleyball. Do you want to sign up and play?”  

This segment is part 1 in the series : Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM
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