Posted on Monday, May 10th 2021
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Kristi Herold, CEO of JAM, 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?”
Our conversation continues
here. This segment is a part in the series : Best of Bootstrapping . Bootstrapping to an Exit . Why is Bootstrapping Important? . How Can You Play this Low-Probability Game Intelligently? . Do NOT Go to VCs as Beggars - Go as Kings . Excess is NOT Required for Success . Bootstrap First and Raise Money Later . Some Bootstrapping to Exit Case Studies . The Buy Side of Bootstrapping to an Exit . Blitzscaling vs. Bootstrapping . Bootstrapping to Unicorns More »» . Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million . Mailchimp Bootstraps to $600M Revenue . Bootstrapping from Arizona to $10 Million . Bootstrapped Basecamp Executes a No Nonsense Strategy . How Under30Experiences Bootstrapped to $5 Million . Bootstrapping with a Paycheck . How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan . Seed Investors Who Like Bootstrapped Businesses . How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million . Bootstrapping with Services . 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