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    • Jun 2, 2023
    • 4 min read

Stephen Kearley

2012 Newmarket

Stephen Kearley, owner of Benson Kearley IFG[i], began his entrepreneurial journey in high school. He sold designer jeans out of his locker for less than they could be purchased in retail stores, and went on to build a sportswear company. He had vision and the courage to follow his dreams, and along the way he’s been able to use his success to help transform the lives of others.


Born in Toronto and raised in a faith-based family, Stephen learned about helping others early in life. It’s a value he’s never strayed from. Whether it’s raising money for the homeless or reuniting estranged families for the holidays, Stephen has discovered unique ways to benefit others.


Deciding to grow his sportswear business rather than go to university, Stephen supplied t-shirts, school uniforms and other items specifically branded to meet needs he was astute enough to notice in his teenage years. Outgrowing that business, he sold it and went into advertising. His jump to insurance was not a planned move. As Stephen says, “no one ever intends to get into insurance.” He was offered a sales position and it clicked for him. When the opportunity came in 1991 to purchase an insurance brokerage, Stephen’s unfailing entrepreneurial vision saw opportunity and he grabbed onto it. He has taken Benson Kearley IFT from a 3 million dollar-a-year company to a 60 million dollar-a-year company[ii].

While financial success is an essential goal in following his passion, Stephen says that it is only one element driving his pioneering approach to life. “It’s more about having the freedom to create, build and design your life” that has been the catalyst to his achievements. Director and long-time member of Entrepreneurs Organization (EO)[iii], Stephen assigns much of his personal and business growth to his connection with this group[iv]. “Personally, I believe entrepreneurship is in the DNA. It is through my contact with other members of EO that I realized we have something that connects us; we all understand each other.”


Stephen has utilized his entrepreneurial creativity in developing charity endeavours. Co-founder of Hockey for the Homeless (now Hockey Helps the Homeless[v]), this organization was conceived thirteen years ago when Stephen and six other business men were playing hockey at Maple Leaf Gardens. They saw the potential to raise funds for charity because, as Stephen says “who doesn’t want to play hockey at Maple Leaf Gardens?” They decided to focus on homelessness in Toronto. In initial years they generated enough money to put together “survival kits” consisting of: sleeping bags, knapsacks, gloves, hats, socks, toiletries etc. that they personally handed out on the streets. However, they soon realized that, in addition to putting themselves in risky situations, they were not making the long-term impact they wanted. They decided to partner with organizations already helping the homeless. As of 2012, Hockey Helps the Homeless has grown to include tournaments and fundraising events in six cities across Canada: Ottawa, Montréal, Toronto, Niagara Falls, Vancouver and Calgary. They have raised 1.5 million dollars in support of homelessness. While Stephen is no longer personally active in this organization, Benson Kearley IFG is a big supporter through participation and donations.


However, Hockey for the Homeless was just the beginning. Applying the same creative energy at Benson Kearley IFG Stephen has developed several ongoing charitable initiatives. The brokerage is a big supporter of kids’ sports, sponsoring hockey camps for children in Newmarket, Aurora, Georgina and surrounding areas. They are also running a two year campaign that donates ten dollars to Southlake Regional Hospital for everyone who calls them for a quote – no questions asked[vi]. A warm approach to reuniting estranged family members at Christmas began in 2011 with Home for the Holidays[vii]. Enacting a Benson Kearley IFG core value, "We are an integral part of our community, striving to make a positive impact where we work and live", they paid all travel expenses to fly a brother from Jasper BC to spend the holidays with his sister and family. The initial intent was to reunite one family, but they decided to extended their generosity to a second family and flew a father in from Nova Scotia for a first-ever opportunity to spend Christmas with his son, daughter-in-law and grandchildren!


2012 will see the exciting beginning of a program designed to offer scholarships, mentorships, guidance, and resources to selected local high school students. Benson Kearley IFG will launch Students Making an Impact in September 2012 by canvassing local high schools, searching for those students who are making an impact through philanthropic works or entrepreneurial initiatives. High school students will have a chance to build an organization, and potentially create new jobs. As someone who has taken his company from seven employees to sixty-five, Stephen sees value in generating employment opportunities. “There is no bigger impact you can have on a community than creating a job.” Stephen says this is just the beginning. “Five, two thousand dollar scholarships is a starting point – we want to do more.”


When Stephen saw the impact of Home for the Holidays he thought, “WOW – we made such an impact but at the end of the day it did not take a lot of sacrifice. It gives you the resolve to want to do more. You say, ‘I can do more. I can stretch myself more. We can get more creative.’” Stephen does not intend to quit anytime soon. The teenager who had the vision to run a business out of his locker, the entrepreneur who has spent his life taking the risks necessary to create a successful business, continues to envision ways of creating positive change. “The first part of my life was about building. The second half of my life is about leaving a legacy. If you make an impact on one or two people – if everyone did that – think of the benefits those actions would have for us all! What if someone had reached out to that twenty-three year old shooter at the Eaton’s Centre? What if I could impact one person and change the course of their life?” What if?

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