He wanted me to be a keynote speaker at a University of Ottawa event he was organizing, so he camped out in front of Sens headquarters at 5 a.m. on a freezing winter's day and waited for me to arrive just after 7. I invited the cold kid in for a coffee and we talked. He got his wish.
Now having just turned 40, married with three kids of his own, Mr. Jayaraman runs a holding company that controls four operating businesses and some real estate. He is thinking of adding more.
"I am a terrible operator and not really good at detail, but I'm surrounded by really good operators," says Mr. Jayaraman.
"In fact, I get immersed enough in a business just to become dangerous. I enjoy creating a business model and then putting it into the marketplace to see if it'll work. It usually takes a year or two to find out."
Mr. Jayaraman uses three tests before he'll make any investment. His head, heart and gut all have to be in agreement - with the most important being his gut check.
"It's that part of your brain that you can't articulate. It's that huge part of your brain that you should be in touch with," he adds.
He started GreenStop, an early player in biodiesel. In fact, Mr. Jayaraman says his was the first all-renewable fuel station in North America. More recently, GreenStop has pivoted away from fuel in Canada to become a convenience store chain, one with differentiated value. In the United States, GreenStop is still a biodiesel fuel trader.
GreenStop has replaced candy bars with healthy organic, tasty treats and it focuses on fresh food. This is unusual for convenience stores, as anyone who has visited one in the last 15 years will know.
Mr. Jayaraman's plan is to franchise GreenStops, with a goal of having 10 shops within 12 to 18 months. Mr. Jayaraman believes there is a market for 500 of these in North America.
He will only put them into neighborhoods that are safe, walkable places. In this sense, GreenStop is similar to another homegrown success story - Bridgehead Coffee, which refuses to locate any stores in car-centric suburbs. Both don't want to contribute to greenhouse gas emissions if they can help it.
GreenStop also offers what its calls the "100-mile lunch," which, as the name suggests, means sourcing all ingredients within a limited radius of each store. It's a point of differentiation and represents a commitment to core values.
Mr. Jayaraman's holding company also manages Asus Medical, which provides support for medical specialists, including billing, scheduling and other back-office functions. He's also president of Kettleman's Bagel Co. in Orleans. It sells to both retail and wholesale customers, supplying Costco with Montreal-style bagels.
Its key differentiator? All-natural, no-preservative bagels.
Mr. Jayaraman's basic investment strategy is to acquire companies that are entrepreneurially stagnant but have a strong local presence. Kettleman's is but one example.
"I want to add entrepreneurial culture to main-street businesses," Mr. Jayaraman says.
Somehow, all this makes sense - at least to Mr. Jayaraman. Just don't talk to him about focus. If you do, don't be surprised if he tells you he has focus, just on one business idea at a time.
He credits much of his success to his membership in Entrepreneurs' Organization. EO has 8,000 members worldwide, more than 800 in Canada and 40 in Ottawa. Each member must be an active owner, founder or co-founder of a company with annual revenues of at least US$1 million.
The group pools their valuable experiences, and it's the first community where Mr. Jayaraman has felt that everyone shares the same values: a thirst for learning, a desire to make a mark, to boldly go forward, trust and respect and to have some fun.
One of the things he was taught via the association's leadership training program was to address his bottom five per cent.
"These are the five per cent of things that you are most scared of. Face them. Address them. Take that aspect of leadership everywhere with you and wear it easily," Mr. Jayaraman answers with a smile.
Professor Bruce M. Firestone is entrepreneurship ambassador at the University of Ottawa's Telfer School of Management; founder of the Ottawa Senators; executive director of Exploriem.org; and a broker at Century 21 Explorer Realty Inc. Follow him on Twitter @ProfBruce.