A veteran of tours in Afghanistan and Bosnia, Bolle is the president of Hero Dog Treats, a three-year-old company that makes natural, dehydrated dog treats that are sold across the country.
Next week, Bolle and Gino Savard, another veteran, head to Melbourne to speak with Australian veterans about starting their own businesses.
Bolle explained one of the challenges Canadian veterans face when they leave the military.
"In the military, if we're being asked to execute a mission, we sit down and come up with a plan and then we reach out to our people with experience and ask them for advice," the 16-year veteran told CBC News.
"When you leave the military, you have no one to reach out to but yourself. You tend to have a false sense of confidence," he added. "There's always a group of likeminded people around you, so if you throw out an idea you get instant feedback. That builds confidence."
"When you're on your own, you have no feedback."
Bolle confessed that he always had "an entrepreneurial spirit but never had the courage to follow through with it" — that is, until a friend who worked in the pet food industry approached him with the idea of manufacturing dog treats.
Bolle enrolled in Based In Business, a seven-day boot camp offered by the Prince's Operation Entrepreneur, a national program of The Prince's Charities Canada which helps transitioning Canadian Armed Forces members who are interested in starting their own business.
Bolle says he still refers to the notes he took during the all-expenses-paid course, and adds that it would've been very challenging to create a business plan.
He says veterans who leave the military have a difficult time finding the support network they enjoyed while serving.
"Having done Based In Business, I now have a support network," he says. "I want to be a veteran who creates a business, hires veterans and as (the business) grows, hires more veterans.
"We can help build a veteran community so there is life post-military."