Jonathan Kennedy | Founder & CEO at HeyCarson & Storetasker
By Ryan Chatterton
May 26, 2020
Jonathan Kennedy is the founder and CEO of HeyCarson and Storetasker, two niche technical service providers for Shopify merchants. We’ll get more into how they work later. Jonathan is also the creator behind the largest and most active Shopify group on Facebook: Shopify Entrepreneurs. This is a story about Jonathan’s entrepreneurial experiences as well as a lesson in why persistence is king.
Jonathan grew up in Ottawa, Canada, where he spent most of his life. Eventually, at age 19, his love of sports took him to Montreal, in pursuit of a kinesiology degree from Concordia University.
“I loved sports, Jonathan told me, “and I thought, you know, somebody told me you have to line up your career path and education with something you really like. So kinesiology did that for me at first, and I jumped into a four year degree. But by the second year I started to understand that it might not be the career for me.”
So, in 2002 Jonathan started selling on Ebay while still attending university. His aim was simple: to make up some gaps in his income. But the experience would prove a bit more profound to young Jonathan.
“I got really into it,” Jonathan said. “I got so into it that I started to really lose interest in what I was doing at school and started to gain interest in business and the idea of buying things low and selling them high. Ebay was just taking off. People were buying things online, mostly from Ebay at that time.”
Entrepreneurial Tug of War
After completing his degree, Jonathan stuck with his dream to work in sports, and landed a sales internship with Canadian professional baseball team, the Toronto Blue Jays. It was this initial break into the business world which eventually led to Jonathan’s first real job with the Montreal Canadians, working in the marketing department.
And it seemed like Jonathan had ticked all the boxes for his career dreams. Business: check. Sports: check. The problem: he wasn’t making much money.
“So that was my first job,” Jonathan told me. “And as great as it was, as cool as it looked on the outside, I wasn't making money. I had huge student loans and I felt stuck because I felt like I was an entrepreneur. I should be selling online. And I kept toying with the idea. I kept starting stores and not really getting any traction because I had bills to pay and I had to commit to work.”
You wouldn’t know this if you haven’t met Jonathan, but I can tell you based on my conversation with him that he’s always looking for the positive in the worst situations. It’s is a theme that’s played out many times throughout his life, and his first-job-blues were no different. Jonathan set about getting the most out of the situation.
“I was put in charge of a full business segment to basically build their memorabilia channel and their merchandising department,” Jonathan said. “And this was really my entry into business. So I was able to start a project with somebody else's money. I had to hire people, I had to find suppliers, I had to merchandise online and offline. And so I got myself into the idea that, for the years that I was there, this was my chance to learn on someone else's dime.”
With valuable lessons in-hand, Jonathan left the Montreal Canadians in an attempt to start his own ecommerce store, hoping to replace his income. The attempt failed and Jonathan took up another job. This time with better pay.
Now, if your innate pattern-recognition bioware is working, I’m betting you know what’s coming next.
The Escape
Jonathan’s second attempt at a store came in 2011.
“I had a buddy who was already traveling around the world,” Jonathan told me. “He had an ecommerce site and he wanted me to come and partner with him on the ecommerce store and another project. He saw that I had been a bit in a rut. I was working a project manager job at the time for a software company. It was a well-paying job, but it was, you know, it wasn't inspiring to me at the time. My friend bought me a ticket to come over to Portugal where he was set up. I only had three weeks to quit my job and pack my stuff and come and meet him.”
So Jonathan moved to Portugal and the two of them worked on the ecommerce store, plus started building a chat tool, a relatively new idea at the time. After eight months and some early traction, they moved to the Philippines.
From here, things took a turn for Jonathan. For better or worse? I’ll leave that up to you.
Going Dark
Jonathan isn’t too fond of this part of his business career, but he still feels it taught him valuable lessons about entrepreneurship, which again is on-theme with his “lemons-to-lemonade” personality.
“I was marketing for orthofill.com, which was owned by my friend, and I was really supporting the marketing,” Jonathan said. “We were driving SEO, driving social media. And at that time Facebook just started to get lift. Like people just started to care about how many likes their pages had back then. They were known as fans then. And we bought Facebook likes one day and the next morning I woke up and there were 500 more real people on our Facebook page. And so we kind of diverted from the chat tool and got into this darker industry. We were the first ones to start selling Facebook likes, Twitter followers, and YouTube views at scale.”
Jonathan doesn’t like to go into much detail about that business, and for good reason. While that business delivered value to thousands of people, it was operating in a very grey area of the internet. That said, regrets or not, Jonathan firmly recounts the lessons he learned running his first successful business.
“As fast as the money came, the competition came in just as fast and it was a very dark place on the internet,” Jonathan told me. “No rules. People could hack you, DDoS attack you, take your clients. It was pretty ugly. But I learned a lot of lessons in those three and a half years. How to hire people, how to deal with people in other cultures.”
These lessons would be valuable instruments for Jonathan going forward, but regardless of lessons learned, a now-more-mature Jonathan had had enough. His moral compass was screaming and he wanted out of the business. So he left.
