Jonathan Kennedy | Founder & CEO at HeyCarson & Storetasker

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, 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.

The HeyCarson team is truly global. Here's some of the Serbian crew.

Into the Light

Once again, Jonathan found himself in a position with little resources and a lot of time on his hands. So of course he started another store. What’s the saying about the definition of insanity?

But Jonathan wasn’t crazy. He was onto something, and as you’ll see by the end, that something wasn’t running an ecommerce store.

“I started the store on WooCommerce,” Jonathan told me, “and I don't know if you've ever worked on a WooCommerce store, but it was a struggle. I was a non technical person, so I really needed to get good at hiring developers to navigate the platform for me and make sure everything stayed live and working. Then, just a couple months after starting the WooCommerce store, I signed up to this thing called WP Curve.”

WP Curve, which sold to GoDaddy in 2016, is a small task service for Wordpress sites. For a fixed fee per month, Wordpress site owners can have small improvements made to their sites with the help of the in-house team at WP Curve.

Jonathan at Calgary Shopclass.

“At the same time, a friend said I should try out Shopify,” Jonathan said. “I switched over and as a nontechnical person, I got more done on my store by myself in four or five days than I was able to get done with a talented developer in two months on WooCommerce. So I really felt the learning curve drop when I moved over to Shopify. Not only that, but I could move faster and I was spending less money on an external developer.”

Eventually Jonathan got as far as he could with the Shopify platform as a non developer. And he recalled his old friend WP Curve, the small tasks service for Wordpess sites.

“I really thought it was a cool business model,” Jonathan said, “and I wasn't getting traction with my new store. I realized, no matter how far you can get as a nontechnical person, you still need the help of a developer or designer at some point. If you have a growth mindset with your store, Shopify is way better than WooCommerce or Magento, but there are still limitations. And that's why you have a really healthy app ecosystem. It's why you have a really healthy expert, developer, and design ecosystem. It’s because that line in limitations has gotten further down the road for people. But there's still so much technology and so much to think about that merchants still need smart humans to help them glue this stuff together.”

Copy and Paste Business Model

This is when the first iteration of HeyCarson, a monthly subscription service for small-task development for Shopify stores, was born. But where HeyCarson was born is more important to its development as a business. And that where was none other than a small coworking space in Bali, Indonesia. 

“Everybody was traveling and running Shopify stores, but they were all nontechnical like me, Jonathan said. “And I had a couple of good technical resources. So from one day to the next I put up this site offering technical support for small projects on Shopify stores. We got our first five to six clients from this coworking space. And most of them loved it. I think I offered it for free to a couple people and then offered it at a really low price for a couple others. What I learned there is you really have to charge a price to get good feedback and to get engagement. We got the best engagement and feedback from the people who were paying us.”

Jonathan's old team at ClickLabs 2012

Jonathan’s MVP had worked. HeyCarson would begin selling a monthly subscription service for unlimited Shopify development tasks, so long as those tasks were under one hour. And the model remains the same to this day.

At this point, you may recall that Jonathan was still running his ecommerce shop at this point, but it wasn’t going well. He was running into licensing issues with some of his products and, if there’s anything his previous business selling social media engagement had taught him, it’s that he wasn’t comfortable being in the grey areas of business. 

“I wanted to do something that was completely transparent where I would be proud to have my face on the about page of whatever I was doing,” Jonathan told me. That’s when Jonathan opted to shut down the store and give HeyCarson his full attention.

One Facebook Group to Rule Them All

At the same time HeyCarson was being built, Jonathan started the incredibly popular and large Facebook group, Shopify Entrepreneurs. 

“I was working from Bali thinking I was pretty alone,” Jonathan said. “I knew some people in the coworking space, but I was still kind of alone trying to figure out the internet. I felt there may have been other people out there that were feeling the same. So I started a group called Shopify Entrepreneurs. It was really early on when groups were just getting started and it became this really cool outlet for me and maybe a dozen other people around the world who found the group just through the suggested groups feature on Facebook.”

The group would discuss problems and solutions for their stores on a daily basis. And as the Facebook group grew, it created a positive feedback loop for HeyCarson, feeding new leads into the business. Jonathan had a virtual goose that was laying golden eggs.

But golden eggs aside, Jonathan’s intuition was to open the group to more experts and app developers.

“When we got to a few hundred people in the group, all I wanted to do was share this platform with other people who I thought were doing really cool stuff for merchants and merchants themselves,” Jonathan told me. “ The response from other Shopify experts and partners and app developers was great. It turned out that my willingness to share the platform actually only helped it grow. I would catch partners on Twitter or LinkedIn and I would say, ‘Hey, I just shared your link in my group. There's only a few hundred people, but join us.’ And then somehow they would turn around and share it with their audiences, which were mostly Shopify merchants.”

Today, the Shopify Entrepreneurs group is 100,000 strong and more engaged than ever. If you’re not a member, you’re missing out on an amazing community of Shopify experts and merchants that really love helping each other.

The Gap in Shopify Development Services

Even with the benefits and affordability of HeyCarson’s small task service, many Shopify entrepreneurs were left in the lurch. Their projects were either too big for HeyCarson’s small task model or too small for most Shopify agencies.

“About 30 to 40% of the requests coming in were getting turned down because they were too big for us,” Jonathan said, "and so we had nowhere to send these people. We still couldn't send them to agencies like Ethercycle, for example. Agencies have a project minimum that’s usually between $10,000 and $20,000. And even if they do sell banks of hours, you have to pay upfront for a bank of 20 to 40 hours at a $100+ per hour. That's a really cool strategy for the agency. That's how you serve really cool clients. But there's a wave of new store owners coming in; small businesses that can't afford that. So we were rejecting projects that were too big for HeyCarson yet still too small for more most agencies.”

Jonathan’s solution was simple and brilliant. Instead of creating a higher price tier or package for HeyCarson’s subscription model, Jonathan created a new business entirely: Storetasker.

Now, before I tell you what Storetasker does, I’d like to go over HeyCarson again because we didn’t explain it fully in the story arc. Plus, Jonathan told me he still struggles to explain the difference between HeyCarson and Storetasker, so I thought I’d take a stab at the simplest explanation possible as I see it.


HeyCarson is a monthly subscription service providing unlimited credits for up to one hour of development work for Shopify stores. At this writing, the price for the service is $299 per month. Alternately, you can buy a single credit for up to one hour of development work for $99.

This is a valuable service for people who need to make small tweaks to their stores or need to install and configure new apps, but lack the confidence or technical know-how to do so. 


Storetasker is completely different.

Storetasker works a lot like Upwork, which is possibly the world’s largest freelancing marketplace where subject-matter experts bid on projects posted by potential clients, with the client selecting the best offer. However, Storetasker has a few critical differences.

  1. Storetasker’s service is incredibly niche. They only offer freelance developers for Shopify stores, period.
  2. The rates are fixed at $65/hr (at the time of this writing), which means there’s no rate competition. No more hiring developers based on price.
  3. All the experts at Storetasker are vetted by the Storetasker team.
  4. Storetasker maintains a private Slack group for their experts, so clients aren’t just getting one freelance developer, but the hive mind of the entire Storetasker expert community.

Similar to Upwork, all Storetasker payments are held in escrow until the client is happy with the work provided by any given Storetasker expert.

Simply Put

To put it simply, Storetasker is the Upwork for Shopify development, with a fixed price, on steroids. 

HeyCarson is a super simple monthly service for unlimited, under-one-hour, development tasks for Shopify stores.

What’s Next for Jonathan

Jonathan didn’t have any major announcements to share with us. Suffice to say that he’s planning on doing even better with HeyCarson and Storetasker, and despite people’s unwarranted advice, he’ll keep moderating the Shopify Entrepreneurs group because he just loves it too much to give up. So stop telling him otherwise!

Jonathan and team at Shopify Unite 2019.


I absolutely loved talking with Jonathan. From his candid and detailed stories to his refreshingly positive nature, it was a pleasure. 

Part 2 of this interview with Jonathan will be out in the near future, and trust me, it’s a great one! In it, he’ll share some absolutely amazing tips for Shopify merchants (seriously, I was blown away). If you want to be notified when it’s released, be sure to follow us on Facebook, Twitter, and LinkedIn, plus subscribe to our newsletter.

Ryan Chatterton Editor, Content Strategist, Digital Nomad, Coworking Influencer, Lover of Wine & Tacos