There is a common misconception that online businesses have no company culture, nor that they need one in order to thrive.

Jon Gillham thinks this idea is absurd.

“I know a lot of people roll their eyes at culture, I certainly did,” said Jon. “But work is where you spend most of your life, and at the end of the day, having a strong culture is actually more profitable.”

A proud husband and father of three, Jon is a former engineer who used his love of system-building to build and grow a slew of online businesses, allowing him to leave his day job for good.
To this day, the majority of his work revolves around building, buying and selling online businesses.
He now has a staff of 35 employees based in Canada and 50 freelance workers worldwide. And while all of his businesses operate independent of a location, Jon makes a point to have staff outings for those in the area as much as possible. Over the years, they have become a family.

“Even if someone told me it wasn’t more profitable to cultivate a culture… It’s more fun to work with people who share the same values and visions as you,” he added.

Originally from Collingwood, Jon and his wife met in public school and started dating in high school. A higher education brought them south — Jon to Hamilton and his wife to the United States — before the young couple settled in Sarnia for several years. Jon graduated as a mechanical engineer and began working for Imperial Oil at the refinery. It was a cool job with an “obscene amount” of responsibilities right from the start, but it wasn’t the end goal.

“We always knew we wanted to get back to Collingwood, mainly for the skiing and biking,” Jon laughed. “And then once we started to have kids it became an even bigger priority.”

So Jon began building online businesses on the side. A geek when it comes to automating and outsourcing any activity, it started out as a side hustle — nothing more than a fun way to generate a passive income. But as life went on, the call to move home got louder.

Jon would spend long days at the refinery and then sit online all evening, identifying problems and then using his knowledge of systems to address them. He restructured his side hustle and set targets, proclaiming that when he hit them, they would hit the eject button and head home.

“I am super risk-averse, and so is my wife,” Jon said. “So it was about finding a way to make this move but not be ridiculously irresponsible.”

Jon has since tried and tested many different methods, and built up well over 150 websites.

To this day, the majority of his work revolves around building, buying and selling online businesses. He often isn’t knowledgeable about the site’s area of expertise, but he has become an expert on implementing systems to solve specific problems each site encounters. Jon joked, “It’s not like I am a plumber and then started running a plumbing company. I can’t write content, I am a terrible writer, but I have a business that writes a boat load of content.”

“It’s the building of the machine that runs the businesses that I like,” said Jon. “Here is a problem, how do I make a system that solves it.”
It started as a side hustle that has grown and allowed me to live my other passions.
Jon is the idea generator, and then he hires the proper people to take his ideas and run with them. Once Jon has a system in place, he brings a manager on board to run the newly built or bought site.

“It’s like creating entrepreneurs,” said Jon. “Seeing the managers come into their own and achieve success is my favourite part.”

His companies include Motion Invest, helping people buy and sell profitable sites; AdBank, an online ad platform; SiteBuddy, helping entrepreneurs build stronger businesses; and Content Refined, a complete end-to-end content marketing solution; among many others.

In 2016, Jon, his wife and their three children officially moved back to Collingwood, and they have never looked back. One of the things he loves most about the area is the ability to do “weekend quality activities during the week.”

In addition, Jon has a self-imposed target to hit 75 days on snow and 50 at the cottage each year — a goal he of course uses a system to measure.

“I track most things so this is definitely one of them,” he laughed. “It’s hard for me to not put metrics around something I care about.”

Jon has come full circle. Building his side hustle in such a sizable way gave him the ability to move back to Collingwood, allowing him to live his other passions daily. But ironically, moving back to Collingwood has also helped him find the right people to continue building his businesses bigger than ever before. While all of his companies are location-independent, the majority of his full time staff reside in Collingwood or somewhere nearby.

“Hiring culture is incredibly important. We try to identify the types of people that will thrive in our weird organization and the ones that won’t. And filtering for that first,” Jon said.

“We are fortunate that our company culture is congruent with Collingwood culture, therefore using that as a first filter when choosing to hire has proven really successful.”

Given the number of local staff he had, Jon initially opened an office space downtown Collingwood. But due to the nature of the businesses and the freedom of flexibility the team has with their schedules, Jon started to realize the cost wasn’t efficient and office energy was lacking. So he moved his team to the Collingwood Foundry in 2018, which allowed them to be surrounded by like minded people at all times, even if other colleagues weren’t present that day.

“I think the Foundry is a great space… It’s an interesting group of people across the spectrum doing different kinds of things,” Jon said. “It has been great to have the shared energy of working in the same space.”

Everyone working on flexible schedules has also made it easier for Jon to maximize family time and achieve his goal of 75 days on snow and 50 at the cottage — this year notwithstanding.

“We try to have that combined hyperflexibility, hyper location dependence, as long as you keep working, but then still have the, ‘we’re in this together, we’re not a bunch of talented people doing an input and that’s it,’ team mentality,” said Jon.

Working in the online space means there are always going to be strategies that are shifting, and Jon said with his team he feels more equipped than ever to continue growing. At the same time, he hopes the year ahead will simply bring more of the same.

“Is my passion content marketing? No. I mean it’s neat, and I am having fun geeking out with AI tools that are coming out, but it’s not a crazy passion of mine,” Jon said. “It started as a side hustle that has grown and allowed me to live my other passions.”