Toronto’s Johnathan Hicks — a 44 year old YouTuber known online as Johnny Strides — has turned his daily city walks into a full-time money-maker. Six years ago, what began as a side hustle filming pedestrian tours around the city has now climbed to “well over six figures” in earnings, he told CTV News.
Hicks launched the Johnny Strides channel in 2018 after buying a GoPro. His early timelapses evolved into narrated walking tours that often last between 30 to 45 minutes, including walking, cycling, transit and livestreaming content filmed in all seasons and all weather conditions. With more than 136,000 subscribers and over 46 million views, Hicks now earns more from YouTube than he ever did working in insurance.
He recalls transitioning from his underwriting job — “a global program underwriting (for) big multinational companies” — into a toxic new role just as the pandemic hit. But as views soared, he made $1,500 one month part time, eventually deciding that “it was just the perfect storm” to go full time.
Toronto may be “stupidly expensive,” he admits, but thanks to a rent-controlled apartment at $1,100 monthly, “the risk management going full time on YouTube…wasn’t that difficult a decision."
Of course it’s not always sunny sidewalks. He recalls filming a blizzard when his boots failed and his feet were “frozen and soaking” as thousands tuned in to watch. Audience bonds built through raw, real content fuel engagement, also known as parasocial relationships.
Still, burnout runs high in content creation because creators must always be “on."
Economics professor Obeid Ur Rehman sees this shift toward unconventional side hustles as part of a larger trend, arguing that with rising unemployment and a more precarious job market, Canadians are increasingly turning to flexible, entrepreneurial income paths. However, he cautions that platform algorithms can change fast, suddenly halting a creators’ earnings potential.
Yet for Hicks, the freedom and community behind the lens are worth it: “Not having a boss and working for yourself is pretty awesome…I love the community. That in itself is rewarding enough to keep going.”
Canadians finding unique paths to wealth
Hicks’s story is inspiring, but he’s not alone. Across Canada, others have found creative, unconventional ways to build wealth. Here are five standout stories of how other inspiring people followed their passion straight to the bank:
1. From basement beginnings to cybersecurity titan: Robert Herjavec
Robert Herjavec’s journey began in 1962 in Varaždin, Croatia. As a child, he arrived in Toronto with his family, carrying only a suitcase and speaking very little English. Early jobs delivering newspapers, waiting tables and collecting money shaped his customer-first mindset. “The most important relationship in business is the one between you and your customers,” he later said.
He got his foot in the door at a tech firm by working six months unpaid while waiting tables at night to pay rent. Before long he became general manager before getting fired in 1990. Undeterred, he started BRAK Systems from his basement. The firm grew fast and in 2000 was sold to AT&T for $30.2 million.
Not ready to slow down, he founded The Herjavec Group in 2003 with $400,000 in sales and three staff. It eventually grew into one of Canada’s biggest cybersecurity firms — reportedly hitting $200 million in annual revenue before rebranding as Cyderes. By mid-2025 his net worth hovered around $300–320 million.
Most notably, Herjavec became a familiar face on TVs Dragon’s Den, Shark Tank and Shark Tank Australia, investing more than $16 million on Shark Tank alone.
2. Homegrown genius revives an island: Zita Cobb’s Fogo Island revolution
Zita Cobb grew up on Fogo Island, a remote outport in Newfoundland that lacked running water or electricity during her childhood. After a successful career in fibre-optics and cashing out US$69 million in stock options from JDS Uniphase, she returned home with a vision.
In 2004, she co-founded Shorefast with her brothers, a social enterprise rooted in place-based economic development. They built studios, workshops and most notably, the Fogo Island Inn, which opened in 2013 and is a striking architectural testament to local heritage and “economic nutrition” transparency.
Guests don’t just stay — they connect. Local hosts, meals showcasing 80% local ingredients and furniture crafted by boatbuilders turned artisans make the inn an immersive cultural experience.
Profits are reinvested into the community, which ultimately support artists, quilters and small-scale food enterprises — nurturing a sustainable micro-economy.
In 2023, Cobb spoke about her belief that “place holds all our relationships,” a philosophy deeply embedded in every visitor experience and business decision on Fogo Island.
3. From junk to franchise joy: Brian Scudamore’s trash turnaround
Brian Scudamore’s career started with junk. Spotting a gap in the market while in a drive-thru, he bought a beaten-up truck in 1989 for $700 and launched what became 1-800-GOT-JUNK.
He refined the business with clean trucks, friendly staff and consistent service tied to a catchy phone number. That branding helped it scale across North America. Scudamore later coined “entrypreneurship,” inviting people to start small through franchising.
Today, O2E Brands (parent of 1-800-GOT-JUNK, WOW 1 DAY PAINTING and Shack Shine) includes hundreds of franchises. Scudamore has also appeared on Dragon’s Den as an investor and authored a book, WTF? Want the Future, sharing his playbook for building trust-based businesses.
4. Humble house flip sparks real estate legacy: Peter Wall
When Peter Wall immigrated to Canada with only $6,000 sent to him by his mother — he used that money to build a modest house, eventually selling it for $13,000 before she had even moved in. This showed him how profitable real estate could be.
He founded Wall Financial Corporation and grew it into a leading real estate firm in Vancouver. His developments shaped parts of the city’s skyline and made him one of British Columbia’s wealthiest developers.
In 1991 he made headlines, and history, by donating $15 million to the University of British Columbia, establishing the Peter Wall Institute for Advanced Studies. His story is proof that small investments can build both wealth and generous legacies.
Create the life you want
From these stories, you can deduce the following as steps towards successful business building:
- Look for opportunity in ordinary places
- Cultivate roots, community and authenticity
- Scale modest gains to build a foundation of wealth — and give back while growing
- Channel success into change
- Reinvent yourself with purpose
Each of these individuals show that creative income can spring from grit, locality, empathy and values. They were open to experimentation, stayed resilient in their path towards success all while leaning into what excites them, because that’s often the spark that leads to both prosperity and fulfillment.
Sources
1. CTV News: This Toronto man films his walks around the city for YouTube. He makes ‘well over six figures’, by Jermaine Wilson (Aug 17, 2025)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.