Seven years ago Jackson Cunningham made an unfortunate realization: he hated his job.
As a realtor in the greater Vancouver area, his role relied heavily on meet-and-greet events and in-person networking, something he didn’t enjoy. What he did like and was particularly good at was getting his realtor profile to show up at the top of Google’s search results page.
“I realized that I only liked the marketing part, not anything else about it," said Cunningham of his past life as a real estate broker. That realization led him to explore the world of internet marketing and launch his first e-commerce business. If he was lucky, he thought, he'd be able to earn a little passive income to help cover his rent.
Unmasking an unexpected business
What Cunningham decided to sell was a surprise, perhaps even to himself. He remembered seeing high-quality, artisan masquerade masks on a previous trip to Italy, and that’s how VIVO Masks was born.
At first, he only received a few orders, and he didn't even have inventory to sell. He simply wanted to test whether there was an online appetite for masks. Initially, he refunded anyone who made a purchase, but when he started to receive two or three orders a week, he invested in a shipment of masks and found a third-party warehouse to drop-ship them.
But as Halloween approached, the number of orders kept growing. Six months after he'd started his site, he'd already sold more than $30,000 in masquerade masks, enough to costume hundreds of adult revelers who still enjoy cosplay. "By October I had basically given up everything else that I was doing and started growing that [site] as much as I could," he said.
The site's surprising success brought a new kind of problem: Cunningham couldn't keep up with the demand. "We were always out of stock," he said. It wasn't until the monthly orders leveled out that he started taking money out of the business for himself. Until then, all surplus cash went into ordering more masks, which range from simple ones fashioned out of leather to fancier models featuring punched-metal detailing and Swarovski crystals. And for those who take masquerading seriously, there’s even a replica of the elaborate full-face mask Nicole Kidman wore in the movie Eyes Wide Shut.
Less than a year after starting his first e-commerce shop, Cunningham let his realtor's license expire and he never looked back.
Fascinators, kimonos and dream catchers: a failure to launch
While Cunningham was already earning a passive income through VIVO by devoting a few hours of work per month, he was ready to branch out.
After a few failed attempts at diversifying the business—he dabbled in fascinators (read: fancy hats), floral crowns and cloaks—Cunningham went back to what he knew best: figuring out what customers want based on their online search behavior.
He would research some keywords to see what people wanted, then quickly build a site on the e-commerce platform Shopify. Next, he would list some products he didn't even have, then run ads on Google and Facebook to see what sold. "If the conversion rate is good enough, then you invest in growing it over six to twelve months," he said.
"Your main assumptions need to be validated," said Cunningham. "For the masks, it was: Will people pay $100 for a nice Italian mask? That’s a bit of a leap. Sure, if they’re in Venice they’ll buy it, but will they actually buy it online when you can buy one for $5 on Amazon? So we needed to test that [for other items]."
He ran several products through his new formula for launching a viable e-commerce business: kimonos, dream catchers, costumes. Finally, in 2013, he landed on his next sure success—suspenders.
A (pant) leg up on the wedding industry
Like his masks, people were surprisingly interested in suspenders. And while masquerade attire had Halloween to boost sales, suspenders had the power of love and a season’s worth of weddings to help it along. The only problem was that most of the suspenders sold online were very cheap. Cunningham was confident that the masks he sold were the best in the world. He wanted the same to be true of his suspenders, so he decided to design his own.
He picked fabrics, clips, buttons and everything else he thought was necessary to create the world's best suspenders, then he ordered samples from a factory. He put photos of the products up on his site, JJ Suspenders, then waited for people to tell him which suspenders looked like the perfect wedding party attire. Some of his favorite designs got no traction, while others made a ton of sales. Once he got an idea of what types of designs people were interested in, he bought some stock and started filling orders. Sure enough, the business took off. Four years after launching, JJ suspenders still hasn't stopped growing. In addition to steady online sales, the products are now available in 150 stores in the U.S.
Within three years of quitting his job as a realtor, Cunningham had devised a recipe for success in e-commerce, but the serial entrepreneur was still looking for his passion project. This time the answer didn’t first come from the internet, but rather from the furry cohabitant in his apartment named Toshi-san.
Building the West Elm of cat furniture
In 2016, Cunningham and his girlfriend adopted a cat, Toshi. The couple lives in Vancouver, where real estate is expensive and apartments are small. "We shop at West Elm, because when you have so little space, you want your stuff to be nice," he said. "But when we looked at cat furniture, we thought, man, this is so sad."
After doing some quick research, Cunningham realized that he wasn’t the only one looking for clean-lined, modern cat furniture, but the options out there were uninspired at best and downright ugly at worst. So, together with his girlfriend, Vanessa Koo, Cunningham decided to launch his most ambitious business yet: Tuft & Paw.
Cunningham wanted to challenge the way humans made accessories for cats. "Let’s not just take a bed and make it a little bit prettier,” he said. “It’s more like: what makes a cat happy? Why do cats scratch? Why are scratching posts these small rectangular beams; could you make them pyramids?”
"You don’t want to find the stuff that’s easy to find on Amazon," he said. Instead, he scoured Reddit threads to find the countries with the best furniture designers. Next, he found himself on Google Korea, searching for the words "cat tree" in Korean.
With a list of artisans from Korea, Japan, Germany, Poland and the U.S. who were pushing the envelope on furniture design, Cunningham created a marketplace to sell their products. Then the couple took the leap and started designing their own cat furniture, with a mission to rethink the way cats and humans live together.
If you build it, they will pounce—eventually
Of all the companies Cunningham has started, Tuft & Paw is the one that means the most to him. But so far, it hasn't produced the same passive income as his other two e-commerce shops.
"It’s a whole different set of challenges that I’ve never had to do with other companies," he said. "I thought I had it nailed down: you just hire a third-party warehouse, and everything is automated. Instead, Cunningham has had to do a crash course in learning about international shipping rates and how to store containers efficiently on different coasts. “Your job is constant problem-solving, and you’ll never fully know, and it’s always changing," he said.
Without any outside funding or small business loans, Tuft & Paw is profitable and growing—if at a slower rate than Cunningham's other e-shops. But that hasn't spoiled his enthusiasm. "I find that my biggest challenge is stopping working," he said. "I’ll wake up and I really feel like I’m always behind to get something done. So I start working on that thing, and I actively have to stop myself from doing it."
To help, he's automated most of his daily chores, like buying groceries and cooking meals. "The thing I value most is convenience," he said. "Basically, I am trying to design my ideal life."
But a man can only look at so many cat scratching posts (even if they're made out of aesthetically pleasing, powder-coated aluminum) before he loses his mind. So, to keep himself sane, Cunningham makes sure he gets out of the house daily.
"There’s an indoor rock-climbing gym just two blocks from my house," he said. "I’m enjoying it more than any sport I’ve ever done because it’s a mix of problem-solving and exercise. Every day I try to go rock climbing and do either yoga or meditation from home."
And while Cunningham still has a lot of work ahead of him to make Tuft & Paw a household name, he has plenty to be proud of. Between his three businesses, he makes more than $1 million in sales annually and he's working on a project that inspires him.
"We think we’re going to change the game with the litter box, cat toys and just general problems that humans have with cat [furnishings]," Cunningham said. "Little annoyances that nobody else has bothered to solve."