Few people are lucky enough to get paid for doing what they love. Between paying the bills and pursuing your dreams, there’s usually little contest. For Ruth Stephensen and Scott Thomas, however, the two needn’t be mutually exclusive. They’ve built a $1 million startup that helps creatives – both hobbyists and pros – earn a lucrative income through visual storytelling.
In today’s noisy world, never has the cliche, “a picture is worth a thousand words” rung truer. As brands compete for our ever-shrinking attention spans, visuals help pull focus from competitors and deliver a resonant message. Over half of professional marketers, for example, believe visuals are indispensable, and Creatively Squared delivers a full spectrum of visual goods.
Ruth and Scott refer to Creatively Squared as a “managed” marketplace. They find the brands, onboard the creatives, and match the two according to the brief. It’s a global business, with content creators in over 30 countries syncing up with brands like Google and Heineken. Having an international team means they can deliver customized, localized content within weeks.
“We connect brands and creators around the world, but it’s not self-serve,” Scott said. “We match the brief with the creator and support the relationship on both sides. Our creators aren’t always used to working with professional marketers and the marketers aren’t used to working with everyday people, so it’s more of a three-sided marketplace.”
Ruth and Scott are onto something. Cisco predicts that videos alone will make up 82% of all internet traffic by 2022, and consumers today demand more visual media from their brands than any other medium. Creatively Squared might be a bootstrapped business, but it’s bang on trend, and as you’re about to learn, it’s boom time for those in the visual storytelling business, too.
Fresh Starts, Fresh Challenges
Like many people, it was a while before Ruth found her calling. While treading water as a designer at NewsCorp, she studied an MA in Advertising and won her first freelance gig at a children’s clothing brand. While shooting products and working with creators, Ruth saw a need for a community to elevate the social media content she was producing in the studio.
“I spent a lot of time trying to find people to take the pictures I needed,” Ruth said. “I wanted variety – different kids, families, parents – but nothing in the market served that need. So I decided to start a creative community on Instagram. I knew a lot of people were interested in this type of photography as a hobby or were bored in their job or wanted an extra income.”
In just two years, the community grew to over 20,000 members. Without geographical restrictions, anyone could submit content, and Ruth saw incredible work from everyday people residing all over the world. This community was the proof-of-concept, the Creatively Squared “MVP”, that gave Ruth the confidence to bring Scott aboard.
“We wanted to be ultra inclusive,” Ruth said. “We didn’t want just influencers or people with fancy houses or anything like that. We wanted everyone to feel their creativity was welcome. The talent was phenomenal but many didn’t have large audiences. For us, follow counts aren’t important as the value lies in their creative ability so it was great to be able to offer them work.”
Creatively Squared grew out of Ruth’s desire for a fresh start, but it was the challenge of scaling a bootstrapped startup that attracted Scott. He’d worked in science and pharmaceuticals and then a stint in the oil and gas industry before doing an MBA in 2015. After a few years of strategy and innovation consulting at EY and others, his entrepreneurial senses began to tingle.
“I’ve always been interested in new business models and problem-solving,” Scott said. “That’s the common thing, and saving 0.1 percent of some balance sheet item wasn’t a challenge anymore. So starting a global business without funding seemed like a much bigger challenge. It was the challenge of building it and doing something different every day that drew me to it.”
Scott left his top-four consulting position to work on Creatively Squared full-time while Ruth continued working flexible hours at NewsCorp to supplement their income. Later, she gave birth to their first child, Jett, and when her maternity leave ended, joined Scott to focus her energies on Creatively Squared. The first six months, Ruth remembers, were incredible.
Scott working from the maternity ward after Jett was born (Nov 2018) 
Ruth’s workspace alongside her son, Jett, who kept her company
“I still remember signing our first big international customer,” Ruth said. “It was a brief from J&J in Singapore for about 750 images. We had no staff so I was managing it myself at home with a two-week-old baby! That’s when I realized this wasn’t a side hustle anymore.” Here lies a lesson for all entrepreneurs: you needn’t start big, just start, and who knows what you can accomplish.
Scott was equally proud, and having reeled in some pretty big fish early on, could see a business with a future. “Once the big brands started coming to us, I knew the business would grow,” Scott said. “All we had to do was keep customers and creators happy.” While that sounds simple enough, as with any marketplace, balancing two different sets of needs wouldn’t be easy.
How They Brought Brands and Creators Together
This is the Creatively Squared business model: Brands submit a brief with the help of the Creatively Squared online tool, which takes minutes. The team then matches them to a visual storyteller who can best fulfill their needs. Once the assets are ready, usually in a couple of weeks, the team makes any required final edits before delivering them to the client.
But where did those first big clients come from? Before pandemic-induced travel restrictions hit, Ruth, Scott, and Jett flew as a family around the world asking brands for a moment of their time to show how Creatively Squared could benefit them. No stranger to the corporate world, Scott charmed his way past gatekeepers to demonstrate how effective visual storytelling could be.
Ruth and Scott brought Jett’s grandparents on the road to attend meetings (London 2019). 
Many of Creatively Squared’s first big customers came from Singapore.
“I’d call them up and say, ‘I’m going to be in your city next week. Can we grab coffee?’ And that led to our first big customer in Singapore,” Scott said. “And once you get one big name, you get the credibility to go after others. We did that for about two years, these round-the-world trips to London, New York, Singapore, Sydney, and places like that having in-person meetings.”
Today, those meetings are virtual. And while acquiring clients has relied on traditional business development techniques, finding content creators has relied on building a collaborative, educational space where visual artists can improve their craft. The niche tutorials and themed challenges Ruth offers help content creators monetize their hobbies or start new careers.
“Creative people don’t always want to run a business,” Ruth said. “That’s why a platform like ours fits around their lifestyles. For those that do, we help them build their portfolio. And the good thing is that everyone generally sticks around as part of the community to help everyone else and offer support. So it’s a really collaborative space that we’ve built for the creators.”
It’s not about counting heads, Scott argues, but finding the right creator at the right time. This is where the global community shines: fostering a talent pool of diverse styles, expertise, and locations means brands enjoy an extraordinary level of customization. And for creators, it means they get exposure to big, household brands that need local insight.
“We’ve built an amazing and talented creative community,” Scott said. “We’ve worked in 35 different countries now. Even if they’re not working with us, we’re always trying to help them explore their creativity and find their own work. Some have never worked with brands before. We’re always helping people who, like Ruth, want to escape the nine to five.”
Think of Creatively Squared as an incubator for creatives. If you don’t have the skills, Ruth and Scott encourage you to participate in the community until you’re ready for your first brief. In other words, these co-founders have turned passions into profits for many people who might never have had an opportunity to monetize their gifts, resulting in happy, motivated creators.
“We screen their Instagram account and any personal websites or portfolio,” Ruth said. “It’s pretty easy to tell whether someone’s going to be a good fit for a project or for the type of work we do. If they need a bit more experience, we push them to participate in the community and hope they’ll learn from the content we publish and from other creators around them, too.”
Growing Pains: Fairness, Culture, and Other Challenges
Any entrepreneur will tell you that to grow a business, you need to understand the problem you solve. You might assume in Ruth and Scott’s case, it was on the client side: delivering great visual content that converts. But Scott is also keen to stress they wanted to elevate creators to stand on equal footing with professional marketers, making the transaction fair for both parties.
“Our role is finding the optimal balance between what marketers and creators need,” Scott said. “That sometimes means our decisions aren’t always client-first decisions. We would never do a crowdsourcing model, for example, where marketers would get a lot more content and just pick what they like without having to pay for everything. That wouldn’t be fair to the creators.”
This idea of fairness spread to Creatively Squared’s company culture. As working parents with a two-year-old son, Ruth and Scott wanted their teams to enjoy work-life balance rather than be chained to their desks or devices all day. Even when working remotely, it can be difficult to switch off, and Ruth and Scott knew they had to address this quickly.
“Work should revolve around life, not the other way around,” Scott said. “Yes, you’ve got to be efficient with your time to stay productive, but also take your weekends to relax and recharge. We knock off on a Friday night to focus on family. If we want to build something long-term, there’s no point rushing to do it in 12 months. It’s a marathon, not a sprint, and life comes first.”
Scott had worked at BP and Ruth at NewsCorp under very different company cultures. Those experiences, combined with their ideals, led to building an environment at Creatively Squared where they and their employees would enjoy working every day. They might not have been able to offer Silicon Valley salaries, but they could offer time.
“We’re bootstrapped so we can’t always compete with big organizations on salary,” Ruth said. “But we can compete on work-life balance and culture. We attract people who find culture important and appreciate that attribute of our company. We want our teams to work in ways that complement their lives because that’s what helps them do meaningful work.”
Being so open and employee-friendly to the global market has presented some challenges, however. “Because we chose to be global from day one, we’ve had customers and creators in different timezones,” Ruth said. “We’ve had to manage language barriers – even use Google Translate – to offer and manage jobs.” But with today’s tech tools, it’s a challenge worth bearing.
What Could They Have Done Better?
Ruth and Scott have done an amazing job of helping creators connect with brands. Whether you’re a commercial photographer or aspiring content creator, these co-founders have created a space where you can build your portfolio as well as earn money. Have they had any regrets along the way? Ruth believes they should’ve trusted their instincts a little more.
“I think we could have trusted our instincts rather than taking the stance that we’re not experienced in this industry,” Ruth said. “I think we could’ve trusted our guts and intuition and made the best choice rather than seeking help from external parties or hiring people we felt were more experienced but didn’t bring what we wanted to the table.”
Scott took Ruth’s point a little further. “People say you can’t scale, you can’t go global, or you can’t build this or that without funding. But we never invested in branding or fancy websites. We did everything ourselves. We stuck it together with low code to see if someone would pay for it and things grew from there.”
Ruth and Scott winning a pitch competition to be named best creative tech company in Australia. 
Scott speaking at an event in Bangkok. 
Scott in the Australian startup pavilion at Startup Grind in Bangkok.
Does this mean Creatively Squared will stay bootstrapped forever? Perhaps not. Ruth and Scott believe funding is all about timing. If you’re bootstrapped and scaling under independent momentum, why give up slices of your company and set a deadline for your success? Startups need to stay agile and they can’t do that under the weight of investor-backed growth goals.
“Never say never, but funding only helps if you’ve validated everything and the only thing preventing you from scaling is funding,” Scott said. “I don’t think we’re there yet and I don’t think money would help us get there. But if we did hit a point where the only thing stopping us from scaling quickly was financing, we might consider it. But at the moment, it’s not on our agenda.”
And what about expanding into other forms of content to widen their market? “Not at this stage,” Ruth said. “I think that we’re pretty comfortable in the visual space. I mean, I guess you’d never say never. We do want to help creative people, but right now I think that we’ve hit a sweet spot with the kind of product and lifestyle we offer.”
And who could argue with that? Ruth and Scott run a $1 million startup helping a global community monetize their passions. Complicating matters with funding or new forms of content doesn’t seem right or in keeping with their life-friendly culture. And as long as Creatively Squared continues upwards momentum, funding will be available if and when they need it.
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