How Oliver Garside Built 99% Customer Satisfaction by Serving the Forgotten
There’s a sheep ultrasound specialist somewhere in rural Australia, traveling from farm to farm with portable equipment, scanning ewes to determine pregnancy rates for farmers planning their seasons. He runs his business using software built by Oliver Garside and the team at Rounded App – software that achieves something the accounting industry claimed was impossible … 99% customer satisfaction.
This isn’t a story about sheep or software. It’s about the profound wisdom that emerges when we build for the humans everyone else forgets.
The Market Others Refused to See
When Oliver Garside took redundancy from his corporate role in 2015, he didn’t set out to revolutionize accounting software. He discovered two technical founders who had built something elegant but didn’t know how to bring it to market. What they’d created challenged a fundamental assumption – that financial software must be built for accountants, not the people who actually use it.
“For us, the first principle has always been the customer,” Oliver shared in our recent conversation on The Wisdom Of… Show. “Freelancer finances are quite simple. It’s tracking money in and tracking money out. There’s no reason why that can’t be done in a way that’s not intimidating.”
This seems obvious now. But in 2015, it was heretical.
The accounting software industry had spent decades building increasingly complex systems for increasingly sophisticated users – accountants, bookkeepers, financial professionals. Meanwhile, the fastest-growing segment of the economy (freelancers, sole traders, creative professionals) were left struggling with tools that felt like learning a foreign language.
First Principles in the Age of Increment
Most business innovation happens at the margins. Companies take existing solutions and make them slightly better, slightly faster, slightly cheaper. Oliver and his co-founders at Rounded chose a different path: they returned to first principles.
What does a freelance photographer actually need? What about a graphic designer? A sheep ultrasound specialist?
They need to track money coming in and money going out. They need to send invoices that get paid. They need to understand their tax obligations without becoming tax experts. They need confidence, not complexity.
“We made very clear decisions about what it wasn’t going to contain as well as what it was,” Oliver explained. This discipline, knowing what to exclude, might be the most important skill in building anything that matters.
The Beautiful Complexity of Human Enterprise
What emerges from Oliver’s work at Rounded is a window into something remarkable – the infinite creativity of human enterprise. Beyond the expected photographers and designers, Rounded serves customers creating value in ways most of us never imagine.
The sheep ultrasound specialist. The custom yacht sail maker crafting equipment for Sydney-to-Hobart racers. The endless variety of specialized trades, services, and creative pursuits that make up the modern freelance economy.
“It never ceases to amaze me, the diversity of ways that people make a living,” Oliver observed. This diversity isn’t just interesting, it’s instructive. It reveals that opportunity exists everywhere, in forms we haven’t yet learned to see.
The Philosophy of 99% Satisfaction
Achieving 99% customer satisfaction isn’t about perfect software. It’s about perfect understanding … of what your customers actually need versus what they think they need, what they can handle versus what they think they should handle.
Oliver’s team built for the end user, not their accountant. They removed intimidation factors. They made complex financial concepts understandable through better language, turning “debtor’s ledger” into “list of overdue invoices.” They applied B2C thinking to B2B challenges.
The philosophy is profound in its simplicity – respect your customers’ intelligence while acknowledging their limitations. Give them tools that make them feel capable, not inadequate.
Stewardship Beyond Software
As Rounded has grown, Oliver has maintained what he calls “mission beyond product” … supporting conferences, sponsoring freelancer groups, creating educational content. This isn’t marketing – it’s stewardship of an entire community.
The freelance economy is growing globally, but it remains underserved by traditional business infrastructure. Someone needs to champion these individuals who create value outside conventional employment structures. Rounded has accepted that responsibility.
The Wisdom of the Forgotten
Oliver Garside’s story illuminates a timeless business truth – the greatest opportunities often lie with the customers everyone else has forgotten or dismissed. Not because these markets are small (the freelance economy is vast and growing) but because serving them requires a different kind of thinking.
It requires seeing humans, not just market segments. It requires building for actual needs, not perceived sophistication. It requires the courage to simplify in a world that rewards complexity.
The sheep ultrasound specialist doesn’t need enterprise-grade financial software. He needs tools that help him serve farmers better, manage his business efficiently, and sleep well at night knowing his finances are in order.
That’s not a small thing … that’s everything.
