Episode 127: Simple Systems for Sole Traders | Massage Business Tips with Oliver Garside of Rounded
Most massage therapists don’t struggle with their treatments. They struggle with everything around them. The invoices that get left until later, the receipts that pile up, the quiet uncertainty about tax, GST and BAS. The tools available often don’t help. They feel built for accountants, not for people running a hands-on business. That’s where Rounded enters the picture. Not as another complex system, but as a response to a simple question: what would accounting software look like if it were built specifically for sole traders?
Rounded is an Australian accounting and invoicing platform designed specifically for sole traders to manage income, expenses, and tax with simple, easy-to-use tools.
Simple Systems for Sole Traders: A Conversation with Oliver Garside (Rounded)
Running a massage business has two distinct sides, and most therapists feel the tension between them very early on. There is the part we train for, the hands-on work with clients, the problem-solving, the relationships, and the satisfaction of helping someone move better or feel relief. Then there is everything else. The invoicing, the expenses, the GST, the BAS, the tax, the record keeping, and the systems that sit quietly in the background but have the potential to create a lot of stress if left unattended.
In this episode of the Folding Towels Podcast, we sat down with Oliver Garside, co-founder of Rounded, to explore what really happens when clinicians step into the role of business owner. The conversation moved well beyond software. It became a practical discussion about how sole traders actually operate, where things tend to go wrong, and what small changes can make the biggest difference over time.
A Career Shift Without a Clear Plan
Oliver’s path into Rounded did not begin in accounting or finance. His early career was in recruitment, first in the UK and then in Australia, before moving into recruitment software. That transition eventually led him to LinkedIn, where he was part of the early expansion of the platform in Australia. It was a period of rapid growth, exposure to startup culture, and working alongside people who were building something at scale.
At some point, that experience created a shift in perspective. Rather than continuing along a defined corporate pathway, Oliver reached a point where he wanted to try something for himself. What is notable is that this decision was not driven by a perfectly formed business idea. Instead, it was driven by the recognition that waiting for the perfect opportunity can often mean never starting at all.
He made the decision to leave LinkedIn without a fixed plan for what would come next. That created space to explore, to have conversations, and to assess opportunities without the comfort of a steady salary shaping those decisions. It was during this period that he was introduced to a small software project. Two engineers were building an app, and they needed someone to help bring it to market. That app would become Rounded.
What stands out here is that Oliver entered the business without a background in accounting and without experience as a sole trader. He was learning the problem at the same time as helping to solve it. That mirrors the experience of many massage therapists who move into business ownership. Very few start with a complete understanding of what is required. Most learn as they go.
The Problem Was Simpler Than It Looked
Rounded did not begin as an attempt to overhaul accounting software. It began with a much more straightforward problem. Oliver’s co-founder, Grant, was a freelance creative trying to manage the financial side of his business. The tools available at the time did not align with how he worked. They were often too complex, too expensive, or built around business structures that did not reflect the reality of a sole trader.
This is a familiar experience for many massage therapists. The systems available are often designed for larger businesses, with features that are unnecessary for a solo operator and terminology that assumes a level of financial literacy that many do not have. The result is friction. Not because the user is incapable, but because the tool does not match the task.
Rounded was built from the perspective of the end user rather than the accountant. That meant focusing on clarity, usability, and relevance. It also meant making deliberate decisions about what not to include, rather than trying to replicate the full complexity of enterprise-level software.
When Tools Create More Work
During the conversation, David shared his own experience of moving from a paper ledger to a spreadsheet and eventually into accounting software. The expectation was that adopting a more “professional” system would make things easier. Instead, it introduced a new set of challenges. The software was difficult to navigate, the terminology was unfamiliar, and the overall experience created more resistance than it removed.
Oliver’s response to this was direct. Many accounting platforms are designed with accountants in mind, not the person using them day to day. For a sole trader, this creates a mismatch. The user is required to adapt to the software, rather than the software adapting to the user.
Rounded approached this differently by simplifying language and focusing on how people naturally think about their business. Instead of using technical accounting terms, the platform translates them into plain language. While this may seem like a small adjustment, it significantly reduces the barrier to engagement. When the system makes sense, people are more likely to use it consistently.
The Real Constraint Is Time
A recurring theme throughout the conversation was not a lack of knowledge, but a lack of time. Massage therapists often operate in tightly scheduled days, moving from one client to the next with little space in between. By the end of the day, the energy required to sit down and manage financial admin is often depleted.
This leads to a predictable pattern. Tasks are postponed with the intention of catching up later. Over time, those tasks accumulate. What might have taken fifteen minutes at the end of the week becomes a multi-hour exercise months later. At that point, it feels overwhelming, which increases the likelihood of further avoidance.
Oliver’s advice in this area was consistent and practical. Regularity matters more than intensity. Small, consistent actions are far more effective than infrequent, large efforts. He used the analogy of training for a marathon. You do not prepare by running the full distance once a month. You prepare by building a consistent routine that gradually develops capacity over time.
Applied to business admin, this means setting aside a small amount of time regularly to stay on top of tasks. The exact frequency will vary depending on the business, but the principle remains the same. Consistency reduces complexity.
Deciding What to Keep and What to Let Go
An important part of the discussion centred on the idea that not every business owner needs to manage every aspect of their business personally. While there is value in understanding your numbers and maintaining visibility over your finances, there is also a point where outsourcing becomes a practical decision.
Oliver highlighted the importance of being honest about your preferences and capabilities. Some people enjoy the process of managing their finances and are motivated to stay on top of it. Others find it frustrating and avoid it. Recognising this difference allows for better decision-making.
If outsourcing bookkeeping or administrative tasks allows you to focus on higher-value activities, such as seeing clients or developing your business, it can be a worthwhile investment. The key is not whether you do it yourself or delegate it, but whether it is being done consistently and effectively.
Creating Clarity Through Separation
One of the most straightforward and impactful recommendations Oliver offered was the importance of separating personal and business finances. Using a dedicated business bank account creates immediate clarity. It simplifies record-keeping, reduces the time required to sort transactions, and makes it easier to understand the financial position of the business.
While this may seem like a basic step, it is often overlooked in the early stages of business. The result is unnecessary complexity that compounds over time. Establishing this separation early creates a cleaner foundation for everything that follows.
Learning to See Patterns
As a business matures, patterns begin to emerge. Income becomes more predictable, recurring expenses are easier to anticipate, and seasonal fluctuations become clearer. This allows for more proactive planning rather than reactive decision-making.
Good record-keeping plays a central role in this process. It provides the data needed to identify trends and make informed decisions. Over time, this shifts the experience of running a business from uncertainty to a more structured and manageable rhythm.
Navigating Uncertainty and Self-Doubt
Beyond systems and processes, the conversation also touched on the psychological side of running a business. Many sole traders experience imposter syndrome, particularly in the early stages. There is a perception that others are more organised, more capable, or more experienced.
Oliver’s perspective was that most business owners are learning as they go. The difference lies in how they respond to that uncertainty. Rather than viewing it as a weakness, it can be seen as part of the process. Experimentation, adaptation, and continuous learning are inherent to building a business.
David framed this in a practical way “I adopted the phrase ‘and no body died.’ Sometimes I try new things that don’t work ‘and nobody died’, but I learned something I didn’t know before.”, and as long as the consequences are manageable, they contribute to learning and improvement.
Addressing Problems Early
For those who find themselves behind on their financial admin, the advice was clear. Engage with the issue early and seek support. Accountants, bookkeepers, and resources from the ATO are all available to assist. Delaying action tends to increase the complexity of the situation, whereas early intervention creates more options.
There is often a degree of hesitation driven by embarrassment or uncertainty. However, addressing the issue directly is typically less difficult than anticipated and provides a pathway back to control.
Looking Ahead: The Role of Technology
Looking forward, Oliver identified technology as a key differentiator for sole traders. The ability to leverage tools that automate or simplify administrative tasks will increasingly influence how efficiently a business operates. For massage therapists, this presents an opportunity. While the core service remains hands-on and human, the systems that support the business can become more streamlined.
Those who adopt tools that align with their workflow and reduce administrative burden are likely to have more time and capacity to focus on their clients and their growth.
Bringing It Together
The conversation with Oliver ultimately returns to a set of simple but effective principles. Keep systems simple, engage with them regularly, and be honest about what you are willing and able to manage. Seek support where needed and make use of tools that reduce friction rather than adding to it.
Running a business does not require perfection. It requires consistency, clarity, and a willingness to adapt over time. For massage therapists, this means creating an environment where the business supports the work, rather than competing with it.
If this is an area of your business that has been sitting in the too-hard basket, it may be worth taking a closer look at your systems and finding something that actually fits the way you work. Rounded is one option designed specifically for Australian sole traders, and if you’re curious, you can try Rounded for yourself with a 30-day free trial. There’s no credit card required, so you can explore it at your own pace and see whether it helps bring a bit more clarity and structure to the business side of what you do.