I asked Cathal O’Reilly a simple question on the first episode of the Exit Ready podcast. When did it stop feeling like you were a freelancer with a team, and start feeling like you ran an actual business?
His answer is the most useful thing a growing agency owner can hear, because the honest version is that it took him about three years, and the headcount had very little to do with it.
Cathal started Rooftop Twenty Two in January 2020, just before the pandemic. Him, a laptop, a desk and no clients, in a box room. Today he has 14 full-time staff and three part-time, serving Irish and international businesses. By any measure, that is a real agency. But for years it did not feel like one to the person running it.
“For years I felt like the imposter. I started off in 2020 and I used to say ‘we’ instead of ‘I’. I still laugh at our first website, which says ‘we will take care of this’. But it was me, in that box room, fulfilling those requests.”
A lifestyle business and a real business are two different things
The frame Cathal used is the one I use with clients constantly. There are two kinds of business hiding under the word “agency”.
One is a lifestyle business. You, maybe one other person, doing the work, earning a good wage, keeping good relationships with clients. There is nothing wrong with that. For a lot of people it is the goal.
The other is a business that has to keep moving. You remove yourself from the work to a degree, you hire, and you commit to running the thing rather than doing the thing. As Cathal put it, you work on the business rather than in it. The two look similar from the outside in year one. They end up in completely different places.
He was honest about why the transition was slow.
“It probably took me three years to make that transition. If I did it again it would be quicker. But me being me, I quite enjoy the marketing, I quite enjoy building websites. So for the first two or three years, I was very much in it.”
The tell was the profit, not the workload
Here is the part every founder doing good work needs to hear. Cathal was earning a good wage. The business was busy. And at the end of the year, the profit was not there.
“I was more of a marketing person than a business person. I was thinking, why didn’t we make the profit that I felt the year deserved? It came down to not taking the business as seriously as it needed to be taken.”
A busy, well-paid founder can hide a structural problem for years, because the wage feels like success. Profit is the number that tells the truth. When the year’s effort does not show up as profit, the business is being run as a job with extra steps, not as a business.
The fix was a sequence, not a single move. He started delegating the work instead of doing it. He put in a monthly profit and loss account with live numbers through the month, so he could see reality instead of waiting for the year-end. And he raised prices.
“We decided to increase our prices. That increased our margin, which let us earn more profit and put those profits back into the business, hire more people, free up time to chase work, and start that again and again.”
Raise the margin, reinvest the margin, buy back your own time, use the time to grow. That loop is the difference between a lifestyle business and one that compounds.
The hire that proves you have stopped being a freelancer
The clearest signal Cathal had crossed over was a single hire: his first ever full-time production manager. A non-billable role.
“This person is not going to work on any clients. He is going to service Rooftop Twenty Two. He will help the team with capacity planning, give the business a helicopter view, and increase customer satisfaction.”
A freelancer with a team will not hire someone who does not touch client work. Every head has to earn its keep on the billable line. A business owner understands that the right internal hire is what lets everyone else deliver better. It is the same logic as removing yourself from the day to day: you spend money to buy back capacity and oversight.
His one regret was timing.
“I probably would have made that hire 18 months earlier. That would have solved some of the obstacles we faced over the past year.”
Be your own best customer
The last shift is the one almost every agency gets wrong, and Cathal named it perfectly.
“It’s like the painter who hasn’t painted their own house in 10 years because he’s too busy looking after everyone else.”
Agencies pour their best work into clients and leave their own brand, website and marketing to rot, because paying work always comes first. When we were in our high-growth years, we fixed that by ring-fencing 10% of the revenue from every big project and putting it straight back into our own marketing. Some of that was internal design and staff time, some was ad budget. It was not optional spend. It was the engine that kept the pipeline full.
Cathal is now redeveloping his own site, pushing his own social, and running his first client event. The painter is finally painting his own house.
What to take from this
If you do good work, earn a decent wage, and still feel like the business is just you with extra steps, the move is the founder shift Cathal made, not another body on the billable line:
Stop doing the work and start delegating it. Watch profit monthly, not yearly, so the truth cannot hide. Price for the margin that funds growth. Make the internal hire that buys back your capacity. And treat your own agency as your most important client.
A team does not make you a business. The founder deciding to run a business does.
Go deeper: Hear the full conversation with Cathal on Exit Ready episode 001, then read how to scale a creative agency without it depending on you and the owner extraction method.