Ross Dwyer came into this with the objection half the creatives reading this page are carrying right now: I'm a filmmaker and an artist. I don't want to become some guy just selling stuff.
When he joined Video Agency OS, Do Good Studio was generating under $2K a month — and he's honest that even that flatters it. Within six months he'd built it to $20K a month in recurring revenue. His first year: around $150K, from a standing start, while staying — by his own account — more creative than he's ever been.
"I Don't Know If You Can Even Call It a Business"
Ross's background is filmmaking, voiceover and acting. Before joining, he was working part-time as an entertainer at the children's hospital, doing consistent voiceover work, and running video as the thing on the side:
"It wasn't really making money at all. It was actually just costing me a lot of money. I was doing these odd jobs for people, bending over backwards, and then having to pay other people to help me do them."
His marketing was the classic creative's version: portfolio pieces he thought were ads, posted in the hope someone would say "cool, we'll hire you." His pricing strategy was copying what other companies' websites said and waiting. His sales conversations went budget-tennis until someone finally said "we've got $200 for this."
"I felt like I was fishing in the wrong pond. I didn't even know what a retainer client was, or what a package could look like. If you'd asked me if I was good at sales, I would have told you I probably was — but really I had no idea how to actually sell something."
The Scariest Purchase Since Camera Gear
Joining was, in his words, the most money he'd ever spent on anything apart from camera equipment — and the panic set in immediately: "I was like, what have I done? Am I actually going to be able to translate this?" His response was to spend that first weekend furiously working through the program, because "I've got to make this work — I have to be able to pay for this."
Four weeks later, almost to the day, he made his first sale: a $5K package. The next day, a $7.5K package.
"In the space of 24 hours I made $12.5K in sales. I'd paid for the program and some. When the second one came through, I ran out and found my now-wife and literally just started dancing around and jumping up and down with her. I'd never seen this as a possibility — getting paid properly for doing what I love. And I was like: if it's that easy, why have I not been doing this for so long?"
He then immediately went and bought a new tripod — which, for the record, breaks one of our standing rules for new clients (no new gear in the first 90 days; reinvest in the business). He owns it with a laugh. We're keeping it in because that's what actually happens.
The Messy Middle: Authority and the Empty Month
Then reality did what it does. Another month passed before the next sale. Some prospects said yes and pulled out later. And as a newcomer selling content services to coaches, he kept hitting the same wall:
"They'd be like: where is your authority? Can I see how you help people grow their businesses? And I was like — ah. I don't have that. That was a really hard thing to face. So it was twofold: I worked my ass off to get results for my clients so I had the authority, and I had to learn how to steer the conversation so they felt safe and trusted me from the get-go."
What carried him through that stretch was showing up — relentlessly. The weekly Q&As ("there'd be people who wouldn't turn up and I did not understand why — no one else is asking questions? Ask away"), and the sales roleplays: "As scary as they are — standing up, getting in the hot seat, getting torn apart — you almost want to. I'd do a roleplay, go into a call the next day, and make a sale." The Queensland mastermind turned the community into something else again: "It's literally built a whole new circle of friends. People who'll message you — hey, you said you were doing that thing, how did it go? And you're like: oh, I'm accountable to a whole group of people I respect now."
From Feast-and-Famine to "The Doors Won't Close"
Ross's first-year revenue landed at around $150K — "if you told me the business could generate that in the first 12 months, I would have been like: no chance." But the early shape of it was still spiky: a $20K month, then two months of one sale. The shift came when he stopped chasing lump sums and rebuilt around retainers, resigns and an actual customer journey:
"Now I'm at about $22K of monthly recurring revenue, with additional project sales on top — sitting around $25 to $30K some months. When I went past the $10K recurring point, it was like: the doors won't close. My clients finished their initial three months and signed on for a year. I can look at growth and build a pool of wealth at the same time."
The life on the other side of that: a wedding paid for, a honeymoon he can actually take without panicking about the pipeline — and, as he shared on camera, he and his wife are now talking about having a kid. "Before all of this, I would have been like: oh god, a kid? Something's going to have to change. Now it's a legitimate conversation we can have." Both of them came from acting, where, as Ross puts it, the income pattern is "feast or famine — mostly famine." Consistency was the whole prize.
To the Artist on the Fence
Which brings it back to the objection he arrived with. His answer to it now:
"I very quickly learned that's not what this was at all. The amount of creativity involved and the amount of fun we get to have with clients — I could not trade that for anything. I have not had a shoot day that hasn't been full of laughter. It's actually made more space in my life for the other creative projects I want to do. Who says you can't be an artist and learn how to be good at business as well?"
And his advice for anyone considering it: "Do it — and if you do it, lean in and give it your all. The systems are all there for it to work. It will give back as much as you put in."
The Lesson
The fear that business skills kill creativity has it exactly backwards. Ross's creativity was never the thing at risk — it was the thing being wasted, spent on $200 projects for the wrong pond because nobody ever taught him how to package, price and sell it. Learning the business side didn't turn the artist into a salesman. It bought the artist room: recurring revenue that keeps the doors open, clients worth doing great work for, and space for the creative projects that never had oxygen before. The craft was never the problem. The pond was.