How Jack Graham built a thriving video business thanks to a big heart, honesty and a busking rock star
There are origin stories, and then there is Jack Graham’s.
Most freelance videographers will tell you they started with a camera and a dream. After a few years working in the charity sector, Jack started with a year of travelling and a chance encounter with a tattooed, one-man rock ‘n’ roll band busking for change on the streets of Romania.
Nearly four years later, he runs Raccoon on the Run, a Manchester-based video production company with a growing reputation, a full calendar, and — crucially — the kind of confidence that lets him turn down work that isn’t right and charge what he’s worth. How did he get there? It starts, as all the best stories do, with a bit of adventure and taking a chance on yourself.
The 18-Year-old YouTuber who changed everything
Jack was in his late twenties, travelling through Eastern Europe in the aftermath of the COVID lockdowns and losing his father, when he stumbled across a young YouTuber who had built a substantial following. The encounter was revelatory — not because Jack wanted to be a YouTuber himself, but because it proved something he hadn’t quite dared believe: that ordinary people with a camera and a story could build something real.
“He had, like, 300,000 subscribers,” Jack recalls. “And I thought, how has this happened? This is a guy, probably 18, just like documenting his trip. And I thought, there’s something here.”
The YouTuber encouraged Jack to get in front of the camera himself — to become a travel vlogger. Jack politely declined. What he felt, instinctively, was the pull of being behind the lens. He went out and bought a Canon EOS 850D, started reading books, watching tutorials, and making, in his own words, “stuff that was rubbish.” He was learning.
“I took out-of-focus pictures, you know, generally just kind of learning very, very basics.”
It was a cathartic experience to just get away from it all and reset my head, and ultimately figure out what I wanted to do next in life.
Captain George and the documentary that started it all
It was in a medieval town about an hour and a half north of Bucharest that Jack’s first real project found him. Walking through the old town, he spotted a busker unlike any he’d seen before: a wild-eyed, tattooed man playing guitar while simultaneously operating a foot drum, singing with the abandon of someone who had decided long ago that the world owed him nothing and freedom owed him everything.
Across his chest was a tattoo that read ‘Captain George.’ His mantra: freedom, rebellion and what it truly means to follow your dream.
“I found him a bit later in a pub,” recalls Jack, “and said, ‘How are you, Captain George? How would you fancy me following you around for a bit and making a documentary about you?”
Captain George, a Slovakian one-man rock ‘n’ roll band who funds his travels by busking, said yes with the enthusiasm of any rocker who had always known he was destined to be documented. What followed was months of travel: through Romania, into pre-war Ukraine, and back to Slovakia, Jack’s camera rolling all the way.
The resulting documentary, Captain George Moves, was a 25-minute documentary that Jack is justifiably proud of — not because it was technically perfect, but because it was alive. In the summer of 2022, it won Best Indie Short Film at an international film festival in Slovakia.
Something can be as beautiful as you like, and as polished and all that kind of stuff — if I’m bored watching it, it doesn’t matter how nice it looks. It’s an automatic zero.
That principle, that storytelling is the only thing that truly matters, has never left him. It is, to this day, the backbone of everything Jack does professionally.
From documentary filmmaker to commercial videographer
Back in the UK, Jack made a second documentary — this time about a homeless man he’d befriended through his previous work in the charity sector and street fundraising. Where most homelessness documentaries leave viewers feeling grim and helpless, Jack was determined to make something different.
“There are tons of documentaries about homelessness,” he says, “mostly pretty depressing. Mostly, you come away going, well, yeah, being homeless is shit. I already knew that. I didn’t really learn anything.”
His version had humour, warmth, and a focus on the friendships, dreams, and relationships his subject still maintained. It was, he says, “really rewarding” — and the craft had noticeably improved.
By late 2022, Jack had spent the last of his savings on equipment, a website, and branding. Raccoon on the Run was open for business. The name — deliberately nonsensical in an industry full of generic-sounding agencies — was chosen for exactly that reason. “I’ve been told I’m slightly raccoon-like, which I’m fine with. I like raccoons,” he laughs.
A long way in a short time
Four years in, Jack Graham has come a considerable distance from that first documentary. He now shoots on a Sony FX6, works with clients across England — from Manchester and Birmingham to London — and has recently entered what he describes, with characteristic understatement, as “a really good” period of business growth.
The feast-and-famine cycle that plagues so many freelancers has largely receded. So, what changed? How has he managed to bring in just one month this year, almost half the amount of last year’s earnings? What’s changed with his business? With clients?
My sales process probably comes in at number two on that list. Number one is the fact that I started putting a lot into networking about a year and a half ago now. It’s seeds planted — with individuals, but also with building a broader reputation, a LinkedIn following, all that kind of thing. It’s the seeds that were planted a year and a half ago. They’re now blooming.
The case for networking — Even if you’re shy
Ask Jack whether networking is essential for freelancers, and he won’t hedge. “I literally don’t see how you run your own freelance business without it. Not in any sort of long-term way. Not in a way that you can make a real living out of.” He pauses. “If you’re not a big fan of networking, in my eyes, you’re going to have to learn to like it.”
He attends in-person events at least every two weeks — evenings suit him better than early mornings, which he notes were not among the reasons he became a freelancer. But he’s equally an active engager on LinkedIn and specifically shares how most people use it wrong.
If you’re not a big fan of networking, in my eyes, you’re going to have to learn to like it.
“For every post I make, I probably make around ten comments on other people’s things. The thing people really drop the ball on is commenting on other people’s stuff.”
It’s in the comment sections, he explains, that real relationships form. You start to recognise the same faces, develop a sense of someone’s personality and values, and eventually — almost naturally — the message arrives: “Hey, we keep seeing each other in the comments. Do you fancy jumping on a Zoom for half an hour?”
Most of the time, people say yes. Some of his biggest clients have come from exactly that process, conversations that began not with a sales pitch but with a shared rant about the state of the world.
“I’m pretty left wing, and I’m not afraid to make that known,” he says. “I’ve had some of my biggest clients through being quite outspoken, just chatting, because our values aligned outside of business. The initial conversations never even had anything to do with business.”
For those who find all of this daunting — and Jack knows many do — his message is: everyone is winging it, even the people who look like they aren’t.
“When you start to feel more on parity with these people, you start to realise that everybody’s kind of winging it. Nobody’s quite the superman you thought they were.”
The sales process that changed everything
The second pillar of Jack’s recent success is a more structured — and more honest — sales process. It begins the moment a lead comes in. The first conversation has one purpose: to establish whether the potential client can actually afford him and whether what they’re asking for is something he does well.
“I’m not really a heavily scripted, heavy special effects TV commercial type person,” he says. “There’s no point in pretending otherwise. I try to stick to what I’m good at.”
From there, a discovery call gives the client space to “offload everything” — their goals, their audience, their references, their budget. Jack listens, asks questions, and — crucially — starts to gently correct misalignments between what they want and what will actually work. It’s a process he describes with warmth but also rigour.
“You’re on this discovery call, thinking, ‘I love your goals — but what you’re asking me to do here isn’t going to get anywhere near that. It’s going to be a waste of money.’ It’s always quite an entertaining conversation, trying to say that in the most practical way possible.”
After the discovery call, a proposal call follows — booked before the discovery ends, so there’s no ambiguity about next steps. The proposal itself is a structured document: context, deliverables, two quotes (one basic, one comprehensive), a process overview, a responsibilities section, and a clear next steps page.
The process section, Jack says, is one of the most underrated parts. “To us, it’s second nature. Pre-production, production, post-production. But the client has never done this before. They want to know their next few months aren’t going to be a shit show. Reassuring people on that is really important.”
He insists on going through all of this across two or three meetings before a contract is signed — even when clients would prefer to skip ahead:
I really try and insist on it. Because I just find it increases conversion so much from my end, but also, if you do sign, it makes the whole project easier. We’re all on the same page from the start.
The honesty that wins clients
Running through everything Jack does is a principle that sounds simple but is surprisingly rare in practice: radical honesty. He will tell a client when their idea won’t work. He will tell them that one video on its own is unlikely to deliver meaningful ROI. He will tell them, warmly but plainly, that they don’t know much about video — and that this is completely fine, because that’s what they’re paying him for.
“Almost nobody I work with knows a great deal about video,” he says, “so that’s all fine. But that’s what you pay me for. I’ll guide you through the bits you don’t know. I’m never going to lie to you about it. I’m never going to say we can buy the moon for you.”
The response, almost universally, is relief. “People breathe a sigh of relief. They say, oh right, yeah, God — I really don’t know a great deal about this, and we don’t have to pretend that we do.” It builds trust quickly, and it keeps clients coming back.
Measuring the results of that trust is harder. Video, unlike pay-per-click advertising, resists clean data. Jack is honest about this, too.
I long for a world where I could have data read out like a PPC person — ‘we’ve seen a 70% spike because of this video.’ But it just doesn’t really work like that.
Most of his feedback is qualitative: clients telling him that new customers mentioned the video, that the company feels more human, and that trust was built before the sales call even happened.
The freelance network that gives back
Jack’s generosity extends beyond his own clients. He has built a network of trusted freelancers — social media managers, copywriters, photographers, motion designers — and regularly introduces them to leads and clients, even when it means no direct financial benefit to himself.
“I really think that in freelance, what goes around comes around,” he says. A recent example: a golf course irrigation startup that came to him with a tiny budget and a vision for a slide-show style promo video. Two years ago, Jack might have taken whatever he could get. Today, he told them honestly that a slideshow would look cheap and wouldn’t serve them — and then referred them to a motion designer he trusts.
“It just builds such a level of trust and authority when you’re happy to relinquish short-term gains to actually help out a potential client in a way that doesn’t benefit yourself.”
I really think that in freelance, what goes around comes around.
He’s also learned — the hard way, through one collaboration that ended sourly — to be selective about who he recommends. “I’ve been burned by that before,” he says. “It reflects on you. I need them to do a good job.” The experience, in which a social media collaborator consistently underdelivered and eventually tried to hold a client’s accounts hostage when the arrangement ended, left Jack more rigorous in his due diligence but no less committed to the principle of a generous freelance ecosystem.
On rates, free work and knowing your worth
On the subject of pricing, Jack is direct. He has raised his rates considerably over the past year — from around £450 per shooting day to £650, with editing at £500 per day — and plans to raise them again within a few months. Paradoxically, each rate increase has brought more clients, not fewer.
“People like paying more for marketing sometimes. It is an indicator of quality. You know, if Armani started discounting their items, no one would buy them. People trust something that’s more expensive, which is wild, but it really makes sense when you look at the consumer market. And it clearly applies in B2B too.”
To those starting out, Jack’s advice on free work is nuanced but firm. A small amount, done for the right reasons — charity, a creative project you genuinely care about, a cause aligned with your values — can be worthwhile for portfolio building. But the trap of becoming “the free freelancer” is real and difficult to escape.
Really try and get out of doing free or massively cut-price work absolutely as soon as you can. If you get 300 quid for a project you might one day charge two grand for, that’s still better than nothing. You’re on the ladder. If you’re doing it for free, you’re not even on the ladder yet.
He applies the same principle when bringing junior freelancers onto his own projects, insisting on paying decent rates — well above market minimums — on the practical as well as ethical grounds that accountability requires fair compensation. “If I’ve paid you less than you’d get from shelf stacking in Tesco, I can’t really hold you to account if you drop the ball.”
Captain George and the thread that runs through it all
The last time Jack and George met, George was working as a ski instructor in Austria. Jack went to visit, slept on the floor of his room, borrowed ski gear and a lift pass. As reunion and travel stories go, it suited them both.
The film that started it all — a 25-minute portrait of a man who decided that freedom and a guitar were enough — won its award and yet was never monetised. That said, it shaped everything that came after: the instinct for storytelling, the commitment to genuine human connection on camera, the belief that the most important quality in any video is whether it makes you feel something.
“Coming from a documentary background,” Jack says, “I really do focus on storytelling. I know the other side” — and he means it. His roster now includes charities, social enterprises, and industrial clients for whom he literally straps cameras to conveyor belts and calls it, entirely accurately, like making a Discovery Channel show with a commercial objective.
But the through-line is always there: people first. Honesty. The long game. The seeds you plant eighteen months before you need them to bloom.
If you do that enough times over the years, you just end up with a stellar, widespread reputation. People learn who you are. And that’s the key to being long-term successful.
Jack Graham can be found on LinkedIn, where he describes himself as someone who produces “occasionally useful stuff” alongside “a lot of rambling thoughts.” Based on the evidence, the ratio is rather more productive and business-building than he lets on.
Raccoon on the Run | Find Jack on LinkedIn
Here is a video project Jack is particularly proud of for Great Ormond Street Hospital (GOSH), a children’s hospice charity
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