How Digital Skills founder Mike Cheeseman broke free from economic cycles to build something bigger
Mike Cheeseman is lying on his office floor, stretching out his back, when he tells me about the moment everything went wrong. It feels a bit like a therapy appointment. It’s a fitting metaphor really.
“It was horrific,” he says of early 2020, his voice carrying the weight of someone who’s lived through genuine business trauma. “We had a triple whammy of disaster to work through.”
For nearly a decade, Mike had been building Digital Skills into what he calls “a bit of a bellwether for the economy”, a successful recruitment business that placed contractors and permanent staff across both public and private sectors, working with the likes of Adidas, Booking.com, and various government departments. But being a bellwether, Mike learned the hard way, means you feel every economic tremor first and hardest.
When Everything Falls Apart
The story of what changed Mike’s perspective begins with a sequence of events so perfectly timed to cause maximum damage that it almost reads like dark comedy. Almost.
First, the IR35 changes. The government’s planned implementation for early 2020 spooked major clients into getting ahead of the curve. They took contractors off Digital Skills’ books entirely, moving them onto their own payroll as fixed-term employees. “We had our contractor book decimated by that,” Mike recalls, the frustration still audible.
Then the pandemic hit, removing any chance to pivot or recover. But the third blow was perhaps the cruelest: Digital Skills had been developing a solution for a large systems integrator, helping them navigate IR35 compliance and providing a fully compliant workforce. Just as COVID took hold, the government delayed IR35 implementation by a year.
“They said, ‘Oh, it’s been delayed a year, we can figure this out within a year. We don’t need you,'” Mike remembers. The client was gone, just like that.
Three separate income streams, wiped out in the space of months. “It was horrific,” Mike repeats, and you can hear that this isn’t business-speak hyperbole. This was genuinely frightening, staff depending on you, bills to pay, and suddenly the future looking very uncertain indeed.
“We had contractors working in the Home Office,” Mike continues, “and the furlough scheme came up. We were able to say to the team, look, you guys get on furlough, I’ll do what I can, and keep things sort of limping along.”
The word choice is telling: limping. Not strategically repositioning or pivoting, just trying to survive. A familiar story for many during COVID.
The Cycle Trap
What followed was a masterclass in the emotional rollercoaster of economic dependency. The furlough scheme worked, Mike admits, “more generous than it needed to be, but that worked in our favour.” By 2021, work came back with what he describes as “a tsunami.”
“All of a sudden we had to just build back, and we were able to do that very effectively,” Mike says. “It was a war for talent out there, DevOps engineers, platform consultants. We were filling loads and loads of roles, everyone was getting counter-offered, rates and salaries were going up and up.”
For two and a bit years, it was brilliant. Digital Skills was making hay while the sun shone, picking up new clients, placing people left and right. But then 2023 brought the familiar summer slowdown that just… never picked up again.
“We were still sort of bumping along,” Mike says, using the kind of understated phrase that masks genuine worry. “But that’s around about the time I reached out to Rachel.”
Because Mike had realised something fundamental about his business, and it wasn’t comfortable: “We’ve always been a bit of a bellwether for the economy,” he admits. “We kind of ride those waves.”
For a founder who’d spent nearly a decade building something, that’s a brutal piece of self-awareness. Your success isn’t really yours, it’s defined by the economy. You’re not building; you’re surviving, over and over again.
The Moment of Truth
“I don’t want to survive,” Mike tells me, with the kind of quiet intensity that comes from genuine frustration. “I want to thrive.”
It wasn’t a dramatic epiphany, no bolt from the blue or crisis-driven revelation. Instead, it was the accumulated weight of watching the same patterns repeat, of feeling your business success rise and fall with forces almost entirely beyond your control.
“I thought to myself, you know what, we’ve been in the ups and we’ve been in the downs several times before. Just keeping riding them out is not what I want to do.”
Mike had known Rachel Murphy for years, had watched her grow and eventually exit her last business, a business that shared a lot of DNA with Digital Skills. He’d seen what was possible when recruitment evolved beyond “bums on seats” into proper project delivery, real services that created genuine value.
“The old adage,” Mike says, “if you keep doing the same thing and expect different results, you’re mad. So let’s do something slightly differently.”
But there was a problem, and Mike is brutally honest about it: “What I hadn’t actually really done is proper project services and project delivery.” He had a hunch it was the right direction, but knowing and doing are very different things when you’re running a business.
The Confidence Gap
When Mike talks about working with Rachel and The Grafter, he cuts straight to what really matters for founders: confidence.
“You know how it is sometimes when you’re in a small startup or bootstrapped business,” he says, and there’s recognition in his voice of something every founder knows but rarely admits. “You think, how do I do that?”
The technical capabilities were there. The market opportunities existed. But between knowing what needed to be done and actually having the confidence to do it stretched a gap that felt impossible to bridge alone.
“Coming on board with somebody like Rachel, it actually opens up a very capable and competent person who can talk through that, gives a little bit of credence to us doing it, as opposed to being just a recruitment business.”
“For me as a founder, it gives me that extra layer of confidence and comfort to say, yeah, I can do that.”
But Mike is careful to explain what this support actually looks like in practice: “It’s a case of someone on the shoulder to say, hey, I’ve got this opportunity. What do you reckon? Should we do it? How come?”
It’s remarkably simple when he puts it like that. Not revolutionary strategies or complex frameworks, just having someone who’s been there before to help you think through the decisions that keep you awake at night.
The Fear of the Unknown
“Sometimes the biggest problem is mapping out the different.” Mike admits, “You’ve got to pull the trigger at some point in time, but it’s going to be painful to do so.”
But as he talks, it becomes clear this is about something far more fundamental: the fear of stepping into territory you’ve never navigated before. Mike had built Digital Skills around recruitment, he knew that world inside out, understood its rhythms, could navigate its challenges. Project delivery was different territory entirely.
“You’ve spent years building credibility in one area,” Mike explains, “and suddenly you’re asking clients to trust you with something you’ve never actually delivered before. That’s genuinely intimidating.”
The status quo, even when it’s limiting, feels manageable. You know its problems, its cycles, its constraints. But transformation can mean risking a lot of what you’ve built for something you can’t be certain you can execute.
“Just having that support to say it’s the right thing to do as opposed to, I’m not sure, that sort of thing. Do you know what I mean?”
The vulnerability in that question, “do you know what I mean?”, speaks to something deeper. It’s not just business uncertainty; it’s the isolation of being responsible for other people’s livelihoods while contemplating a fundamental shift in how you operate.
“Sometimes you know what the problems are and you know exactly what the kind of external eye on your business would say, but you need to hear it anyway.”
Beyond Survival Mode
The partnership with Rachel brought practical benefits, new networks, fresh opportunities, additional credibility. But it also helped Mike recognise something Digital Skills had been doing well without fully understanding its strategic value.
“We’ve been doing some good work in terms of diversity,” Mike explains, “specifically women in digital, women in technology.” Working with Rachel, a female founder who’d successfully built and exited her own business, suddenly gave that capability much more weight.
“With Rachel partnering with us as a female founder, an exiteer, and a digital leader, we’ve got a little bit more to shout about on that.”
In a sector where diversity is a genuine challenge, this isn’t just about press statements and initiatives, it’s about having the network, experience, and credibility to help clients build the kinds of teams they actually need.
The Quiet Revolution
Ask Mike about the future now, and there’s something different in his voice. Not bravado or unrealistic promises, but a kind of steady confidence that comes from knowing you’re no longer just reacting to events.
“We’ve got some great opportunities which I might have wimped out of before and I’m not going to do that,” he says simply.
The honesty of “wimped out” is striking. How many founders would admit to backing down from opportunities? But Mike’s willingness to acknowledge past hesitation makes his current confidence more credible, not less.
“I would imagine that in 12 months time we’ll have a number of proper service based deliverable contracts that we’re working on… It means growth and it means diversification.”
The Real Value of Support
When I ask Mike what he’d tell other founders considering similar support, he’s characteristically direct about what it is and isn’t.
“It’s not necessarily someone’s going to wave a magic wand and all your problems go away,” he explains. “It’s a case of you just get somebody who understands, knows what the problems are and knows what the pitfalls are to support you in making the right decisions.”
The practical elements matter too: “Getting your credentials right, getting your service proposition right, getting your data right… those are other things which maybe some founders like myself have in their heads. They know what’s going on, but not actually down on paper, not necessarily in the right level for a third party to analyse.”
But underneath the practical support lies something more fundamental: permission to act on what you already know needs doing.
Breaking the Cycle
Mike Cheeseman is still running the same company he founded in 2015. Same core team, same fundamental expertise, same commitment to finding and placing digital talent. But Digital Skills is also becoming something different: a business that creates value instead of just capturing it, that builds capability instead of just riding waves.
“I feel pretty confident catching and running with opportunities that we may have not necessarily have caught and run with before,” Mike says, and there’s genuine satisfaction in his voice.
The economic cycles will keep coming, Mike knows that. But this time, instead of being their victim, he plans to be ready for them. Not just to survive the next downturn, but to use it as an opportunity to prove that Digital Skills has become something more resilient, more valuable, more future-proof than a simple bellwether for the economy.
“Happy days,” as Mike would say. And that feels like more than just optimism.
