Why the over-50s are building businesses the young never imagined
The mythology of entrepreneurship has a particular uniform: a grey hoodie, unwashed hair, a face unmarked by anything so inconvenient as decades of actual experience. The Silicon Valley archetype demands youth-the younger the better – on the peculiar theory that ignorance of how things work is somehow advantageous when building things that must, eventually, work.
We had better hope this mythology dies quickly, because the demographics are unforgiving. By 2030, more than half of the UK workforce will be aged fifty or over, a cohort expected to contribute some £730 billion to the economy. The proportion of over-50s in work has already grown from 21% to 33% in the past three decades – and the trend is accelerating. The story in America is similarly stark: a 65-year-old woman now has a 40% chance of living to ninety; for men, the odds are roughly 30%. That is far too long to spend without work and earning. No economy can sustain a top-heavy collapse borne on too many people requiring financial support while too few remain productive. The maths is brutally simple: we absolutely have to postpone full retirement, and that means we need people in their fifties, sixties, and seventies not merely employed but building – creating enterprises, generating jobs, solving problems that younger founders cannot even perceive.
This orthodoxy about youth is, to put it charitably, nonsense. And a growing cohort of entrepreneurs is proving it so – not by arguing the point, but by simply getting on with it.
The First Woman to Found a British Bank
If we want to understand what older entrepreneurs can achieve at scale, consider what Anne Boden and Mark Winlow built. In 2014, Boden was fifty-four, Winlow fifty-one. Both had spent decades in traditional banking – Boden at Lloyds, Standard Chartered, UBS, ABN Amro, and as Chief Operating Officer at Allied Irish Banks during its post-crisis recovery; Winlow as a partner at EY and KPMG, with advisory roles across British financial institutions. They had, in other words, precisely the kind of establishment credentials that should have guaranteed comfortable sinecures until retirement.
Instead, frustrated by the failure of traditional banks to embrace new technology, Boden decided to do something genuinely radical: build a digital-first, mobile-based bank from scratch. “My entrepreneurial journey began when I was 54,” she has said. “Prior to this I’d spent my whole career working as a corporate executive in a big bank and I decided to quit my job and start one of my own.”
Boden sold her weekend house in Swansea to raise funds. Winlow became the second employee. What they created was Starling Bank – now a fintech unicorn valued at £2.5 billion, with over four million customers, £14.7 billion in assets, and more than three thousand employees. By 2024, Starling had achieved three consecutive years of profitability, with pre-tax profits exceeding £300 million. It was the first UK digital bank to turn a profit – a feat still elusive for many of its younger, flashier competitors.
Boden became the first woman ever to found a British bank. She received an MBE for services to financial technology. Starling was named Best British Bank three years running. And when she stepped down as CEO in 2023, it was not to retire but to start another company – this time in artificial intelligence.
The Starling story demolishes every assumption about age and entrepreneurship. These were not naïve outsiders stumbling into disruption; they were consummate insiders who understood exactly what was wrong with the industry and possessed the technical sophistication to fix it. Boden’s degree from Swansea combined chemistry and computer science – she had been thinking about technology in banking since the 1980s. Winlow had served on eighteen boards and chaired eleven of them. They knew how regulation worked, how capital requirements functioned, how to navigate the labyrinthine process of getting a new bank approved.
“At Starling Bank it was a little like learning to ski,” Winlow has observed. “You can spend hours learning to ski well, or you can just put on your skis and lean forward.” This from a man who had spent four decades in financial services. The confidence was not youthful naïvety; it was the earned certainty of people who had seen enough to know what would work.
Fired at Sixty-Four, Founder at Sixty-Six
Paul Tasner had a successful career working in consumer products and supply chain. He had held roles in several top-tier companies like The Clorox Company, Clif Bar, and Method Products. His last full-time position was as a director at a consumer products company in San Francisco. However, just before Christmas in 2009, the white-slip dismissal letter arrived.
At sixty-four he was fairly certain that any application he submitted would be screened out at the earliest opportunity. Rather than go through the soul-destroying rejection process depicted in films like Up in the Air, he decided it was better to go down the independent route.
At first he followed the time-honoured path of consulting, where a variety of old-timers put out to grass are occasionally thrown a bone of opportunity. However, he rapidly discovered that he preferred more involvement than consulting could offer. He wanted something else.
He also wanted to reverse something that, in his earlier jobs, he had been instrumental in rolling out – very strong plastic packaging. As an industrial engineer, he spent most of his career making plastic. He made “blister packs”, the plastic wrap around consumer products that are very hard to open, even with scissors.
Appalled by the mounting plastic pollution on our planet and his earlier role in it, he set out to create a safe, eco-friendly packaging for consumer products. With his background he knew that industry needed something similar to plastic, but able to be composted into soil.
After a period of experimentation, using paper and agricultural waste, he launched PulpWorks in August 2011. Their boast was to turn garbage into planet-friendly products. His client base now spans North America. By then he was sixty-six.
Since launch, PulpWorks has become a leader in “green” packaging. The company makes packaging for major brands including T-Mobile, Burt’s Bees, Max Factor, Cover Girl, and Leapfrog Toys.
“Every package that we produce replaces a piece of plastic that is not going into a landfill. What could be better than that? Except to do it a billion times over – and that’s our goal.”
But what struck Tasner most was not the operational challenges. It was the prejudice. “It was almost as if I was gatecrashing a community that felt I had no right to be there,” he recalls of his early encounters with the start-up world. “Why did I have wrinkles? That was not in the start-up script.”
He yearned, at the beginning, to find other first-time entrepreneurs his age. “I had no role models, absolutely none.” Now he argues something counterintuitive: age means fewer mistakes, a safer lift-off.
The Accidental Patriot
The dismissive, sneering tech bros – so confident in their disruption credentials – might note that genuine disruption sometimes looks like a grandmother from Northern Ontario who simply understood the problem better than they ever could.
Karen Hastie spent over three decades building and running a fitness retail chain in Northern Ontario. Not necessarily the background for a SaaS software social start-up.
When the pandemic arrived, she sold the business in a seven-figure transaction. She was sixty. Most people might have reckoned they’d done enough and retired. But she is not most people. She had no intention whatsoever of slowing down.
What she created next was the Chamber Perks App, a bilingual technology platform designed to connect Canadians with local businesses through their Chambers of Commerce.
The significant detail here is that Hastie had precisely zero background in technology. She built a software company anyway. Three-and-a-half decades of understanding how small businesses actually function; what they actually need; what the Chamber network could become if properly digitised – all of this proved rather more useful than a computer science degree.
Trump – unbeknown to him – may have given her idea new impetus. In an era of American tariffs and rising economic nationalism, Hastie’s platform has become an unexpectedly potent instrument of Canadian self-reliance. “Buy Canadian” was already a sentiment; she built the infrastructure to act on it.
“Even when Canadians want to shop locally, they often don’t know how to find local businesses or have the financial flexibility to do so,” Hastie observes. “That’s why we built the Chamber Perks App – a solution for chambers to help businesses navigate today’s economic challenges and empower consumers to shop Canadian.”
The scale is already considerable: fifty Chambers across Canada representing approximately twenty thousand businesses, with over fifteen hundred perks available to any Canadian consumer looking to keep their money circulating domestically. The ambition is larger still – all four hundred-plus Chambers nationwide.
The best bit? It’s solving an old problem with new technology.
Not Everyone Aims This Big
Not every reinvention needs to be a unicorn. The venture capital obsession with billion-dollar valuations has always been faintly absurd – as if the only businesses worth building are those that might one day swallow the earth. But there is another kind of entrepreneurship, quieter and no less determined: people who look at the actuarial tables, note that they may have another thirty years of existence ahead of them, and decide that golf might cost more than they can afford. They are ready to return to the drawing board and come up with smaller ideas that help them and maybe their communities too.
Disrupting the Disruptors
Mary Rawles launched a fitness career targeting older women – a demographic routinely patronised by an industry that struggles to imagine anyone over forty lifting anything heavier than a small pink dumbbell.
“Until recently,” Rawles observes, “if you Googled ‘older woman strength training’, you would get images of women with these tiny little pink weights, and usually they have a young woman next to them holding their shoulders.”
Today that imagery is widely seen as outdated. We don’t feel fragile, nor do we feel incapable of improving our physique.
Rawles, along with famous names like Dr Gabrielle Lyon, is not just talking a new language of empowerment; she is disrupting the whole industry – slashing prejudice.
Rawles describes herself as a “disruptor of ageing”, taking the language of Silicon Valley and giving it a feminist twist. She is part of a movement changing how ageing is represented, insisting on images of actual strength rather than managed decline.
The Professor Who Understood Her Own
For many women – especially those who have found themselves derailed by the act of caring for parents and children – the case of Charlotte M. Bishop may provide the most hope.
She spent forty years at the Borough of Manhattan Community College, eighteen of them chairing the Office Administration department. She raised two sons as a widow and then juggled her work while caring for her elderly mother.
When she retired from the City University of New York, she had accumulated a huge amount of experience that she knew instinctively was undervalued. What she also noticed was that many of her friends, and friends of those friends, were overwhelmed by the need to have countless documents in order to manage their lives.
Perhaps younger people can muddle through with papers in disarray, hidden in some computer drive or box. But later in life, paperwork – or at least the capacity to identify your rights – becomes more important. Medical records, insurance policies, legal documents – any one of these may be the key to accessing vital help. If you can’t find them, you may be depriving yourself of thousands of dollars or pounds.
Whereas she had learnt from her earlier career to be meticulously organised, many of her friends were fumbling around their houses searching for something vital they couldn’t lay their hands on. They would waste hours searching for a piece of paper that might just alter their lives.
So Bishop founded Life Files Professionals, a company specifically designed for those in their mid-50s in need of a file overhaul. It is also that much-sought-after business idea that replenishes itself – an evergreen business on speed.
What makes Bishop’s story particularly significant is its universality. She represents millions of women who have spent years as carers and may wonder whether they have anything left to offer the world. She proves they do. There are corners of the economy that perhaps only older women can understand – problems invisible to younger eyes because they have not yet lived them. One of the pressing challenges of the modern age is the number of people finding themselves trapped in caregiving roles, uncertain what comes after. Charlotte Bishop shows you can restart.
It is difficult to imagine a twenty-five-year-old entrepreneur perceiving the need for Life Files Professionals, let alone understanding how to serve that clientele. The insight required years of lived experience – organising her own documents, managing her mother’s care, watching friends struggle with the administrative chaos of ageing. This is not a business that could have been invented by youth. It required exactly the wisdom that Silicon Valley has taught us to dismiss.
The Uncomfortable Truth
There is, however, a darker reading of this phenomenon. As Harold Mansfield, an AI consultant, put it bluntly on LinkedIn: “I think often the path to entrepreneurship is involuntary (they have difficulty finding traditional corporate track jobs/ageism).”
The responses were illuminating. “After 50 no one will hire you to do anything other than greet people at Walmart,” wrote one commenter. “Hell, companies start looking at you funny mid-40s – that’s if you can even get an interview at that age without some kind of inside connection.”
So let us be honest: many of these entrepreneurs are not choosing adventure over security. They are building businesses because corporations have decided they are surplus to requirements – despite decades of proven competence.
But here is what the corporate world has failed to understand. The same qualities that make someone “too old” to hire – deep expertise, pattern recognition honed over decades, the calm that comes from having survived previous crises – make them formidable founders. The rejection is corporate loss, not personal failure.
The Energy Question
The ageist assumption is always about energy – the notion that building something new requires the frantic all-nighters of a twenty-three-year-old subsisting on Red Bull and desperation. But watch Anne Boden methodically building a bank that would achieve profitability while her flashier competitors burned through capital, or Paul Tasner navigating manufacturing challenges, or Karen Hastie learning to build software from scratch, and you see something else entirely.
You see energy, yes – but directed energy. The kind that knows which problems are worth solving and which are merely noisy. The kind that has seen enough failures to recognise them early. The kind that understands sustainable effort over performative exhaustion.
Women of a certain generation, as one observer noted, “absorbed all that conditioning about not being too competitive, spent decades being interrupted and overlooked, were told repeatedly that we should step aside for men or younger women.” They are now, at fifty, sixty, seventy, “actively reinventing what it is to be” those ages. Taking consulting gigs. Building portfolios. Writing books. Launching podcasts. Starting businesses.
“Refusing, essentially, to shuffle off to Pilates class and garden design, which is apparently what we were supposed to do.”
The Verdict
Perhaps the young men of Silicon Valley were simply far too prejudiced. They built an industry mythology that excluded anyone who looked like their parents, then expressed surprise when those excluded people built remarkable things anyway.
Anne Boden’s Starling Bank – a multi-billion-pound unicorn built by a woman in her mid-fifties – stands as perhaps the most emphatic rebuttal to the cult of youth the financial services industry has ever witnessed. Paul Tasner’s view is worth repeating: age means fewer mistakes, a safer lift-off. Karen Hastie’s understanding of small business needs was not available in any curriculum. Mary Rawles’ determination to disrupt patronising imagery came from lived experience of being patronised. And Charlotte Bishop’s insight into the document chaos facing older adults could not have been learned at an accelerator – it required years of caregiving, years of administrative expertise, years of watching people struggle with problems that younger entrepreneurs simply cannot see.
These are not people making the best of diminished options. These are people finally freed from the organisational constraints that never deserved their talents in the first place.
The start-up world fetishises disruption. It might consider disrupting its own assumptions about who gets to build the future.
