Clearly your path to where you are now has not been a smooth one, but going back, what were the pivotal moments early on in your life that contributed to where you are now?
My working life started in commission-only direct sales, double glazing, door to door. You were given leads, expected to open and close on the same night, and paid nothing if you failed. On my very first evening, I was still knocking on doors past midnight. No one told me to. I just refused to stop until I had made a sale.
That experience set the tone for everything that followed. It taught me resilience early on. Rejection became normal, and effort became the differentiator.
A second pivotal moment came much later, when I lost an online hotel broking business almost overnight due to currency movements. Sterling collapsed against the euro, and we had not hedged properly. What had been a very good business simply stopped working.
At that point, I already had Staysure, but it was very much secondary. The collapse of the hotel business forced me to focus entirely on insurance. In hindsight, that failure was one of the most important moments of my career.
What was your first taste of success in business?
If you mean success in business generally, then as early as 1986 I earned £100,000 in a single year selling burglar alarms, commission only. That was a big moment for me, and it proved what was possible if you kept showing up.
If you mean my first sizeable business, it was an early Groupon-style company in the mid-1990s. We ran two discount card propositions. One focused on restaurants, called Good Life, and another on nightlife, free entry to clubs, half-price drinks, that sort of thing. The business turned over £3.5 million with very high gross margins. I was about 30 at the time.
I would not say sales came effortlessly, but I was obsessed with improving. I studied people like Zig Ziglar and Tom Hopkins and applied what I learned relentlessly. Even at 17 or 18, canvassing for double glazing, I realised I had more determination than most people around me. I simply stayed out longer and tried harder.
Did this business have legs, or did it end up on the learning side of the mental balance sheet?
It absolutely had legs, but I made a critical strategic mistake.
Our main route to market was selling cards at train stations and other major venues around the country. It was scalable, profitable, and the venue hire was a variable cost. Staffing cost around £2,000 a week per location and worked brilliantly because you could turn it on and off with demand.
I decided to open retail stores instead, moving from variable to fixed costs. At the same time, the internet was starting to emerge, and I began negotiating a deal to sell access to our youth customer base to a new internet service provider (ISP) launching to target that market.
The deal was agreed in principle, £1 million in publicly listed shares and a CEO role. At contract stage they tried to reduce the consideration, so I pulled out. Unfortunately, during that period I had taken my eye off daily trading. With high fixed costs, that loss of focus was fatal. The business closed.
Ironically, the shares I walked away from went up around 400% the following year, although the company ultimately failed as well. The lesson was permanent. Fixed costs magnify mistakes, and focus is everything.
When did you realise that entrepreneurial success was not a one way street?
I do not think I ever believed entrepreneurship was easy. Most genuine entrepreneurs will tell you it is hard graft.
My first real business was satellite TV, which I started at 22, selling dishes and receivers door to door. We turned over around £1 million in the first year. What I did not understand was profit and loss.
I treated cash in the bank as my own money and spent it, cars, houses, clothes. It was the classic mistake of spending revenue rather than profit. The business failed through poor cash management, not because the idea was wrong.
It was painful, but essential. After that, I became far more disciplined in how I thought about growth.
Was it onwards and upwards from then on, or did life throw some further lessons your way?
There were plenty more lessons.
Most of the businesses I tried actually worked, but they were undercapitalised. I did not properly understand accounts, and strangely, it never occurred to me that I could raise outside investment. Even Staysure started with less than £20,000 and had no external capital until 2024.
Looking back, I am convinced I would have succeeded much earlier with either a better understanding of financial management or access to capital.
That said, for just over 20 years now, since the inception of Staysure, it has been largely onwards and upwards. The setbacks sharpened the edge, and the discipline became an advantage.
What types of businesses have you been involved with over the years, and how did you decide which ventures to pursue?
Satellite TV, fitted kitchens, discount cards, golf holidays, two-for-one golf vouchers, hotel broking, insurance.
Early on, I was always looking for a unique angle. Over time, I realised you do not always need to invent something new. Sometimes it is better to take an existing model and re-engineer it, so it works better for customers and for the unit economics.
One thing I strongly believe is the importance of cash-flow-positive businesses. If you can get paid before you pay suppliers, you can fund growth without outside investment. But that only works if your metrics are sharp and you understand the drivers.
Today, my core focus is travel, insurance, and sport, particularly golf through the Legends Tour.
What would you say has been your most successful business venture so far, and why did it stand out?
Staysure, without question.
I would estimate the business is valued at £1 billion plus today. We were the first to put medical conditions front and centre of the proposition and take that message to television. We then built deep pricing and analytics capability to ensure we charged appropriately for risk.
That combination, clarity of proposition and data at scale, created a commanding market position. It would be extremely difficult to replicate from scratch today, not least because the market is far more mature and the cost of customer acquisition has changed.
I am proud of what we have built, but I am also aware it came from understanding a need that had been ignored for too long.
You made the bold decision to relocate from Sheffield to Dubai. What inspired that move, and how has the experience been?
I actually left Sheffield at 20, moving to Northampton. I left the UK entirely in 2004 to live in Gibraltar and Spain, and only moved to Dubai in 2022.
Dubai works for several reasons. The tax system is clearly advantageous, but beyond that there is a strong growth mindset, excellent infrastructure, and a genuinely global outlook. I also run a tech and shared-services business in Sri Lanka employing around 400 people. Being four hours away makes a big difference.
Add good weather, great golf, and a lot of energy, and it is an easy place to be productive. I now split my time roughly four to five months in Dubai, three to four in the UK, and three to four in Spain.
What would it take for you to run your business empire from the UK?
The UK does not seem to recognise that it is competing globally. Starting a business there can feel like starting a football match five goals down.
Tax compounds just like investment fees. Over time, small differences become enormous. In the UK, 70% to 80% of value can disappear through taxation in one form or another. Compare that to Dubai. Zero income tax, zero capital gains, and 9% corporate tax.
Counter-intuitively, higher taxes often lead to less total tax being collected because growth slows. Until that mindset changes, the UK will struggle to attract and retain entrepreneurial capital.
That is why I commissioned the Centre for Economics and Business Research (CEBR) to model a practical alternative. The idea is simple. Give founders the option to pay a £5,000 flat fee in return for a 10% capital gains tax (CGT) rate when they ultimately sell their business. CEBR's modelling suggested this could generate around £640 million for the Treasury in the first year, building towards an additional £4 billion a year by year five, driven by increased business creation and productivity gains.
For me, that is the direction of travel. If the UK created a more competitive, founder-friendly tax environment that rewards long-term commitment, risk taking and growth, it would be far easier to justify running everything from the UK.
Outside of your professional life, do you have hobbies or interests that help you unwind and stay balanced?
Golf is my main hobby. When I play, it is like meditation. I think of nothing other than the shot in front of me, and that mental switch is valuable when your head is full of business problems.
For many years I put golf aside to focus on building businesses. Now I have integrated it into my professional life through the Legends Tour. But personally, it remains my way of switching off completely.
I have learnt that rest is not a luxury. If you want to perform at a high level, you need something that clears your mind and resets your energy.
What trends or industries excite you most right now, and are you planning to explore any of them?
I am building three main ecosystems, insurance, travel, and golf, all running on a shared technology stack I am branding as 28.ai. The aim is to run businesses end-to-end using modern technology and AI, while keeping the customer experience simple.
I am particularly passionate about helping entrepreneurs start and scale faster, avoiding the mistakes I made. It is a shame that real business and money are not taught properly in schools, because the basics are learnable.
I did recently look seriously at acquiring Sheffield Wednesday with my friend Simon Jordan. Ultimately, the capital required to stabilise the club without future penalties exceeded what I felt it was worth. A shame, it would have been a fascinating journey, but it has to make sense as an asset as well as a passion.
What advice do you give to aspiring entrepreneurs balancing personal passions and business goals?
I put my golf clubs down for 20 years, so balance is not easy.
My core advice would be:
- Know your cockpit. If you do not understand your numbers, you are flying blind.
- Make sure the margin is there. You need enough headroom to acquire customers profitably at scale.
- Find a niche you can win in, then build properly.
Stay focused. This is still my hardest challenge.
Finally, AI is a massive leveller. You can now disrupt huge businesses with a fraction of the cost they incurred. Become competent in AI, or you will be disrupted by someone who is.
