You’ll Never Beat the Bookie
Over the last twenty-five years I have had the great pleasure of working with some fantastic people, who became incredible entrepreneurs.
As someone genuinely interested in people, and developing authentic relationships over the long term, the fact that I was getting direct access to such a unique community of people through my work is something I have always been grateful for.
The really interesting thing for me being I have gotten exposure to people who have built incredible businesses across a range of sectors including retail, finance, technology, real estate, hospitality, healthcare, farming, renewables and many more.
As I reflect, considering the huge numbers of people I have had the pleasure of working with over the years, I often get asked who was the sharpest mind, best kind of entrepreneur I came across throughout my career?
For me, and this is my own personal experience, I would say the business minds I have had the pleasure of working with that stood out the most came from the bookmaking industry.
I have worked with quite a number of families who have built great bookmaking businesses over the years, and for me, the people involved always seemed to have an edge and a unique approach to business / decision making, which struck a chord with me.
The reason I say this is quite simple – the bookie is always the guy who will figure out the risk profile on any opportunity the quickest. There’s a saying I often say when describing such people: “they can hear the grass grow.”
As we all know, the economy ebbs and flows and is cyclical in nature, but another observation I would make on people in business is although the best entrepreneurs keep an eye on what’s happening across the economy, and events that sit external to them and their businesses, it often will not deter them in pushing on and executing their business plans.
When I left a very successful Commercial Real Estate Practice in Belfast in 2010, after ten years, and set up our debt restructuring business (GDP), little did I know at the time that over the next five years I would engage in work which I felt captured the subject matter and skillsets which was often the missing part of so many business people’s armour, when talking about the complete entrepreneur.
This all prompted this week’s article, where I would now like to set out, in my own experience, the five traits and characteristics that I feel make a brilliant entrepreneur.
What Makes a Brilliant Entrepreneur?
Five Traits That Separate the Best from the Rest
Every week I speak to business owners across Northern Ireland and further afield. Some are scaling fast. Some are stuck. Some are close to going bust. Some are bust and getting ready to go again. Some have brilliant ideas, real energy, and genuine talent — but they’re going nowhere – fast.
The difference almost always comes down to the same handful of things.
After years working in the business and finance industry, I want to share with you what I believe to be five characteristics that every brilliant entrepreneur must master. Get this right, and you give yourself a real chance. Ignore them, and even the best idea/business in the world might not go very far.
Let’s start with the one most people leave until last — and shouldn’t.
1. They Understand Money — and Know How to Fundraise. They are FINANCE ENGINEERS
This is the big one. And it’s the one most entrepreneurs neglect.
A brilliant idea without capital is just a hobby. Ambition without financial literacy is just noise. I’ve seen genuinely talented business owners fail — not because their product / service was poor / wrong, not because the market wasn’t there — but because they ran out of road financially. They didn’t raise enough capital, or possibly didn’t know how to. They raised at the wrong time. They structured it badly and paid the price later.
Brilliant entrepreneurs understand their numbers deeply. Not just revenue and profit, but cash flow, cost of capital, debt structure, and what their business is worth, at any given moment. They know the difference between a good loan and an expensive one. They understand when to bootstrap, when to borrow, and when to bring in outside investment. They know the difference between debt and equity. Two very different elements of money.
Finance isn’t a back-office function for these kinds of people — it’s a strategic weapon. The ability to raise capital at the right time, on the right terms, is what allows great business owners to move fast when opportunity knocks. It’s what keeps you alive when the market turns. It’s what funds the next hire, the next location, the next phase of growth.
If you’re serious about building something significant, get close to your numbers. Understand your funding options. Build relationships with lenders and advisors before you need them. The entrepreneurs who treat finance as a core skill — not an afterthought — are the ones still standing when others have folded.
2. Relentless Resourcefulness
Great entrepreneurs don’t wait for perfect conditions. They find a way with what they have and move forward.
They treat constraints as creative fuel, not excuses. When one door closes, they move on quite quickly to the next door, and repeat. This isn’t blind optimism — it’s a practical, steely determination to keep moving regardless of what’s in the way.
The best business builders I know have all faced moments where it looked like it was game over. What separated them from those who quit was a refusal to accept that there was no solution — just solutions they hadn’t found yet. They ask lots of questions and often have access to people who will know the answer. This can be the difference between failing and succeeding.
3. A High Tolerance for Uncertainty
Most people are wired to seek certainty before they act. Entrepreneurs don’t have that luxury — and the brilliant ones I’ve had the pleasure of working with have made peace with that.
The ability to make decisive calls without all the information is a genuine superpower. Brilliant entrepreneurs are semi-comfortable living in the grey. They weigh the evidence, back their judgement, and move. They don’t freeze waiting for a green light that never comes. They are often more patient and can deal with the pain and anxiety that comes with the territory.
This isn’t recklessness — it’s calibrated confidence. They know they’ll be wrong sometimes. They plan for it, learn from it, and move on quickly. Again, they have access to people smarter than them who know the answers they don’t. This allows them to become a lot more tolerant, in the face of challenge or adversity.
4. Obsessive Customer Focus
The best entrepreneurs are almost annoyingly focused on the people they serve. “The Customer is always right.”
I remember selling a building in Belfast over 20 years ago, which is now a 5-star hotel and owned by one of the City’s best known hospitality entrepreneurs. When I was showing this guy the building, walking through what was the old Ulster Bank at the time, I recall him telling me how important it was for him and his staff to have an almost obsessive approach to customer satisfaction. It hit home and never left me.
The best entrepreneurs listen more than they talk. They solve real problems rather than imagined ones. They understand that every great business is ultimately built on trust earned one customer/client at a time — and that reputation, once lost, is the hardest thing to rebuild.
Customer obsession isn’t a marketing tactic. It’s a mindset that shapes every decision, from product development to how you handle a complaint on a bad day.
5. The Ability to Sell — We are all in Sales…
If you can’t sell, you can’t build.
Brilliant entrepreneurs, I mean the truly brilliant ones, understand that selling isn’t just for the sales team. They are constantly selling — their vision to family, friends, investors and partners, their culture to the people they want to hire, their product to customers, their credibility to the market.
The best of them don’t feel like they’re selling at all. They’re so clear on the value they create, so genuinely convinced by what they’re building, that conviction does the work for them. That kind of authentic belief is magnetic — and it’s almost impossible to fake.
The fascinating thing I find about humans is that so many people don’t understand that we are effectively all salespeople. We are all selling something, regardless of whether you think you are or you’re not. Teachers, doctors, joiners, retail assistants, every one of us, from the moment we leave the house are in the sales business. The best entrepreneurs know all of this of course, and have mastered the art of selling.
The Bottom Line
Starting your own business and then building that up to something of meaning and success is one of the hardest things a person can choose to do. It demands courage, resilience, and a set of skills that no classroom or university fully prepares you for.
There is one thing reaching success in business, but it’s another thing to maintain this success over the long term.
What I have tried to do in this piece is share with you some of the traits I have seen in the flesh - literally, and in my experience, if you master them, will allow you to push on and achieve long term success.
The best of the best stay close to their customers, they act with conviction, they find a way when others give up — and above all, they treat the financial side of their business as seriously as the creative side.
That last point, as I have said, is where most people fall short. And it’s where the gap between a good business and a great one is often found.
If you want to talk about funding your next stage of growth in your own business, get in touch with me.
Until next week, look after yourself.
All the best,
Conor