There was a time when Welsh businessman Rob Lloyd had so much money coming in, he didn't give a second thought to: "How much fuel I was going to put in the Bentley?" or "How much the chauffeur had been paid that year?".

As one of the richest men in Wales, with a net annual salary of around £350,000, and many millions more sitting in his bank account, Rob was revelling in having "all the trappings of success".

It was 2006, he'd floated his property firm Eatonfield Group, which he'd built from nothing, on the stock exchange and the best estimates put his worth at circa £37 million.

As Rob says himself, "it was happy days".

Read more: At home with the Welsh entrepreneur who flopped on The Apprentice but now runs a £16m business and drives a Ferrari

He spent £6 million on creating a racing yard and another £2 million on horses, not to mention buying up a couple of farms too. The now 57-year-old, who lives in Rhos on Sea, Conwy, even starred in Channel 4's hit show The Secret Millionaire in 2009.

But by July 2011, the Cheshire-born tycoon was reported to have up to £26 million of debts following the property market collapse. He was also ripped off by a conman in the Bahamas, who stole thousands from him through a dodgy deal, around the same time.

Then in 2017, there was the "ill-advised" appearance on The Real Housewives of Cheshire alongside Ester Dee, his then partner with whom he had a daughter. He doesn't want to dwell on that rather farcical situation, which saw Ester reveal that as well as being engaged to Rob, she was married to millionaire John Temple.

And in 2020 he was given the bombshell news he had cancer after a series of nosebleeds since running the London Marathon.

"I had the chauffeur-driven Bentley, the Range Rover, all the fancy type of things," Rob said without a trace of bitterness.

"And you think it's never going to stop. Everything I touched, I was just making money. You just think it's going to get better and better and better."

Rob Lloyd

In its final year, he reckons he got the profits of Eatonfield to around £7 million. But for all his seemingly magic ability to turn dilapidated property into cash, not even Rob foresaw what was just around the corner: the 2008 recession, or what he calls "the worst depression for 80 years".

For Rob, who's empire was built on retail property around the UK, it spelled disaster.

Ironically, as the banking crisis took hold, Rob was at a roadshow in the city trying to raise more money from investors.

"We were looking to raise another £50 million to expand because we were just doing so well," he explained. "And it was the second or third day of the roadshow. I got a call from our broker. He said: 'We may as well pull it, the markets are in freefall'.

"Taylor Wimpey shares had crashed, Barrett shares had crashed. It was just in complete turmoil. Unless you were actually within the industry itself, you'd never have believed how share prices were just collapsing. And banks didn't know what to do. They were falling off a cliff. And it just went from bad to worse."

The Eatonfield board admitted that the company had been in severe financial difficulty since the summer of 2008, when the construction sector began to feel the impact of the credit crunch. By 2011, it was unsalvageable and the company went into liquidation.

For Rob himself, despite desperate attempts to buy back his company, it meant he lost everything: the racing yard had to be sold off, the horses went, the farms too. His second marriage failed and he wound up living in a caravan in a field with a bank balance with just one zero rather than six.

"It really brings everything into perspective," said Rob.

"From one minute, you've got all the toys, all the race meetings, and you're flying here, flying there. You're just living the five-star treatment and then, all of a sudden, it hits you.

"For just over a year I was living in the caravan and for that first year it was grim, cold and damp. The second year wasn't much better.

"But then I had started doing the odd deal. That's the good thing with property. You can make and lose money. One decent property deal can get you back to where you need to be. And then you just start building it back again."

Rob Lloyd in The Secret Millionaire

For all his ambition and motivation to make money, Rob is incredibly grounded and matter of fact. There's a sense that it's not really about the money at all, but rather a drive to succeed.

His "wheeler-dealer" mentality is something he's always had, ever since he was a kid, he said. In turn, that was driven by the fact he was brought up on a dairy farm in Cheshire where his father struggled to send him to Rydal boarding school in Colwyn Bay.

"It was hard for him to pay the school fees," Rob admitted. "And I suppose I was around a lot of pupils whose families had a lot of money. They were quite well off and they arrived in their fancy cars when they got dropped off at school. I suppose that gave me quite a bit of drive and ambition.

"I liked to earn a shilling as I call it - wheel and deal, buy and sell type of thing. As a kid I was particularly good at marbles. So I used to win all these marbles and then sell them back to the pupils at school. So that was the start of it."

But as Rob finished school, having failed his O-level English six times, his dad, who had just 20 cows, was forced to sell up. Rob had a public school education under his belt and was on his own.

"My father said: 'Look, it's down to you now; there's nothing there where you can step into a family business or anything like that'.

"I've always been interested in property. So it went from there."

Despite pressure from his dad to get a university degree, Rob had little interest: "Because I was at boarding school for so long, I'd had enough of the education system," he said. "I just really had the appetite to earn money."

He did attempt university, heading to Reading to do a course at its college of estate management, but he only stuck it for a year. He said: "I just didn't like it at all. I just wanted to get into making money I suppose."

After a spell working for a surveyor in Oxfordshire, he moved back north to work for Grimley and Son chartered surveyors. He did mainly lettings on big office buildings and retail units. Acting for some quite large clients Rob saw what young entrepreneurs were doing and fancied giving it a go himself.

"I wanted to get on the other side of the fence and do it in my own right," he said. "My first deal when I started Eatonfield was in Cardigan and I bought Canolfan Teifi, a four-storey development right in the town centre which I bought off the receivers. I paid £175,000 for it and a year later I sold it for £800,000.

"So I think that was a start of the taste of making money."

Businessman Rob Lloyd was once one of the richest men in Wales

He snapped up more property in Cardigan including the showground field and the abandoned Woolworths unit in the town centre. After building up his portfolio he sold it all for £4.5 million, having only paid £500,00 in total.

"I made a huge profit on that," said Rob, admitting that a lot of his success was simply getting the timing right. "So that was the start of the wheeler dealer adding value to sites approach."

He was in his late 30s and things all started coming together for him.

"We were buying from distressed sellers," he explained. "And that could have been private owners who just wanted to dump their piece of land or property, or we used to buy a lot of receivers at the time. Anything with an angle where we could add value.

"The philosophy was you bought something that day at the right money knowing you could exit it the next at a profit. That was always my philosophy - if you can't nick it, leave it type of expression. Having set up Eatonfield Group in 1998, he floated it on the London Stock market in 2006.

"It was a weird experience," he said. "I had so much money around me and so much money in the bank."

He added: "All the trappings of success gave me the ability that if the family wanted to go somewhere and stay somewhere on an expensive holiday, or going to London for a long weekend to stay in the best hotels or have the best meals, I knew we could do that. It wasn't a problem.

"I wasn't worried about how much fuel I was going to put in the Bentley or how much the chauffeur had been paid during that year. That just didn't bother me because it was a bit of a roller coaster. There was just money coming in.

"It happened quite quickly. I built it up it, floated it quickly. And then all of a sudden, you don't think it's going to stop, but then it does. You do think: 'Bloody hell if only I'd done this or done that differently'."

He does regret a particularly bad experience in the Bahamas. Perhaps wrapped up in the fact that he'd floated Eatonfield and had millions at his disposal, he bought what he thought was a government contract to build thousands of Bahamian properties.

"I spent about a million pounds thinking I bought this building plot fronting onto the ocean backing onto the golf course in Paradise Island," said Rob. "But the solicitor I used out there embezzled all the funds which was about £2 million at the time."

The solicitor was arrested and in a strange twist of fate, Rob has just had the trial date set for next August, 12 years later.

"Whether I get anything of it back I don't know," Rob said. "Going first class over to the Bahamas and having the office there - it was a lifestyle of luxury. And I was due to build a 14,000 square foot mansion. When I realised this guy had stolen all the money, that was an experience and a half.

"After the guy got arrested I just drew a line under it and came back and focused on the UK. And then in 2010 and 2011, it more or less went off the cliff."

Rob was forced to "literally start all over again".

He continued: "I went back to my roots trading, trying to do some wheeler dealer type deals and just get by. I had to sell the racing yard, sell the other farms as well. And just asset stripped everything to the point where I just had a base to work again.

"And that's what I've been doing for the last 10 years. It's been quite a journey but now things are good. We're in a good place, we're expanding like hell, I've got a good team around me and it's exciting times again."

Rob has spent the last decade building his company, Bearmont Group, which does a similar thing to what he did with Eatonfield. Much of his focus is on high street retail and he's snapped up a lot of the old Arcadia portfolio off the receivers like Dorothy Perkins and Burton's and more recently an M&CO building in Aberystwyth. There's also a house building department and a strategic land division where they assemble big chunks of land for mixed-use development including residential and commercial.

He's just sold a parcel of land for £3.5 million and the group is an "ambitious deal-led company".

Have his life experiences taught him anything or served to rein in the ambitions of this maverick businessman, I ask. He admits that age has made him a lot more cautious.

"I'm always looking at how I can get out of the deal," he said. "I don't want to be stuck with something that's going to bury me alive. I just kept chipping away. And 10 years later, I've got quite a healthy business."

He also admits to being quite an "open book" when it comes to talking about his business highs and lows. He means it in the literal sense, having written a book about his experiences, but also in the general sense.

"There's nothing to hide as far as I'm concerned," he said. "People are interested in how you've gone from humble beginnings, although admittedly I did go to public school. But with building a business from scratch, some people like to see how the journey has taken me and how I've made a lot of money over the years.

"There's no hidden agenda with me - you take me as you find me. You either like me as a person or you don't. I've always got on on the basis that in business you always leave a ladder that you can climb out of. Business can be quite difficult and deals don't go quite according to plan. I try not to fall out with people."

With three adult children from his first marriage, Rob has just married his third wife, Maria.

"She's been really good for me," he said. "I'm enjoying married life. I'm enjoying life generally and I'm enjoying the little one, my daughter, who's six now.

"For some reason in my head, I always wanted to be chief executive of a public company. I don't know why it was just something I wanted to do. One of my peers said: 'You'll never be able to do that Rob, you're good at school but you're not bright enough to lead a big company'. And when that was said to me, I thought I can do it. And nothing's impossible.

"The point is, if I can do it, anybody can do it. The only thing is I've got to try and do it all over again now."

It's not the only thing he's got to do though, because in 2019 Rob was diagnosed with cancer. Not only is he rebuilding his fortunes, he's also rebuilding his health. He's had to undergo gruelling chemotherapy and is still on medication for his lymphoma. He only went to the doctors after struggling around the 2019 London Marathon in seven hours. He kept getting nose bleeds and feeling rough afterwards.

Rob (left) has put his business activities on hold to raise money for charity Sense

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For now, his business activities have been put on hold to raise money for Sense, the charity he ran the marathon for.

"I really liked what they were about, helping the severely disabled," Rob said about his early research into what charity he wanted to run for. "You sometimes don't realise how lucky you are. They gave me a place for the London Marathon and I did it in seven hours, which was not normal for me. I thought maybe five hours because I've always been quite into sport.

"But at that time, I was getting a lot of nosebleeds so I knew something wasn't quite right. Straight after the marathon, I'd never experienced anything like it - I felt so ill. I went to get a blood test and within 24 hours, I was in the cancer unit and then diagnosed with lymphoma.

"I spent nine months there going through all the chemotherapy and it puts everything into perspective. You begin to think life is too short. The cancer that I've got is treatable but not curable. So I'm going to have it for the rest of my life.

"Fortunately, touch wood, I feel good at the moment. I can keep moving forward and forget that I've got it. That's not a bad way to be - to take every day as it comes and see it as just a normal day."

That philosophy on life has brought Rob round to a hare-brained idea of completing a year of daring and gruelling challenges to continue raising funds for Sense. He has already put himself through a terrifying skydive, tortuous training with the SAS and a marathon bike ride. He has spent the first 10 days of December doing a grand tour of Wales by running, cycling and walking 379 miles from Wrexham to Newport.

"I felt that I wanted to do something different," he said. "I was thinking about what fundraising challenge I could take on to support Sense, and then I thought, why not do a series of challenges? So that’s what I’m doing. Everyone thinks it’s a bit crazy, so I named it a 'Sense-less Challenge'."

So far this year, he's raised about £75,000.

The 57-yerar-old businessman flies by the seat of his pants in life as well as business

When it comes to bombshell news about business and health over the years, which was worse, I ask. Rob's answer is surprisingly philosophical.

"Both are similar but also different," he said.

"It gets to the point where, with having the cancer treatment, you just don't know what the outcome is because they won't give you the diagnosis. When you ask them: 'How long do you think I'm going to live?' the specialists won't tell you. It's treatable and I could still be around for a long time. I still have to go back and have the blood tests done every quarter.

"I think that's the unknown so it's a difficult one to quantify. With your health, you just don't know what's around the corner. I never thought I'd get cancer. I never thought I'd become really ill because I've always been healthy all my life. And then this thing happens and it puts a different light on it.

"With the business side, I think it's market forces. I built up the company, we were very successful, and then all of a sudden this depression hit. The problem was when the banks were in freefall, there's not a lot I could do about it. The market just stopped and it was out of control. You just have to try and get through the wave of it.

"It's difficult - you just keep your head down in the trenches, and keep battling and battling.

"I'll always remember before my father died I had a particularly difficult day at the plc when a board meeting didn't go well. I was a bit grumpy and moody and I came back home and moaned and he said: 'I tell you when you've had a really bad day is if you think about those soldiers in a trench with the ammunition being fired at them. And what some of these armed forces have to go through to protect this country. That's when you're having a bad day'.

"I've never forgotten that to this day. So I don't tend to have that many bad days now."

Find out more about Rob's Sense-less challenge here: https://justgiving.com/campaign/RobsChallenge.