Aged 22, Simon Dolan was close to rock bottom. On the dole for 15 months, he was drowning in debt and living off credit cards.

In desperation he spent his last £10 on an advert in the local paper offering to do cheap accounting for small businesses, having worked in an accountants office for 18 months.

Three weeks later he got a phone call from a local florist, and SJD Accountancy was born. In 2014 he sold the firm for a nine-figure sum.

Now 51, Simon owns a huge business empire in areas as diverse as accountancy, PR and aviation, including The PHA Group, Oneserve, Jota Aviation, BajaBoard, COAST Autonomous, Jota Sport and Snag Tights.

Last year he launched a legal battle over the legality of lockdown.

What was the first memory of having any money in your pocket?

I had a paper round at the local hospital when I was about 12. I earned £3 for my first shift and it took me all morning to complete the round. I think I realised at that point the special feeling and personal rewards of earning your own money. That said, I still can’t stand the smell of hospitals to this day.

What did you spend it on?

David Bowie records. That’s where most of my money went. I think of money as a tool. You convert it into something you like.

When you left school at 16 did you ever think you would be financially successful?

I never gave it much thought, to be honest. I suppose the pertinent thing is that I never thought I wouldn’t be finally successful.

What financial advice would you have given to the younger you?

There is no easy way to earn money. My parents taught me that if you want money, you have to earn it. From age 10 I was pushed to be self-sufficient. I’ve tried hard to instil this mentality in my own children.

You lived off credit cards at 22 – is credit ever advisable?

Yes of course, provided you can afford it at the time, and also, crucially, even if you lose your job. I am not like my parents who were of the generation that believed you should save up for something you wanted to buy, instead of getting into debt.

The first thing I did after I turned 18 was get a £2,000 bank loan to buy music equipment. I have never had any qualms about borrowing money to buy something and I don’t mind being in debt – but I make sure I can pay back whatever I borrow.

That said, it’s not really advisable to take out loans on depreciating assets.

What was your big break financially?

That £10 turned into £200m over the years, so it would be difficult to top that.

Age 22 I was living hand-to-mouth on £40 a week and I had racked up debt out of necessity. I was unemployed with a £200-a-month mortgage and I had to buy food.

I was desperate, so I went to a newsagents near where I lived in a grotty part of Manchester, and asked the owner if he had any paper rounds.

He asked: ‘For your son?’ I said: ‘No, for me.’ He said: ‘No, sorry.’ That was a pivotal moment. Straight afterwards I had the idea to put an ad in a local newspaper offering to do end-of-year accounts for people.

What happened next?

A client phoned three weeks later and I did her accounts. That meant I could place another ad, which got another client. Spending £10 on that advert in 1992 was the best money decision I ever made.

It was how my business SJD Accountancy was born. Twenty-two years later I sold it for more than £100million.

I guess that’s when you knew you were financially secure for life?

I don’t. The world can change in a heartbeat, 2020 is testament to that.

Being worth £200million, how do you interact with that much money?

You simply live life. It’s not something you think about. What you probably appreciate above all else is the freedom it gives you – to travel and to experience new things.

Do figures like that seem like something you can understand in your head?

Yes, I have always been good with numbers, but it doesn’t feel like anything. It’s relative. Most Western people are infinitely richer than billions who live in impoverished countries but I’m sure they don’t spend time thinking about it.

Are you still careful with your money?

Probably more so now, ironically. It’s about choosing things that bring value to your life. The days of buying trinkets are, I think, gone for me. I’m careful how I invest money, how I look after it.

Most extravagant purchase?

David Bowie’s Balinese mansion in Mustique. It’s probably the purchase that brings me most joy.

What do you regret buying?

I don’t do regrets. I’m of the mindset that whatever happens in the past makes you the person you are today. If I was pushed, though, investing in Contracts For Difference in 1999 wasn’t a good move. I lost £100,000.

What would you do if you only had a tenner left in your pocket now?

Panic. It took me a long time to get where I am today. I’d rather not start again from scratch.

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