Simon Dolan: ‘In 1992 I spent £10 on the best financial decision I ever made’

The Government’s ‘overeaction’ to the pandemic made his airline company bankrupt, says Dolan – John Nguyen/JNVisuals

British businessman and investor Simon Dolan, 54, is the founder of JD Accountancy, which he sold for more than £82m in 2014 – the largest ever sale of a private accountancy firm. He went on to create a broad business portfolio encompassing everything from aviation and PR to autonomous vehicles and tights.

He has also been a champion kickboxer and recorded a class win at the 24 Hours of Le Mans in 2014. During the Covid pandemic he founded the Keep Britain Free campaign which took the Government to court over the lockdown regulations. He and his wife Sabrina, with whom he has two sons, own multiple properties around the world.

Dolan was the focus of film Journey To Le Mans which followed Jota Sport as they won the 2014 24 Hours of Le Mans – Danny Martindale/WireImage

Did you have a good financial start in life?

I had an ordinary middle-class upbringing. Dad was an accountant, Mum an occupational therapist. I grew up in a three-bed semi in Chelmsford in Essex. I did get a job quite young, however, which was probably the making of me. From the age of 14, I worked on a cheese and eggs stall at Chelmsford Market. My boss, who was only seven years older, made me realise that you didn’t need a business plan and an education to earn good money.

Didn’t you perform well at school then?

I was top of the class at primary school but when I reached grammar school I couldn’t see the point of Latin and ancient Greek, so I switched off. I was thrown out, aged 16, with virtually no qualifications.

What did you do next?

I did a Btec national diploma in business finance while continuing to work at the market. After flailing around in a band, my dad, knowing I was good with numbers, suggested I write to a couple of local accountancy firms. I got an interview and was offered a full-time job for £50 a week. I remember laughing because I thought it was a joke. I’d earned more at Chelmsford Market.

After 18 months they showed me the door because I demanded a pay rise. I tried various sales jobs, but was pulled over for drink-driving, 10 yards after getting into the car, and lost my driving licence. I was forced to sign on for 15 months and quickly racked up debts because I had a mortgage.

How bad did things get?

I got so desperate that I walked into a newsagent’s and asked if I could take on several paper rounds. The guy behind the counter said, “Is it for your son?” I said, “No, it’s for me,” and he just looked sad and shook his head.

Falling back on the only thing I knew, I placed an advert in a local newspaper offering to do end-of-year accounts from £99 a month. I got a call from a florist and it grew from there. Spending £10 on that advert in 1992 was the best financial decision I ever made.

How did you take the business to the next level? 

My big breakthrough came in 1996 when I moved to Hemel Hempstead in Hertfordshire with my then-girlfriend. I tried to place the same advert in the local press there but it didn’t work, so I decided to target one-man limited companies. I advertised in a computing magazine and got three clients within the first week. I quickly realised I’d hit on something.

Didn’t you create a virtual office to appear bigger than you were?

I needed more credibility, so I rented out a telephone number from a real estate company for £100 a month to make it appear as though I had a Mayfair address. The calls came through to my home phone. I also undercut my competitors by charging £35 a month rather than the standard £69. By the time I sold the business, I had 14,000 clients, around 180 staff and was making £1m profit a month.

Why did you become known as the ‘Twitter Dragon’

In 2010 I invited start-up companies to send me business pitches via Twitter. I don’t think I invested in any of them, but I was up for a ‘millionaire investor’ slot on the BBC show Dragons’ Den until they decided Hilary Devey was a better candidate. I was a white male and think that may not have fit their remit. That show has got no more to do with business than Big Brother has to do with normal relationships. It’s not how business works.

Why did you sell JD Accountancy?

I got an offer I didn’t want to refuse. Also, because of the niche I was in, there was the worry that government regulation would scupper the market – which it did three years later.

Is it true you’re worth £200m?

That’s not far off. I didn’t own any of those businesses that made ridiculous amounts during the pandemic. Neither was I involved in any that lost much, other than my airline company, Jota Aviation, which was made bankrupt by the Government’s handling of Covid. My planes were grounded and I lost £10m.

In 2014 Dolan made the largest ever sale of a private accountancy firm and is now known as the ‘Twitter dragon’ – Sam Pearce

Is that why you founded Keep Britain Free?

I can see why people might think that, but by the time we went to court the damage to my business was done. It was an ideological thing for me – the Government telling us not to leave our homes was a massive overreaction. Just look at inflation now. I launched the most successful legal crowdfunder ever to fund the proposed action – we raised £490,000 by the end. The court costs came to £790,000, so it cost me £300,000 of my own money. But the case went all the way to the Supreme Court.

What do you spend your money on?

I used to collect sports cars, but I sold the flashy ones for about a £4m profit. My other passion is guitars. My pride and joy is a guitar Mick Ronson played during David Bowie’s Ziggy Stardust years. I also own Noel Gallagher’s 57 Les Paul Standard.

How much property do you own?

Dolan’s chateau in south-west France is just one of his 10 properties – John Nguyen/JNVisuals

I own about 10 homes. Last year I bought casino billionaire Steve Wynn’s estate in Las Vegas, Nevada, for $17.5m (£14m). It’s by far the most beautiful house I’ve ever seen, but it’s back on the market because my business is now taking me to different places.

We also own a chateau in south-west France and David Bowie’s former home on Mustique in the Caribbean, which I bought for $18m from the publisher Felix Dennis. I’ve loved Bowie ever since I heard Space Oddity when I was 12. It’s a Balinese-inspired house on a hillside overlooking blue seas and white sands. It’s paradise.

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