‘I was staring at 25 years in a US prison. Then I went straight and made millions’

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Unlike many businessmen, entrepreneurship did not come naturally to him.

“You hear these stories of people selling multipack Mars Bars for profit when they’re at school, but that was just never me,” he explains. “Even in prison, the guards were always annoyed with me because my cell was the last to close at night, because people were always coming to me asking to borrow my CDs. I could have charged them for it but didn’t, because it just didn’t occur to me. I did have a strong internal drive though, I really don’t need other people to tell me that I’ve done well.”

On his release, Mr Jackson reconnected with the Prince’s Trust, who helped him start up shop as a one-man web developer. He soon changed tack and began developing software for sale.

“I had a baby daughter on the way and I was determined to properly support her and my then-girlfriend, who’s now my wife. I realised it was a better idea to sell a product than to sell my time, so I changed my focus and created some of the first invoicing software,” he says.

In 2013, Mr Jackson sold his first business for £20m. He now rubs shoulders with the likes of Elon Musk, and has met the King on several occasions. He still works closely with the Prince’s Trust, of which he is now a patron. But his most crucial connection has been Lord David Young, former trade and business secretary to Margaret Thatcher.

“Through the Prince’s Trust I met Lord Young, who became my mentor and my sounding board, as well as the chairman of that first company,” Mr Jackson said. 

“Tech investor Michael Jackson reached out a few years in and asked if we could chat, so I went and met him. He said that he wanted to buy my business for a million pounds, and I laughed at him – and then I realised he was being serious. I told him that it wasn’t for sale – he said, ‘of course it is, I’ll give you two million’.”

Lord Young offered Mr Jackson a £100,000 loan to be paid back when, or if, the business was sold. 

“In 2011 I met Natie Kirsh, the South African billionaire, who bought some shares from me for a million in cash – so I didn’t even have to wait until I’d exited to make my first million,” says Mr Jackson.

“It’s one thing having a business that’s worth that much on paper, and another thing altogether to actually see it in your bank account,” says Mr Jackson. “It was surreal, but the main thing for me was the security that it gave me. I’ve always moved about a lot. When I was younger living in children’s homes, and then again in prison, most of my belongings had to fit in a bin liner so that I could move them at a moment’s notice. Being in a position to buy a home outright was the big thing for me.”

Mr Jackson has made sure to hire people who have been to prison, a decision that has given his business an edge, he says. “I’ve hired a lot of ex-cons. Stereotypes are there for a reason – plenty of us do get out of prison and go on to reoffend. But the people who get out of prison and decide to go straight, like I did, are the most honest folk that you will meet. Accounting software isn’t exactly exciting, so that does set us apart from our competitors.

“On the other hand, we’ve lost some deals because of my background, so it does cut both ways,” he adds.

Did Mr Jackson’s experience smuggling drugs across continents give him a head start in the world of above-board business? “I was either very brave or very stupid,” he admits.

“People are always telling me that I have a lack of fear. When you end up in a maximum security American prison as a nineteen-year-old-boy from England, it certainly doesn’t get much scarier than that – so since then I’ve always thought, what’s the worst that could happen?”

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