How a drug smuggler who got caught with 6,500 Ecstasy pills went on to build a $30 million tech business

Duane Jackson, a 21-year-old from east London, arrived at Atlanta airport in 1999. Head down, he collected his suitcase from the conveyor belt and darted straight toward the “Nothing to Declare” lane.

“Step this way please,” a member of airport security interrupted, before Jackson had reached the anonymity of the arrival lounge.

After a close but inconsequential inspection of his suitcase, Jackson nervously nudged his shoulder bag behind him, hoping it would be ignored.

“And that one,” the officer snapped.

Jackson’s suitcase was clean, but inside his shoulder bag were 6,500 Ecstasy pills, hidden in a big bottle of talcum powder and a pair of gutted Walkman speakers.

As the airport security officer ripped open the talcum-powder bottle, hundreds of Ecstasy pills wrapped in cling film dropped out. The eruption of powder hid nothing: Jackson’s guilt was obvious.

“There was no cleverness to it at all,” Jackson told Business Insider, in the lounge of the Hilton Hotel near London Bridge, 17 years later.

In the years since he got arrested at Atlanta airport, Jackson has spent time locked up on both sides of the Atlantic as a convicted drug smuggler. On release, he built KashFlow, an online accountancy business The Guardian reported was sold in 2013 for around £20 million ($30 million.)

Now he is campaigning for prisoners to be encouraged to make use of their misused entrepreneurial urges on release. According to a new report from the Centre for Entrepreneurs, this could save the UK taxpayer £1.4 billion (about $2 billion) a year, through dramatically lowering recidivism rates.

We sat down with Jackson to ask more about his own incredible journey from convict with no qualifications to multimillionaire tech entrepreneur.

Jackson grew up in Newham, in the east end of London. From early on, family life was difficult.

Aged 11, he was separated from his mum and sent to a children’s home.

“It certainly wasn’t a loving environment, but nor was it an abusive environment. It was a safe environment I guess,” Jackson said, describing the home.

Jackson, who comes across calm and confident during the interview, admits that his time at children’s homes made him “emotionally detached.”

However, he thinks this may have helped him in the business world, comparing his own coolness to that of Bill Gates and British entrepreneur Sir Alan Sugar.

Jackson said his time at the home was “neutral.”

However, this description clearly hides real difficulties. He explained that he was kicked out of various schools before being left to spend his whole day with social workers at the children’s home.

This was a problem for the staff at the home, because they were legally obliged to make sure that children between ages 3 and 9, like Jackson, were “doing something classed as education.”

One day, aged 14, Jackson spotted an unopened ZX Spectrum computer lying in the corner.

Timidly, he asked if he could use it.

Staff at the home were pleased to let him do so: They were glad he was doing anything other than watching TV.

The teenager quickly became obsessed with the Spectrum, spending hours each day trawling through the manual that came with the computer, learning to code.

“The thing I loved about it was if the computer does something wrong, or not what you were expecting, there’s a very simple reason for it: You programmed it wrong. It was your fault,” Jackson explained.

“Whereas normally in my life, if someone had done something wrong or not what I expected, it could have been because they didn’t get laid last night. It could have been because they shouldn’t have been a social worker in the first place. It could have been because they think you’re an arrogant little s— that they don’t like. It could be for a million different reasons that I couldn’t decipher,” he said.

Jackson found reassurance in the logic and reliability of computer programming. However, his life was about to get a whole lot more chaotic.

On leaving the children’s home at 16, with no formal qualifications, Jackson moved into a flat in a council estate. Unlike the majority of his peers, he managed to find regular work as an office junior.

However, by the time Jackson was 18, he became “very short of cash,” resulting from a combination of high rent and “no financial-management skills.”

“In the east end, you don’t fall into crime, you grow up around it,” Jackson explained. “If you’re not committing some level of crime, whether it be drug dealing, or breaking into cars, then actually you’re the odd one out. So I was around crime all the time.”

One group of guys Jackson had grown up with in east London had built a profitable business of their own. It involved smuggling drugs by passenger plane to the US.

During the 1990s, rave culture on both sides of the Atlantic was booming, largely fueled by high-quality ecstasy, a lot of which came from European dealers.

Jackson was not involved initially, but then one of the mules dropped out from a deal last minute.

“Stupidly, I volunteered,” Jackson said. “It looked like a way to get some money. It paid the rent. I got a trip to the States out of it.”

Jackson’s first few trips to New York went without a hitch. As a result, he became overly confident, even “ridiculously blasé” about the job.

He enjoyed making the call back to London after a successful trip.

A coded “Hello mate, just to let you know, I’m in the States for a long weekend, so I’m not going to make the drink” became: “‘Yeah, job’s a good’un” after a few successful trips.

It was only when Jackson was caught out in Atlanta that the gravity of the crime dawned on him.

Though he was not a drug user himself — apart from “a bit of weed as a teenager” — Jackson was confident that MDMA was not as serious a drug as cocaine or heroin, because of its ubiquity in ’90s London.

“I genuinely thought that if I got caught it would be a slap on the wrists and that would be the end of it,” Jackson said.

However, when he was arrested, the US police officer explained that he was looking at 25 years behind bars and a $1 million fine.

Jackson spent a “bloody scary” two months in a US prison, which he described as his “lowest point.” Inside, he learned that “correcting black guys from Atlanta on Tupac lyrics doesn’t go down very well.”

Jackson was then transferred to the UK, where he was put on bail for one year, while police gathered evidence to take him and eight other members of the east London drug-smuggling syndicate to trial.

In his own words, Jackson “got off very lightly.” He was expecting to be sentenced 10 to 12 years in jail, but ended up with five. As a result of good behavior in prison, he was only inside for two and a half.

British prison, Jackson said, was much easier than Atlanta’s penitentiary: “It’s a much more controlled environment than it is in the US, where you get the feeling that it could blow up any minute.”

Inside a British prison based on the Isle of Wight, Jackson “showed off” by completing a computer course, which was meant to take many weeks, in just one morning. Soon after, the teacher became sick and Jackson was asked to take over teaching the course.

While inside, an ex-girlfriend from his teenage years got back in touch. The prison he finished his sentence in was “very open” and Nadia became pregnant while he was still incarcerated.

Behind bars, with hours of free time, Jackson began to reflect on his life choices.

“What I realized was I didn’t make a conscious decision to go into crime … it sounds very glib, but I realized I could be the master of my own destiny,” Jackson said.

“While I was in there I had always been grateful that I wasn’t one of the older guys I had seen with pictures of their kids on the wall, missing their kids grow up,” he said. “When I found out my girlfriend was pregnant, I realized that if I carried on down this route I would become that guy.”

So Jackson decided to go clean.

He was inspired during a talk by the Prince’s Trust — a charity led by Prince Charles — at Ford Prison about the type of aid that could be provided to ex-prisoners looking to start their own businesses. Entrepreneurship was not something Jackson had ever considered as an option because of his lack of education.

It wasn’t easy for Jackson to give up crime. While on bail before the trial, Jackson had slept with a woman called Amanda, who was the girlfriend of the boss of the drug-smuggling ring.

On release from prison two and a half years later, Jackson was given a choice: Get back involved with crime and get protection, or face the wrath of his violent boss, Dillon, who was known as “one of the top guys in east London.”

At first, out of fear, Jackson agreed to carry on doing “dodgy stuff.”

Then, aware of the young family around him, he changed his mind: Jackson refused to do more crime, hoping to face up to boss and move on.

“He’s not going to kill me, so just face up to it. Get it out of the way,” Jackson reasoned.

The next day he got a call from a mutual acquaintance. “You’re the luckiest guy I’ve ever met,” the man said. “Dillon dropped down dead last night from a brain tumor, out of nowhere.”

Now in the clear, Jackson moved to Essex with his wife and baby. With the help of the Prince’s Trust, he began his own one-man computer-programming business, charging clients by the hour.

He was doing OK and making enough money to feed his young family. However, he struggled with managing accounts on top of a busy schedule.

The available software was “all incredibly difficult,” Jackson said. “So I decided to write something myself. Being a web developer, it made sense to create a folder on my web server and stick the code and develop it there, rather than on the desktop.”

Soon, other small businesses began asking if they could borrow Jackson’s software, suggesting small changes and new features as they used it.

“It took a good six months, maybe a year, for me to realize that actually my focus should be on monetizing this as a product for other businesses rather than selling my time by the hour,” he said.

KashFlow was born in 2005.

The major competitor in account-management software at the time was Sage.

“We ended up getting into some big PR wars with Sage, who were a big player, and that really is what set us up. It gave us a lot more exposure than we would have otherwise had,” Jackson said.

Kashflow was a web application, while Sage produced desktop software. Sage described web applications as “a fad that will pass,” according to Jackson. “So we took the opportunity to say: ‘This is the future and we will eat Sage’s lunch.'”

Jackson’s eyes lit up as he reminisced about one of the more memorable PR stunts he had used against the much larger software company.

He had released a statement that said: “Send us your copy of Sage and we’ll give you Kashflow free for a year and build a bonfire out of all the boxes of Sage we’re going to get.”

As Jackson’s success grew, Lord Young of Graffham, an enterprise adviser to British Prime Minister David Cameron and former trade secretary to former British Prime Minister Margaret Thatcher, became a substantial investor in KashFlow and even chairman of its board.

It took eight years of “all-absorbing, all-consuming” work before Jackson eventually sold to payroll company IRIS in 2013.

Jackson is contractually obliged not to reveal the exact figure, but The Guardian reported the sale price as close to £20 million ($30 million).

Now Jackson lives with his wife and three daughters in a large house by the coast in Brighton, England.

In-between “chilling out” and baking banana bread, Jackson has founded another company, Supdate — software designed to make sending shareholder updates simpler.

Jackson hopes his example can be a lesson to prisoners and policymakers alike.

Working with The Centre for Entrepreneurs (CFE) and The Prince’s Trust, Jackson is campaigning for prisons to run more entrepreneurship courses.

“I think you’ve got a lot of natural entrepreneurs in prison, especially those from the drug-dealing side of things because there are a lot of parallels … If they use these skills for good rather than evil, these guys are well placed to be good entrepreneurs,” he said.

According to a report from CFE, the “large scale introduction of prison entrepreneurship programs” could save the UK government “up to £1.4 billion (around $2 billion) per year.”

This is calculated based on the effects of such programmes on a small scale on prisoner recidivism rates.

We spoke to Maximilian Yoshioka, the lead researcher behind the report to find out why this is a good idea.

“From a practical perspective, it makes sense that prisoners will be doing things in prison that will give them a greater likelihood of supporting themselves when they’re out,” Yoshioka said.

Ethically, the scheme is viable because “prison in itself is a punishment because of the deprivation of liberty” and therefore it is unjust to make prison a deliberately unpleasant, cruel place.

Jackson was happy to admit that trajectory of life had been satisfying to experience.

“I wouldn’t change anything,” Jackson said. “It’s kind of like Jenga. If you remove one piece — the time I spent in prison, or any of it — the whole thing comes tumbling down, and I wouldn’t be where I am now.”

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