Duane Jackson

Published: 06/02/2019

From a beneficiary of the Prince’s Trust to a patron of the charity, Duane Jackson transformed his life after serving time in prison. He’s using his success as an entrepreneur to help other inmates turn their life around.

Serving a prison sentence for drug trafficking, Duane Jackson had an epiphany: “It suddenly dawned on me that I was inside because of actions I had taken, largely without giving much thought to them,” he explains.

How it started

Duane was determined not to end up in the same situation as other offenders he’d met. His partner was expecting a baby and he wanted to be there: “I didn't have kids or any family around [when I started my sentence], but there were plenty of other guys who did. I saw they had pictures of their kids on the wall, and I was thankful that I wasn't that guy, I wasn’t missing my children growing up. When I was released, my girlfriend fell pregnant and I realised that if I did go down that path, I would be that guy. That was a big motivation.”

Naturally good with computers, Duane trained as a web developer. Finding the existing accountancy packages clunky, he designed his own. Support from the Prince’s Trust helped him create KashFlow, a web application for managing the accounts of small businesses. He sold it to IRIS in 2013 – for a rumoured £20 million.

In 2015, Duane developed Supdate, a tool he originally created to enable him to share company news and metrics with KashFlow shareholders: it sold to Crowdcube in September 2018.

How it’s going

Duane became a Patron of the Prince’s Trust and works with Code 4000, helping to give ex-offenders career opportunities after prison. He knows they lack options, and many wouldn’t naturally consider entrepreneurship or programming.

There are those that fit the cliché of what you think prisoners will be like, but others have a lot of potential. Code 4000 teaches inmates to programme, with the aim that they’ll work for industry employers on release. My hope is that they’ll eventually start their own businesses.”

Inevitably, starting out as an entrepreneur had its challenges. Duane says that whenever he started to lose hope, he’d focus on small achievements. “When I was building KashFlow, I would get that feeling that I wouldn’t be able to take it any further,” he says. “I eventually recognised that it was a state of mind that passes. The way I dealt with it was by picking a relatively short-term task. I’d choose something I knew I could affect, get my head down, and focus on that. When you start achieving on that short-term thing, you start to feel more positive.”

Lessons learnt

The biggest lesson Duane has learnt from the business world is the importance of people: a really good business comes from the right team.

Duane says he doesn’t focus on wanting to change the past, because it brought him to where he is now; he’s interested in what you can change today. He says that if he could offer advice to somebody in a similar position to him at age nineteen, he’d encourage them to have a plan.

“I speak to lots of people who have a goal: for example, somebody I know told me he’s going to be a millionaire by the time he’s thirty. I asked him, how are you going to get the first £50k? £100k? £250k? It’s always going to be a dream unless you work out the steps.

With the sale of Supdate in 2018, Duane moved back into the world of accounting to fill a gap he’s spotted in the market. He then successfully launched Staffology, a SaaS Payroll application with a comprehensive API. In 2021 Duane sold Staffology to IRIS, one of the UK’s largest software companies, of which Duane became a Senior Technical Director.

The best thing about success, Duane says, is the luxury of choosing your work. He never loses sight of how much his life has changed. In May 2018, Duane attended Prince Charles’ 70th birthday party at Buckingham Palace – a far cry from Camp Hill prison. “Whenever we pull up outside our house after being away,” he says, “I think ‘Wow, how did we end up here?’”