1 Duane Jackson
Duane Jackson describes himself as “having grown up with the wrong crowd” in East London care homes. In his early years he struggled to escape the trouble his upbringing exposed him to – being expelled twice by the time he reached school-leaving age.
His record only got worse after leaving school. At only 19 he was arrested for attempting to smuggle class A drugs into the US. He recently wrote about the arrest in his blog post My Night with the DEA and 6,500 ecstasy tablets.
But even before his arrest Jackson was learning the skills that would later bring him success. Social workers who were responsible for his education introduced him to computer coding and he took to it instantly – first on a ZX Spectrum.
He also used these skills in prison; he taught fellow prisoners IT skills and started work as a web designer. In 2006, four years after leaving prison, he started his business KashFlow, a system aimed at simplifying accounting methods for those who struggled with the more complex aspects.
With the help of The Prince’s Trust and Lord Young his business was a great success. He eventually sold the business to IRIS in 2013 in a very lucrative deal and is currently a patron of The Prince’s Trust.
2 Mark Wahlberg
Now Mark Wahlberg is one of Hollywood’s best-loved actors – famed for playing loveable if slightly wayward characters. But away from the screen he is also a prodigious entrepreneur and investor. In 2013 he made an equity investment in the Barbados Trident cricket team, declaring himself “a huge cricket fan”.
His burger chain Wahlburgers is also huge in the US. But his past, in which he seemed to be a pretty unsavoury individual, has not been completely left behind.
Before finding fame Wahlberg was involved in low-level crime and gang activity in his hometown of Boston.
One particularly unpleasant incident saw him, along with his fellow gang members, racially abuse and attack a Vietnamese man. He was sentenced to two years in prison for his part in the incident.
Recently he asked for a pardon so that he could obtain a licence to sell alcohol, something his criminal record won’t allow him to do.
So, however successful you become in film or entertainment, it’s a salutary warning that you can never completely outrun a criminal past.
3 Derek Jones
Back in 2003 Derek Jones was languishing in a Winchester prison. A life of petty crime meant he had been in and out of institutions for most of his adult life. But now in his thirties, things were about to turn around.
His idea was very much the product of his surroundings. He was frustrated about the lack of available email access for himself and other prisoners, so decided to do something about it.
Under the premise, people wishing to email prisoners set up an account and were charged 30p per email (prisoners were not charged).
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His pilot scheme was a great success and when he was released he sought to turn it into a scaleable business. At first he struggled for funding due to his criminal record, but many 12 hour shifts washing dishes and some sheer bloody-mindedness allowed him to get the business off the ground.
It was adopted across the UK and latterly in Holland. He has since sold the business for a very tidy profit and is doing pretty well for himself as director of SALT Academy.
4 Ryan Blair
ViSalus CEO Ryan Blair had one of the hardest starts to life of any on this list as his abusive father was a long-term user of crystal meth.
He was involved in criminal and gang activity as early as 13 and had been arrested several times by the age of 16.
But Blair refused to succumb to his fate and turned his fortunes around in quite spectacular fashion. He started his first business, 24/7 Tech, at the age of 21 and has since gone from strength to strength.
He has been the CEO of ViSalus for a decade now. In 2010 he won the DSN Global Turn Around Award for turning a $6m debt to a $150 turnover in a year and a half.
For long-term entrepreneurship and executive success from less than auspicious beginnings, Blair is pretty hard to beat.
5 Jay Z
Jay Z’s music streaming business Tidal may not be setting the world alight, but the world’s most famous rapper has plenty of more successful business interests.
From buying Scandinavian streaming service Aspiro for $56 million to acquiring world-renowned champagne brand Armand de Brignac, his business portfolio is varied and very lucrative.
But before his music or business mogul activities took off, he was engaged in much more legally dubious activities. Dealing crack and allegedly stabbing rivals is not a great way to get your entrepreneurial career off the ground: but as we’ve seen with all five of these characters, it’s never too late to turn it around in business.
Further reading: My first year as an entrepreneur