Business Law & Compliance

6 entrepreneurs who shook off criminal records to dominate the business world

15 min read

26 October 2015

Former deputy editor

Certain professions, which we won't name, are often dubbed criminals and crooks. But what about those who find themselves on the wrong side of the law then into a profession? We've highlighted six recognisable individuals who have turned around their situations for the better to dominate the business world.

1986-founded rap group N.W.A witnessed a new lease of life this year with the arrival of Straight Outta Compton, a film adaption based on the crew’s struggle of growing up in the crime-riddled Californian city.

The members, which included Dr. Dre and Ice Cube, were often caught up with police clashes as the Los Angeles area was condemned for police brutality and racial discrimination.

Of course, Dr. Dre and Ice Cube have transitioned to become huge success stories. Indeed, the former had the last laugh when his Beats Electronics business was acquired by Apple for $3bn in May 2014.

As such, we’ve looked at six other individuals who defied their shaky beginnings and run-ins with the law to become leaders in their fields, and we start by continuing on the theme of rap with…


1. Jay-Z

Today, people around the world know Jay-Z, real name Shawn Carter, as a successful millionaire rapper and businessman in his own right – as well as the husband of the equally successful Beyonce.

However, he hasn’t always been such a law-abiding family man.

In fact, years ago, Carter was somebody you’d have wanted to avoid on a dark night.

Growing up in New York’s Brooklyn, Carter had a rough childhood and witnessed a murder at the age of nine, a father abandoning the home at 11 and at 13 he’d become a crack dealer.

Speaking to Oprah in an interview, he said of his old neighbourhood: “Navigating this place was life-or-death.” The rapper added that the streets taught him loyalty because breaking your word to someone would result in you being dealt with personally – not in a court of law.

And speaking of law, Carter’s life of crime went beyond narcotics as he admitted to stabbing a music executive in 1999 – by which time he’d already secured rap fame.

These days, Carter is much more respectable. In September 2015, Carter ranked number two on the Hip Hop Cash Kings list, having brought in $56m this year alone.

This was generated from a combination of shows with his wife, summer launch of streaming business Tidal alongside other celebrity faces, and the acquisition of premium champagne brand Armand de Brignac in late 2014.

Image source

Read more on the crossover between celebrities and business:


2. Bill Gates

Taking down the violence a notch, we have billionaire tech genius Bill Gates.

These days, the man responsible for Microsoft uses his presence and $79.2bn wealth to spread philanthropic wisdom across the globe.

One of the most notable moves he made this year saw him champion a new process that purifies waste into drinking water and call upon entrepreneurs to seize the opportunity.

“I think it could be a great fit in India, where there are lots of entrepreneurs who could own and operate the processors, as well as companies with the skill to manufacture many of the parts,” he said.

But back in 1975, when the businessman was aged 19, he was arrested for speeding – and driving without a licence.

Interestingly, it’s also the same year that Microsoft was founded and it’s reported that the shaggy-haired boy racer had enough to pay for his own bail at this point. 

He was arrested two years later in 1977 for a similar offence and is said to have been seen speeding around in his Porsche on a regular basis.

Fortunately for Gates, should he be caught speeding, when he isn’t busy talking about poo-based beverages, he can probably just bribe the law enforcer and speed off into the sunset.

Meanwhile, there’s a theory that suggests Gates used the outline of his mugshot for the photo outline featured on Microsoft applications.

Continue reading on the next page for the Hollywood A-lister that left his violent streak behind for Tinseltown and a growing burger empire, and a man who made it onto the FBI’s Most Wanted list.

3. Kevin Mitnick

Making it onto the FBI’s Most Wanted list is quite an accomplishment – and that’s exactly what happened to Kevin Mitnick after a series of cyber crimes.

Remarkably, however, he has turned his life around to become a security consultant to firms in the Fortune 500 and governments across the globe.

It was aged 16 in 1979 when Mitnick made his first foray into cheating the system when he found a way to travel across his native city of Los Angeles on the bus network.

The same year he went on to hack into a computer network and stole software, which resulted in his imprisonment for a year in 1988 and then supervised release, but during the latter he hacked once again and went on the run as a fugitive for two and a half years.

In 1995, the FBI finally caught up with the outlaw and in 1999 he was sentenced to five years in prison for his fraudulent hacking activities involving 40 organisations, but he had developed a following of fans over this period of incarceration.

Today, Mitnick can be found running Mitnick Security alongside his “Global Ghost Team”. The firm boasts a 100 per cent success rate of breaking into any system they’re paid to infiltrate. On the other side, the security chief also teaches consumers how to protect their information from harm.


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4. Mark Wahlberg

It could have all gone so wrong for Boston boy Mark Wahlberg, who today is worth around $225m while his 2015 earnings reached $32m.

Aged 14, Wahlberg – the youngest of nine children – started to skip school in favour of the streets where he would steal and sell drugs. At one stage he found himself caught in a lawsuit accusing him of hurling racial slurs and rocks at other youths.

Things escalated wildly when he was jailed at 16 for the “savage beating” of a Vietnamese man who was left blind, in what was believed to be a racially motivated assault.

The 45 days he spent in prison gave him clarity and he started to focus by working out and now claims to be a devout Irish Catholic, calling religion “the most important part of my life”.

Following his older brother into the music world gave Wahlberg to shake off his past, while his “charisma” led him into the world of film.

Showcasing entrepreneurial spirit, the actor started to produced Entourage, which has achieved great success, as has Boardwalk Empire – another of his productions.

More recently, Wahlberg got into the food industry with his family. The initial Wahlburgers venue opened in Boston in 2011 and commenting on the company’s growth this year, he said: “I’m the driving force behind the business aspect of it, and I don’t think they’re used to their little brother telling them, ‘Well, this is how we’ve got to do things.’ But we’re in a good place now.”

“We have almost 70 restaurants under contract right now, with various franchisees and deals in different places. I think we will have nine or 10 open by the end of the year in places like Fenway Park in Boston and airports in Philly and New York. 

“We’re opening in Coney Island, Long Island, the D.C. area, Las Vegas — and we’re looking for locations in L.A. We also just made a deal in the Middle East for 20 restaurants.”

Continue reading on the next page to discover the MBE-awarded young entrepreneur who got arrested at school for a furniture-based attack, and the man who had his conning exploits transformed into a Hollywood film.

5. Jamal Edwards

Looking at 25-year-old SBTV founder Jamal Edwards today, a man awarded an MBE at Buckingham Palace, and you’d have no idea he was arrested as a teenager.

Having grown up on an estate in Acton, West London, Edwards had a trouble-free upbringing – something his mother saw to.

However, an altercation at school resulted in his arrest. A play fight saw a student spray deodorant into Edwards’ face, which prompted him to retaliate – by grabbing a nearby chair and smashing it into the toiletry-wielder’s face.

“The next thing I knew, a police car pulled up in the playground and I was being arrested and taken away,” he said.

Edwards was stripped, forced to sit in a cell, and had to ring his mum to explain what had happened, which he claimed was a wake-up call.

He revealed: “That was the point when I realised I didn’t want this to be me. Mum was so upset; I could tell she was really disappointed.”

The only was up after that and after Edwards received a videocamera for Christmas when he was 15, the concept for entertainment business SBTV, which is highlighted as the platform that jumpstarted the career of Ed Sheeran, was born.

He would record local rappers and then upload the videos onto YouTube, which was just one-year-old at the time, in a bid to challenge MTV.

“It was a frustration of going to school and everyone talking about: ‘How do we get our videos on MTV?,” he recalled.

“Everyone was looking at me like, ‘What are you doing, like you can compete with these major corporations’ but I think I was early enough to believe that I could make a change.”

Edwards is now worth an estimated £8m, counts Richard Branson as a pal and was named an MBE this year.


6. Frank W. Abagnale

Frank Abagnale has advised and worked with hundreds of financial institutions, corporations and government agencies globally, and is considered a respected authority forgery, embezzlement and secure documents.

That’s because he used to be responsible for forgery, embezzlement and penetration of secure documents.

In fact, his status as a world-famous conman was depicted by none other than film royal Leonardo DiCaprio in Hollywood movie Catch Me If You Can, which also starred Tom Hanks and was directed by Steven Spielberg.

It was adapted from Abagnale’s best-selling book of the same name, which has also been transformed into a broadway musical.

During his time on the wrong side of the law, Abagnale impersonated an airline pilot, doctor and assistant attorney general, and cashed in fraudulent cheques worth more than $2.5m.

His scamming days came to a close when he was just 21, having been caught by the French police, while international exploits meant time in prisons across France, Switzerland and the US.

A deal was struck after five years and freedom was granted to Abagnale on the condition he would aid the federal government by teaching and assisting law enforcement agencies – without pay.

Abagnale has now had his programmes used by more than 14,000 corporations and he works as a lecturer and consultant.

According to his company website, it “does not sell products or provide services with the exception of his public speaking engagements which are handled through Keppler Speakers in Washington, DC”.