Elliot Castro was 16 and selling mobile phones from a Glasgow call centre when he first conned someone out of their bank details.
Soon he was enjoying a champagne lifestyle, that included first class flights and luxury watches.
The teenager would go on to mastermind the theft of £2.5m from an audacious series of scams before finally brought to justice in a department store toilet in Edinburgh.
Castro, who now works as a fraud prevention expert, shared his remarkable story in a new BBC Scotland documentary, Confessions of a Teenager Fraudster.
It chronicles his rapid rise from leaving school with no qualifications to spending $1,000 (£786) on a bottle of champagne for friends in a New York bar.
Castro, now 42, recalls the first time he conned a customer after they called in with an order.
Instead of putting the order through as normal he pretended there was a problem with the credit card and then proceeded to dupe them into thinking he had their bank on the line.
Seconds later he had their details and a scam was born.
He recalled: "I don't remember having that Eureka moment, if you like.
"It was just something that I did one time and I thought 'I wonder if I can do this?'"
Castro's spending was modest to begin with but, like his offending, it rapidly escalated.
He told BBC Radio Scotland's Mornings programme: "That was the beginning of five years of absolute craziness from the time I was 16 up until 21, 22.
"The first time I ever got hold of a card it was CDs and haircuts and t-shirts at that point.
"There was no hint of how mental it would get later on."
The fraudster was born in Aberdeen in 1982 and attended eight different schools before he moved to Glasgow with his family in 1998.
He described himself as a dreamer and admitted lying on the application for his call centre job and said he was 18 instead of 16.
Castro, who is half Chilean, said: "I had it in my head that I would just have this amazing lifestyle."
His criminal career eventually bankrolled exclusive holidays, five-star hotels, lavish parties and limousines.
During one trip to London in 1999 Castro bought a Gucci belt for £300 - which he said was more than he earned in a week in the call centre.
The Home Alone fan later splashed more than £8,000 on a first class flight to New York, where he stayed in the Plaza Hotel, which features in the celebrated movie.
His trip featured a three-day $15,000 (£11,791) spending spree on the city's exclusive Fifth Avenue.
Castro admitted: "A general day in my life at that time was wake-up, go shopping, buy things, go drinking, go back to whatever hotel I was staying in that night, sleep, wake up the next day and repeat.
"But all of this time I had to be aware that I was possibly being followed or that someone would be looking to catch me."
In 2001 he enjoyed trips to Germany, France and Spain.
The following year he spent time in Ireland, where he stayed at The Clarence Hotel in Dublin and claimed he rubbed shoulders with U2 stars.
Castro said: "It's a hotel owned by Bono and the Edge and we had a conversation one night in the bar where I told them I was working for the Ministry of Defence or a hotel consultant."
The con man had several brushes with the law, dating back to 2001 when he spent four months in a young offenders' institute in Lancaster.
Months later he was arrested at the Balmoral Hotel in Edinburgh and taken to Manchester, where he was sentenced to 18 months at HMP Hindley.
During this time he got a job in the prison library and read up about the internet.
This research led him to use internet cafes on his release to make anonymous flight bookings with stolen credit cards.
In 2002 he was arrested in Toronto and jailed for 87 days before being deported in 2003.
His international crime spree eventually came to an end in the Harvey Nichols department store in Edinburgh the following year.
Castro said: "I was beginning to feel done with it, I'd started for the first time in my life to make friends.
"But the downside was I couldn't tell them who I really was.
"The situation became unbearable.
"So I do wonder, was there a subconscious part of me that wanted to give it up?"
That day he bought £2,000 of vouchers with a card that wasn't in his name.
The receptionist called the card company, who approved the transaction.
But, acting on a hunch, she called them back.
He said: "They got in touch with the real card holder who verified it was fraudulent and stupidly I came back to the shop less than an hour later and that's the moment it ended.
"I went to the toilet quickly and when I opened the cubicle door there was a plain clothes police officer there and that was the beginning of the end."
The following year at Isleworth Crown Court in Middlesex, Castro admitted fraud offences amounting to more than £73,000 and was sentenced to two years.
Castro admits he benefited from a lack of co-operation between law enforcement agencies and card companies.
He said: "Through the five years, if they'd had better communication then they might have managed to stop me quicker."
Today he is a different man, full of regret over the misery he caused and keen not to glamourise theft.
He is also helping to stop sophisticated scams and catch credit card fraudsters.
Castro said: "When I started doing this I never actually thought of people.
"I never met these people. That doesn't make it right.
"What I understood about the way credit cards worked at the time was that if the cardholder hadn't authorised the transactions - which in my case they didn't - then they wouldn't lose anything financially."
More than 20 years on, he feels he is making amends for his actions as a teenager and a young man.
He said: "I'm not making excuses, but it is a very, very long time ago and I like to think since then I've made reparations.
"Fortunately I'm in a position now that I'm working with financial institutions, travel companies and businesses.
"I'm fortunate and lucky to be known as a trusted advisor in the industry now, which is great.
"It's been an interesting journey."
Confessions of a Teenage Fraudster is available on BBC iPlayer.
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