Behind the Wheel Life

From prison to owning supercars and... a boat - with Jason Cunningham


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A multi business owner and serial entrepreneur, Jason started working at 14 doing a paper round earning a whopping £5.50 for delivering 180 papers, before working at ASDA stacking shelves and manning the checkouts. 

As life progressed, Jason started a career in double glazing and sales, and at the age of 19 he was the number 1 branch manager in the company out of 88 branches. Life was good. Being so young and earning good money, Jason took his first step into buying sports cars. First came the Porsche at 20, followed by a Ferrari 360 spider at the age of 21… BUT in 2008,  the recession hit hard. The company he was working for went bust and Jason was out of a job. He had no option but to go bankrupt. For the next few years he worked within double glazing before moving on to solar panels. Solar panels was a time in his life he regrets, and it ended badly. He was prosecuted and sent to prison for a short time.

Jason walked out of prison with £110 to his name and no idea what he wanted to do, knowing that he was no longer employable to any business. He was lucky enough that he had bought a Rolex in the past so off to the pawn shop he went, sold it and started to buy and sell second hand cars. Jason did that successfully for 6/7 months but it wasn't going to give him the life he wanted. 

So 2017 Jason researched property and that’s what he decided he was going to do. He bought a business in a box estate agency and set off on his journey in property. Running an estate agent started well but it again just didn’t produce the income he wanted. He started looking at different property strategies, rent to rent, service accommodation, HMOs, property developments and many others, and Jason soon built a property and business empire. And the rest is history!

A real rags to riches, to rags again and then riches story, at just 33 Jason genuinely believes there is nothing in life he hasn’t been through and fought tooth and nail through, including, struggling at school being dyslexic,  marriage, kids, bankruptcy, divorce and prison.

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Behind the Wheel LifeBy Muhammad Haji