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Jimmy Bennett: From Homeless to A Successful Entrepreneur



Jimmy Bennett
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Jimmy Bennett’s life is like a rollercoaster ride, with dizzying highs, and crushing lows. From homeless to successful entrepreneur, author, and speaker in less than a decade, Jimmy’s story humbly begins in the classroom where, at the age of 15, he’d already been completely dismissed as a lost cause.

Early Life

After dropping out of high school at 15, Jimmy bounced from dead-end job to dead-end job. Between selling narcotics and working for £4/$5 an hour at Domino’s Pizza (less than the minimum wage), things looked bleak.

Indoctrinated with a disbelief mindset through many years in the UK school system, his perceived academic shortcomings ultimately culminated in ending up homeless.

“To me, sleeping on a park bench for months on end only confirmed what I’d been told throughout my teenage years – that I was destined for failure. The holes in the pair of jeans I’d worn for three months straight were a clear visual representation of what was inside myself. I’ve had more dead-end jobs than most people I know… I’ve certainly learned what success was not!” Jimmy relays. “At the time, I had no idea why failure was a habit/result that followed me everywhere. I’d never completed anything successfully in my life.

“By the age of 24, I had lived in 7 different cities, lived out of a suitcase for the majority, and had totally exhausted all of my friend’s good graces to be able to couch surf. I was given the opportunity to live in my uncle’s garage, and I zealously took up his offer. In honesty, I am grateful and attribute much of my success to my exposure to so many different cultures and characters, so many of which left a mark on me as a person.”

A major turning point came when a close friend, one on his own journey of self-discovery, related how knowledge was power. The decision soon followed to cast off others’ doubts, enroll in a local college, and therefore return to education.

Jimmy Bennett’s Interview

Most stories would perhaps amicably end here. And yet Jimmy recalls three mentors that influenced him to do more, to be more, after such a difficult period.

“I’ll be honest, my local basketball coach Kevin Robbins was the only person who kept me on some sort of path. He was the only authority figure in my life I actually respected, and no matter how many times he told me to get a grip on my life, I felt that he respected me too.

“Two that also stand out for me are Chichester College’s athletic tutor Matt Wright, and music teacher Aldith Smith; they were really the first teachers who saw my potential and helped me to believe in myself.”

Yet Jimmy’s life has not been plain sailing since this; he would encounter many adversities, including being declared bankrupt and diagnosed with a chronic, incurable disease, to name just a couple of the hurdles he has overcome, of which his new book release goes into more detail.

Today is a far cry from his days of darkness. Jimmy now runs a successful financial services consultancy, a thriving foreign exchange trading team, has been a speaker at many events, and has been sharing his story to inspire those who also have had little or no support. Jimmy is also a soon-to-be-published author with his first book being released early next year titled “0 to 100”.

Within himself is now a desire to give back everything he has learned. Jimmy runs a charity called Mentors for Minors, created after the realization that he was far from being alone in having experienced a lack of good mentors in his life. His aim is now to ensure that he can have a positive impact on those who need someone supportive in their life.

“A place for those young people who are in the shoes I was once in, Mentors for Minors focuses primarily on providing advice and guidance to those who have none. I also want to do everything I can for the homeless and vulnerable, and so I always do things throughout the year to help these communities.”

In times of hardship, he’s always recalled Winston Churchill’s famous quote: “Success is going from failure to failure without losing enthusiasm.”

“My power comes from my mindset and what I’ve overcome. Self-belief and a positive mentality don’t always come easy to everyone, but with the right mentor’s people can turn their lives around from a position of hopelessness and go on to achieve their potential,” Jimmy concludes.