You may know Simon for his famous street interviews asking people 'Would you ever start a business of your own?'. His videos have had over 1 billion views on social media. Simon has spent the last 30 years as an entrepreneur. He started his first company when he was homeless at 15-years-old, and he sold his last company Fluid to PwC.  His life imploded when he was 15 years old. His father died in front of him and after a fall out with his mother, he left home and was penniless, jobless and forced to sleep in a stairwell. But today Simon is the founder of the world's first Help2Earn platform - HelpBnk - which helps people learn how to start and scale a business for free. He has also invested in over 70 startups in the last 15 years. In this episode we talk about how he turned his life around from sleeping on the streets, how luck played an important part in his success story and why he thinks retirement is bullshit.