This feeling of indestructibility led to Mr Hill making poor choices, which led to mounting personal and business debt.
He was caught selling drugs at a music festival in an attempt to pay off his debts, and was sentenced to 28 months in prison.
But while serving 294 days of his sentence, the now 23-year-old had a turning point, which led to him launching Offploy – a HR company that looks to support large organisations with designing and implementing an ex-offender hiring strategy.
“We want to help large organisations through the ethical and legal minefield that is hiring ex-offenders,” says Mr Hill.
Speaking about his own path to offending, he said: “It all boils down to me thinking I was indestructible. Many have said that I rose too quickly.
“It was a form of empty success. I still believe I was untouchable and went completely against everything my parents stood for and I ended up selling drugs at a music festival.”
Before he ended up behind bars, Mr Hill says he never understood ex-offenders and how they came to offending in the first place.
He told The Yorkshire Post: “Both my parents are retired police officers. I was brought up with the idea that prisoners are bad people. That’s what was instilled into me.”
While in prison Mr Hill was sewing boxer shorts, when he got talking to a fellow inmate.
“I remember talking to one chap who was six foot tall and had a scar down his face. He was what you would call a typical ex-offender,” he said.
Mr Hill realised that this inmate wanted to get on in life but was never given an opportunity and that he suffered from low self-esteem.
Mr Hill said: “It was at this point that I realised that these guys want more. Re-offending is just as much a self-esteem issue as it is a lack opportunities issue.
“Many of these ex-offenders do have a low self-esteem. I’m not saying that you need pity every ex-offender, a lot of people are there because they deserve to be there.”
Mr Hill became a peer advisor with St Giles Trust and he ended up meeting prisoners from all sorts of backgrounds.
“You meet more and more ex-offenders and you realise they are not bad people. They are human beings. People who have made a mistake,” he said.
“This is why a big part of our business is taking CEOs on guided prison tours,” he added.
When he was released Mr Hill was faced with a situation that many ex-offenders face. He ended up on jobseekers allowance and while looking for a job was rejected at every turn. But then one investor took a chance on him and Offploy was born.
The 23-year-old said: “I was declaring my criminal conviction in a paragraph at the top of my CV because I wanted to be open.
“I wanted to send the message out that I’m a normal person who has made this mistake. I got rejected for all sorts of jobs. It came down to that one investor who believed in me.”
In his previous life Mr Hill was selling camping gear for festivals, but he is more at peace with himself with this venture.
He said: “I regret what I did and what it did to my family at the time. But at the end of the day it’s the best thing to ever happen to me. It has given me some direction in life. I’ve never had that before. Now I feel like I’m actually doing something which is useful to the world.”
Offploy has also already attracted investment for growth. Mr Hill has been awarded grant funding and support from charity UnLtd. He has also attracted investment and mentoring from Hull businessman Nigel Stabler.
Battle to overcome stigma
One of the things Jacob Hill, who is from Brighouse, wants to achieve with Offploy is remove the stigma attached to ex-offenders.
Mr Hill says many business leaders don’t know what an ex-offender is.
He said: “My advice to employers is to go to a prison. Meet and speak to ex-offenders. They’ll be pleasantly suprised.
“There’s a good group of ex-offenders that will jump at the opportunity.
“Look at Timpson, they have incredible retention rates with their ex-offenders because people are grateful for the opportunity.”