Jacob Hill: Hiring People with Criminal Convictions | Episode 179Jacob Hill: Hiring People with Criminal Convictions | Episode 179
Brain Shaman
Jacob Hill shares how debt, drugs and a prison sentence led him to create Offploy, a social enterprise helping people with criminal convictions into work. The conversation challenges stereotypes about crime and highlights the value and loyalty that can emerge when people are given a genuine second chance.
1:05:54•22 Jul 2026
Second Chances at Work: Jacob Hill on Crime, Desperation and Hiring Ex‑Prisoners
Episode Overview
- Crime often stems from desperation, poverty and unaddressed mental health issues rather than inherent "evil".
- Labels like "ex‑prisoner" can trap people in shame and low expectations; focusing on character and circumstances offers a fairer view.
- Prison can reveal strong values and skills, and people with convictions frequently show high loyalty and long‑term retention when hired.
- Employers should assess the risk of the role first, then the individual, and use structured questions to understand context, change and motivation.
- Meaningful goals beyond a pay cheque, such as reconnecting with family or repaying a "debt to society", can drive powerful, sustained change.
“I thought I'd find evil and horrible people in prison... but the majority are just looking for some direction in life, some hope, a new opportunity.”
How do different strategies aid in addiction recovery and life after a criminal conviction? This conversation on Brain Shaman brings together Jacob Hill’s raw honesty and Michael Waite’s curiosity to unpack crime, desperation, mental health and second chances at work. Jacob shares how a seemingly "wonderful upbringing" and early entrepreneurial success collapsed into debt, drugs and eventually a 28‑month prison sentence. He openly admits, "I wanted to be the best at drug dealing...
I was just desperate to succeed at something," while pointing to poverty, mental health and desperation as common drivers behind many offences. Inside prison, Jacob’s assumptions shattered. Instead of monsters, he found "incredible human nature" and people full of kindness, ambition and regret.
The story of Ralph, a fellow prisoner who obsessively checked every pair of boxer shorts they sewed because "this is your first set of clean, dry clothes" and a defect might break someone on their first night, becomes a powerful example of unseen value behind the label "ex‑prisoner".
From this experience Jacob founded Offploy, a UK social enterprise helping people with criminal convictions into work and advising employers on culture, policies and risk so they can safely hire this often overlooked talent pool. He argues that the real issue is less criminal records and more desperation and self-belief, stressing that people with convictions often have higher loyalty and retention once given a genuine chance.
The episode suits anyone curious about addiction, crime, stigma and practical routes to rehabilitation, especially employers wondering whether to hire someone with a record. You’ll hear how labels shape behaviour, why "we need to address that bit first" when someone assumes they’ll fail, and how meaningful goals like reconnecting with children or repaying a "debt to society" can drive lasting change.
It leaves you asking: what labels are you putting on yourself or others, and how might loosening them unlock unexpected potential?
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