Ep324: Defying the Odds With Extraordinary Couple Shelley Winner and Jeramia Dupre

Hi, I’m Jules
I’m Jules, founder of Unconventional Life, born from a dream after a near-death experience seven years ago. As a 2x TEDx speaker, global event host, multi-millionaire entrepreneur, and artist, I’m passionate about guiding you to unleash your soul’s greatest gifts. Together with my two sisters, I’ve expanded UL’s mission by co-creating Pink Lemon Agency, a creative marketing agency designed to help bring bold visions to life.
Follow Me
Blog Categories
Ep324:Shelley Winner and Jeramia Dupre

Recidivism (noun) – The tendency of a convicted individual to re-offend.

According to current statistics, 76% of people released from prison will re-offend and return to prison.

Shelley Winner and Jeramia Dupre both grew up in less than ideal environments – their parents had problems with drug use and addiction. It didn’t take long for them to fall into the same pattern. Jeramia is currently 43 and has spent 17 years locked up in some capacity, and another 5 to 6 years on probation. Being in prison gave them access to rehabilitative programs, which they utilized greatly. It was the catalyst for the reversal of their mindset.

We don’t know what we don’t know, and that makes education crucial. Shelley and Jeramia spent their days serving time finishing programs. Discovering a new way of life through these programs shifted their mindset and gave their self-esteem, confidence, and motivation a huge boost.

It wasn’t a drastic change by any means – neither did it happen overnight. The transformation happened after a series of decisions, no matter how insignificant they seemed to be at the time. Deciding to choose the positive option and ignoring the temptation of falling back into negative behaviors worked as those micro-steps started adding up for the couple. Taking in the whole picture has been overwhelming at times, but ultimately, what worked was breaking down the goal into little steps, which made the whole process more digestible and attainable.

Getting out of prison was another challenge, as it is for the majority of people with negative records. They were both aware that the odds of being employed were not in their favor. Formerly incarcerated individuals are systemically kept from getting good jobs.

Shelley was a spiritual person, so she prayed for a very specific thing – she wanted a career in tech. At the halfway house, she saw a commercial from Code Tenderloin and instantly signed up. She finished the program but encountered a hiccup when Microsoft rescinded her job offer due to a flagged background check.

She had nothing to lose and everything to gain.  Shelley fought for her job at Microsoft. San Francisco had a Fair Chance ordinance that advocates for anti-discrimination of formerly incarcerated individuals. The ordinance has never fought an entity as big as Microsoft, but they proceeded to take Shelley’s case and ended up winning. That was the beginning of Shelley’s very interesting journey at the tech giant.

Despite all the setbacks and roadblocks, they powered through and kept their ground. Shelley and Jeramia defied all odds stacked against them and are now doing really well, living their best life. Jeramia is successfully running his own construction business, and Shelley is the #1 Microsoft B2B Surface Sales Rep in the world! They continue to advocate for formerly incarcerated people by volunteering their time and spreading the word about their cause. If you are moved by this story and are called to participate, check out these organizations that they highly recommend:

This week’s generous giveaway is an opportunity to volunteer in prison with Shelley and Jeramia for a day! If that is not generous enough, Shelley and Jeramia are subsidizing the airfare for any giveaway winner who is not currently residing in California. Volunteering will not only benefit the prisoners but is also an experience guaranteed to expand your perspective.

More from Shelley and Jeramia: