113: Entrepreneurs in Recovery with Jesse Harless113: Entrepreneurs in Recovery with Jesse Harless
You're Sober! Now What?
Tamar Medford talks with Jesse Harless about his journey from trauma, addiction and legal trouble to long-term recovery, authorship and entrepreneur-focused facilitation. The conversation highlights cold showers, holistic support and a strong sense of purpose as central themes for people sober and ready to build something new.
46:43•5 Jul 2021
From Cold Showers to Calling: Jesse Harless on Entrepreneurs in Recovery
Episode Overview
- Recovery can begin through court-ordered structures but grow into a self-directed, purpose-led life.
- Holistic support from counsellors, mentors, employers and 12-step communities can reduce the need for incarceration and deepen healing.
- Cold showers, combined with focused breathing and gratitude, may help ease anxiety and build daily resilience for some people.
- Writing out one’s story and sharing it publicly can be a powerful therapeutic tool and inspire others in recovery.
- Many people in recovery are high-achieving by nature; directing that intensity toward meaningful goals can turn past pain into purposeful work.
“A lot of us live halfway. We don't go the whole way. We live halfway.”
How do people find strength in their journey to sobriety? This conversation between host Tamar Medford and guest Jesse Harless spotlights recovery as a starting point for purpose, not a finish line. A long-time facilitator and resilience coach, Jesse talks openly about childhood trauma, losing his father to addiction-related brain injury, and the spiral into internet gaming, pornography, alcohol, opioids and cocaine that led to federal felonies and court-ordered recovery.
Readers get a clear sense of the episode’s style: honest, conversational and practical, with plenty of humour and real-life detail. Tamar and Jesse swap stories about being "overachievers" in addiction and in business, showing how the same intensity that once chased a drug can later drive recovery, entrepreneurship and service to others.
Jesse explains how a judge, an understanding employer, a skilled counsellor and a pastor formed a holistic support system that helped him stay out of prison and build a new life. One standout section focuses on Jesse’s first book, *Smash Your Comfort Zone with Cold Showers*. He shares how straight cold showers reduced his long-standing anxiety and became a daily mindfulness practice: he uses deep breathing, gratitude and present-moment focus under icy water to centre himself for the day ahead.
His second book, *If Not You, Then Who?*, grew out of a decade-long urge to tell his full story and offer a framework built around the acronym FEARS. This episode will appeal to people in recovery who feel restless, driven or "meant for more", especially those curious about entrepreneurship. It’s geared toward anyone who wants examples of turning grit into growth, mixing 12-step foundations with coaching, mindfulness and purpose-focused work.
By the end, you’ll be asking yourself Jesse’s favourite question: if not you, then who will use your experience for good?
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