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CASE STUDIES
John Jackson: Turning a Life Sentence Into a Second Chance
In this episode of Case Studies, Casey is joined by John Jackson; a former gang leader who rose through the ranks of one of the most powerful prison organizations before choosing a path of transformation. From maximum security yards to solitary confinement at Pelican Bay, John shares how trauma, prison politics, and the underground economy shaped his life—and how entrepreneurship helped him rewrite it.
He reveals how gangs inside prison operate like corporations, complete with hierarchies, rules, and revenue streams. John breaks down the incentives that drive violence and control, while also exposing the perverse economics of private prisons. His story shows how the same discipline and leadership that once sustained chaos can be redirected toward growth and purpose.
From orchestrating survival in solitary to joining an in-prison entrepreneurship program, John and Casey explore the pivotal moments that shifted his trajectory. This conversation offers a rare inside look at resilience, influence, and the possibility of change in even the harshest environments.
Chapters
00:00 | Welcome & setup
00:18 | Why this world feels “foreign”
00:42 | John’s origin story begins
01:03 | First encounter with law enforcement
01:20 | Taking the drug charge at 17
01:35 | Four armed robberies & max prison
02:21 | Siblings, loss, and isolation
03:14 | Environment vs. guardrails
05:40 | Probation, parole & stacked obstacles
06:20 | Private prisons & perverse incentives
08:10 | Cartels as local “employers”
09:11 | Crime’s inevitable endgame
10:14 | Why he took the fall
11:12 | Acceptance as a survival need
12:07 | Jail ecosystem: drugs, fights, status
13:04 | Race lines and prison structure
14:00 | Negotiation skills behind bars
16:10 | Cutting off family to “go all in”
17:10 | First robbery & the dangerous win
18:00 | Dopamine, risk, and escalation
19:23 | “I knew I’d thrive in prison”
20:13 | The cafeteria incident & mentor
21:07 | Sentencing math: stacking charges
22:02 | Centinela: max prison near the border
23:20 | Why jail can be more volatile
24:05 | Joining the largest prison gang
26:16 | Gangs as parent companies & franchises
26:40 | Smuggling supply chains (incl. dirty cops)
28:05 | Earning status: debts & discipline
29:06 | Prison entrepreneurship (gambling, alcohol, phones)
31:01 | Corporate politics—just higher stakes
31:26 | Power, money, and “don’t do politics”
33:08 | The written rulebook & paperwork checks
33:47 | Who’s excluded—and why
35:11 | Internal punishments & order
36:20 | 18 years inside: the ladder
37:01 | Pelican Bay & four years in the SHU
39:20 | Solitary reality vs. myths
41:27 | Transfers, levels, and riots
42:36 | Use of force: towers & rifles
43:06 | The peace treaty & hunger strikes
44:09 | “Yard time” myth in solitary
44:40 | Breaking point: wanting to go home
45:01 | New charges from inside
48:23 | Stepping down from leadership
49:14 | A lifer’s blessing to leave
50:09 | Entrepreneurship program that changed everything
51:25 | His future wife: VC to prison reform
52:21 | Scaling Defy & big-name allies
52:42 | A force of nature walks into Pelican Bay
54:10 | She saw potential—before he did
More episodes
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120. Juliana Del Aguila: Highlight Episode
31:55||Season 1, Ep. 120In this inspiring episode of Case Studies, Juliana Del Aguila takes us on a deeply personal and powerful journey through her life as a leader, a woman in a male-dominated industry, and a member of a family with an iconic legacy. Juliana shares the extraordinary story of her family, from escaping the Armenian genocide to building transformative businesses in Argentina and Armenia, including their groundbreaking ventures in textiles, wine, and airport development.Juliana opens up about her unique position as the only female leader in her family’s businesses, the challenges she has faced, and the lessons she has learned about resilience, vulnerability, and embracing authenticity. She reflects on balancing personal ambitions with family commitments, coping with loss, and preparing for future roles as a mother and mentor.Through her story, Juliana explores profound themes such as the importance of faith, the role of community impact in business, and the journey to discovering and owning her true self. Whether you’re drawn to stories of entrepreneurship, family legacy, or personal growth, this episode is a must-listen for anyone seeking inspiration to live with purpose, make meaningful contributions, and leave a lasting legacy.120. Dave Checketts: From Running Sports Empires to a New Life in Private Equity
01:34:36||Season 1, Ep. 120In this episode of Case Studies, Casey Baugh sits down with Dave Checketts, the youngest president in NBA history and former CEO of Madison Square Garden. From saving bankrupt franchises to leading iconic sports organizations, Dave shares the defining moments that shaped his career and his character.This conversation goes far beyond headlines and trophies. Dave opens up about faith, injustice, loss, and the unseen preparation behind opportunity. He reflects on how early rejection fueled resilience, how mentorship changed the trajectory of his life, and why building “championship culture” matters more than talent or capital alone.Now operating in private equity after decades in the global sports spotlight, Dave explains why influence without attention has become more fulfilling than power with a platform. This is a rare masterclass on leadership, readiness, and building a life of meaning long after the applause fades.⏱️ Episode Chapters00:00 | Admiration, Sports, and a Life in Leadership03:35 | Growing Up in Bountiful & Learning to Hustle Early08:34 | Rejection, Injustice, and Missing High School Basketball12:20 | Turning Setbacks into Fuel for Growth15:25 | Making the BYU Basketball Team Against the Odds20:14 | Faith, Obedience, and a Defining Spiritual Promise24:19 | Why That One Year of College Basketball Mattered28:19 | Ambition at 70 and Never Being Finished30:48 | Business School, Bain, and Early Career Acceleration35:27 | Clayton Christensen, Mentorship, and Consulting41:31 | Helping Danny Ainge and Entering Pro Sports47:26 | Walking into the NBA Office Unannounced52:58 | Sparring with David Stern—and Earning His Trust57:09 | Why the Celtics Deal Fell Apart59:17 | Being Chosen to Save the Utah Jazz at 2701:02:42 | Championship Culture vs. Winning Culture01:09:14 | Painful Partnerships and Hard Lessons01:16:21 | Tragedy, Loss, and Perspective01:20:04 | Faith, Gratitude, and the Experiences You Wouldn’t Choose01:22:14 | Raising Capital to Save the Jazz01:27:00 | Legacy Beyond Sports and the Spotlight119. Chad Willardson: Highlight Episode
35:06||Season 1, Ep. 119On this week’s episode, Casey sits down Chad Willardson - Chad shares his inspiring journey of building a successful wealth management business from the ground up, emphasizing the importance of adding value, maintaining integrity, and fostering positive relationships.Chad reveals his unique approach to helping others overcome their fears, illustrated by a moving story of encouraging a stranger to take a leap of faith. We delve into the critical distinctions between building and preserving wealth, the significance of focusing on what you do best, and the power of giving while living. Chad also discusses the role of faith, family, and personal growth in achieving a fulfilling and successful life.Whether you’re an aspiring entrepreneur, a seasoned business owner, or someone looking to better manage your finances, this episode is packed with practical wisdom and profound insights. Tune in to discover how to harness your fears, invest with confidence, and build a legacy of wealth and purpose.119. David Bearss: How a Gene Discovery Sparked a Career Saving Lives
01:08:38||Season 1, Ep. 119In this episode of Case Studies, Casey sits down with David Bearss – a trailblazing scientist, cancer researcher, and biotech founder, for a compelling conversation about faith, innovation, and the extraordinary journey from a biology lab to life saving breakthroughs. David shares how an early gene discovery altered the course of his life, launching him from a white coat in academia to the unpredictable world of entrepreneurship. With humility and clarity, he reveals what it’s like to develop treatments that not only extend lives but have saved the lives of people he loves. They explore how Halia, his latest venture, is revolutionizing Alzheimer’s research by studying those genetically at risk who never get the disease, and how AI is accelerating discoveries that once took decades. David also opens up about the mentors who believed in him, the moral weight of investor trust, and why scarcity breeds the best innovation. This conversation is an inspiring masterclass in conviction, purpose, and the science of resilience; for anyone committed to solving hard problems and building something that truly matters.118. Highlight Episode: Talk to Me About Faith (Part 2)
40:27||Season 1, Ep. 118As we step into a new year, we’re taking a moment to pause and reflect on one of the most meaningful questions asked in every episode of Case Studies:“Talk to me about faith.”This episode is Part One of our 2025 faith reflections, featuring half of this year’s guests sharing how faith shapes their leadership, decisions, relationships, and sense of purpose. The answers are thoughtful, honest, and deeply personal, offering a powerful look at how faith is showing up in real life and real business.As we move into the year ahead, these conversations create space to reflect on our own journeys and consider how faith is impacting each of us right now.Part Two drops next week, where we’ll share the remaining guests’ responses and continue the conversation.Whether faith is central to your life or something you’re still exploring, this episode is an invitation to reflect, reset, and step into the new year with intention.118. Andrew Smith: Three Exits by 33 and What Most Miss About The Food And Beverage Industry
01:31:39||Season 1, Ep. 118In this episode of Case Studies, Casey sits down with Andrew Smith, serial entrepreneur, multi-exit founder, and co-founder of Savory Fund, for an unforgettable deep dive into resilience, reinvention, and the sacred power of food.Andrew opens up about building three successful tech companies before the age of 33, selling to Fortune 100s, and navigating the dot-com bust and 2008 financial crisis. But it was a surprising pivot—supporting his wife Shauna’s dream to open a Kneaders Bakery; that shifted his trajectory and ultimately led to launching a wildly successful F&B Investment firm.From selling streaming tech in the ’90s to washing dishes in a café post-exit, Andrew shares raw lessons on humility, grit, and what it means to start over. They explore how family, faith, and a relentless drive to solve real problems shaped his entrepreneurial DNA, and why he believes restaurants are uniquely positioned to thrive, even in chaos.This conversation is a masterclass for founders on navigating ego, building with purpose, and finding meaning in the margins.117. Highlight Episode: Talk to Me About Faith (Part 1)
26:21||Season 1, Ep. 117As we step into a new year, we’re taking a moment to pause and reflect on one of the most meaningful questions asked in every episode of Case Studies:“Talk to me about faith.”This episode is Part One of our 2025 faith reflections, featuring half of this year’s guests sharing how faith shapes their leadership, decisions, relationships, and sense of purpose. The answers are thoughtful, honest, and deeply personal, offering a powerful look at how faith is showing up in real life and real business.As we move into the year ahead, these conversations create space to reflect on our own journeys and consider how faith is impacting each of us right now.Part Two drops next week, where we’ll share the remaining guests’ responses and continue the conversation.Whether faith is central to your life or something you’re still exploring, this episode is an invitation to reflect, reset, and step into the new year with intention.117. Casey Baugh: A Christmas Challenge To Live Abundantly
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01:22:10||Season 1, Ep. 116In this powerful episode, Casey Baugh sits down with long-time friend and All-American wrestler Ben Kjar for an unforgettable conversation about resilience, adversity, and becoming the kind of person who stands out—on purpose. From surviving childhood bullying to becoming Utah Valley University’s first All-American, Ben shares what it takes to turn pain into fuel, pressure into performance, and setbacks into legacy.Ben opens up about living with Crouzon Syndrome, calling his shot as a teen, building elite discipline, and the upcoming release of his inspiring feature film Stand Out. This isn’t just a story of success—it’s a blueprint for how to live bold, focused, and fully committed to your calling.00:00 | Missionary Beginnings & Lifelong Friendship03:58 | Wrestling Origins & Crouzon Syndrome06:39 | Calling the Shot: Becoming a 3X State Champion08:55 | Childhood Trauma That Sparked Transformation12:39 | Choosing Power Over Victimhood18:10 | Lessons from Jesus: Grace vs. Retaliation24:31 | UVU Wrestling & Sacrificing for the Dream26:45 | Be Disobedient to Average29:42 | The Power of Shot-Calling & Deadlines32:57 | Translating Athletic Principles to Life35:07 | Expanding Worldviews Through Experience41:56 | Letting Go to Go All In44:43 | Becoming UVU’s First All-American48:01 | Grit, Redemption & Spitting in Fear’s Face54:15 | Impact of Focused Commitment57:25 | From Real Estate to Life Purpose01:02:00 | Family, Adoption & Unwavering Support01:06:09 | Speaking with Purpose & Creating Legacy01:09:03 | Trust, Belief & Living with Intention01:15:08 | Behind the Film “Stand Out”01:21:00 | Final Reflections & Lasting Impact