The Second Act with Michael and John
Michael and John take you on a mission-driven, story-telling journey where a diverse group of people share unique perspectives on trying something new in life. From corporate executives to military veterans, consultants to entrepreneurs, the conversations delve into the backgrounds and inspiring transformations of guests to highlight the power of grit, persistence, perspective, purpose and community.
Episodes
Jason Middleton didn’t just reinvent himself once. He built an entire life around jumping into the unknown. Growing up as an overweight kid in Bakersfield with little confidence and no clear direction, he found salvation in endurance sports, eventually becoming a professional triathlete before pushing himself even further into the savage world of Eco Challenge adventure racing, battling jungles, oceans, sleep deprivation, and seven...
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She did everything right, and it still didn’t work. Eileen Nebhut built a decades-long career across publishing, energy, and fintech, earned her MBA, and followed the traditional path to success, only to find herself after COVID unable to land the roles she expected and questioning where she truly fit. Shaped early by a childhood of standing out and learning to navigate being “other,” she developed deep empathy and self-awareness t...
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Angie Callen didn’t plan a radical career reinvention. It found her. She began her career as a civil engineer and moved to Colorado for what seemed like the perfect opportunity, but the 2008 financial crisis forced her to question everything about the path she was on. Walking away from engineering, she spent a year trying anything that crossed her path, from running an artist’s gallery to selling advertising, simply gathering clues...
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Ron Johnson’s journey is a powerful testament to reinvention, resilience, and purpose across every chapter of life. Raised on Chicago’s West Side by a single mother and grandparents, Ron learned early that excellence could be a way forward, earning his path to West Point and embarking on what he thought would be a short Army commitment that ultimately became a 32-year career of service. Rising to Major General and Deputy Chief of E...
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January 9, 2026 • 31 mins
To celebrate two years of The Second Act Podcast, this special anniversary episode distills the most powerful parting advice ever shared by our guests into a single, focused conversation for anyone standing at the edge of what’s next. Across founders, operators, creatives, coaches, and leaders, a clear pattern emerges: second acts aren’t about reinvention for reinvention’s sake, but about curiosity, courage, self-trust, and taking ...
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What happens when everything you thought defined you, your title, your income, your path, suddenly stops feeling true? For JB Bolton, that question ignited a transformation he never saw coming. Growing up in Colorado Springs, he watched his parents navigate change with resilience, a lesson that later fueled his own nonlinear path from retail sales to finance to tech. But it was the birth of his daughter that triggered a radical res...
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She never set out to be a coach. In fact, she thought she’d be a doctor. But when a single question from her boss changed everything, Cara-Lyn Giovanniello discovered her true calling: helping people evolve into the leaders they were meant to be. From her beginnings in a family of educators to shaping leadership cultures at UC Berkeley, Booz Allen, Square, and Nextdoor, she’s built a career around courage, connection, and emotional...
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Adam Contos turned unconventional beginnings into an extraordinary career, rising from hands-on hustle to lead RE/MAX as CEO. Along the way, he built resilience and sharpened his decision-making in high-pressure environments, lessons that fueled his entrepreneurial spark and opened the door to new opportunities. At RE/MAX, what began as teaching safety to real estate agents evolved into an 18-year climb to the top, proving that con...
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What do a foster kid, a West Point boxer, an Olympic Trials competitor, and a NASA engineer have in common? They are all chapters in the extraordinary journey of Giovanna Camacho. From being taken from her family at 12 to carving her way into West Point and creating the women’s boxing team, she proved early on that grit and resilience would define her path. She went on to lead medical operations, compete at the highest levels of sp...
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Joey Odom began his journey in Tulsa, Oklahoma with no clear path, transitioning from theology to marketing at Oral Roberts University before building a 15-year career in commercial real estate. Everything changed when he missed his son’s first soccer goal while looking at his phone, a moment that revealed how deeply technology was affecting his relationships. That experience, combined with a timely conversation with a friend, spar...
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Michaella Gallina grew up in a rural town of 4,000 where hard work and grit were ingrained early, riding horses to track practice and dreaming of something more. Determined to create her own path, she earned a full scholarship to the University of Denver, studied finance, and broke into Wall Street, eventually managing multi-billion dollar portfolios, meeting CEOs like Zuckerberg and Cook, and becoming CFO of a $100 million fintech...
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Collin Strachan began life battling severe autoimmune disorders that nearly left him blind and bedridden, but through resilience, fitness, and mindset, he overcame his health challenges and reclaimed his future. After working in corporate marketing in Dallas, he walked away from the comfort of a steady paycheck in 2017 to pursue a deeper calling for creativity and adventure. With his wife Kendall, he launched Every Mile Creative, a...
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Ali Schroer, MSW, LCSW, C-PD grew up in California and Indiana, where early experiences navigating change and hardship sparked her passion for supporting others. Inspired by a deep love for children and a family legacy in mental health, she pursued a career in elementary education, only to realize that her true calling was in helping people with their emotional wellbeing. After witnessing firsthand the profound impact of stress on ...
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After a high-powered Wall Street career and a life defined by achievement, Paul Kent’s world was upended by a rare genetic condition that triggered a decade-long health crisis that nearly took his life. Facing relentless infections, 21 surgeries, and the gradual erosion of his wealth and identity, Paul made a radical decision in 2020: to undergo an experimental double amputation that ultimately saved him. Emerging from surgery not ...
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April 4, 2025 • 56 mins
Brett Murphy grew up in Colorado, inspired by his grandfather’s small-town five and dime store and his father’s relentless work ethic in real estate. Watching his father pivot from a struggling teacher to a top producing real estate investor instilled in Brett a deep understanding of grit and opportunity. After earning his real estate license in college, he thrived in a booming market, but years of relentless hustle left him burnt ...
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Jasmine Motupalli's journey is a testament to courage, adaptability, and purpose-driven leadership. Growing up in a supportive, education-focused household, she excelled in academics and athletics before attending West Point as part of the first class to enter after 9/11. Commissioned as a military intelligence officer, she deployed to Iraq and Afghanistan, where she led with innovation, turning challenges into strengths despite be...
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Ayush Gharat grew up in Bangalore, India, surrounded by entrepreneurs and innovators, which sparked his early fascination with technology. At just 10 years old, he began teaching himself coding, earning an Android development certification by eighth grade. During the COVID-19 pandemic, he founded Aashwas, a social initiative that provided thousands of healthcare workers with essential protective equipment, leading him to present at...
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February 21, 2025 • 51 mins
Born in Orlando and raised in Kissimmee, Joshua Young, known as Saint Josh, wrote his first rap at six years old and, by 11, set a bold goal to pursue music, inspired by artists like Eminem and Lil Wayne. Struggling with shyness, music became his outlet, helping him build confidence and develop his craft—first mastering lyrics, then flow, performance, and storytelling. As he grew, he realized that success in music required not just...
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February 7, 2025 • 56 mins
Jordon Allard grew up in the Midwest, inspired by her hardworking father, who instilled in her the values of balance, perseverance, and family-first priorities. Initially unsure of her exact career path, she explored various healthcare roles before choosing occupational therapy for its deep personal impact. After gaining experience in the field, she unexpectedly found herself with an opportunity to launch her own therapy business d...
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Henry Oliver’s life journey is a testament to the power of reinvention and embracing one’s unique path. A writer and speaker based in Southeast London, Henry’s early career was shaped by talent attraction marketing and insightful essays on literature and history. However, it was during a challenging period of illness and time away from work that his perspective shifted, sparking the idea for his book, Second Act: What Late Bloomers...
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