David Oliver, deputy wellness editor at USA TODAY, award-winning journalist, and journalism professor at the University of Maryland, joins Zach for a deeply human conversation on grief, mortality, and why death has become one of today’s most important wellness conversations. Drawing from his own experience losing his father suddenly to a rare neurodegenerative disease, David shares how that loss reshaped his perspective on life, relationships, ambition, and what it really means to be present.

Together, they explore why modern society has become so disconnected from death, how grief shows up in waves rather than neat stages, and why the workplace, our healthcare systems, and our culture as a whole still struggle to support people through loss. They also discuss the rise of longevity culture, the limits of biohacking, what COVID changed about the public conversation around grief, and why confronting mortality may actually help us live with more clarity, gratitude, and purpose.

This is a thoughtful, honest episode about the pain of loss, the value of remembering what matters, and how facing death can teach us how to live.

David's Writing at USA Today

David on Instagram

Zach and Reflecting Back on Instagram

In this episode, Zach sits down with two leading voices in modern dating: Blaine Anderson and Tim Molnar. Blaine is a dating coach, founder of Dating by Blaine, and host of Help Me I’m Single, known for her simple, effective advice that has helped more than 7,000 clients and built a following of over 600,000 people. Tim is a dating coach and bestselling author of Date Smarter: A Strategic Guide to Navigating Modern Romance, drawing on behavioral science, psychology, and his background as a former university lecturer with both a JD and PhD to help people approach dating with more clarity and intention.

Together, they explore why dating feels harder than ever, even as connection matters more than ever. Zach opens with striking statistics on loneliness, marriage trends, and modern dating behavior, including the idea that 70% of our happiness comes from the quality of our relationships, that one in six people feel lonely most or all of the time, and that 45% of men ages 18 to 25 have never approached a woman in person. From there, the conversation dives into dating app burnout, the shift back toward in person connection, unrealistic standards shaped by social media, the pressure to “have it all together” before dating, and what actually predicts long-term compatibility. They also cover rejection, friendship, belonging, vulnerability, and practical ways to build a fuller life that makes real love more likely.

datingbyblaine.com

datingbyblaine on Insta

TimothyMolnar.com

Tim Molnar on Insta

Zach on Insta

In this episode, Zach sits down with endurance athlete, sports physiotherapist, university lecturer, and HP3 coach Tim Pigott to explore what long-term success in sport really looks like. Tim shares the story of a near-fatal car crash at age 20 that left him with multiple broken bones, months in a wheelchair, and years of surgeries and rehabilitation. Despite being told he might never run again, he rebuilt his life and eventually returned to endurance sport, going on to win major ultramarathons including Race to the Stones (100 km) and setting the course record at the Montane Summer Spine Challenger South (174 km). It’s a powerful story of resilience built not on motivation alone, but on consistently doing the next right thing.

The conversation then shifts into the practical side of performance and coaching. Tim breaks down how to set meaningful goals, structure a season around real-life constraints like work and family, and why flexible systems often matter more than rigid plans. They discuss mental fatigue, problem-solving when races or training go off script, and lessons Tim learned preparing for and racing some of the world’s toughest endurance events, including UTMB. At its core, the episode is a reminder that the finish line is only one moment, while the real value comes from the journey that gets you there.

In this episode, Zach sits down with Nicole Davis, a two time Olympic silver medalist with Team USA Volleyball, 2014 world champion, and former USC standout who helped win back to back NCAA national titles. After retiring from elite competition, Nicole earned her doctorate in psychology and has since become a trusted voice in high performance, working with Olympic teams, professional athletes, military operators, and senior leaders through Finding Mastery and Warrior’s Edge. Her career bridges the worlds of elite sport, psychology, and leadership under real consequence.

Zach and Nicole explore what separates excellence from mastery, why high performing environments can still feel empty or exhausting, and how meaning often erodes as organizations scale. They dig into mindfulness as a trainable performance skill, not a wellness trend, and discuss grit, routines versus superstitions, leadership, trust, and vulnerability. From aircraft carriers to Olympic finals, this conversation offers practical insight into how people and teams can perform at a high level while staying grounded, connected, and resilient when the pressure is on.

Langdon Root shares his journey from growing up in rural Indiana to a 26-year Air Force career as an F-16 fighter pilot and Special Warfare leader, followed by a transition into civilian life focused on mentorship, service, and building veterans’ projects. Drawing on combat deployments, years of leading young Airmen, and hard lessons from marriage, Langdon explains how early exposure to pornography, an emotionally absent father, and cultural confusion around masculinity shaped his beliefs and eventually forced a reckoning. He distinguishes toxic masculinity (selfish use of strength), healthy masculinity (selfless strength), and biblical masculinity (selfless strength rooted in Christ), grounding the discussion in 1 Corinthians 16:13–14 and emphasizing vigilance, courage, discipline, and love. The conversation explores why men need deep male friendships, why vulnerability is an act of courage, and how responsibility gives men direction and purpose. Langdon also addresses the misunderstood idea of submission in marriage, arguing that it only works when paired with a man’s sacrificial love, integrity, and accountability. The episode ultimately challenges men to stop chasing approval, comfort, or status, and instead pursue faith, purpose, community, and the kind of inner strength that leads to healthier relationships and a more meaningful life.

Chapters

00:00 The Impact of Culture on Masculinity

06:53 Biblical Masculinity Explored

07:32 The Role of Masculinity in Family Dynamics

10:28 Positive Masculine Role Models

12:42 The Decline of Masculinity in Society

14:40 Biblical Masculinity: A Framework for Growth

18:47 Healthy vs. Toxic Masculinity

21:09 The Importance of Male Relationships

26:23 Being On Guard: Spiritual Vigilance

32:36 Standing Firm in Faith

36:22 Courage and Emotional Resilience

40:22 Expectations vs. Outcomes in Masculinity

42:49 The Journey of Masculinity

45:58 The Dynamics of Attraction

48:53 Building Masculine Skills

51:29 Understanding Love and Submission

58:06 The Role of Men and Women in Marriage

01:10:07 Lessons from the Youth Retreat

In this episode, Hillary “Hillygoat” Allen takes us inside one of the most extraordinary comeback stories in endurance sport.

In 2017, at the peak of her career and ranked #1 in the world in skyrunning, Hillary fell 150 feet off an exposed ridge during a race in Norway—an accident that should have taken her life. She broke 14 bones, lost her identity as an athlete, and was told she might never run again.

But what followed wasn’t just physical recovery—it was a complete reconstruction of self. Hillary opens up about the shame, fear, and isolation she faced, how vulnerability and community became essential to rebuilding, and how she redefined strength, success, and who she believed herself to be.

We explore the neuroscience behind resilience, the psychology of identity collapse, and the deliberate practice and mental frameworks that allowed her not only to return to running, but to rise all the way back to the world stage—ultimately qualifying for Team USA.

This episode is a raw, honest, and deeply human conversation about the power of mindset, the role of vulnerability in high performance, and what it takes to build a life that can withstand being broken open.

In this essential episode of Reflecting Back, Zach breaks down barriers around a topic most men ignore—menopause. Inspired by the eye-opening South by Southwest panel, "Hotter Than Ever: The Truth About Sex in Midlife," Zach is joined by Dr. Rachel Pope, a renowned gynecologist and menopause expert, to shine a light on the vital importance of communication and awareness around women’s health. They discuss why menopause isn’t just a "women’s issue," how desire discrepancies can impact relationships, and why open conversations about sexual health are crucial. With women more empowered than ever to advocate for their well-being, it's time men step up, educate themselves, and become the supportive partners their relationships need.

Links:

Dr. Pope’s

• Insta: @drrpope @mim.menopause
• FB: @drrpope @mim.menopause
• TikTok: @thevulvadoctor

Insta: https://www.instagram.com/zachstiffler

In this episode of Reflecting Back, Zach sits down with Gavin Greenberg and Jess Pink, founders of Travel World Culture (TWC) and the speakers behind the impactful TEDx talk, "The American Dream is Making You Lonely." They discuss their bold decision to leave corporate life to create a travel business focused on building community and meaningful experiences. Gavin and Jess share how living abroad reshaped their views on personal fulfillment, community involvement, and cultural awareness. They also explore the real-world challenges of entrepreneurship, particularly during the COVID-19 pandemic, and offer practical advice on travel safety, building genuine relationships, and thoughtfully balancing privilege with empathy. This conversation will prompt you to reconsider your own ideas of success and connection.

Links:

Travel World Culture’s Insta: https://www.instagram.com/travelworldculture/

Zach's Insta: https://www.instagram.com/zachstiffler

Guests: Couples Therapist - Baya Voce, Austin-Based Dating Coach - Kate Durocher, and Hot Takes Hot Dates Host - Joel Monteleone

This episode charts the full journey of modern relationships—from building unshakable self-worth to navigating long-term connection with depth and clarity. Kate Durocher shares how embracing solitude and doing the internal work laid the foundation for finding a healthy, aligned partnership. Joel Monteleone, Founder of Austin’s “Hot and Sober” and Host of “Hot Takes Hot Dates” events, highlights the power of in-person connection and why play, presence, and risk are essential antidotes to dating app fatigue.

Baya Voce delivers a masterclass in conflict and repair, breaking down her five-step framework that turns rupture into reconnection. She explains why most relationships don’t fall apart because of conflict—but because of the lack of meaningful repair. This conversation is an invitation to reimagine what love looks like when it’s rooted in accountability, emotional attunement, and the courage to stay in the mud together.

Together, we challenge outdated ideas of what dating and relationships “should” look like. We explore how to build resilience in a culture that avoids discomfort, how to spot the patterns we inherit from our caregivers, and how to step into relational maturity by taking ownership of our emotional experiences.

Links:

Baya Voce:

• https://bayavoce.com
• https://www.instagram.com/baya_voce/

Kate Durocher:

• https://coachkatedurocher.com
• https://www.instagram.com/coachkatedurocher/

Joel Monteleone:

• https://www.instagram.com/joel_monteleone/

Zach Stiffler:

• https://www.instagram.com/zachstiffler/

In this episode, Omid Scheybani—global storyteller and tech entrepreneur—shares his insights on time, purpose, and personal growth.

He reflects on the rewards and challenges of a nomadic lifestyle, the power of cultural exploration, and the importance of curiosity in fostering empathy. Drawing from experiences in living in China, visiting North Korea, and embracing his Iranian heritage, he challenges media-driven narratives and highlights the profound impact of human connection.

Omid also discusses setting ‘moonshots’ for growth, embracing discomfort, and the role of gratitude and perspective in shaping a fulfilling life.

Links:

Omid’s Insta: https://www.instagram.com/omidscheybani/

Insta: https://www.instagram.com/zachstiffler

Chapters:

00:00 Introduction and Purpose of the Podcast

00:52 Reflections on Time and Life at 34

05:33 Life in China and the Decision to Move

10:37 The Nomadic Lifestyle and Its Challenges

15:28 Curiosity and Empathy: A Global Mindset

20:18 Experiencing Iran: A Journey of Discovery

25:18 Influencing Perspectives on Iran

26:50 Adventures in North Korea

33:32 Haunting Memories from North Korea

35:44 The Reality Behind the Scripted Experience

39:03 Emotional Expression in a Controlled Society

40:46 Travel Opportunities for North Koreans

43:42 Defining Moonshots and Personal Growth

50:53 Setting Intentions and Themes for Life

55:13 Gratitude Through Painful Experiences

01:03:13 Introduction to Amid's Journey

01:03:41 Reflections on Loss and Moving Forward