Podcast
High, Low and Unexpected
Hosted by Shaun Gordon · EN
In this podcast, we explore the remarkable successes, challenges, and unexpected turns that entrepreneurs encounter in their careers.
44episodes
Episodes
Newest firstAll episodes
When Success Feels Empty: How Inner Work Transformed His Life and Business (ft. Ben Chernivsky)
Sep 901:10:14Tap to summarizeIn this honest and energizing episode, Shaun sits down with his longtime friend and fellow entrepreneur Ben Chernivsky for a conversation that goes far beyond business.Ben shares what it was like to build a life that looked perfect on paper—successful companies, financial freedom, a beautiful family—and still feel deeply unsettled, until he was able to rebuild from the inside out.You’ll hear about:The surprising emptiness Ben felt after reaching financial goalsHow unspoken loneliness impacted his marriage and mental healthWhy your business often reflects what’s going on internallyThe role of community and mentorship in healingFatherhood, presence, and rewriting your personal legacyThis one’s full of wisdom, reflection, and encouragement for anyone who’s ever asked, “Is this really it?”
Transcribe →It’s Okay to not be Okay: Navigating Mental Health and Creative Identity (ft. Brit Nicole)
Aug 1901:06:54Tap to summarizeIn this powerful and vulnerable episode, Shaun sits down with his friend Brit, a photographer and educator who shares her deeply personal story of loss, survival, and the journey of finding identity after a suicide attempt.Together, they discuss the pressures of entrepreneurship, how creativity and mental health intertwine, and what it means to choose healing in the midst of pain.This episode is a raw, honest look at what happens when life feels too heavy—and how we can show up for ourselves and each other through it.This episode covers:The quiet struggles behind outward successRebuilding identity and purpose after a mental health crisisThe importance of rest, boundaries, and authentic communityWhy conversations like these matter in the creative industryWhether you’ve walked a similar road or you love someone who has, this conversation will help you feel less alone—and remind you that your story matters.⚠️ Trigger Warning: This episode includes open discussion of suicide and mental health struggles. Please take care as you listen.
Transcribe →The Truth About Healing and Never “Arriving” (ft. Julia Woods)
Aug 5, 202500:45:40Tap to summarizeIn this vulnerable and profound episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with his longtime friend and former coach, Julia Woods—a relationship coach known for her powerful in-person event, Breakthrough. Together, they unpack what it means to chase intimacy, embrace the mess, and accept the fact that we never fully “arrive.”From a tornado that changed the course of her career to the gut-punch realization that healing is lifelong, Julia shares what it really takes to live fully alive—and lead others to do the same.In this episode, you’ll hear:Why couples keep showing up for hard conversations (and how real change happens)What Julia learned from her own season of insomnia, grief, and surrenderHow a tornado led to the unexpected start of her second careerWhat it means to be a “wounded healer” and walk in your calling anywayThis one is for anyone craving deeper relationships, real growth, and a life that’s led from the heart.
Transcribe →Burnout, Breakups, and Starting Over with Purpose (ft. Roy the Photographer)
Jul 22, 202500:51:02Tap to summarizeWhat happens when life pulls the rug out—and you decide to rebuild everything from the ground up?In this deeply honest episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with destination wedding photographer and creative entrepreneur Roy the Photographer. From a canceled proposal and health issues to a radical shift in work and location, Roy shares what it means to burn down the life you built and start again—with clarity, purpose, and a whole lot of heart.In this episode, you'll take away:How personal and professional burnout sparked a creative “Renaissance”What Roy learned after walking away from coaching to return to storytelling through photographyWhy hardship sometimes reveals what truly matters—like connection, health, and faithA fresh perspective on rebuilding: how controlled burns can lead to better growthIf you’ve ever been through a season where everything changed, this episode will encourage you to stay honest, stay curious, and keep showing up.🎧 Listen now and share your favorite takeaway with us!
Transcribe →What Honest Leadership Really Looks Like (ft. Adrian Koehler)
Jul 8, 202500:49:09Tap to summarizeIn this raw and reflective episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with executive coach and leadership advisor Adrian Koehler for an honest conversation about what it really means to show up, both in business and in life. From a pivotal moment on an empty stage to a professional low that cost him trust and opportunity, Adrian shares what it takes to lead with courage, own your missteps, and keep moving forward.In this episode, you'll hear about:What a professional misstep taught him about trust, repair, and leading with humilityHow to confront hard truths in leadership by "riding the elephant" instead of avoiding itWhy saying yes to an unpaid opportunity led to six figures in unexpected revenueWhat it looks like to build real influence through transparency, not titlesIf you're a leader, entrepreneur, or anyone navigating growth, this episode will challenge and encourage you to lead with honesty, humility, and purpose.Listen now and let us know your favorite takeaway in the comments!
Transcribe →How Pivoting Through Pain Builds Purpose (ft. Mycha Mills)
Jun 24, 202500:28:09Tap to summarizeIn this inspiring episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with Mycha Mills—photographer, branding expert, councilwoman, and mom—to talk about the beauty and challenges of designing a life that truly reflects your values. From photographing weddings on the Amalfi Coast to building a new life as a single mom living above her studio, Mycha shares what it looks like to embrace grit, growth, and grace in seasons of transition.In this episode, you’ll hear about:How travel with her daughters became a powerful bonding and growth experienceThe unexpected pivot from wedding planning to photography during COVIDWalking through divorce while building a business and creating a new visionThe beauty of branding photography and working with businesses in new waysWhy being present in each season matters more than perfectionWhether you're in a season of change, questioning your next move, or simply looking for honest stories of resilience, Mycha’s wisdom and strength will speak to you.
Transcribe →How Grief, Photography, and Vulnerability Shape an Entrepreneur’s Journey (ft. Louisa Vilardi)
Jun 10, 202500:53:20Tap to summarizeIn this episode, Shaun is joined by Louisa Vilardi, a portrait photographer and writer, to share her inspiring journey into entrepreneurship. Louisa talks about the transition from a secure teaching career to pursuing her passions in photography and writing, after experiencing profound personal loss. She reflects on how grief, while difficult, has shaped her life and work, reminding us of the power of vulnerability and how we can use our unique talents to document life's most meaningful moments.We’re talking:How Louisa pivoted from teaching to entrepreneurshipThe power of vulnerability in life and workPhotography as a tool to preserve memories and healThe importance of being present in the moment
Transcribe →When Fear Meets Faith: Building a Dream from Loss, Betrayal, and Grit (ft. Taylor Petrinovich)
May 6, 202500:51:36Tap to summarizeIn this powerful and emotionally rich episode of High, Low, and Unexpected, Shaun Gordon talks with Taylor Petrinovich—wedding filmmaker, educator, and co-founder of The Level Up Co.—about the rollercoaster journey of building a dream business while navigating motherhood, betrayal, and personal loss.Taylor opens up about how her entrepreneurial spark was ignited after the tragic loss of her father, how fear and grief fueled her first (failed) business, and how that “failure” taught her to try again. She shares candidly about what it means to trust (and be betrayed), how she turned loneliness into partnership, and why niching down in business has brought the greatest growth.Topics Covered:Grieving the sudden loss of her dad and how it launched her entrepreneurial journeyWhat she learned from her failed candle business—and why she doesn’t regret itThe birth and explosive growth of The Level Up Co.Finding the right business partner and pivoting from solo to shared successCoping with betrayal from a mentor and the emotional falloutLessons on trust, boundaries, and building from a place of healingHer Enneagram 3w4 wiring and how it plays into business, leadership, and relationshipsTaylor’s story is a testament to grit, courage, and the belief that dreams—even the scary ones—are worth chasing.
Transcribe →From Burnout to Becoming: Finding Purpose Beyond Success (ft. Kelley Gilster)
May 5, 202501:24:07Tap to summarizeIn this deeply vulnerable and relatable episode of High, Low, and Unexpected, Shaun Gordon sits down with Kelley Gilster—wedding filmmaker, serial entrepreneur, and co-founder of The Level Up Co.—to talk about the emotional cost of success, rediscovering purpose after burnout, and building a business that supports your real life, not just your goals.Together, they unpack Kelley’s journey through motherhood, running four businesses, hitting her financial peak in 2024 while feeling at her lowest emotionally, and the wake-up call that brought her back to herself. Shaun also reflects on his own recent retreat experience and shares how emotions, the Enneagram, and a deeper awareness are shifting the way he shows up as a leader.Key Topics Covered:The myth of “having it all together” and what happens when you don’tKelley’s unexpected path into motherhood and entrepreneurshipThe emotional weight of 2024—and why success felt emptyBuilding Level Up Co. and the power of aligned partnershipsEnneagram Type 3w2 and how it shaped Kelley’s mindsetThe power of awareness, therapy, and showing up as your whole selfThis is a must-listen for anyone juggling ambition and real life, and anyone who’s ever felt like their achievements weren’t enough. You’ll walk away challenged, inspired, and seen.
Transcribe →Learning to Rest: Embracing Fulfillment Beyond the Hustle (ft. Jon Hayes)
Apr 29, 202500:57:02Tap to summarizeIn this episode, Shaun chats with Jon Hayes, founder of a brand photography company and educator for aspiring photographers, about the unexpected pivot towards rest and fulfillment in both life and business. Jon shares his journey from an achiever mindset to embracing a new pace of life—learning how to prioritize family, rest, and intentional living over the constant hustle. He talks about his career highs, his struggles with ambition, and the most difficult lesson he’s learned in balancing productivity and personal fulfillment.This episode covers:Jon’s journey from corporate to entrepreneurThe unexpected wisdom of slowing downWhy achieving success doesn’t always bring fulfillmentHow Jon and his family have found balance in FloridaThe importance of setting a new pace for a meaningful lifeTune in for an inspiring conversation about redefining success and learning to embrace rest.
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