Out Here Wingin It

Tommy Sessions, Devin Hess, Tyler Bergeren

Life’s not about being perfect, it’s about being real. Out Here Wingin It Podcast, hosted by Tommy Sessions, goes beneath the surface with people who’ve lived it, entrepreneurs, creators, and everyday fighters with stories that hit home. This isn’t self-help. It’s straight talk about what it means to live with purpose, rebuild your identity, and face life head-on. No filters. No fake. Just life, raw and uncut.

  1. FEB 20

    EP. 24 | Lyssa Scott | Part 2 Live Life at Maximum Potency

    The conversation delves into moments of divine intervention and spiritual connection, the significance of receiving and perceiving meaningful experiences, and the expression of love and appreciation for others. It also explores the concept of living funerals and the importance of witnessing one's feelings. Lyssa discusses her journey of self-discovery, physical fitness challenges, financial stability, and her transition to a new role. She shares insights on personal growth, leadership, and the pursuit of excellence. The conversation covers a range of topics including the immersive retreat experience, the concept of masterminding, the power of deep connections, and the transformative impact of events like CCV. It also delves into the journey of self-discovery, the importance of setting intentions, and the pursuit of personal growth and fulfillment. Takeaways Divine intervention and spiritual connectionThe significance of receiving and perceiving meaningful experiencesThe expression of love and appreciation for othersThe concept of living funerals and the importance of witnessing one's feelings Self-discovery and personal growthChallenges in physical fitness and healthTransition to a new role and leadershipPursuit of excellence and financial stability Immersive retreat experiences can be transformative and offer a unique blend of personal growth and connection.Deep connections and meaningful conversations are essential for personal and professional growth.Setting intentions and looking for the good in everything can lead to transformative experiences and personal growth. Chapters 00:00 Divine Intervention and Spiritual Connection08:06 The Expression of Love and Appreciation for Others17:00 Living Funerals and Witnessing Feelings29:47 Journey of Self-Discovery and Personal Growth36:25 Challenges in Physical Fitness and Health45:45 Transition to a New Role and Leadership53:45 Pursuit of Excellence and Financial Stability01:09:27 Setting Intentions and Personal Growth

    1h 28m

  2. FEB 19

    EP. 23 | Lyssa Scott | Live Life at Maximum Potency

    In a long-form podcast conversation, Lyssa describes vivid “signs” from her late father, including following a white Chevy Silverado with a Pennsylvania plate for miles during a solo Texas drive while a meaningful song played at sunset, and seeing what she believed was his face and a wink in the ocean while scattering his ashes. The discussion explores how to notice and receive moments of significance through pattern interruption (breathwork, hypnotherapy, nature), identifying physical cues like goosebumps, praying with openness, and avoiding forced interpretation of signs. They talk about music as an emotional trigger, watching sunrises and sunsets, and the “green flash” phenomenon in Hawaii. Lyssa shares practices such as informal written prayer through morning journaling (morning pages) and reframing emotions by witnessing them rather than identifying with them. The conversation includes stories about faith and action using biblical examples (Noah’s ark, Moses and the Red Sea), skepticism about organized religion, and a faith-based spirituality centered on conversation and community. They discuss personal growth, including letting go of anger as a fuel source after a friend’s blunt feedback, and Alyssa’s desire to increase capacity to better serve others while dealing with escalating unexplained back pain and balancing fitness, finances, and presence. The hosts share ideas about “living funerals,” daily compliments, and compiling video tributes for loved ones, plus a humorous festival story involving an unexpectedly strong psilocybin dose during a Tyler Childers set. Alyssa explains her entrepreneurial shifts from business coaching to creative brand work, launching content road trips and rapid branding/website offers, then joining Rob Bailey’s team after a bold DM (“what are we closing?”) and relocating to support his mission, navigating ego death, sales repetition, and learning leadership and speaking. The host reflects on quitting his job after physical stress reactions, tracing his path from a branding playbook and CCV event to fundraising, coaching, and starting a podcast. They close with reflections on reframing the “cost of freedom,” building teams carefully, creating deeper connection at business events through personalized follow-up conversations, and a final principle: use your gifts to serve at the highest level while continually expanding capacity.

    2h 17m
  3. EP. 22 | Kindi Berry | A Teen's Courageous Battle with Cancer

    FEB 6

    EP. 22 | Kindi Berry | A Teen's Courageous Battle with Cancer

    Meet Kindi Barrie: A Teen's Courageous Battle with Cancer. In this heartfelt episode of the Out Here Wing'in It Podcast, meet 16-year-old Kindi Berry who shares her courageous battle with cancer. Kindi, who recently had her lower leg amputated due to the disease, opens up about her journey, the emotional and physical challenges, and the unwavering support from her loved ones including her boyfriend Maddox. Despite ongoing treatments and obstacles, Kindi's story is one of resilience, humor, and hope. From heartfelt gift-giving moments to the significance of community support, this episode is a testament to human strength and the impact of love. Hosted by Devin, the episode also touches on the technical hiccups the podcast has faced and the ongoing efforts to upgrade their equipment. Join us to get inspired by Kindi's remarkable story and find out how you can show support and love to those battling similar challenges.

    1h 16m

  4. JAN 7

    Ep. 21 | Devin Hess & Tommy Sessions | Founder of $1 dream and Real Estate investor

    The conversation delves into the concept of resolutions and the speaker's perspective on them. It also explores the idea of setting specific goals and the speaker's personal goals for the future. The conversation delves into the impact of kindness and compliments, highlighting their significant influence on people's lives. It also explores the reevaluation of the role of money and success, emphasizing that money brings a range of emotions and is not the sole measure of success or happiness. Additionally, it discusses the importance of being the person you want to be and the challenges of self-acceptance and personal growth. The conversation delves into the challenge of reaching out to others, the impact of changing social media, and the power of small acts and stories. It emphasizes the importance of human respect, connection, and the influence of sharing kindness and personal experiences. The conversation delves into the discomfort of silence and the search for answers within it. It also explores the constant need for entertainment, the impact of short attention spans and social media influence, and the importance of reframing the past and embracing the journey. Takeaways Resolutions as wishesSetting specific goals Kindness and compliments make a big difference in everyone's life.Money brings a range of emotions and is not the sole measure of success or happiness. Small acts create big impactThe power of sharing stories and kindnessThe importance of human respect and connection Silence holds the answersConstant need for entertainmentShort attention spans and social media influenceThe journey is as important as the destination Chapters 00:00 The Problem with Resolutions48:47 The Impact of Kindness and Compliments57:14 Reevaluating the Role of Money and Success01:18:40 Being the Person You Want to Be01:31:02 The Challenge of Reaching Out01:37:00 Changing Social Media and Personal Impact02:13:00 The Search for Answers02:21:32 Short Attention Spans and Social Media Influence02:32:22 Reframing the Past and Embracing the Journey

    2h 32m

  5. JAN 7

    Embracing the journey

    Do you embrace the journey or wish it away?

    1 min
  6. Ep. 20 | Kelsi Petersen | Founder of Kelsi's Kitchen

    2025-11-30

    Ep. 20 | Kelsi Petersen | Founder of Kelsi's Kitchen

    In this engaging conversation, Kelsey Peterson shares her journey from a family-oriented upbringing to becoming a successful entrepreneur with Kelsey's Kitchen. The discussion delves into her experiences in CrossFit, the importance of nutrition, and the mental challenges faced in sports. Kelsi reflects on the balance of motherhood and ambition, the impact of personal loss, and the role of spirituality in her life. The conversation emphasizes the significance of affirmations, emotional connections, and the lessons learned from grief, ultimately highlighting the journey of self-discovery and the power of open-mindedness.

    2h 21m
  7. Ep. 19 | Stu Draper | Founder/Angel Investor

    2025-11-20

    Ep. 19 | Stu Draper | Founder/Angel Investor

    Summary In this conversation, we discuss the importance of choosing supportive influences over naysayers in life. Stu Draper reflects on his upbringing, emphasizing the role of his parents in fostering a positive mindset and belief in oneself. Through personal anecdotes, he illustrates how encouragement can shape one's confidence and outcomes in various endeavors. Find Stu on Startups with Stu

    2h 41m
  8. Ep. 18 | Aaron Wilburn | Master Blade Smith |

    2025-11-12

    Ep. 18 | Aaron Wilburn | Master Blade Smith |

    In this episode, we sit down with Aaron Wilburn, a master blade smith renowned for his expertise in crafting exquisite knives. Aaron shares his journey into the world of bladesmithing, revealing the intricate techniques and creative processes behind his stunning 320-layer Damascus blades. Whether you're a knife enthusiast or simply curious about the art of forging, this episode offers a captivating look into the dedication and craftsmanship that define Aaron’s work.

    2 hr
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About

Life’s not about being perfect, it’s about being real. Out Here Wingin It Podcast, hosted by Tommy Sessions, goes beneath the surface with people who’ve lived it, entrepreneurs, creators, and everyday fighters with stories that hit home. This isn’t self-help. It’s straight talk about what it means to live with purpose, rebuild your identity, and face life head-on. No filters. No fake. Just life, raw and uncut.

Information

  • Creator
    Tommy Sessions, Devin Hess, Tyler Bergeren
  • Years Active
    2025 - 2026
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © 2025 Tommy Sessions, Devin Hess, Tyler Bergeren
  • Show Website
    Out Here Wingin It