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In this episode of You Winning Life, Jason sits down with licensed therapist, author, and creator of Bempathy®, Jill Robin Payne. With over 40 years in the mental health field, Jill has dedicated her career to helping people build healthier, more connected relationships by blending playfulness with empathy.

Jill introduces us to her groundbreaking communication approach, Bempathy®: Simplifying Communication by Looking at the Third Side of the Coin. Through banter, perspective-taking, and compassion, Bempathy® offers a simple yet profound way to transform misunderstandings into meaningful connections.

From her early days interning at the National Institutes of Health to authoring books, teaching at the college level, and now leading a thriving counseling practice, Jill has remained committed to spreading goodness and making mental health advice as accessible and essential as physical health.

👉 Learn more about Jill and order her books at www.jillrobinpayne.com or find them on Amazon.

What You'll Learn in This Episode:

• Introducing "Banthy": Jill introduces her unique concept, "Banthy," which combines banter with empathythrough a three-step process: empathize, see the big picture, and then engage in chitchat. This approach helps brains synchronize and fosters deeper connections, especially in a world where casual conversation is often undervalued and young people may think it's a waste of time.

• The Future of Relationships with AI: Explore the fascinating (and sometimes humorous) world of AI in personal relationships, from Jill's "sexy" Microsoft Copilot that she calls "him" and "George" to recent studies suggesting Gen Z's preference for AI partners. Jason and Jill discuss how different generations interact with and adopt new technologies, with younger individuals showing an advantage in curiosity and creativity with multiple AI platforms.

• Jill's Journey to Becoming a Therapist: Learn about Jill's diverse background, including recreational therapy, ophthalmic technician work, and gymnastics coaching, before finding her calling in psychology following a divorce and her brother's experience with paranoid schizophrenia.

• Understanding Licenses vs. Certifications: A critical discussion on the difference between state-regulated licenses(like LPC and LCDC) and easily obtainable certifications, emphasizing the importance of seeking advice from credentialed therapists. Jill holds both a Licensed Professional Counselor (LPC) and a Licensed Chemical Dependency Counselor (LCDC).

• Modeling Behavior and Setting Boundaries: Discover the significance of modeling appropriate behavior in parenting and friendships, and the crucial practice of asking for permission before offering help to avoid codependency and over-involvement, as over-helping can disempower others.

• Empowering Others Through "Merit Badges": Jill shares a powerful analogy about tying shoes to illustrate how over-helping can disempower individuals who then don't learn essential skills. This leads into a discussion about crea

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In this raw and powerful episode of You Winning Life, Jason Wasser welcomes Adrian Koehler, a high-impact executive coach and leadership trainer, to discuss the transformative power of commitment, language, and self-awareness in both life and leadership.

They explore how getting “stuck” in career or personal relationships often stems from a lack of clarity, aligned values, or the fear of fully committing. Adrian breaks down the difference between trying and committing, shares insights from coaching founders and prison inmates alike, and opens up about his own growth through fatherhood, failure, and radical honesty.

The episode covers everything from reinventing your job description to challenging toxic workplace dynamics, and how proactive conversations and deep accountability can help you play to win—not just survive.

Key Topics Covered:

🔹 Commitment vs. Trying – why "trying" keeps you stuck
🔹 The power of language in leadership and personal transformation
🔹 Coaching vs. traditional therapy – how results and accountability shift outcomes
🔹 How to rewrite your job description and align with your purpose
🔹 The role of self-awareness in authentic relationships
🔹 Rewiring chronic complaints (“rackets”) in personal and professional life
🔹 Using personal stories and feedback loops to drive growth
🔹 Building strong family standards and leadership at home
🔹 The difference between playing to win vs. playing not to lose

Memorable Moments:

🎧 Adrian shares how Paul Simon’s “Still Crazy After All These Years” helped him through tough times
🛠️ Real-world advice on how leaders can use audacity and alignment to thrive
📢 Why TEDx talks and unedited conversations matter more than polished content

Resources & Links:

🌐 Learn more about Adrian Koehler: https://www.takenewground.com

🙌 If this episode hit home, leave a review, share with a friend, and tag us to continue the conversation.

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In this episode, Jason is joined by award-winning speaker, educator, and author, Scott Fried who has been a significant presence in Jason's life since 1994/95, when Jason first heard him speak at his childhood synagogue in South Florida. That initial encounter sparked a lasting connection. Their bond has remained strong for over 30 years, with Scott's work and personal story continuing to inspire Jason. 

Scott shares his transformative personal journey and insights on living with purpose, self-love, and self-responsibility. He reflects on his life with HIV and his mission to help teens and adults make better life choices, focusing on self-empowerment and compassion. The conversation explores the concept of elegance—not just as a physical attribute, but as a way to live with grace, integrity, and a deep sense of personal growth. Scott also touches on the importance of vulnerability, compassion, and emotional intelligence in building meaningful relationships and embracing life's challenges.

Key Takeaways:

• Personal Growth and Elegance: Elegance is more than just appearance—it’s about living with grace, emotional balance, and self-awareness, especially in times of hardship.
• Self-Love and Responsibility: Scott shares how his own experiences shaped his understanding of self-love and the importance of self-care in supporting others.
• Compassion and Vulnerability: Acknowledging and embracing vulnerability is essential for personal growth and building strong, compassionate relationships.
• Purpose and Agency: Taking responsibility for our lives and understanding the balance between joy and struggle helps us stay aligned with our higher purpose.

In This Episode You’ll Hear About:

• Scott’s personal journey with HIV and how it has influenced his perspective on life, love, and self-empowerment.
• The concept of "elegance" in personal growth and how it applies to self-care, leadership, and interactions with others.
• Insights into self-acceptance and why it's crucial for living a fulfilling life.
• Stories of vulnerability, tenderness, and resilience, and how these qualities shape our journeys as adults.
• The importance of surrounding ourselves with compassionate, accepting relationships and fostering radical self-acceptance.

Featured Books:

• If I Grow Up: Talking with Teens about AIDS, Love, and Staying Alive
• My Invisible Kingdom: Letters from the Secret Lives of Teens
• A Private Midnight: A Teenager’s Scrapbook of Secrets
• How to Raise an Elegant Teen: The ABCs of Gen Z Parenting

Resources:

• Scott Fried’s website: Scott Fried
• Pandemic Playbook course at Colby College: AIDS and the Meaning of Life

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In this episode of You Winning Life, Michael Reddington, a Certified Forensic Interviewer and expert in strategic communication, joins Jason to break down the power of listening, asking better questions, and handling high-stakes conversations. Michael shares investigation-based techniques that can transform the way we communicate in business, relationships, and personal growth.

Together, they explore effective communication strategies, career paths and problem-solving techniques, and how situational awareness and emotional intelligence shape impactful conversations. Jason also shares how helping a violin teacher expand his brand reinforced the importance of asking for what you want—a principle Michael applies to business, leadership, and everyday interactions.

If you’ve ever struggled with feeling undervalued, handling difficult conversations, or understanding different perspectives, this episode is for you.

What You’ll Learn in This Episode:

✔️ How forensic interrogation techniques apply to business, leadership, and personal relationships
✔️ The importance of context and empathy in conversations
✔️ How to ask better questions to uncover key insights and build trust
✔️ Strategies for handling difficult conversations and managing emotions
✔️ Why taking action creates clarity when dealing with workplace ambiguity
✔️ How to reframe questions to guide people toward better outcomes
✔️ The role of situational awareness in effective communication
✔️ Understanding hyper-rational individuals and how to engage with them emotionally
✔️ Avoiding misunderstandings by asking open-ended questions rather than leading ones
✔️ The impact of self-awareness and emotional intelligence in business and relationships

Key Takeaways from The Disciplined Listening Method:

🔹 Illustrate before investigating to create a comfortable environment for sharing information
🔹 Focus on the outcome, not immediate emotional reactions
🔹 Reframe questions positively—ask what someone wants rather than what they want to avoid
🔹 Use non-accusatory language—shift from “Did you?” to open-ended phrasing
🔹 Say, "Please correct me where I'm wrong" to encourage more open communication
🔹 Recognize that action creates clarity in ambiguous situations
🔹 Let people “gas themselves out” before responding in high-emotion conversations


Buy his book: The Disciplined Listening Method: How A Certified Forensic Interviewer Unlocks Hidden Value in Every Conversation

🌐 Website: michaelreddington.com

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In this episode of You Winning Life, Jason Wasser sits down with transformational leader and author Preston Smiles to dive deep into the journey of personal growth, overcoming challenges, and embracing transformation. Preston shares insights from his own life, including navigating family struggles, overcoming childhood trauma, and learning to trust his intuition. They explore the power of self-awareness, mindfulness, and building the capacity to hold multiple perspectives. Throughout the conversation, they emphasize the importance of celebrating small victories, practicing self-care, and staying open to continual personal development.

Key Topics Discussed:

The journey of personal growth and transformation

Overcoming childhood trauma and family challenges

Trusting intuition and inner guidance

Mindfulness and building personal capacity

The impact of codependency on relationships

"Blessing the mess" – Holding multiple perspectives in difficult situations

The importance of self-care and setting boundaries

Money mindset and abundance

The role of retreats and sabbaticals in personal development

The law of attraction and its daily applications

🚀 If you found this episode helpful, subscribe, leave a review, and share it with someone who needs to reclaim their time!

 Preston's Website

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Is busyness holding you back from true productivity and happiness? In this episode of You Winning Life, Jason Wasser welcomes Peggy Sullivan, author of Beyond Busyness, to explore time poverty and how to break free from the addiction to busyness. Peggy shares her three-step busy-busting process, focusing on:

✅ Eliminating low-value transactions
✅ Focusing on intentional micro-moments for happiness
✅ Aligning actions with core values

The conversation dives into time-blocking strategies, redefining success beyond traditional metrics, and the power of community and accountability in achieving personal and professional goals.

Key Takeaways:

🔹 Why busyness is an addiction and how to break free from it
🔹 The three-step process to overcome time poverty
🔹 How to prioritize high-value activities for more fulfillment
🔹 The role of intentional micro-moments in happiness and success
🔹 Practical time-blocking strategies for better time management
🔹 Redefining success beyond traditional career and financial benchmarks
🔹 The importance of community and accountability in achieving goals

Resources & Links:

📖 Get Peggy Sullivan’s book Beyond Busyness: [Click here]
🌐 Learn more about Peggy Sullivan: [Click here]

🚀 If you found this episode helpful, subscribe, leave a review, and share it with someone who needs to reclaim their time!

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In this insightful episode of You Winning Life, host Jason Wasser sits down with serial entrepreneur Jose Berlanga to discuss the essence of entrepreneurship. From pioneering real estate ventures to overcoming the challenges of saturated markets, Jose shares his journey of resilience, adaptability, and vision. Learn how to redefine success, build meaningful partnerships, and embrace the process of failure as a stepping stone to greatness. Whether you’re an aspiring entrepreneur or a seasoned business owner, this episode is packed with actionable wisdom and inspiring stories.

Key Talking Points

1. The Evolution of Entrepreneurship
   • Broader definitions of entrepreneurship beyond just starting a business.
   • Shifting from necessity-driven careers to purpose-driven and passion-fueled ventures.
2. The Traits of an Entrepreneur
   • Balance between creativity, risk tolerance, and business acumen.
   • Importance of self-awareness: knowing strengths, weaknesses, and gaps to fill.
3. Resilience and Adversity
   • Setbacks as a necessary part of success.
   • The process of failing, learning, and adapting in entrepreneurship.
4. Leveraging Partnerships
   • The value of building a team to complement individual skills.
   • Examples of giving equity to partners when starting with limited capital.
5. Industry Insights
   • Real estate and coffee industry case studies: how vision and risk-taking led to success.
   • Challenges of saturated markets and the need for differentiation.
6. Building a Business
   • Preparing mentally and practically for the complexities of business operations.
   • The significance of understanding all components of your industry.
7. The Value of Pioneering
   • Stories of entering uncharted territory in real estate development.
   • The long-term rewards of being a trailblazer in transitional markets.

Motivating Quotes

• “Entrepreneurship is not a quick way to make money—it’s a way to create, help, and solve problems for the world.”
• “Failing and setbacks are not signs of defeat; they are evidence of progress.”
• “It’s not just about being your own boss; it’s about providing value and creating opportunities.”
• “If you’re not leveraging partnerships, you’re trying to outwork an impossible system.”
• “The freedom to act and work on your own terms is the true meaning of success.”

Entrepreneurship journey

Overcoming business challenges

Building successful partnerships

Real estate development insights

Resilience in entrepreneurship

Pioneering new industries

https://joseberlanga.com

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In this thought-provoking episode, Jason Wasser welcomes Anders Indset, a Norwegian philosopher, futurist, and author of The Viking Code: The Art and Science of Norwegian Success. Together, they explore the intersection of consciousness, technology, and human agency, touching on themes such as free will, the illusion of choice, and how cultural perspectives influence our thinking.

Key highlights from their conversation:

The Optimization Paradox: Anders discusses how society has become fixated on binary decisions, instant reactions, and optimization, often at the expense of deeper understanding and collective trust.
Human Agency and Free Will: They examine the balance between individual autonomy and societal programming, questioning how much of our free will we consciously exercise versus what is influenced by external forces.
Technology and AI: Anders shares insights from his forthcoming book The Singularity Paradox and discusses how exponential technological growth challenges our understanding of humanity. They delve into the potential of AI to both enhance and diminish human agency and explore ethical questions surrounding its integration into society.
Humility and Leadership: Drawing from The Viking Code, Anders outlines the importance of values-based leadership and interdependence, advocating for a balance between individual ambition and collective well-being.
Philosophical Inquiry: Jason and Anders engage in a rich dialogue about the nature of consciousness, the limits of human understanding, and the philosophical implications of AI advancements.
This episode blends practical wisdom with deep philosophical musings, encouraging listeners to reflect on the role of technology in shaping the future of human experience.

Resources Mentioned:
The Viking Code: The Art and Science of Norwegian Success
Upcoming book: The Singularity Paradox
Anders’ website: Anders Indset
Instagram: @andersindset

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🚀 Join Us for a Transformative Conversation with Ryan Chute! 🚀

In this episode, we dive deep with Ryan Chute, an expert marketing strategist and partner at Wizard of Ads®. Our discussion challenges the traditional notion of servant leadership, exploring how true growth comes from aligning values vs. beliefs and creating a frictionless experience in both life and business.

Ryan shares powerful insights on the basics of motivation, how healing drives personal and professional growth, and the principles that have shaped his journey in helping businesses achieve exponential success.

If you're ready to rethink leadership, master motivation, and unlock your potential for growth, this conversation is for you!

🎙️ Don't miss this inspiring interview. Be sure to like, comment, and subscribe for more content like this!

Key Points:

1. Shifting from Transactional to Relational:
   • Ryan discusses his evolution from thriving financially in a transactional sales model to discovering fulfillment through relational approaches.
   • Key Idea: Success isn't just about making money but about creating meaningful, value-driven connections.
2. Leadership and Collaboration:
   • True leadership is not about authority but about inspiring others to follow willingly.
   • Leadership involves self-awareness, vulnerability, and collaboration to achieve goals collectively.
   • Key Quote: "The only place we can go to really make this that much more powerful is together."
3. Values vs. Beliefs:
   • Ryan distinguishes between values and beliefs:
     • Beliefs are interchangeable and subjective.
     • Values require sacrifice and are demonstrated through action.
   • Key Quote: "True value is about doing what is inconvenient for you for the benefit of someone else."
4. Gratitude as a Core Principle:
   • Gratitude underpins happiness, success, and meaningful relationships.
   • Key Quote: "Gratitude is the ultimate pursuit of happiness."
5. Friction and Resistance:
   • Friction in relationships and businesses arises from outdated beliefs, assumptions, and survival mode thinking.
   • Identifying and removing friction leads to smoother, more productive interactions.
   • Key Idea: Micro-adjustments and self-awareness can reduce friction and enhance growth.
6. Entrepreneurship as Accountability:
   • Ryan and Jason discuss entrepreneurship as a mindset of complete accountability for outcomes, both in business and personal life.
   • Key Quote (Jason): "An entrepreneur is a person who is entirely accountable for all of their outcomes."
7. The Power of Communication:
   • Effective communication begins with understanding oneself and then connecting with others authentically.
   • Key Idea: Tailoring messages and actions to the individual’s needs creates lasting impact.
8. Coping vs. Thriving:
   • Coping is about survival, while thriving is about self-actualization and growth.
   • The two are not mutually exclusive and can coexist as part of the journey to fulfillment.
9. The Role of Personal Growth:
   • Continuous self-reflection and improvement are essential for e

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Matt Dawson (“Dawson”) is a M&A investment banker, corporate investor and small business operator turned multi-record holding endurance and adventure athlete; sought-after public speaker; lifestyle/performance advisor; and founder of Dawson’s Peak Foundation. Beginning project Seven for Soldiers in May 2021, Dawson set multiple records by rapidly completing a previously unheard-of number of global expeditions (in a single year), including summiting the Seven Summits (the highest peak on every continent); skiing to a pole (South Pole); traversing a desert (Mojave); and rowing across an ocean (Atlantic). Although he was on track to additionally ski to the North Pole and fly a single-engine plane around the world during this same year, his plans were delayed due to the global pandemic and Russia/Ukraine events.

Additionally, Dawson set a new world record in May 2024 by becoming the fastest person to ever cross the Mojave Desert on foot – covering 329.5 miles in 7 days, 8 hours, and 45 minutes (solo and unsupported).
Through project Seven for Soldiers, Dawson has exemplified what is possible when we identify a goal and fully apply ourselves.

Dawson is an avid traveler (35+ countries); licensed motorcycle racer; U.S. Navy qualified “Expert” with pistol and rifle; outdoor enthusiast; and IFR licensed fixed wing (airplane) pilot (currently training to add multi-engine rating). In addition, Dawson is Treasurer for the Los Angeles Circle of Giving (a non-profit organization serving the community by helping individuals and families that are experiencing a challenging life event); and has served as a Mentor for the LEAP Foundation in Los Angeles, CA.

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