🎗️You Winning Life🎗️

🎗️You Winning Life🎗️

Most people know something is holding them back. They just can't quite name it. You Winning Life is the podcast for high-functioning people who are done settling for "fine" — hosted by Jason Wasser, LMFT, Certified NET Practitioner, and Entrepreneur Coach based in South Florida. With 20 years working with entrepreneurs, athletes (MLB, NBA, USTA), and everyday high-achievers, Jason brings a rare blend of clinical depth and straight talk to the conversations most podcasts are too polished to have. Each episode pulls back the curtain on the patterns, beliefs, and nervous system responses that drive your decisions — at work, in your relationships, and in your own head. Guests include psychologists, performance coaches, wellness experts, and people who've navigated real transformation. No jargon. No toxic positivity. Just the kind of honest conversation that actually moves the needle. Work with Jason → thefamilyroomsfl.com

Episodes

January 1, 2026 47 mins

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In this episode, Jason speaks with Myra Salzer, CFP® & Melissa Hoyer, CFP®, CPCC of The Wealth Conservancy to explore how individuals navigating inherited or sudden wealth can shift from overwhelm to clarity, agency, and purpose. Rather than treating money as a purely financial matter, Myra and Melissa illuminate the emotional, psychological, and relational realities of wealth — and h...

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In this episode, Jason sits down with Eliana Goldstein, a certified career and executive coach, the resident Career Coach for CBS New York Morning News, and a member of the Forbes Coaches Council. Eliana’s coaching strategies have been featured on MSNBC, Business Insider, and Fast Company, and she has spoken at leading companies including Peloton and LinkedIn.

Together, Jason and Eliana ex...

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Today we’re sitting down with Jay Sapovits, founder and president of Inked Stores—a swag company that’s not only grown past $5 million a year in revenue, but has also built more than a thousand online stores for big names like Pen Entertainment, DoorDash, and Crocs.

Jay’s path isn’t just about building successful ventures. It’s about resilience, reinvention, and choosing to keep moving for...

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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®: Simplif...

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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 f...

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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 con...

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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.

T...

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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...

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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 f...

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January 15, 2025 61 mins

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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 p...

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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.

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December 9, 2024 72 mins

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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.
<...

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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 num...

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I met Aleeza around 2002 when we both attended retreats for a Jewish spirituality organization called Isralight. I am so proud of her amazing success as a Matchmaker and her show Jewish Matchmaking on Netflix. 

  • Matchmaking Origins: Aleeza's journey as a matchmaker started organically by setting up friends and recognizing matchmaking as her calling.
  • Vision and Goals: The importance ...
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Welcome to the You Winning Life podcast, your premier destination for mastering a positive existence. In this empowering episode, host Jason Wasser, a licensed marriage and family therapist and certified entrepreneur coach, sits down with the extraordinary Jay Sapovits, founder and president of Inked Stores.

Jay's story is a masterclass in resilience and reinvention. He's a man w...

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Unresolved trauma can dramatically impact our personal lives. But what about professionally? Business leaders with unresolved trauma may eventually find that it cannot only hinder their leadership abilities, but also impact their organization’s bottom line. 

This episodes guest is Kelly L. Campbell (they/she), a certified trauma-informed leadership coach and author of Heal to Lead: Revolut...

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Ty Hoesgen is a top communication coach, #1 best-selling author, and the Founder of Advanced Growth Institute. He helps professionals from around the world communicate with confidence, charisma, and clarity — so they can get more respect, become stronger leaders, and advance their careers. 

Motivated by his past struggles, Ty has spent many years and thousands of hours researching, practic...

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Kendall Wallace is a dynamic leader in the field of marketing and team development, with over a decade of experience driving growth and innovation. As the founder of Executive Offsites, Kendall specializes in creating impactful team-building experiences that enhance employee satisfaction, team cohesion, and communication. Her approach focuses on fostering deep human connections and facili...

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In this enlightening episode, we welcome Allison Guilbault, a Licensed Therapist, International Speaker, and Mindset & Transformation Coach. Allison specializes in helping individuals navigate anxiety, trauma, and intimacy issues through her online practice, Mindful Mental Health out of New Jersey.

Starting off as a researcher for the FBI specializing in Sexual Assault, Allis...

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Discover the transformative power through a profound conversation with Ajit Nawalka, the mind behind EverCoach and the Dharma Coaching Institute. Our dialogue unveils Ajit's inspiring ascent from a crowded household in India to a luminary in the personal growth sphere, underscoring the undeniable influence of mentorship and the pivotal instances where coaching propelled him toward fu...

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