🎗️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
199 episodes
Ep.198- Transforming Wealth into an Ally w. The Wealth Conservancy
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 ...
•
Season 1
•
Episode 198
•
47:20
Ep. 197-Quiet Cracking: Why We Ignore Red Flags in Careers (and How to Stop) w/Eliana Goldstein
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 strategi...
•
Season 1
•
Episode 197
•
52:56
Ep.196- Jay Sapovits: From Marquee Jets to $5M Inked Stores – Entrepreneurship Lessons in Resilience & Growth
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 Entert...
•
Season 1
•
Episode 196
•
55:15
Ep. 195: The Lost Art of Empathy with Jill Robin Payne
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 bui...
•
Season 1
•
Episode 195
•
50:00
Ep. 194- Leadership, Language & Living Fully with Adrian Koehler
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...
•
Season 1
•
Episode 194
•
1:04:09
Ep.193-Becoming an Elegant Adult: Personal Growth, Self-Love, and Embracing Life's Challenges with Scott Fried
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 i...
•
Season 1
•
Episode 193
•
1:03:09
Ep. 192-Mastering the Art of Communication, Negotiation & Personal Growth w/ Michael Reddington
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. ...
•
Season 1
•
Episode 192
•
1:01:12
Ep. 191- Overcoming Trauma & Building Abundance with Preston Smiles
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 fr...
•
45:29
Ep. 190-Beyond Busyness: Overcoming Time Poverty with Peggy Sullivan
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 fr...
•
Season 1
•
Episode 190
•
37:23
Ep. 189- "Be A Pioneer" w. Jose Berlanga
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 saturat...
•
Season 1
•
Episode 189
•
1:01:01
Ep. 188- "Lessons From A Modern Viking" w/Anders Indset
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, techno...
•
Season 1
•
Episode 188
•
1:02:55
Ep.187-Be Frictionless w/Ryan Chute
🚀 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 leade...
•
Season 1
•
Episode 187
•
1:12:10
Ep. 186-"Strength in Surrender" with Extreme Athlete Matt Dawson
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...
•
Season 1
•
Episode 186
•
57:56
Ep. 185- "Getting Real" with Netflix's Jewish Matchmaking Aleeza Ben Shalom
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...
•
Season 1
•
Episode 185
•
1:05:42
Ep. 196- Nice Guys Really Finish First w/ Jay Sapovits
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 wit...
•
Season 1
•
Episode 196
•
55:15
Ep. 184- Please Heal Your Trauma with Kelly Campbell
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...
•
Season 1
•
Episode 184
•
57:39
Ep. 183: Elite Communication Skill with Ty Hoesgen
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, becom...
•
Season 1
•
Episode 183
•
55:21
Ep. 182- Unleashing Team Potential w/Kendall Wallace
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 ex...
•
Season 1
•
Episode 182
•
1:03:37
Ep. 181: Empowered Confidence and Authentic Living with Allison Guilbault
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 he...
•
Season 1
•
Episode 181
•
46:43
Ep. 180-Crafting a Purposeful Life: The Power of Coaching and Mentorship with Ajit Nawalka
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 th...
•
Season 1
•
Episode 180
•
50:55
Ep. 179-Unlocking Genuine Growth Beyond Achievement with Jacob Kaufman
Have you ever wondered why some transformations stick while others fizzle out like forgotten New Year's resolutions? Join us as transformative coach and author Jacob Kaufman unpacks the journey toward authentic change. In a heartfelt discussion...
•
Season 1
•
Episode 179
•
39:41
Ep. 178- Rick Warner's Real Estate Journey Through Neuroscience, Recovery, and Mentorship
Embarking on a personal journey can sometimes feel like navigating a labyrinth; every turn reveals new challenges and insights. That's why we invited Rick Warner, a titan in the real estate industry with a keen interest in neurology and self-im...
•
Season 1
•
Episode 178
•
1:09:37
Ep. 177-Navigating Business Growth and Work-Life Harmony with Eric Esteves
Embark on a transformative journey with us as Eric Esteves, a luminary in the entrepreneurial landscape, unfolds the map to his ascent from a corporate cog to the creator of a bustling mortgage empire. By tuning in, you'll grasp the essence of ...
•
Season 1
•
Episode 177
•
39:55
Ep. 176-Dr. Wendy Trubo's Guide to a Healthier, Stress-Free Existence
Embark on a journey to uncover the subtle yet profound ways stress shapes our existence with Dr. Wendy Trubo, a guiding light in the world of integrative and functional medicine. This conversation is a deep dive into the hidden corners of well-...
•
Season 1
•
Episode 176
•
38:28
Ep.175- Dr. Bobby Grossi's Journey of Leadership, Growth, and Change
Have you ever witnessed a masterful blend of artistry and science? Dr. Bobby Grossi's journey from musician and athlete to revolutionary dentist is just that - a symphony of skill, heart, and entrepreneurial spirit. Join us as we uncover the tr...
•
Season 1
•
Episode 175
•
42:58