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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 how aligning values with financial decisions can transform wealth into a meaningful ally rather than a burden.

They discuss the unique identity challenges faced by inheritors, the central role of fiduciary responsibility, and the importance of proactive communication, legacy planning, and intentional philanthropy.

Key Highlights & Insights

Decoding Financial Jargon — What the Terms Really Mean

• Certified Financial Planner (CFP®): A CFP® serves as a strategic integrator overseeing a client’s entire financial ecosystem — taxes, estate strategy, insurance, investments, and long-term planning — rather than focusing only on asset management.
• Fiduciary Standard: A fiduciary is legally obligated to put the client’s interests first, which often contrasts with institutions whose primary duty is to shareholders.
• Redefining Wealth: Derived from historical roots meaning “well-being” and “health,” true wealth expands beyond finances to include emotional, spiritual, intellectual, physical, and community well-being.

The Human Reality of Inherited & Sudden Wealth

• The “tsunami effect” of sudden financial responsibility often occurs without emotional or practical preparation.
• Paradox of Self-Worth: Entrepreneurs may connect identity to productivity, while inheritors may experience declining self-worth as net worth increases.
• The “Luxury of Doing Nothing” Dilemma: Without survival-driven motivation, inheritors must intentionally create purpose, challenge, and structure.
• Wealth as an Amplifier: Money magnifies existing traits — generosity, anxiety, creativity, or avoidance.

Legacy, Family Dynamics & Proactive Planning

• Fair vs. Equal: Families frequently confuse equality with fairness — and the distinction matters.
• The biggest estate-planning risk is surprise; open, multi-generational dialogue reduces conflict and shock.
• Purpose-Driven Philanthropy: Giving should reflect authentic values — not obligation or performance.

Their approach integrates both technical financial strategy and coaching-informed human insight.

Programs, Resources & Mentions

• The Way Into Wealth Program — An eight-session, one-on-one coaching experience aligning inner values with financial reality.
  Visit: wayintowealth.com
• The Wealth Conservancy — A retainer-based fiduciary advisory firm specializing in complex wealth strategy and stewardship.
  Visit: thewealthconservancy.com | twwcinc.org

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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 explore the growing workplace trend of “quiet cracking”—when professionals, overwhelmed by today’s tough job market, settle for roles that don’t align with their values or strengths, ignoring obvious red flags along the way.

This powerful conversation uncovers the mindset shifts, strategies, and frameworks that can help you navigate career transitions with confidence, advocate for yourself in the workplace, and embrace change without fear.

🧭 What You’ll Learn in This Episode

• Why “quiet cracking” is becoming the new workplace trap—and how it mirrors relationship dynamics
• Red flags to look for (and stop ignoring) when evaluating career opportunities
• The role of self-advocacy in building fulfilling, financially rewarding careers
• How to align your work with your strengths and values through self-audits and strategic career planning
• Eliana’s journey from corporate marketing to career coaching, and how her personal growth shaped her mission
• Practical tools for career clarity: journaling, asking the right interview questions, and building authentic networks
• How to confidently frame career pivots, even when they don’t follow a “traditional” path
• Why evolving your definition of success matters—and how to embrace transitions from technician → manager → entrepreneur

🚀 Episode Highlights

• Quiet Cracking vs. Quiet Quitting — how fear, desperation, and uncertainty push people to take the wrong roles.
• Mindset Shifts — breaking free from imposter syndrome and cultural narratives that keep you stuck.
• Career Fulfillment — Jason and Eliana share stories of how small shifts in perspective can transform both work and relationships.
• Self-Advocacy & Growth — strategies for negotiating roles, realigning job responsibilities, and prioritizing satisfaction over short-term paychecks.
• Career Evolution — embracing change with confidence and redefining what success looks like at each stage.

⚡ Rapid-Fire Takeaways

• One career myth you should stop believing
• The best question to ask before accepting a new job
• One thing to stop doing on LinkedIn right now
• The first action to take in the next 24 hours if you feel stuck
• The career advice Eliana lives by, no matter what

🎧 Listen Now

This episode is for anyone feeling stuck, burnt out, or overwhelmed in today’s job market. If you’re ready to stop ignoring the red flags, advocate for yourself, and design a career that truly excites you and pays you well — this conversation is your roadmap.

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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 forward after setbacks that would have made most people walk away. Before Inked, he helped scale Marquee Jets alongside Jesse Itzler and Ken Dickler. Along the way, he’s lived through both the highs and lows of entrepreneurship while staying rooted in relationships, humility, and service.

In our conversation, Jay talks about his knack for spotting opportunities—what he jokingly calls “desperation”—and how early patterns of escapism shaped his career. We get into his shifting view of happiness: not as something to chase, but as a way of being that comes from deliberate choices, meaningful work, and strong relationships, including nearly three decades of marriage and raising three kids.

Jay also opens up about ego, humility, and why keeping active is essential for his mental health. In his words: “when I sit around and relax, my life gets worse.”

For anyone on the entrepreneurial path, Jay offers practical wisdom:

• Sell your product or service first, before you pour time and money into building it.
• Don’t obsess over the “big idea”—you don’t need to invent something new, just solve a real problem.
• You don’t have to be perfect to start. What matters is truth, self-awareness, and the willingness to take the first step.

As Jay puts it, “You can’t lie to yourself.”

Jay's LinkedIn

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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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