The Hidden Entrepreneur Show with Josh Cary

If you have ever wondered what truly high level leaders are craving behind the polished LinkedIn profiles and impressive titles, this conversation pulls back the curtain. This is the inside story behind a remarkable day when seven vYve members, leaders, and entrepreneurs across a range of industries came to the New York iHeart Studios for a full immersive experience. Together, they workshopped their messaging, clarified their stories, and stepped up to the mic for one on one interviews that captured their insight, energy, and personality.

In this kickoff episode, Andrea Sullivan and James Orsini share how vYve by Vayner was created to support executives and entrepreneurs who feel lonely, stretched, and stuck at the very moment they are expected to have it all figured out. You will hear how the iHeart day came together, why it became a breakthrough moment for the group, and what it revealed about the power of community, confidence, and storytelling. This episode sets the stage for the individual conversations that follow, each one showcasing a different vYve member and the work they are doing in their world.

What You’ll Learn in This Episode

• How vYve by Vayner emerged during the uncertainty and emotional weight of COVID

• Why even the most impressive leaders quietly struggle with loneliness and burnout

• How Andrea and James built vYve around community, accountability, and personal breakthroughs

• What makes vYve’s mix of entrepreneurs and Fortune 500 leaders so unique

• How the iHeart studio day became a podcast playground for seven vYve members

• Why shaping your message is as important as knowing your story

• The concierge style support vYve offers, including curated connections and expert guidance

• How vYve measures progress, momentum, and personal transformation

• Who vYve  is for and how to know if the program is the right next step for you

About Today’s Guests

Andrea Sullivan is the CEO of vYve by Vayner and a long time marketing leader who served as chief marketing officer for Gary Vaynerchuk for more than six years. She co founded vYve to help leaders grow their businesses while also becoming healthier, happier humans.

James Orsini is the President of Startup Operations at VaynerX and a trusted operator who has helped launch multiple companies and offerings within the Vayner ecosystem. As co founder of vYve and its lead business and personal coach, James focuses on strategy, accountability, and connecting members with the right resources to move forward with clarity and confidence.

...

The vYve Thrive Series

Stories about the unlocking of dreams that lead to business and personal growth… ignite YOUR thrive.

The vYve Thrive podcast series was born from a simple vYve NYC meetup—an intimate gathering centered around charting our dreams and finding our true voice. What began as a small circle of leaders quickly evolved into something much bigger: founders, creators, and executives opening up, shedding old limits, and discovering what becomes possible when you allow yourself to be seen and heard.

At vYve, we are more than a business-growth mastermind. We are a community grounded in honesty, courage, and the belief that our dreams—big or small—are meant to be pursued together and made real.

Through our work at the New York Summit in October with The Podcast Playground, these stories now have an even broader platform to resonate, inspire, and remind others that their next chapter is entirely within reach.

If you’re feeling the pull to explore your next chapter, we would love to hear from you.

Reach out to us on social @thrivewithvyve on IG or just @vYve on Linkedin!

This is vYve Thrive—where leaders chase their dreams, claim their voice, and ignite the spark for others to do the same.

Retirement is supposed to feel freeing, but for many people it becomes disorienting, lonely, and far from the dream they imagined. Recorded live inside the iHeart Studios in New York, Sylvia Toense shares how a frightening health scare at 58 pushed her to rethink everything, leave her corporate career, and develop a framework that helps others thrive in their next life chapter.

If you want clarity, purpose, better health, stronger relationships, and a plan you can actually put into practice, this conversation gives you the roadmap. Retirement is not an ending. It is a shift. And Sylvia shows you exactly how to navigate it.

What You’ll Learn in This Episode

• The most common patterns among people who retire and feel unhappy

• Why losing work based friendships leads to loneliness and depression

• How Sylvia’s cardiac wake up call changed her life priorities overnight

• The practical steps she took to design her next chapter with intention

• Why people need more self reflection before they retire

• How to experiment with retirement through small trials, hobbies, and test runs

• Why purpose matters more than the idea of “free time”

• The biggest trap people fall into and how to avoid it

• Why planning for friendships, health, and meaning is more important than finances alone

About Today’s Guest

Sylvia Toense is the author of The Shift Playbook and a mentor for individuals preparing for retirement or major life transitions. After a successful 25 year career in financial services, a health crisis forced her to reassess her priorities and rethink her future. Today, she helps people design a purposeful, energizing, and connected life after leaving full time work, guiding them through mindset shifts, planning exercises, and practical steps for thriving in their next chapter.

...

The vYve Thrive Series

Stories about the unlocking of dreams that lead to business and personal growth… ignite YOUR thrive.

The vYve Thrive podcast series was born from a simple vYve NYC meetup—an intimate gathering centered around charting our dreams and finding our true voice. What began as a small circle of leaders quickly evolved into something much bigger: founders, creators, and executives opening up, shedding old limits, and discovering what becomes possible when you allow yourself to be seen and heard.

At vYve, we are more than a business-growth mastermind. We are a community grounded in honesty, courage, and the belief that our dreams—big or small—are meant to be pursued together and made real.

Through our work at the New York Summit in October with The Podcast Playground, these stories now have an even broader platform to resonate, inspire, and remind others that their next chapter is entirely within reach.

If you’re feeling the pull to explore your next chapter, we would love to hear from you.

Reach out to us on social @thrivewithvyve on IG or just @vYve on Linkedin!

This is vYve Thrive—where leaders chase their dreams, claim their voice, and ignite the spark for others to do the same.

If you have ever wondered whether calm, connected parenting actually works, Avery Rubenstein is living proof. As the adult child of parenting expert Randi Rubenstein, Avery grew up in a home built on perspective seeking rather than punishment.

In this conversation, recorded live at iHeart Studios in New York, Avery shares how that upbringing shaped her confidence, empathy, and calling as a social worker working with foster youth. This episode gives you a deeply human look at what happens when a child is heard, understood, and treated like a whole person.

What You’ll Learn in This Episode

• What it feels like to be raised in a home without yelling and why that matters

• How perspective seeking creates emotional safety for both parent and child

• Why Avery realized as an adult that her childhood was very different from the norm

• The moment Avery recognized the impact of their upbringing while babysitting

• How children sense when adults are truly listening

• The surprising behavior shifts that happen when a child is given choice

• What Avery has learned working with foster children who have experienced trauma

• A simple but powerful message for parents who want to do better

About Today’s Guest

Avery Rubenstein is the co-author of a children’s book series developed with their mother, parenting expert Randi Rubinstein. Avery is pursuing a master’s degree in social work and works in foster care settings, helping children process difficult emotions through play and perspective-based communication. Her work is centered on helping kids feel heard, respected, and understood.

...

The vYve Thrive Series

Stories about the unlocking of dreams that lead to business and personal growth… ignite YOUR thrive.

The vYve Thrive podcast series was born from a simple vYve NYC meetup—an intimate gathering centered around charting our dreams and finding our true voice. What began as a small circle of leaders quickly evolved into something much bigger: founders, creators, and executives opening up, shedding old limits, and discovering what becomes possible when you allow yourself to be seen and heard.

At vYve, we are more than a business-growth mastermind. We are a community grounded in honesty, courage, and the belief that our dreams—big or small—are meant to be pursued together and made real.

Through our work at the New York Summit in October with The Podcast Playground, these stories now have an even broader platform to resonate, inspire, and remind others that their next chapter is entirely within reach.

If you’re feeling the pull to explore your next chapter, we would love to hear from you.

Reach out to us on social @thrivewithvyve on IG or just @vYve on Linkedin!

This is vYve Thrive—where leaders chase their dreams, claim their voice, and ignite the spark for others to do the same.

If you have ever found yourself stuck in a cycle of tough conversations, shutdowns, and frustration with your kids, this episode is your blueprint out. Recorded live inside the iHeart Studios in New York, Randi Rubenstein shares her simple, powerful SAP framework for having productive conversations with strong-willed children.

Instead of lecturing, reacting, or pushing too hard at the wrong moment, Randi shows parents how to see their child’s perspective, actively listen, and problem solve together. If you want more connection, cooperation, and confidence in your parenting, this conversation delivers the tools you need.

What You’ll Learn in This Episode

• Why the timing of tough conversations matters more than parents realize

• What dysregulation looks like in kids and how to help them re enter a calmer state

• How the SAP method works and why it transforms communication

• Why empathy is the hidden key to productive conversations

• How active listening reduces defensiveness and opens your child up

• How prompting kids with the right questions helps them solve their own problems

• Why ego, fear, and old school parenting habits get in the way

• How Randi’s new children’s books help parents practice connection through story

• The core belief Randi hopes every child learns: you are worthy of exquisite care

About Today’s Guest

Randi Rubenstein is the founder of Mastermind Parenting, a coaching and education company focused on helping parents communicate more effectively with strong-willed children. A respected voice in conscious parenting, Randi teaches practical frameworks for connection, accountability, and emotional safety. She is currently developing a series of children’s books designed to spark productive conversations at home.

...

The vYve Thrive Series

Stories about the unlocking of dreams that lead to business and personal growth… ignite YOUR thrive.

The vYve Thrive podcast series was born from a simple vYve NYC meetup—an intimate gathering centered around charting our dreams and finding our true voice. What began as a small circle of leaders quickly evolved into something much bigger: founders, creators, and executives opening up, shedding old limits, and discovering what becomes possible when you allow yourself to be seen and heard.

At vYve, we are more than a business-growth mastermind. We are a community grounded in honesty, courage, and the belief that our dreams—big or small—are meant to be pursued together and made real.

Through our work at the New York Summit in October with The Podcast Playground, these stories now have an even broader platform to resonate, inspire, and remind others that their next chapter is entirely within reach.

If you’re feeling the pull to explore your next chapter, we would love to hear from you.

Reach out to us on social @thrivewithvyve on IG or just @vYve on Linkedin!

This is vYve Thrive—where leaders chase their dreams, claim their voice, and ignite the spark for others to do the same.

When the world shut down in 2020, most event and influencer marketing firms folded. Mark Zablow’s agency not only survived, it thrived while serving one of the brands hit hardest by the pandemic: Corona.

Recorded live inside the iHeart Studios in New York, Mark shares how he navigated the collapse of live events, protected his employees, stayed culturally relevant, and positioned his company for explosive growth through Modelo. This is a masterclass in resilience, creativity, and entrepreneurial instinct. If you want a real look at how leaders turn crisis into opportunity, this is the conversation.

What You’ll Learn in This Episode

• What it was like to run Corona’s experiential marketing during the coronavirus outbreak

• How Mark kept his team employed when events disappeared overnight

• Why long term thinking matters when short term chaos hits

• How Modelo became the brand opportunity hiding inside the crisis

• The strategy behind one of the first large scale digital events of 2020

• Why influencer marketing works and how brands misuse it

• How communities, not campaigns, create lifelong customers

• Why Bleecker Trading was launched during the worst retail moment in NYC

• The entrepreneurial mindset that spots opportunity where others see barriers

About Today’s Guest

Mark Zablow is the founder of Cogent World, an influencer and event marketing agency with a decade-long track record serving some of the biggest brands in the world. He is also the founder of Bleecker Trading, a lifestyle collectibles and trading card brand based in New York City. Mark is known for turning challenges into momentum, building communities around brands, and leading with strategic clarity in uncertain times.

...

The vYve Thrive Series

Stories about the unlocking of dreams that lead to business and personal growth… ignite YOUR thrive.

The vYve Thrive podcast series was born from a simple vYve NYC meetup—an intimate gathering centered around charting our dreams and finding our true voice. What began as a small circle of leaders quickly evolved into something much bigger: founders, creators, and executives opening up, shedding old limits, and discovering what becomes possible when you allow yourself to be seen and heard.

At vYve, we are more than a business-growth mastermind. We are a community grounded in honesty, courage, and the belief that our dreams—big or small—are meant to be pursued together and made real.

Through our work at the New York Summit in October with The Podcast Playground, these stories now have an even broader platform to resonate, inspire, and remind others that their next chapter is entirely within reach.

If you’re feeling the pull to explore your next chapter, we would love to hear from you.

Reach out to us on social @thrivewithvyve on IG or just @vYve on Linkedin!

This is vYve Thrive—where leaders chase their dreams, claim their voice, and ignite the spark for others to do the same.