Circle This

In this special episode, Dre sits down with her 16-year-old son, the one and only Strummer James Rouse, for a tender, funny, and surprisingly profound look into the emotional world, entrepreneurial drive, and connection language of Gen Z.

Later, they're joined by Strummer's friend and collaborator, 19-year-old entrepreneur Jack Jiang, for an eye-opening second chapter on credibility, reputation, and the real cost of building a brand at a young age.

Sitting together in Tribeca, Dre and Strummer talk about everything from change-of-scenery magic ("even the rain lights me up") to why his generation is struggling with loneliness, and how ego, emotional fear, and screen culture all play a role. For Strummer, texting has become a kind of safe frequency, a channel where vulnerability is easier, and where emotional truth feels less risky.

Raised in circles and supported by a charter school that prioritized emotional intelligence over grades, Strummer shares the early trainings that shaped him: learning to listen, to sit in presence, to share from the heart. He reflects on Covid as a turning point, the blessing and complexity of screen-based connection, and how fashion, and the stories behind what we wear create belonging.

Dre also takes us inside Strummer's entrepreneurial world: Selling his first shoe at nine. Landing his first job at thirteen by boldly walking in and saying, "What's it going to take for me to work here?"

Understanding that people aren't just buying clothes, they're buying the story, the experience, the connection.

Then Jack joins, sharp, vulnerable, and wise beyond his years. He talks about the pressure of growing up online, why reputation is everything, the art of paying attention to details, and how social credibility can make or break a business. He shares the story of opening his first appointment-only showroom at nineteen and explains the trend-based heartbeat of the fashion world.

This episode is a window into Gen Z's emotional landscape, their honesty, their hustle, their heart, and a reminder that connection really is the currency that never loses value.

Follow: @strummer.rouse @saturdayservicepodcast @legossssssssss

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Stay connected with the Circle This team:

@andreabendewald @circlethispodcast

@emkratter @goodmessmedia @talkwithtrace

For sponsorship inquiries: [email protected]

In this episode, Dre welcomes storyteller and community-builder Tylah Jordan for full circle conversation about the unexpected pregnancy that changed the entire trajectory of her life.

Tylah opens up about discovering she was pregnant just one month into a new relationship, while navigating the weight of secrecy, shame, and a religious upbringing where she had never known anyone who became a mother outside of marriage. What could have been an isolating chapter instead became the doorway into a new identity, a deeper spiritual maturity, and the beginnings of Unfiltered Motherhood, the platform she now uses to support and anchor mothers in a world that often leaves them feeling alone.

Dre and Tylah circle around the real initiation of motherhood, the profound beauty, the need for connection and the parts rarely posted about, up until now.

Tylah shares effortlessly about her earlier experiences that shaped her, moving to LA at 18, financial separation from family, surviving sexual assault, toxic overload, and a period of being stalked that rewired her sense of safety.

These chapters became the soil of her spiritual awakening and the reason she felt drawn to women's circles years before she became a mother herself.

In one of the most beautiful full-circle moments, Tylah reveals how a meditation class she found on Instagram led her back to Dre, the same woman who facilitated her first-ever circle at The Den Meditation six years earlier, the circle that sparked her entire spiritual path. You couldn't script a more FULL circle moment!

This episode is a reminder that motherhood is not just about raising a child, it's about meeting the woman you're becoming. And that when one mother is supported, an entire family and the next generation is positively effected.

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Stay connected with the Circle This team: @andreabendewald @circlethispodcast

@emkratter @goodmessmedia @talkwithtrace

For sponsorship inquiries: [email protected]

Recorded in New York City where it all began, Dre and Em reflect on how everything in life unfolds in systems, patterns, seasons, and cycles.

They circle around their love–hate relationship with social media, exploring the irony of creating a podcast about connection while spending so much time in virtual spaces and what happens to our nervous systems, creativity, and sense of belonging when we finally gather in person.

They also touch on the rise of "outsourced intimacy" from dating apps to digital wellness and how we're losing the art of being with one another. Together, they reframe what's "hard," remind us that giving and receiving are two sides of the same gift, and share stories that reveal how mindset creates reality.

They end with a call to connection: step away from the screen, gather your people, and create an opportunity to engage with one another in real life. Because luck and love aren't random. We create them.

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Stay connected

with the Circle This team:

@andreabendewald @circlethispodcast

@emkratter @goodmessmedia @talkwithtrace For sponsorship inquiries, email: [email protected]