Start Now, Why Wait: Gen Z Truth & Entrepreneurship with Strummer Rouse & Bonus Guest Jack Jiang

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

 

 

--

 

 

Stay connected with the Circle This team:

@andreabendewald @circlethispodcast

@emkratter @goodmessmedia @talkwithtrace

For sponsorship inquiries: [e-mail]