“I worked at Levi’s for 23 years, worked my way all the way up the ladder from entry-level marketing assistant to brand president.”

“I needed to build a factory. And I didn’t have two nickels to rub together or a bucket to piss in but I did have a singleness of purpose to course-correct this thing.”

“We were very different when we first came out and all the other brands looked exactly the same.”

Entrepreneurs don’t just start businesses; they start revolutions. Founders are driven by a deep sense of purpose, an almost reckless determination to build something that doesn’t yet exist. Unlike traditional CEOs who inherit an established structure, founders have to make every decision, carry every risk, and fight through uncertainty with nothing but conviction. The difference? Founders break the rules to create new ones, while CEOs operate within the system to maximize efficiency.

Today’s guests prove that true leadership requires courage. From launching brands that challenge industry norms to rebuilding domestic manufacturing from the ground up, these founders have faced rejection, controversy, and even financial ruin to stay true to their mission. They share stories of taking radical risks, navigating cancel culture, and making decisions that CEOs in corporate boardrooms would never dare to make. The lesson? Bravery in business isn’t optional—it’s the cost of true innovation.

Jen Sey: Former Levi’s President turned founder of XX-XY Athletics, a brand challenging cultural norms and championing women’s sports.

Pete Roberts: Founder of Origin USA, a company reviving American manufacturing through relentless grit and self-funded growth.

Michelle Watson: Founder of MICHI, redefining activewear for women over 40 by prioritizing longevity, strength, and purpose-driven design.

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