Max Levchin, co-founder of PayPal and founder of Affirm, shares his journey from Soviet Ukraine to Silicon Valley's tech scene. He discusses the formation of PayPal with notable figures like Elon Musk and the challenges they faced, including Musk's ouster as CEO. Levchin reflects on the intense work culture and pivotal moments in the company's rapid growth, driven by innovation. His transition to entrepreneurship after PayPal's acquisition by eBay showcases his relentless drive to create impactful fintech solutions.

Lyndon Cormack, co-founder of Herschel Supply Co., shares insights with early-stage founders seeking success. They dive into crafting compelling brand stories that resonate with customers. Topics include the innovation behind FloorDrobe for decluttering clothes and the unique challenges of designing nursing bras. Lyndon emphasizes adaptability in entrepreneurship, offering practical advice on marketing strategies and staying relevant in a competitive market. This discussion blends personal experiences with actionable insights, inspiring listeners to forge their paths.

Monica Lewinsky shares her journey of reclaiming her narrative and redefining her public image. She engages with guests who discuss overcoming adversity and finding purpose after personal struggles. Emotional turmoil and the challenges of unhealthy relationships are explored through honest reflections and insights. The conversations aim to empower individuals to take back their power and transcend their vulnerabilities, fostering a sense of resilience and connection.

Barry Turner, co-founder of Lenny & Larry's, shares his inspiring journey from American Gladiator to protein snack innovator. He discusses the early days of protein muffins in the 90s and how they stumbled upon the idea of protein-rich baked goods. Barry reflects on the challenges of scaling their brand and the whimsical evolution of their logo. He also reveals his motivation for returning to Lenny & Larry's to revive the brand and introduce new products, demonstrating resilience and a commitment to health-focused snacks.

Ariel Kaye, founder of Parachute Home, leads an insightful discussion with guests Daen Brown, co-founder of King Brown Pomade, and Deanna Blasi-D, founder of Mindset Tapestry. They tackle smart strategies for brand growth, with Daen seeking investment after a decade of self-funding while navigating the grooming market's challenges. Deanna shares her journey of creating an emotional health tool for children, emphasizing the impact of affirmations and effective marketing strategies. The conversation also highlights women breaking barriers in male-dominated industries.

Monica Nassif, the innovative founder of Mrs. Meyer's Clean Day, shares her incredible journey in the cleaning product industry. She creatively shifted from an upscale brand to making her products accessible, targeting chains like Target. The importance of family influences shines through, especially how her mother became a beloved mascot. Monica discusses the delicate balance of launching new products and the critical lessons learned about timing in retail. Her insights into blending nostalgia with modern branding reveal the heart behind her successful venture.

Travis Boersma, co-founder of Dutch Bros Coffee, and Sean Chang, co-founder of Mukja Korean Fried Chicken, share invaluable entrepreneurial insights. They discuss the journey of transforming a simple espresso cart into a national coffee chain, tackling challenges like rising costs and competition. Sean highlights creative marketing strategies for his restaurant, while both guests emphasize the power of word-of-mouth in boosting customer growth. The conversation also touches on the importance of resilience and adaptability for new founders in today’s ever-changing market.

Michelle Wahler, co-founder of Beyond Yoga, shares her inspiring journey in creating an inclusive activewear brand. She discusses the challenges of starting the company with no outside investment and her focus on soft fabrics and body positivity. Wahler emphasizes the importance of strategic hiring and building a strong team, alongside innovative growth strategies. She also reflects on key moments, including a pivotal e-commerce shift and the brand's lucrative acquisition by Levi’s for $400 million, showcasing the blend of resilience and leadership in her entrepreneurial path.

Vicky Tsai, co-founder and former CEO of Tatcha, shares her entrepreneurial journey from finance to skincare, inspired by Japanese beauty rituals. She discusses stepping back into her CEO role and the lessons learned. Brittany Lowe talks about launching her vegan skincare line, focusing on intimate health and the importance of storytelling. Devon Clymer shares insights about her gluten-free mug cake business Mugsy Bakes, including clever marketing strategies. Each guest offers unique perspectives on overcoming challenges and building brand awareness.

Sam and Mariah Calagione, co-founders of Dogfish Head Craft Brewery, share their inspiring journey from high school sweethearts to craft beer pioneers. They discuss innovative brewing techniques and the use of quirky ingredients like cherries and licorice. With humorous anecdotes from their early days, including writing a bill to legalize their brewpub, they reflect on community support and the unique identity of craft breweries. Their remarkable story also touches on the challenges and triumphs that led to their brewery's impressive growth and eventual acquisition.