The Burnouts with Phoebe & Sophia

In a captivating discussion with Phoebe Gates and Sophia Kianni, Simon Squibb, a multi-millionaire entrepreneur and founder of the Give Without Take movement, shares his incredible journey from homelessness to success. He reveals how losing his father at 15 reshaped his perspective on life and success. Simon emphasizes the importance of sales skills, authentic relationships, and turning adversity into motivation. He also discusses the real value of mentorship and urges aspiring entrepreneurs to pursue their passions and start now.

In this conversation, Bryan Johnson, an entrepreneur and longevity researcher, shares his quest to become the healthiest person alive after selling Venmo. He dives into biohacking, revealing the staggering $2M he spends annually on health optimization, from blood plasma treatments to rigorous sleep protocols. Bryan challenges hustle culture’s lies, advocates for the power of sleep, and discusses the impact of food toxins on our well-being. His insights encourage a shift in priorities for entrepreneurs towards health and longevity.

Sophia Amoruso, founder of Nasty Gal and author of Girlboss, shares her incredible journey from thrift store seller to CEO. She candidly discusses the meteoric rise and fall of her brand, detailing lessons learned through bankruptcy and recovery. Sophia emphasizes the importance of empathy in leadership and how failure can be a powerful teacher. Now, as an investor with Trust Fund, she redefines success and champions the entrepreneurial spirit, offering invaluable insights on resilience, risk, and making meaningful connections.

Lilly Singh, a comedian, creator, and author, transitioned from an immigrant upbringing to becoming a YouTube sensation. She shares how storytelling serves as a tool for gender equity and the inspiration behind her raunchy sex comedy, Doing It, aimed at normalizing female sexuality. Lilly discusses the challenges of authenticity in the age of algorithms, the importance of connection with her audience, and her commitment to supporting South Asian creators through her initiative, Hyphenate. She emphasizes the value of therapy, negotiating pay, and unlearning the need for likability.

Rainn Wilson, best known as Dwight Schrute from The Office, shares his journey from fame to fulfillment. He reveals how the success of the show didn’t bring him happiness and discusses his battles with burnout. Rainn dives into his transformation through spirituality and mental health practices, highlighting daily routines that ground him. He shares hilarious behind-the-scenes stories from The Office and emphasizes the importance of finding purpose over chasing external milestones. This candid conversation is filled with insights on success, self-acceptance, and meaningful work.

Bobbi Brown, renowned makeup artist and entrepreneur, shares her inspiring journey from a Vogue makeup artist to building a $160M beauty empire. She reveals the secrets behind launching Bobbi Brown Cosmetics, her emotional connection to makeup, and how she successfully navigated a lengthy non-compete. Bobbi candidly discusses her viral TikTok moment, the importance of a supportive partnership with her husband, and her passion for mentoring young women. Plus, her refreshing take on beauty rules that resonate through generations!

Tommy Hilfiger, a fashion designer and entrepreneur, shares his inspiring journey from a young dreamer to building a $9 billion global brand. He opens up about overcoming dyslexia, surviving bankruptcy, and his transformative billboard campaign that catapulted his brand to fame. Hilfiger discusses key collaborations with stars like Beyoncé and Zendaya, the impact of manifestation on his success, and how he views AI shaping fashion's future. He combines raw honesty with invaluable lessons on resilience, family, and creativity.

Anine Bing, a Danish-born model and entrepreneur, transformed her life from selling secondhand clothes to launching a $100M fashion empire from her garage. She shares her early hustle, balancing motherhood while packing orders and navigating naysayers. Anine discusses her viral moments, including collaborations with Kate Moss and the influence of music on her brand. Her mission? To empower women through timeless designs and self-belief. Join her unfiltered journey from Milan to global fashion icon, filled with inspiring lessons on resilience and authenticity.

Gary Vaynerchuk, aka Gary Vee, is an entrepreneur and bestselling author known for his candid approach to success. In a lively discussion, he explains why most influencers will struggle while emphasizing that patience beats hustle. He shares insights on how his immigrant upbringing fueled his work ethic and why $100K can signify 'making it.' Gary delves into the importance of emotional intelligence in leadership, the rise of live shopping, and how AI can enhance creativity—all while challenging traditional definitions of success.

In this captivating discussion, global pop icon Ava Max opens up about her remarkable journey from a first-generation immigrant to a chart-topping star. She reveals the challenges of surviving a predatory music industry and nearly quitting music altogether. Ava also shares the emotional toll of touring, losing her voice at a pivotal moment, and the importance of protecting her energy. With insights about her new album 'Don't Click Play,' she emphasizes resilience, the power of originality, and the significance of empowering women in the industry.