Tech journalist Kara Swisher discusses her career, reflections on loss and assertiveness, childhood aspirations and disillusionment, the transition to the internet, women and money in the workplace, and admiration for tech industry figures.

Jad Abumrad, MacArthur Fellow and creator of Radiolab, discusses the early days of editing, the meaning of 'OG', the best techno song, growing up in Nashville, the success of Radio Lab, the state of podcasting, and his personal identity.

Mary Ellen Matthews, the chief photographer for Saturday Night Live since 1999, discusses her career and how she creates the distinctive look for the show's images. She shares insights into capturing great shots, talks about her upbringing in Madison, New Jersey with her photographer father, and reflects on her athletic journey. The chapter also explores her experiences in the music industry, photographing Paul McCartney, shooting photographs for weddings and rock and roll tours, and creating memorable moments through photography.

Design royalty Paula Scher, Emily Oberman and Michael Bierut celebrate the 50th anniversary of Pentagram. They discuss the unique structure and success of Pentagram, the power of a strong work culture, the partner-owned business model, competition and inspiration in the industry, the adoption of successful systems, and the unique culture and identity of Pentagram.

Kevin Kelly, digital visionary and bestselling author, talks about the connection between technology and creativity, the significance of a deep balcony or porch, the evolution of symbols and branding, embracing mortality, using technology and social media, the origin and purpose of 'Excellent Advice for Living', minimizing deathbed regret, and the power of fully becoming yourself.

For over sixty years, Gloria Steinem has been at the center of American culture and political life, where she has been instrumental in shaping our ideas about feminism, humanity, and equal rights for all people. She joins to talk about her legendary career as an award-winning journalist, New York Times best-selling author, co-founder of one of the most significant magazines of the 21st century, and an activist whose work has impacted the place women and girls now have in the world.

Jessica Nordell, science and cultural journalist, talks about unconscious bias and ways to eliminate it. They discuss the denial of opportunities for women, storytelling from witchcraft accusations to political contrasts, personal experiences with bias in the workplace, running simulations to analyze gender imbalance, standardizing criteria and checklists to interrupt bias, and exploring anger, grief, and bias.

Steven Heller, legendary writer and author, shares entertaining stories about his coming-of-age in New York's youth culture. Topics include involvement in the hippie porn industry, unconventional parenting choices, writing a memoir, finding solace through reading Russian literature, and the creation and downfall of the New York Review of Sex.

Author of the bestselling book “Queenie”—Candice Carty-Williams joins a very special guest host, Roxane Gay, to talk about her latest novel “People Person” which follows the Pennington family, a cadre of five half-siblings forced together in the wake of a dramatic event.

Chris Evert, legendary tennis player and jewelry designer, discusses her groundbreaking career in tennis and her recent creative endeavor in jewelry design. The podcast covers topics such as Evert's disciplined approach to winning, her talents as a commentator, the influence of her tennis coach father, factors contributing to a tennis victory, resilience and mindset in tennis, and her personal journey with ovarian cancer.