Jack Schlossberg—writer, lawyer, political correspondent, and the only grandson of President John F. Kennedy—joins live at the On Air Fest to discuss political legacy, internet culture, and the future of Democratic leadership. With humor and candor, he reflects on growing up in a historic political family, the power and peril of social media, the spread of misinformation, and why authenticity and risk-taking are essential to reaching a new generation of voters.

Kim Hastreiter—co-founder and longtime editor of Paper magazine—joins to reflect on a life at the center of downtown New York’s art, fashion, and nightlife, from scrappy newsprint beginnings to the cover that “broke the internet.” She also discusses her memoir, Stuff: A New York Life of Cultural Chaos, and why artists must document culture before it’s rewritten.

C. Thi Nguyen—philosopher, professor, and author of Games: Agency as Art—joins to discuss his new book, The Score: How to Stop Playing Somebody Else’s Game, and how metrics, from grades to likes, quietly reshape what we value and who we become. Together, they explore games as “libraries of agency,” the allure of scoring systems, and the vital question: Is this the game you really want to be playing?

Quiara Alegría Hudes is a Pulitzer Prize–winning playwright, composer, and novelist whose work has reshaped contemporary American theater. The co-creator of In the Heights and author of Water by the Spoonful, she has consistently explored identity, family, and belonging across theater, music, memoir, and now fiction in her new book, The White Hot.

Chris Duffy—comedian, writer, and host of the TED podcast How to Be a Better Human—joins to discuss how humor shaped his path from teaching and improv to podcasting and television. Together, they explore why laughing more isn’t about being funny, but about attention, vulnerability, and connection, and how humor helps us stay human.

Ruth Ann Harnisch is an investor, philanthropist, social activist, media producer, and founder of Harnisch Foundation, which supports work that breaks down barriers to equality and opportunity. She joins CreativeMornings live to reflect on her path from teen broadcaster to first female anchor, and how finding her voice in inequitable newsrooms shaped everything that followed.

Brian Chesky is the co-founder and CEO of Airbnb, a company that began with airbeds and grew into a worldwide community built on trust and belonging. He joins to discuss how imagination and design shaped his path from art school to entrepreneurship, and what it means to design the world you want to live in.

For the 20th anniversary of Design Matters, Debbie Millman revisits excerpts from her most memorable interviews. Featuring Jason Reynolds, Marina Abramović, Chris Ware, Richard Saul Wurman, Rick Rubin, and Roxane Gay, this episode gathers voices that challenged, surprised, and have continued to evolve in meaning over time.

For the 20th anniversary of Design Matters, Debbie Millman revisits conversations with renowned poets Eileen Myles, Elizabeth Alexander, Sarah Kay, and Amber Tamblyn. These excerpts reflect on language, identity, memory, and the lived experience that fuels their work. Together, they reveal poetry as an intimate practice that resonates beyond the page.

For the 20th anniversary of Design Matters, Debbie Millman revisits conversations with distinguished actors Claire Danes, Ethan Hawke, Nick Offerman, Kyra Sedgwick, and Josh Brolin. These excerpts explore how they approach their craft, work with directors and fellow actors, and what it means to inhabit a role and sustain a creative life on stage and on screen.