Podcast Summary: Design Matters with Debbie Millman

20th Anniversary Celebration Episode

Guests: Krista Tippett, Ira Glass, Hrishikesh Hirway, Kara Swisher, Jad Abumrad
Date: October 27, 2025

Overview

In this milestone episode commemorating 20 years of Design Matters, Debbie Millman brings together some of the most influential voices in podcasting and radio for a reflective, free-flowing series of interview excerpts. Millman turns the tables on people renowned for their own interview skills—Krista Tippett, Ira Glass, Hrishikesh Hirway, Kara Swisher, and Jad Abumrad—to explore not only their creative journeys and the evolution of their craft, but what it means to design a life through storytelling, inquiry, and courage.

Key Discussion Points & Insights

1. Krista Tippett: Spirituality, Journalism, and Humanizing Doctrine

• Restless Curiosity & Worldview Formation
  Tippett recounts her circuitous post-college journey, from reporting in divided Berlin with no guaranteed paycheck to living in several European countries.

  “I was ready to fail and to, like, go home with my tail between my legs. But it worked out, it seems, that.” (05:29)

• Spiritual Inquiry Born Out of Disillusionment
  Disillusioned by self-serving political circles in Berlin, she found meaning not in power but in witnessing dignity among those with fewer material choices. This led to her pursuit of a divinity degree at Yale.

  “I started thinking about that work of creating a life of dignity and beauty. And it was through that kind of an anguished inquiry that I started to ask what I now would call spiritual questions.” (08:26)

• Reinventing the Religious Conversation in Media
  Tippett identified a void in nuanced, human-focused coverage of religion and strove to “humanize doctrine” through oral histories and what would become On Being.

  “Every single one of those conversations was intelligent, thought provoking and fun. And if there's one word that you never use to describe the public religion at that time, it would not be fun.” (13:40)

2. Ira Glass: Finding His Voice, Vulnerability, and Nosy/Noisy Tendencies

• Evolution as an Interviewer and Persona
  Glass describes how changing his appearance paralleled a life transformation, then reflects on his early radio career and efforts to look the part of an adult, despite youthful appearance.

  “I wore a tie every day and it sort of worked… I would get stopped for a hall pass. Like I know I'm an adult.” (16:39–17:30)

• Approach to Interviewing the Famous
  Glass shares his strategy for drawing out authentic responses by making interviews three-dimensional exchanges:

  “An interview is a party that you are throwing and if you are a three dimensional person, it gives the other person the opportunity to be a three dimensional person back.” (18:37)

• On Being a Noisy/Nosy Introvert
  Glass agrees with his sister’s description as a “noisy introvert” and discusses the duality of being outwardly sociable but inwardly drawn to solitude—an archetype common among writers and creatives.

  “They can manage in a social setting and they're okay for a couple of hours, but really where they'd rather be is alone. And that's a lot of my personality, too.” (19:41)

• Magic, Playfulness & Disarming Interview Techniques
  An impromptu segment sees Glass reminiscing about his magic tricks as a teen and making a balloon “Snoopy” live, capturing the spirit of spontaneity in good radio.

  “I do carry around usually a couple of balloons, because sometimes you're in a situation, a reporting situation, or just you're with a friend's kid...” (22:53)

3. Hrishikesh Hirway: Building ‘Song Exploder’ and Defining Creative Ownership

• Turning Career Stagnation into Innovation
  Hirway explains how the format of Song Exploder—creators breaking down their songs—emerged both from his own musical curiosity and the desire for deeper listener experiences.

  “A podcast could be a place where you could kind of combine these things. You could get to explain these ideas, and then you could also hear these things.” (26:00)

• Courage vs. Confidence in Creation
  After rejections from big networks, Hirway did it independently:

  “I don't know which one it was, if it was courage despite a lack of confidence, or if it was in fact confidence. I just knew that it was something that I really wanted, that I would really benefit from if it existed in the world.” (28:45)

• Creative Authorship and Editing Himself Out
  Initially resistant to making his voice prominent in the show, Hirway reflects on creative process and team effort:

  “The thing that I was trying to make was about this artist and their song. So I didn't understand what I needed to even be doing in there.” (31:04) "I want it to feel like it's not about me or my point of view." (31:36)

• Debate on Authorship in Creative Work Millman and Hirway parallel their approach to design and podcast authorship:

  “There's always somebody that's doing the market research and... implementation... So I wouldn't feel comfortable ever saying that I designed that on my own. Because it was just a real group effort.” —Debbie Millman (32:47)

4. Kara Swisher: Loss, Survival, and Radical Candor

• Impact of Childhood Loss
  Swisher recounts how losing her father at five forged a sense of urgency, clarity, and functionality in her approach to life and journalism.

  “When your parent dies at a young age... you get a sense of mortality at a very early age and two is you can survive a lot of stuff.” (38:13)

• Boldness, Detachment, and the Power of ‘No’ Swisher credits her resilience—and ability to end relationships or projects unapologetically—to this early loss.

  “You get like that you have perspective. Yeah, it'll be fine. Everything will be fine. I'll be fine. And I think having kids does give you a sense of vulnerability that you can't avoid.” (41:00)

• No Regrets About Speaking Her Mind
  Swisher proposes a book series called No is a Complete Sentence, reflecting her trademark bluntness, particularly in male-dominated tech spaces.

  “People are like, did you regret that? I'm like, no, no. I liked that. That was fun.” (43:23)

5. Jad Abumrad: Experimentation, Failure, and Finding a Voice

• From Musician to Storyteller
  Abumrad describes his early, accidental foray into radio, driven by a girlfriend’s guidance, and his gradual adoption of audio as storytelling collage.

  “I started volunteering at a radio station... and I just got hooked, like, instantly. I was like, oh, this is what I should be doing.” (45:22–47:09)

• Learning under Benign Neglect
  Hosting Radiolab began as a graveyard-shift experiment where having no listeners was a gift:

  “I'm really grateful because I feel like we all need that period of benign neglect to figure out who we are.” (52:59)

• Rejecting the “Voice of God”
  The show developed a distinctive, informal tone, with Abumrad and co-host Robert Krulwich exploring ideas through genuine conversation and vulnerability.

  “You could kind of, you know, be as stupid as you actually are. And that was the invitation...” (54:57)

• Growing Through Imitation and Failure
  Early episodes mimicked established voices (Ira Glass, Walter Cronkite), but authentic style emerged only through repeated, public trial and error.

Notable Quotes & Moments

• Debbie Millman on Preparation:
  “My job is to craft questions, ask as many of them as time and good sense allows, and pay close attention to the answers. Easier said than done.” (02:48)

• Krista Tippett on Courage:
  “I don't think of myself that way. I think I actually need to give my younger self a little bit more credit.” (05:29)

• Ira Glass on Interviewing:
  “If you are a three dimensional person, it gives the other person the opportunity to be a three dimensional person back. And so that's just an enormously powerful force.” (18:37)

• Kara Swisher on Saying ‘No’:
  “No is a complete sentence.” (42:50)

• Jad Abumrad on Early Experimentation:
  “If you listen to those old episodes, what you will hear is the sound of Radiolab... it’s just all very sort of like throw it against the wall. Very experimental at times because I wasn't a journalist at that point. I was still learning.” (50:28)

Key Timestamps

• [04:38] Krista Tippett discusses spirituality’s relevance and her disinterest in religion during her early career.
• [15:19] Ira Glass recounts changing his look to change his life and how being “noisy” and “nosy” shapes his work.
• [24:59] Hrishikesh Hirway reflects on launching Song Exploder out of creative frustration.
• [37:55] Kara Swisher discusses the impact of losing her father as a child and the resulting boldness in life and work.
• [44:47] Jad Abumrad describes discovering radio through creative wandering and accidental opportunities.
• [52:59] Abumrad reflects on how “benign neglect” in his early career was a blessing for developing his voice.

Memorable & Humorous Moments

• Ira Glass attempts a balloon animal (Snoopy) live at a festival, revealing delightful quirks about mixing radio and childhood talents. (22:22–24:29)
• Kara Swisher imagines being targeted by vengeful tech billionaires—only to discover it’s a fan wanting a selfie. (44:26)

Summary

This special episode celebrates Design Matters’ legacy by peeling back layers on the creative lives of fellow interviewers. These hosts reflect openly on fears, failures, and learning on the job—reminding listeners that mastery is built through experimentation, mistakes, generosity, and real human connection. The conversation serves as a touchstone for anyone interested in storytelling, creative risk, and the authentic voices that shape our culture.