Design Better Live AMA at The New York Times – Detailed Summary

Podcast Title: Design Better
Hosts: Eli Woolery and Aaron Walter
Guest: Matt Raw, Interim Head of Design at The New York Times
Release Date: July 9, 2025

Introduction: A New Collaborative Experience [00:02 - 00:43]

In this special live AMA (Ask Me Anything) episode, co-hosts Eli Woolery and Aaron Walter welcome Matt Raw from The New York Times. Unlike their usual format of interviewing guests, Eli and Aaron take the stage to share the story of Design Better. Eli begins by reflecting on their unique experience:

"Matt and the Times design team were curious about the origin story of Design Better, what we've learned about creativity and design after more than 200 interviews and how we approach building our business." (00:14)

Meet the Hosts and Guest [01:38 - 03:23]

Matt Raw provides an in-depth introduction of Eli and Aaron, highlighting their diverse backgrounds:

• Eli Woolery: Trained in product design at Stanford, with a rich history in photography, filmmaking, and industrial design. Formerly the director of design education at Envision and founder of the Design Consultancy Out of the Deep Blue.

• Aaron Walter: A seasoned design and technology leader, he initiated the user experience design practice at Mailchimp, contributed to growth strategies at Envision, and collaborated with public health officials during the Covid-19 pandemic. Author of the influential book Designing for Emotion.

Matt expresses admiration for their work, noting:

"Designing for Emotion is one of the more formative books for me as a designer. Super cool to be able to talk to you, and your guidance has helped the White House, Department of State, dozens of major corporations, startups, and venture capital firms." (02:58)

Origin and Evolution of Design Better [03:23 - 06:04]

Matt Raw delves into the genesis of Design Better, explaining its roots within Envision Design Company before becoming an independent entity in 2023. Eli adds:

"It's come out of a natural curiosity that Aaron and I both have about how do we become better designers, but how do we also just be better creatively in general." (03:45)

Aaron discusses the shift from a focus solely on product design to incorporating broader creative disciplines to keep both the hosts and their audience engaged.

Growth and Impact: Beyond Numbers [05:22 - 06:04]

Eli shares milestone achievements and the podcast's reach:

"At the scale we were, we're sort of found ourselves in the top half percent of all podcasts globally, which seems like a lot, but we're still way smaller than the giants like Joe Rogans." (05:33)

Matt emphasizes the qualitative impact, recounting a listener’s story:

"I heard from a young woman who just entered college, she said she started listening to us in high school and actually convinced her to study design in college. I was like, wow, we are having an impact." (06:04)

Expanding Creative Horizons: Diverse Guest Profiles [06:25 - 09:23]

Eli and Matt discuss their strategy of featuring guests from various creative fields beyond traditional design roles. Eli explains how cross-disciplinary guests like astrophysicist Sarah Seager and humorist David Sedaris offer unique insights applicable to design:

"Working across different fields, they teach us how to speak the language of other disciplines and communicate with people who think differently." (07:14)

Matt adds an example with David Sedaris:

"He's a master of prototyping, constantly observing, doing amazing user research... There's a lot of similarity in how you approach the creative process." (07:58)

Audience Engagement and Community Building [09:34 - 34:44]

The conversation shifts to understanding and nurturing their diverse audience. Matt highlights the variety within their listener base, ranging from students to executives:

"We have people who are not designers. We call them design curious." (10:19)

Eli reflects on the value of content that supports listeners in different career stages, from transitioning roles to leading large teams.

Building Community:

Matt and Eli address the challenges of fostering a genuine community:

"Community suggests some sort of interaction. It's not just a broadcast, it's a dialogue... We're protective of the brand and want to avoid negative interactions common in open forums like Slack or Discord." (32:10)

They discuss initiatives like live events and the DesignBetter directory to facilitate meaningful engagement without the pitfalls of unmanaged online communities.

Incorporating Technology and AI [16:48 - 21:38]

The hosts explore how generative AI has influenced their content creation:

Use of AI:

Eli shares:

"We can feed transcripts into AI to pull out common themes... but it still hallucinates, so you have to double-check things." (17:13)

Matt elaborates on various applications of AI in their workflow:

"We've used it to clean up audio, create proposal language, forecast analytics, and even matchmake job postings with audience profiles." (19:29)

Maintaining Human Touch:

Despite AI integration, both agree that human judgment remains crucial:

"Our roles as creatives may become more the producer, curator, the editor... Our taste is very important." (20:06)
"Taste comes from years of experience... We have to be the ones based on the breadth of our human experience to create something that resonates." (20:06)

Future Plans and Vision [36:04 - 37:18]

Looking ahead, Eli and Matt outline their ambitions to expand Design Better:

• Books Library: Releasing a series of books on topics like design systems, design operations, and the business of design.

• Partnerships: Collaborating with companies to offer premium members exclusive software tools.

Matt emphasizes their commitment to providing value by understanding and meeting audience needs:

"How do you build community? How do you keep an audience around, be useful, recognize what are people's interests, what are people's problems... meet them where they are." (36:31)

Audience Q&A Highlights [37:57 - 49:04]

1. Staying Inspired [38:24 - 40:17]

• Eli: Finds inspiration through his children’s music choices, discovering new sounds that he incorporates into potential future episodes (38:24).
• Matt: Emphasizes continuous learning through activities like playing jazz guitar and practicing Jiu-Jitsu with his son, which engage different parts of his brain and connect diverse interests to creative processes (38:55).

2. Recharging Amidst Creation [40:35 - 42:10]

• Matt: Incorporates personal time by waking up early for meditation and writing, viewing passionate work as a way to recharge (40:56).
• Eli: Balances work by spending time outdoors surfing, hiking, and mountain biking, essential for recharging his creative energies (41:30).

3. Favorite New York Times Products [46:38 - 49:04]

• Matt: Loves the Games app for its ability to connect generations and provide stress-relief through interactive puzzles and word games. He shares personal anecdotes about gifting subscriptions and the positive impact on his family (46:38).
• Eli: Also favors the Cooking app for its intergenerational value, using recipes as a means to connect with his parents through shared culinary experiences (48:50).

Closing Remarks [49:03 - 50:23]

Eli and Matt wrap up the episode by thanking Matt Raw for his participation and highlighting how viewers can connect with them through @designbetterpodcast.com. They encourage listeners to share the podcast and leave reviews to aid in its discovery.

Notable Quotes:

• Eli Woolery:
  "We're passionate about creativity. Where is creativity? It's in all the places you look for it." (38:41)

• Matt Raw:
  "Taste comes from years of experience. We have to be the ones based on the breadth of our human experience to create something for other humans to enjoy that resonates." (20:06)

• Eli Woolery:
  "This is DesignBetter, where we explore creativity at the intersection of design and technology." (00:33)

Conclusion

This live AMA episode of Design Better at The New York Times offers a rich exploration of the podcast’s journey, its impact on a diverse audience, and the innovative ways Eli Woolery, Aaron Walter, and Matt Raw are pushing the boundaries of design and creativity. Through insightful discussions and personal anecdotes, listeners gain a deep understanding of the importance of cross-disciplinary learning, the integration of AI in creative processes, and the continuous effort to build a supportive and engaged community.