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Design Better

Design Better

By: The Curiosity Department
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Design Better co-hosts Eli Woolery and Aarron Walter explore the intersection of design, technology, and the creative process through conversations with guests across many creative fields, helping you hone your craft, unlock your creativity, and learn the art of collaboration. Whether you’re design curious or a design pro, Design Better is guaranteed to inspire and inform. Vanity Fair calls Design Better, “sharp, to the point, and full of incredibly valuable information for anyone looking to better understand how to build a more innovative world.”© The Curiosity Department, LLC 2026 Art Economics
Episodes
  • Blaine Billingsley: OpenAI designer on the collaboration problem AI hasn't solved yet, and why the best way to have influence is to be influenced

    Blaine Billingsley: OpenAI designer on the collaboration problem AI hasn't solved yet, and why the best way to have influence is to be influenced
    Sep 23 2026
    Blaine Billingsley is a staff designer at OpenAI, and his path there was anything but a straight line. He studied music composition and comparative religion, played guitar in Texas for a living (he remembers checking his bank account, seeing seven dollars, and feeling pumped), then drove to San Francisco and took a data entry job at a startup. This is a preview of a premium episode. To listen to the whole thing, join our premium membership on Susbtack: https://designbetterpodcast.com/p/blaine-billingsley The engineers taught him to script his way through the work in a couple of hours, and he spent the rest of the day learning from them. From there he went on to companies big and small, including a long run on Gmail. Blaine has an allergy to corporate jargon that we found interesting. He’s known amongst his colleagues for rewriting product specs to get absolute clarity on a project, and for raising his hand in meetings to ask, “what do we really mean by ‘create a command center for work’”. We talk about why a design principle only helps if you could reasonably disagree with it, and his counterintuitive advice for working with a pushy PM: the best way to have influence is to be influenced. Then we get into how design actually works inside OpenAI. Blaine walks us through what goes into an eval, and the product design plugin he built with one engineer, whose biggest fans turned out to be the PMs and engineers who were starved for a design partner. Bio Blaine Billingsley is a member of the design staff at OpenAI, where he works on making ChatGPT a daily tool for designers and built a product design plugin focused on translation workflows like image-to-code. Before OpenAI, he was a Product Design Architect at Slack and a Staff Experience Designer at YouTube, and earlier held design roles at Airbnb, where he created a system of Host Guides, and Google, where he worked on Inbox by Gmail. He was also the sole designer at Pattern Technologies, an AI-powered sales startup acquired by Workday. Blaine studied music composition and comparative religion, played guitar professionally in Texas, and got his start in tech doing data entry at a San Francisco startup. He's known for his allergy to jargon, his love of a clear process, and his belief that a designer's job is to represent the user. Books & links mentioned Show notes Blaine Billingsley blaineb Blaine Billingsley — Design Mentor @blaineranium The Systems Bible The OpenAI Product Design Plugin Mid-air Thief Vargamae: Volume I of the Truth and Justice Pentalogy *** Premium Episodes on Design Better This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: Weekly Portfolio Club calls this summer helped our paid subscribers build portfolios that land great jobs. Experts joined us weekly to provide feedback, and we compiled lessons from each session into a portfolio design guide. We’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community. And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes. Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further. Upgrade to paid *** Learn more about your ad choices. Visit megaphone.fm/adchoices
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    28 mins
  • Mack Paul: Co-author of Miracle Road on designing places where innovation happens

    Mack Paul: Co-author of Miracle Road on designing places where innovation happens
    Sep 17 2026
    In the mid-1950s, North Carolina was one of the poorest states in the country. Its economy ran on tobacco, furniture, and textiles — all three in decline — and its universities were turning out talent that promptly left for somewhere with better jobs. Find bonus content and more on our Substack: https://designbetterpodcast.com/p/mack-paul-co-author-of-miracle-road Today the stretch of pine woods between Raleigh, Durham, and Chapel Hill is the largest research park in the United States. The barcode came out of it. So did AZT, ultrasound, and AstroTurf. Our guest Mack Paul spent years working out how that happened. He’s the co-author of Miracle Road, a history of Research Triangle Park (known as RTP) written with his father — a journalist — and built on about 160 interviews with the scientists, planners, and politicians who were there. It’s out October 6th. Hundreds of research parks have been attempted, and most failed. RTP started later than Silicon Valley or Route 128, with no defense money, no entrepreneurial culture, and universities that were openly uneasy about mixing academia with industry. But it worked anyway. Mack’s answer to why is not what you might expect. The park itself was almost an afterthought. What made it work was a set of long, unglamorous commitments: a governor who went industry hunting, a community college system that promised to train any company’s workers for free, and a decision about desegregation that made North Carolina a better bet than Virginia — which is a big part of why IBM came in 1965. We talk about what made it take off, the challenges now as RTP tries to become something denser and less car-dependent, and what it takes to build a place people actually want to be. We also talk about what it’s like to write a book with your father. Bio Mack Paul is a founder of Morningstar Law Group in Raleigh, where he has spent 30 years on the legal and political machinery behind how places get built — zoning, land use, environmental permitting, public-private partnerships, and public financing for infrastructure, mostly on large mixed-use and urban infill projects in North Carolina’s Triangle region. He’s a LEED Accredited Professional and served six years as the public member of the NC Building Code Council. He sits on the NC State Design Guild board, has advised the modernist preservation nonprofit US Modernist, helped organize the “Build Raleigh Better” symposium, and co-founded a development company aimed at raising design quality in the region. He teaches Real Estate Development Law at NC State. Mack is the co-author, with his father, of Miracle Road: The Story of Research Triangle Park, published by Duke University Press. *** Premium Episodes on Design Better This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: Get design and career support in Design Club Weekly Portfolio Club calls this summer helped our paid subscribers build portfolios that land great jobs. Experts joined us weekly to provide feedback, and we compiled lessons from each session into a portfolio design guide. We’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community. And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further. Upgrade to paid *** Learn more about your ad choices. Visit megaphone.fm/adchoices
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    44 mins
  • Federico Casalegno: Samsung EVP and MIT Design Lab founder on what 20,000 years of human creativity means for design today

    Federico Casalegno: Samsung EVP and MIT Design Lab founder on what 20,000 years of human creativity means for design today
    Sep 10 2026
    When Samsung’s CEO asked Federico Casalegno to redesign the cameras on the company’s phones, Federico told him he was the wrong person for the job. He wasn’t an optical engineer. He didn’t understand cameras. What he understood was storytelling — and he pointed to the Lascaux caves in France, where people were marking walls twenty thousand years ago for the same reason we hold up our phones today: to capture a moment, and tell it to someone we love. Find the full episode on our Substack:https://designbetterpodcast.com/p/federico-casalegno That’s the kind of answer you get from a designer who arrived by way of studying human society. Federico is Head of Samsung’s Global Design Studios, with teams spread across San Francisco, Europe, and Seoul. Before that he spent two decades at MIT, where he co-founded the MIT Design Lab with Bill Mitchell, and before that he was a social scientist embedded with engineers and psychologists at Philips Design in the nineties — back when “cross-disciplinary” wasn’t yet a word anyone put on a job posting. We talk about what that looks like in practice at the scale Samsung operates at. His team builds digital twins of human ears — thousands of 3D and 4D scans across real demographics — then simulates millions of variations to figure out how an earbud should fit. Then they strap the buds onto robots and make them run. Then they test with actual humans, because at some point a person still has to decide what “comfortable” means. There’s a phrase Federico kept returning to: technology without humanity is merely perfection without purpose. The designer’s role is problem making first, problem solving later. We also get into how critique works inside a company that speaks a dozen native languages, what he actually looks for when hiring, and the French philosopher who, at 102, looked at his calendar and said he was booked until next year. Bio Federico Casalegno is Executive Vice President at Samsung, where he leads product experience innovation across business units and heads the company’s Global Design Studios. Reporting directly to the CEO, he builds teams of designers, engineers, creative technologists, and strategists working on advanced design and next-generation experience planning. As head of design and AI, he established Samsung’s Computational Design function and leads digital transformation across the organization. Before Samsung, Federico spent two decades at MIT, where he founded the MIT Design Lab and the MIT Mobile Experience Lab and taught at MIT and the MIT Media Lab, researching the intersection of design, AI, and emerging technology. He previously worked at Motorola and Philips Design, and holds a PhD in sociology from the Sorbonne. *** Premium Episodes on Design Better⁠ This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: ⁠Get design and career support in Design Club⁠ Weekly Portfolio Club calls this summer helped our paid subscribers build portfolios that land great jobs. Experts joined us weekly to provide feedback, and we compiled lessons from each session into a portfolio design guide. We’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community. And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes. Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further. Upgrade to paid *** Visiting the links below is one of the best ways to support our show: Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer. If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com If you’d like to submit a guest idea, please contact us at: contact@...
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    24 mins
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