Design Better

In graduate school, Randy Hunt poured his heart and soul into a poster for Milton Glaser’s class, a picture built entirely from hand lettering that read as an image from across the room and as words up close. Glaser glanced at it, said, “Well, that’s not very good,” and moved on to the next student. Get bonus content and more on our Substack: https://designbetterpodcast.com/p/randy-hunt Randy tells that story fondly. What stayed with him wasn’t the sting but the standard: keep the floor high, and the ceiling keeps rising. He carried that idea from Glaser’s studio, where he apprenticed, through a career leading design at Etsy, at Grab in Singapore, and until recently at Notion. At Notion, that standard meant a design team smaller than anyone would expect, on purpose. Randy argues that limited bandwidth forces a company to prioritize, and that great people have little patience for what he calls “the work around the work.” The team doesn’t talk about titles or levels. Designers ship code in the production app, something Randy built teams around at Etsy in 2010, long before “design engineer” came back into fashion. We also get into what he calls “whole design,” which means treating a push notification with the same care as the main dashboard. He explains why hotels and restaurants inspire him as much as any software, and traces that back to growing up near Disney’s carefully spaced trash cans in Orlando and to the bowl of fresh fruit that always sat in Glaser’s studio. Bio Randy J. Hunt is a designer, artist, and author based in New York City, with more than 20 years of experience building products, brands, and businesses. Most recently, he was Head of Design at Notion. He also chairs the MFA Design program at the School of Visual Arts, a graduate program focused on entrepreneurial designers. Earlier, he led design at Etsy, Artsy, and Grab, co-founded the designer-made marketplace Supermarket, and served as Chief Product Officer at the coffee-tech company Morning. He apprenticed at Milton Glaser's studio, founded the design studio Citizen Scholar, and wrote Product Design for the Web (New Riders, 2013). Books & Links Randy Hunt on LinkedIn randyjhunt.com The Hunt Design Week: “A lot of this is about rituals” MiltonGlaser.com The Creative Act, by Rick Rubin Johnny Cash Project Julia Hoffman Tequila Wars: José Cuervo and the Bloody Struggle for the Spirit of Mexico Widow’s Bay *** 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 4 ad-free episodes per month. 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. Upgrade to paid Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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: [email protected] If you’d like to submit a guest idea, please contact us at: [email protected] Learn more about your ad choices. Visit megaphone.fm/adchoices

We all know that there is something fractured about the workplace, that makes it inefficient, and at times inhumane. If only someone was thinking deeply about those problems, and how to address them… Visit our Substack for the full episode: https://designbetterpodcast.com/p/clay-parker-jones That’s what Clay Parker Jones is working on right now. Clay has spent close to two decades on this problem — first at the consultancy undercurrent, and today as Head of Org Design and Development at Airbnb. He advocates for investment in creativity and humanity at work, something you might think would be obvious for any company, but sadly is eclipsed by short term thinking. His new book, Hidden Patterns: A Playbook for More Human Workplaces, is one of the most cohesive philosophies of organizational structure we’ve come across. And his diagnosis of what’s broken is simple: there aren’t enough real teams. Most of us work in what he calls “co-acting groups” — people who convene for a meeting and then scatter back to their actual work. In this conversation, we get into why psychological safety stays a platitude until you make it structural, what rule of law looks like inside a company, and how to break a manager’s job into atomic pieces and hand away the parts you’re bad at. We also chat about why the org chart is a design problem that designers should be at the table for. Bio Clay Parker Jones leads Organizational Design & Development at Airbnb, refining how a creativity-first company learns and ships new ideas. A former Chief Strategy Officer at Black Glass, co-founder of August, and transformation lead at R/GA, his work has been recognized by B Lab and profiled in a Harvard Business School case study. A former bike mechanic with a BA in Diplomacy and World Affairs from Occidental College, Clay now resides in Brooklyn with his wife Emily and cat Ian. You can find him on the Fort Greene tennis courts in his spare time. *** 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: 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

Like a lot of parents, Eli struggled over the years to get his kids more into reading and away from screens. He wasn’t necessarily on the search for a technological solution, but then an interesting device came our way: the Yoto Player, a screen-free audio player for kids. Eli’s 10-year old son has been loving to read along to the Harry Potter books (and he often finds him after he falls asleep, and the player is still going). Visit our Substack for bonus content and more: https://designbetterpodcast.com/p/ben-drury The story behind Yoto is from a similar moment of parental struggle. About a decade ago, Ben Drury was shopping for a stroller in a London department store and found one with an iPad mount built in. For a newborn. He remembers the reaction being physical — this is just wrong. But if you’re expecting an anti-screen crusade, that’s not quite what happened . The line Ben uses is: we don’t say screens are bad, we say audio is good. Listening is good for creativity and imagination — and there’s research going back to the 1980s to back that up. Ben is the co-founder and CEO of Yoto, makers of a kids’ audio player that works by dropping a physical card into a small speaker. Before Yoto Ben spent about a decade building a B2B digital music platform called 7digital which he took public. What he learned from that experience proved helpful as he and his co-founder started Yoto. Ben and his co-founder became parents at roughly the same time, and wanted a way for their kids to connect with music and books like they did in childhood. So they started hacking on Raspberry Pis with no hardware experience whatsoever. How hard could it be, right? The 3rd Gen Yoto Player Turns out, it’s pretty hard. They took a restrained approach. Yoto is a cube, because it was the simplest shape they could think of. It uses NFC cards that have a Pokemon card feel. The 16 by 16 pixel display presents pixel art that gives Yoto a fun personality. In this conversation, we get into the design principles that came out of Montessori, their experience working with Pentagram on product design and branding, why Paul McCartney became an early angel investor, and what changes when you go from a Kickstarter that raised fifty thousand dollars to nine-figure revenue. Bio Ben Drury is the co-founder and CEO of Yoto, the screen-free audio player that lets children control their own listening by dropping a physical card into a speaker. Before Yoto, he spent roughly a decade building 7digital, a B2B digital music platform he took public. He and his co-founder started Yoto in 2017 with a Kickstarter campaign and no hardware experience between them; today the company employs about 220 people across six countries, sells in 1,900 Target stores in the US, and counts Paul McCartney among its early angel investors. He lives in London with his wife and two sons. *** 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: 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

Fifteen years ago, Eric Ries handed a generation of founders a playbook. When Eli was in a Palo Alto-based startup accelerator in 2011, The Lean Startup felt like the only book anyone in that ecosystem was talking about. It was in the middle of a wildly optimistic moment for tech. Marc Andreessen declared that “software is eating the world,” social media was blooming, and there was a widespread belief that technology was about to democratize everything and bring us closer together. Concepts like the MVP (“minimum viable product,”), the pivot, and build-measure-learn became the operating language of Silicon Valley. This is a preview of a premium episode. Listen to the full interview on our Substack: https://designbetterpodcast.com/p/eric-ries But a lot of the companies built on those ideas went on to get corrupted by forces Eric hadn’t yet named. His new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great, is his reckoning with what happens after you build something great — and how to keep it from falling apart. Buy the book In this conversation, we get into why speed itself wasn’t the problem, but treating a rising stock price as proof of health is like assuming more exhaust means a faster car. Eric explains why doing the right thing 100% of the time is actually easier than doing it 98% of the time, and how companies behave like superorganisms with their own emergent character — a point he illustrates with a genuinely mind-bending study about ants solving a puzzle that no single ant ever could. We talk about the “harder is easier” principle through stories from Patagonia and the long-term stock exchange he built as a design challenge, and why the value a company makes comes from the design of its products. And because we couldn’t resist, we get into AI slop, LLM psychosis, and Eric’s clear, simple antidote: never ask these tools to make you an artifact — ask them to teach you how to make one yourself. Bio Over the last two decades, Eric Ries’s ideas about continuous innovation, long-term thinking, governance, and market reform have reshaped company building and management practices. He is the creator of the Lean Startup method, and the author of the New York Times bestseller The Lean Startup; The Leader’s Guide; and The Startup Way. As a founder, he has put his own ideas into practice with The Long-Term Stock Exchange (LTSE); Answer.AI, an AI R&D lab; the Lean Startup Co, which teaches and supports the implementation of Lean Startup; Virgil, a legal services startup; and IMVU, where the ideas that became the Lean Startup method were forged. On his podcast, The Eric Ries Show, he talks to guests including world-class technologists, thought leaders, and executives working to build profitable companies for the long-term benefit of society. Eric has served as an entrepreneur-in-residence at Harvard Business School and IDEO. He lives in the San Francisco Bay Area with his wife and three children. *** 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: 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. Learn more about your ad choices. Visit megaphone.fm/adchoices