Alastair Simpson: From professional soccer to leading design at DropBox

Hi folks! We hope you’re having a wonderful holiday season, and have plenty of opportunities to relax and spend time with friends and family. This week we’re rewinding to one of our favorite episodes with Jonathan Hoefler, the legendary type designer. Enjoy the episode, and we’ll see you in the New Year! Find the full episode and bonus content on our Substack: https://designbetterpodcast.com/p/rewind-jonathan-hoefler *** It’s still not too late for a last-minute gift for the creative people in your life. Why not give the gift of education and inspiration by with a year-long subscription to Design Better Premium? We’ve even made a 🎁 handy gift card that you can send virtually, or print out and mail, or gift in person. *** Chances are you have a few fonts on your computer designed by Jonathan Hoefler. Since 1991, Apple has included Hoefler Text on every Mac. Ideal Sans, Knockout, Archer, Verlag, and Sentinel—are a few more of Hoefler’s well known typefaces —each is steeped in history and timelessly beautiful. It’s no wonder that Jonathan was featured in the Netflix series Abstract, which explores design and creativity, as he is truly a typography legend. As part of our series on design history, we talk with Jonathan about his typographic influences, his philosophical views on the value of presentation and why he views entrepreneurship as an invitation, and some of the themes in his work like “Unfinished Business” and “Conservation and Preservation.” Bio Jonathan Hoefler (pronounced "HEFF-ler") is a typeface designer, typographer, writer, and inventor, and the creator of some of the world's most influential fonts such as Gotham, Knockout, Mercury, Sentinel, and Hoefler Text. He founded the distinguished type foundry Hoefler&Co in 1989, which he sold in 2021, after publishing more than eleven hundred original tyepfaces. He's currently enjoying a sabbatical, and writing about typography and visual culture on his website, JonathanHoefler.com.

Alastair Simpson is accustomed to adaptation. The first half of his life was spent in the pursuit of a professional football career (or soccer as we call it in the States). But things didn’t go as expected, and he found himself searching for a new path in life. Football taught him discipline and to focus on excellence, traits that transferred well into a career in design. He’s led design teams at Atlassian and today, he’s VP of Design at Dropbox. We spoke with Alastair about how he applies design principles to parenting, the role craft plays in making great products, and creating a work environment that supports the creative process. Visit our Substack to access the full episode: https://designbetterpodcast.com/p/alastair-simpson Bio Alastair Simpson reports to the CEO and serves on the Executive team at Dropbox, where he leads the design team across all creative disciplines, including Brand, Product Design, Research, Content Design, and Operations. He also co-led, designed, and implemented Dropbox's transition to a Virtual-First working model. Previously, Alastair was Head of Design at Atlassian, where he played a key role in scaling the design team from 20 to over 300. *** 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 benefits: Premium subscribers also get access to the documentary Design Disruptors and our growing library of books, as well as 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 *** 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 Atwook, 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. Wix Studio: With Wix Studio, agencies and enterprises can create, develop and manage exceptional web projects with hyper efficiency. And if you're worried about the learning curve eating into time you don't have, don't be. Wix Studio is intuitive by design, so your entire team can hit the ground running. For your next project, check out wixstudio.com. Wine Access: We love wine, but often feel overwhelmed by the options out there. But we recently joined Wine Access who not only ship to your door some of the world’s most inspiring wines, they also educate subscribers with full color information cards that accompany each bottle. You should totally join The Waitlist Wine Club. Just visit wineaccess.com/waitlist and use Promo Code: DESIGNBETTER for $25 off your first shipment. 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]

Jason Giles is tuned into the habits of successful product design teams, not only because he’s been leading them for 15 years, but also because his team at UserTesting makes essential tools used by top design teams around the world. Jason thinks of the collaboration process in his team as similar to a jazz band where improvisation and exploration go hand-in-hand. We’re anxious to learn more. We’re excited to share this sponsored bonus episode, recorded live in Austin at The Human Insight Summit (THiS)—as UserTesting helps designers and product teams gain shared insight—seeing and hearing how another person engages with the world around them and taking in their perspective. Learn more about UserTesting Bio As VP of Product Design at UserTesting, Jason leads a team of designers, writers, and researchers across the US, Canada, and UK with the mission to enable real human insight and lead a movement for empathy. Jason Giles began his professional career as a designer at Microsoft, where he effectively “grew up” alongside the UX discipline itself. Having actively participated in that evolution, Jason transitioned to design management where he has focused on building teams with great cultures that deliver awesome product experiences. Visit our Substack to view the video of the interview: https://designbetterpodcast.com/p/jason-giles

Sometimes, a creative transformation occurs after a painful experience in our lives. This certainly happened for our guest today, Bishop Briggs, who lost her sister at a young age in 2021. After a period of intense grieving, and struggling with depression, her son was born in 2022, and she went on to win The Masked Singer in 2023. Find the full episode on our Substack: https://designbetterpodcast.com/p/bishop-briggs We spoke with Bishop about how her creative process evolved during these life-changing events, as well as how she approaches creating with consistency, connects with her audience, and the surprising results of her experiments with generative AI. Also, a quick note for anyone who might be sensitive about the topics of depression and suicidal thoughts, Bishop does discuss these topics during the course of our interview, most notably around the 10 minute mark of the episode. Bio Bishop Briggs, born in London to Scottish parents, discovered her passion for music early, performing for the first time at a Tokyo karaoke bar at age four after her family relocated there. Immersed in Tokyo's karaoke culture and influenced by Motown and The Beatles at home, she began writing songs at seven. After moving to Hong Kong at 10, where she lived until 18, she pursued her dream of a music career by relocating to Los Angeles to attend the Musician’s Institute. In Los Angeles, Bishop released her debut single, "Wild Horses," in 2015 and rose to prominence with her 2018 debut album, Church of Scars, and her 2019 follow-up, Champion. Her music has since reflected her personal journey, including profound loss, motherhood, and resilience. In 2023, she won The Masked Singer as "Medusa" and released her EP When Everything Went Dark. Her latest album, Tell My Therapist I'm Fine, debuted in October 2024, and she is currently on tour through Spring 2025. *** This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. ✨New benefits: Premium subscribers also get access to the documentary Design Disruptors and our growing library of books, as well as 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 ***

We're at the holidays once again and that means it's one of our favorite episodes, our Design Better holiday gift guide for designers, creatives, and anyone who appreciates well-designed products. This list is perfect for anyone hunting for the ideal gift for that special someone—or, let’s be honest, for themselves. And this year—like last year—we’ve curated some stellar picks. Visit our Substack for the full list: https://designbetterpodcast.com/p/design-better-2024-holiday-gift-guide *** Visiting the links below is one of the best ways to support our show: Wix Studio: With Wix Studio, agencies and enterprises can create, develop and manage exceptional web projects with hyper efficiency. And if you're worried about the learning curve eating into time you don't have, don't be. Wix Studio is intuitive by design, so your entire team can hit the ground running. For your next project, check out wixstudio.com. Wine Access: We love wine, but often feel overwhelmed by the options out there. But we recently joined Wine Access who not only ship to your door some of the world’s most inspiring wines, they also educate subscribers with full color information cards that accompany each bottle. You should totally join The Waitlist Wine Club. Just visit wineaccess.com/waitlist and use Promo Code: DESIGNBETTER for $25 off your first shipment. *** 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]

When Aarron was in college studying painting and drawing, he had an absolute certainty about the path my career would take. He was going to move to New York, make it big as an artist, and never look back. And Eli, as an undergrad in product design, wasn’t sure what a career in his field even looked like. The skillset wasn’t clearly defined yet. The outdoor product companies he was eyeing wanted me to conform to a neat little box: “Are you an industrial designer, or a mechanical engineer?” He wasn’t sure how he fit in. Did our careers unfold as we expected? Absolutely not. Life and careers rarely go according to plan. There’s so much beyond our control. But, despite the unexpected twists, there are lessons that can guide us in the right direction. And that’s what we’re here to explore today in this special live episode of Design Better, recorded right here at the Savannah College of Art and Design. Today, we’ll be speaking with four design leaders who took a winding path but all found their way to significant work. Bios Kate Aronowitz is a design executive who has built her career empowering teams at some of Silicon Valley’s most iconic companies. In addition to her role leading GV’s operations team, Kate coaches GV portfolio companies on cross-functional design processes, scale, product development, and management strategy. Kate has built world-class design teams at eBay, LinkedIn, Facebook (now Meta), and Wealthfront. She joined the first user experience team at eBay before taking her experience to LinkedIn, where she started the user research team. As Facebook’s first design executive, Kate grew the organization from 20 to 200, establishing multidisciplinary design teams in front-end engineering, user research, content strategy, and communication design. Steve Johnson, VP of Design at Netflix, leads a diverse, multidisciplinary, Emmy-award-winning Experience Design organization. His team's commitment to discovery, product innovation, brand development, and personalization has set the standard for streaming media platforms across the world. Prior to Netflix, Steve also led design teams at LinkedIn and Adobe. Jaime Lopez, Chief Design and Marketing Officer at Flatiron Health, Jaime Lopez is the Chief Design & Marketing Officer at Flatiron Health. She has over 15 years of startup product, design and marketing experience with a passion for creative problem solving and building and mentoring teams. In her role at Flatiron Health, Jaime uses her background to create and deliver high-quality experiences to oversee the company’s entire marketing and design suite.  Kat Holmes is EVP and Chief Design Officer at Salesforce where she's driving the future of AI, Data, and CRM experiences. As the author of the best-selling book Mismatch: How Inclusion Shapes Design, Holmes works with multidisciplinary teams to set a foundation for why designing with excluded communities drives better solutions for everyone. Her work has been featured by NPR, BBC, Fast Company, Forbes, The Economist, and many more. Visiting the links below is one of the best ways to support our show: Wix Studio: With Wix Studio, agencies and enterprises can create, develop and manage exceptional web projects with hyper efficiency. And if you're worried about the learning curve eating into time you don't have, don't be. Wix Studio is intuitive by design, so your entire team can hit the ground running. For your next project, check out wixstudio.com. Wine Access: We love wine, but often feel overwhelmed by the options out there. But we recently joined Wine Access who not only ship to your door some of the world’s most inspiring wines, they also educate subscribers with full color information cards that accompany each bottle. You should totally join The Waitlist Wine Club. Just visit wineaccess.com/waitlist and use Promo Code: DESIGNBETTER for $25 off your first shipment.

This is a special sponsored episode of the Design Better Podcast Gali Erez, Head of Wix Studio at Wix, has had quite a journey, from a background in graphic design at CalArts, through transitioning from print to digital in her early work at Warner Brothers, where she helped envision media's digital future. Along the way, she has learned some principles that helped her during her time as an individual contributor, and also guide her as a leader: sharing ideas early, giving tough feedback, and using storytelling as a leadership tool. We speak with Gali about how AI is changing web design workflows, the research process her team uses, and what’s kept her excited to work at Wix for over 10 years. This is a sponsored bonus episode we’re excited to share, as Wix Studio is a product that helps diverse users, from casual creators to professional web designers and developers, with a platform that balances simplicity and customization. *** Learn more about Wix Studio at https://www.wix.com/studio *** Bio Gali Erez is the Head of Wix Studio at Wix and has been with the company for over a decade. She studied graphic design at CalArts, where she experienced the transition from print to digital design. Her early career included a product design internship at Warner Brothers, where she worked on innovative ways to bring media online. At Wix, Erez has held various roles, starting as a UX designer on the DIY editor and later transitioning into management. She played a key role in developing Wix ADI, an AI-driven platform that simplifies website creation, and led the creation of Wix Studio, a professional-grade platform for web designers. Erez's leadership style emphasizes transparency, incremental innovation, and adaptability to changing team dynamics and industry trends. Her work focuses on democratizing web design, balancing accessibility with professional-grade features, and leveraging AI to enhance efficiency and creativity in design processes.

Jazz is a constantly evolving art form, offering some of the richest lessons in creative collaboration. A melody and chord progression provide the foundation, but as each musician brings their unique improvisational perspective, the music takes on unexpected, transformative shapes. If you ask any fan of the genre who’s pushing jazz into new territory, Kamasi Washington’s name will come up—likely at the very top. His 2015 album The Epic won the American Music Prize and stands, in our opinion, as one of the greatest jazz records of the 21st century. Kamasi contributed to Kendrick Lamar’s Grammy-winning To Pimp a Butterfly, scored Michelle Obama’s Netflix documentary Becoming, and has collaborated with musical legends like Herbie Hancock, Wayne Shorter, Lauryn Hill, Nas, Snoop Dogg, Chaka Khan, and many more. In this episode, we spent an evening with Kamasi, exploring his creative process, what he’s learned from his collaborators, his philosophy on collaboration, and his latest album, Fearless Movement. Find show notes, bonus content, and more on our Substack: https://designbetterpodcast.com/p/kamasi-washington Bio Kamasi Washington, born in Los Angeles in 1981, grew up surrounded by music, with a saxophonist father and a flutist mother who nurtured his musical talent from a young age. Kamasi’s journey began with drums and piano in his early years, progressing to the clarinet at age seven and finally to the tenor saxophone at twelve, mirroring his father’s path. His high school years at Hamilton High School Music Academy were pivotal; there, he joined the renowned Multi School Jazz Band and learned from jazz icons like Herbie Hancock and Wayne Shorter. Kamasi’s talent was quickly recognized when he won the John Coltrane Saxophone Competition, and he co-founded "The Young Jazz Giants," which marked his early step into professional music. Kamasi's musical evolution continued at UCLA, where he studied ethnomusicology and expanded his understanding of global music traditions. This foundation supported his wide-ranging collaborations beyond jazz, where he worked with artists like Snoop Dogg, Raphael Saadiq, and Kendrick Lamar. Yet, despite his diverse influences, Kamasi remained firmly rooted in jazz, ultimately channeling these experiences into his innovative sound. His 2015 debut album, The Epic, was a monumental release—a three-disc exploration of jazz that introduced a unique blend of spiritual depth and musical complexity. The album garnered critical acclaim, broadening Kamasi's reach and establishing him as a leader in modern jazz. *** 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. Premium subscribers also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, access to our (small but growing!) library of books and participation in book giveaways, and our new enhanced newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.  Upgrade to paid *** Visiting the links below is one of the best ways to support our show: Wix Studio: With Wix Studio, agencies and enterprises can create, develop and manage exceptional web projects with hyper efficiency. And if you're worried about the learning curve eating into time you don't have, don't be. Wix Studio is intuitive by design, so your entire team can hit the ground running. For your next project, check out wixstudio.com. Wine Access: We love wine, but often feel overwhelmed by the options out there. But we recently joined Wine Access who not only ship to your door some of the world’s most inspiring wines, they also educate subscribers with full color information cards that accompany each bottle. You should totally join The Waitlist Wine Club. Just visit wineaccess.com/waitlist and use Promo Code: DESIGNBETTER for $25 off your first shipment.

We’re students of the creative process, and so is Adam Moss, author of The Work of Art: How something comes from nothing. Formerly the editor-in-chief of New York magazine, these days Moss is on a quest in his studio to understand painting and through it the mysteries of the act of creation.  Questions about why people create—and the diversity of process across mediums—led Adam to write his book, which features interviews with a host of inspiring folks. Kara Walker, Tony Kushner, Sofia Coppola, Stephen Sondheim, Barbara Kruger, Ira Glass, Samin Nosrat, Marc Jacobs, David Simon, and many more share their approach to the work they do in the book.  We talk with Adam about the red threads that run through such varied creative expressions, finding the right creative partners, how to feed creativity, and how his own work has been influenced by his investigation into how creativity unfolds.  Visit our Substack for bonus content and more: https://designbetterpodcast.com/p/adam-moss Bio Adam Moss was the editor of New York magazine, The New York Times Magazine, and 7 Days. As editor of New York, he also oversaw the creation of five digital magazines: Vulture, The Cut, Daily Intelligencer, Grub Street, and The Strategist. During his tenure, New York won forty-one National Magazine Awards, including Magazine of the Year. He was an assistant managing editor of The New York Times with oversight of the Magazine, the Book Review, and the Culture, and Style sections, as well as managing editor of Esquire. He was elected to the Magazine Editors’ Hall of Fame in 2019. *** 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 our monthly AMAs with former guests, ad-free episodes, early and discounted access to workshops, and our new enhanced newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.   Upgrade to paid *** Visiting the links below is one of the best ways to support our show: Wix Studio: With Wix Studio, agencies and enterprises can create, develop and manage exceptional web projects with hyper efficiency. And if you're worried about the learning curve eating into time you don't have, don't be. Wix Studio is intuitive by design, so your entire team can hit the ground running. For your next project, check out wixstudio.com. Wine Access: We love wine, but often feel overwhelmed by the options out there. But we recently joined Wine Access who not only ship to your door some of the world’s most inspiring wines, they also educate subscribers with full color information cards that accompany each bottle. You should totally join The Waitlist Wine Club. Just visit wineaccess.com/waitlist and use Promo Code: DESIGNBETTER for $25 off your first shipment.

One of Aarron’s first jobs as a kid was performing magic shows, and it taught him a surprising amount about creativity. Magic is, at its core, the art of storytelling. It’s about directing attention, making people question assumptions, and blending creativity with technology to change how we see the world. That’s why it’s no surprise that Andrew Evans, founder of the Magic Patio, draws on his training from Stanford’s d.school to craft truly mesmerizing experiences.  We dive into Andrew’s journey, from his childhood dream of designing roller coasters, to creating treehouses, working at IDEO and Nike, and eventually launching a magic show in his own backyard. We also explore how he’s honed the art of engaging an audience, and we share tips on how to craft presentations that pull people in and make them feel part of the experience. Watch the video version of this episode on our Substack: https://designbetterpodcast.com/p/andrew-evans Bio Andrew Evans is founder and magician at The Magic Patio, a uniquely San Francisco magic experience. After entering what appears to be a strange library/candy store on Mission Street, guests discover the hidden wonders of a hand-crafted, secret magic theater with one-of-a-kind magic performances. More than designing and performing magic, my passion is creating unexpected experiences that transport people into new worlds and shift their perspective on what they perceive to be impossible. Think Urban Disneyland rather than David Copperfield. A trip to The Magic Patio will fill you with inspiration and wonder as you witness unexplainable feats in an intimate setting. Buy tickets to The Magic Patio *** 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. Premium subscribers also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, access to our (small but growing!) library of books and participation in book giveaways, and our new enhanced newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.  Upgrade to paid *** Visiting the links below is one of the best ways to support our show: Adobe’s In the Making: As a Design Better listener, we have another podcast we think you’ll enjoy. Adobe’s In the Making hosted by Teresa Au takes an honest look at the challenges and rewards of being part of the creator economy. Building a business around your creative pursuits ain’t easy. Wouldn’t it be great to learn from those who have done this before? Check out In the Making from Adobe to learn more about how to build a creative career and life. Subscribe on Spotify, Apple Podcasts, or wherever you listen. Bluehost: When you upgrade to Bluehost Cloud, you can start managing multiple sites and domains. Not only that, you also get 100% uptime, enhanced security, and priority 24/7 support to keep you online no matter what. That means no crashing from heavy traffic. Go to Bluehost.com and start building your dream website today. Methodical Coffee: Roasted, blended, brewed, served and perfected by verified coffee nerds 🤓 : https://methodicalcoffee.com (use code "designbetter" for 10% off of your order).