Design Of Podcast

What happens when a creative leader realizes that style alone isn’t enough, and decides to build something rooted in idea, intention, and longevity instead? In this episode of Design Of, I sit down with John Pobojewski to explore the tension between style and substance, and what it really takes to create work that lasts. This is a conversation about design, yes—but more importantly, it’s about leadership, conviction, and the responsibility that comes with shaping brands in a world that moves fast but forgets even faster. John has spent his career helping organizations think more clearly about who they are and why they exist. Along the way, he’s seen what happens when brands chase trends, confuse motion with progress, or mistake aesthetic for meaning. His perspective is simple, but not easy: without a real idea, design becomes decoration, and decoration doesn’t endure. This episode is not about making things look better. It’s about making them matter. Key Takeaways “If there’s no idea behind it, it’s just

What happens when a foreign correspondent watches legacy media shrink, and decides to build something more human instead? In this Season 11 opener of Design Of, Justin Ahrens sits down with Nathan Thornburgh, former Time Magazine foreign correspondent and co-founder of Roads & Kingdoms, to explore journalism, leadership, American identity, and the future of immersive storytelling. Nathan spent nearly a decade reporting from Moscow and across Europe during a period of global change. As foreign bureaus closed and media shifted toward digital scale, he saw the rise of compassion fatigue — the growing distance between audiences and the people in the story. Roads & Kingdoms became his response. Built at the intersection of food, geopolitics, and culture, the company became a creative partner to Anthony Bourdain and a home for long-form journalism rooted in shared humanity. Today, it has evolved into a print magazine, curated travel experiences, and a membership community built around real-world connection. Th

What if great communication isn’t about saying more, but saying what actually matters? Sarah Kissko Hersh has spent more than two decades inside agencies, brands, and leadership rooms where words carry weight. She grew up in Indiana, built her career in Chicago and New York, and learned early that clarity, not polish, is what moves people forward. Along the way, she worked across architecture, design, travel, luxury, and global firms, often stepping into messy moments where teams felt stuck and leaders felt unsure of what to say next. What started as a traditional PR career slowly evolved into something deeper. Sarah saw how often people were promoted into leadership without being taught how to manage. How communication broke down not because of bad intentions, but because of fear, burnout, and lack of direction. And how simple, honest language could reset entire teams. Today, Sarah is the founder of Type A, a communications and leadership consultancy based outside New York City. Her work focuses on helpin

What if the most powerful kind of creativity isn’t about making things beautiful, but making them clear? Gordon Kaye never planned to work in design. He studied law, built a career in New York, and handled media and trademark cases before joining NBC as counsel, reviewing everything from late-night jokes to broadcast standards. But when his father’s health declined, he stepped away from law to take over the family publication, Graphic Design USA (GDUSA), a magazine his father had launched in the 1960s to celebrate the people behind design, not just the work itself. What began as a rescue mission became a lifelong calling. Gordon brought his legal mind and curiosity for communication to a creative field that thrives on clarity. Over the decades, he’s evolved GDUSA into more than a design magazine, it’s a respected voice for how ideas move through business, marketing, and culture. In our conversation, Gordon and Justin talk about what design can teach every leader: how to communicate simply, lead with empat

What happens when you stop chasing views and start designing for belonging? When the world went online, most virtual events started to feel the same, flat, distant, and forgettable. But not for Rachel Elnar, Heather Lynn, and David Carr-Berry. Together, they built some of Adobe’s most loved digital experiences: Creative Jams and The Perfect Match, a 1970s-style design game show complete with music, lights, wigs, and real connection. These weren’t webinars. They were living, breathing events that made thousands of creatives feel seen. Each brought something vital: Rachel’s heart for community, David’s director’s eye for rhythm and flow, and Heather’s producer’s instinct for care and calm. Their shared secret? Treat every audience like a room full of humans. When layoffs hit, they took that shared language and built something new: Together By Design—a creative studio helping others build programs with purpose, host events with empathy, and grow communities that last. This is a conversation about saying yes

What if the most honest way to change minds isn’t a new campaign, but a new way to see familiar things? Brian Singer, known as “Someguy,” makes work that lures us with beauty and play, then nudges us to sit with what’s uncomfortable. Brian’s projects cross gallery walls and public space. The 1000 Journals Project sent blank books into the world for strangers to fill. TWIT Spotting put photos of distracted drivers on billboards to make a daily danger impossible to ignore. His recent pieces deconstruct books, flags, and everyday objects to examine censorship, identity, and what we choose to remember. In this conversation, we talk about how design craft and social commentary can live together. We also talk about heritage, silence, and what it means to make work that is both kind and clear. For the Rule29 community, this is a practical lens for client work and culture. Brian shows how to use material, language, and context to create meaning. He shows why public engagement matters. And he reminds us that strong

What happens when you say yes to what brings you joy, even if it starts on the side? For Chicago-based artist and designer Alyssa Low, it began with a quiet sketch. A visual diary during the early days of the pandemic. “I was just trying to express what I was feeling, when words didn’t quite work,” she says. That simple practice of showing up for herself turned into something bigger. One mural became two. Then came the collaborations: Wayfair. The Chicago Bulls. Soho House. Public art that now lives across city walls, basketball courts, patios, and even 10,000 hats handed out at a Bulls game. Alyssa is a multidisciplinary artist and muralist whose work is rooted in bold color, community connection, and movement. But she still holds a full-time design job. And she still approaches every project with the same focus and curiosity that shaped her as a kid, watching her mom run a design studio out of their home, playing competitive soccer, and practicing Tae Kwon Do forms that taught her how to focus, adapt, and

What happens when a designer at the top of his field walks away to chase something simpler, sharper, and harder? Illustrator Craig Frazier did exactly that, leaving a thriving design practice for a life defined by clarity and metaphor. Craig shares how he built a signature style that makes the complex instantly understandable. From Time magazine covers to U.S. postage stamps, his work proves how powerful reduction can be, and why the best ideas often live just shy of obvious. We talk about the moves that changed his career: a humble self-promo that landed Time magazine, a decade-long brand system made of pictures not paragraphs, the discipline of offering three strong options, and why clarity comes from pulling back just before obvious. Craig Frazier is an illustrator, designer, and author whose clients include The New York Times, The Wall Street Journal, Adobe, and the U.S. Postal Service. His work is known for clarity, wit, and staying power. In this episode, you’ll hear: + Why Craig left a successful d

What if the most powerful brand you could build didn’t shout, it whispered, “You’re enough”? That’s the quiet revolution Miss Katie Sings is leading. In this episode of Design Of, we sit down with Katie Norregaard, aka Miss Katie Sings, a musician, educator, and content creator who’s redefining what it means to connect with your audience. With calm clarity and cultural depth, she’s grown from a single homemade video during lockdown to a trusted global presence in children’s music, simply by being herself. She didn’t launch with a marketing team or a strategy deck. She launched with a box of rice as a drum, a $0 brand name, and an unwavering belief that kids deserve better. Her presence, gentle, intentional, and deeply human, has drawn comparisons to Mister Rogers. Not because she imitates him, but because she shares his radical belief: that children deserve to be seen, heard, and taken seriously. Here’s why this one’s worth your time: Because Katie’s story is what every brand leader, creative, educat

What if your next competitive advantage wasn’t a new product, but a new kind of leader? Doug Powell believes designers and design thinkers have the skills business needs most right now, the ability to connect human needs with strategic goals, to navigate uncertainty, and to see opportunities others miss. In a world of rapid technological change and economic contraction, that perspective can be the difference between falling behind and defining what’s next. Doug has spent his career proving it. At IBM, he helped build one of the largest corporate design programs in history, hiring over 1,000 designers, embedding human-centered design across global teams, and aligning design thinking with enterprise strategy. He’s led at the highest levels of AIGA, advised Fortune 100 leaders, and now coaches executives on how to integrate design into the core of their decision-making. This is an essential time for design and designers. In the face of unprecedented global challenges and a rapidly evolving technological land

Billy Oppenheimer is a pattern-seeker, storyteller, and creative thinker who turns curiosity into clarity. His path, from ski towns and side jobs to working alongside bestselling author Ryan Holiday, is a powerful reminder that following what fascinates you isn’t a distraction; it’s a direction. In this episode of Design Of, Billy shares how his instinct to notice, capture, and connect ideas has shaped his creative journey, and how it continues to evolve through deep research, disciplined writing, and his upcoming book with Penguin Random House, The Work Is the Win. Billy’s creative trajectory began with a bold, curiosity-fueled email to Ryan Holiday, whose own career was launched under the mentorship of Robert Greene (The 48 Laws of Power). That lineage, Greene to Holiday to Oppenheimer, reflects more than just professional mentorship. It reveals a shared creative philosophy: do the work, think deeply, and trust that the process itself holds the reward. Now, through his widely followed newsletter Six at

Jerry Takigawa is a rare kind of thinker, someone who approaches the world not just with creativity but with deep awareness, humility, and care. His work as an artist and storyteller explores what it means to carry a legacy, reframe pain into purpose, and make meaning in a world that often feels fragmented. In this episode of Design Of, Jerry shares how his Japanese American heritage, his parents’ experience with internment, and his lifelong creative practice have shaped the way he see, and responds to, the world. This is a conversation for leaders, creators, and anyone navigating complexity. Jerry doesn’t just talk about ideas, he embodies a way of thinking that invites reflection, connection, and change. You’ll hear: + Why embracing uncertainty can lead to more authentic leadership + How silence and heritage shape our voice, and our responsibility vWhat it means to create from both logic and intuition + How storytelling, metaphor, and vulnerability unlock deeper trust + And why making space for mean

Ali Schwanke isn’t just a marketer, she’s a builder of trust, a champion for clarity, and a quiet force of curiosity. As the founder of Simple Strat and the face of HubSpot Hacks (with over 3 million views and counting), Ali has become one of the most trusted voices in helping businesses unlock their true potential, not just in tools, but in people. In this episode, we trace Ali’s journey from a childhood of small-town hustle, selling greeting cards door-to-door, to becoming a sought-after strategist who sees marketing as more than data and automation. For Ali, marketing is about heart: the stories we tell, the ways we listen, and the empathy that holds it all together. Along the way, we explore: + Why “helping is the new selling” became her mantra + How she navigates the balance between data and human connection + What it means to stand out in a world of noise and sameness + The emotional power of B2B marketing—often overlooked, but never absent + And how Ali sees growth as an experiment in courage and car

Peter Aguero isn’t just a performer—he’s a presence. Known for his emotionally charged, wildly entertaining, and deeply human stories, Peter has become one of the most beloved voices in the storytelling world. A longtime host and GrandSLAM champion with The Moth, Peter’s work explores grief, rage, love, redemption, and the quiet moments that define who we are. In this episode, we sit down with Peter to trace the creative arc of his life—from growing up in South Jersey and leaving football behind, to traveling the country with Chicago City Limits, and eventually becoming a core figure in The Moth’s rise to cultural prominence. Along the way, we explore why storytelling isn’t just communication—it’s how we make sense of being human. Peter’s story intersects with some of the greats, including his longtime friendship with creative musician and experimental educator Dave Gould, who introduced him at a transformative moment in Iowa City. Together, their work reminds us that story is not just scientific—it’s deepl

If you’re a business leader, creative director, entrepreneur—or someone curious (or even a little anxious) about how AI fits into your work—this episode is for you. In this conversation, Justin Ahrens talks with Scott Meyer, co-founder of Chipp.ai, about designing AI tools that don’t just automate—but amplify creativity, strategy, and human connection. Scott’s journey—from studying peace and conflict in Norway to building tech startups—has always centered on clarity, access, and community. Together, they explore what it means to make AI more human, more useful, and more aligned with how we actually think, lead, and create.

“Music is completely emotion-driven for me. If I don’t feel it, I can’t fake it. That’s why I keep writing—to stay close to that feeling.” In this deeply reflective episode of The Design Of, Justin Ahrens sits down with musician, composer, and sonic storyteller Ryan O’Neal, best known as Sleeping At Last. With millions of listeners around the world and a body of work that’s as emotionally rich as it is expansive, Ryan shares how he intentionally designs not just music—but meaning. We explore how Ryan’s creative process is rooted in emotion, curiosity, and the desire to stay connected to what truly moves him. From writing songs inspired by the Enneagram to scoring film and television, Ryan talks about chasing wonder, navigating vulnerability, and using music as a mirror for growth. While Ryan is a musician, his approach offers powerful insights for anyone in business, branding, or leadership. His creative process models how to: + Lead with emotional intelligence—understanding the power of empathy in connec

Andy Stoll is the guy you want at your dinner party if you're looking for some serious entrepreneurial wisdom mixed with a dash of world-traveler intrigue. As a Senior Program Officer in Entrepreneurship at the Kauffman Foundation, he's got a cool $25 million philanthropic portfolio to work with, all in the name of strengthening entrepreneurship and innovation across the United States. This Omaha native with family roots in a small Japanese farming community in western Nebraska embarked on a four-year solo trip around the world, visiting a whopping 40 countries. He's been inspired ever since, founding not one, not two, but six entrepreneur-focused companies over the past two decades. Throughout his career, Andy has collaborated with industry leaders such as Steve Case, Paul Allen, and Tony Hsieh. He's now considered one of the leading national voices on how cities can build more vibrant and equitable entrepreneurial communities. From working in Bollywood to living in a mud hut village in Zambia, and even tea

Julie Sims, a global marketing and communications leader and strategist, has had quite a career. Knowing what she wanted to do at age 10, she followed her path and curiosity across the country, exploring different industries and searching for meaning in her work. From working in a newsroom and a staffing agency to dedicating her talents to a non-profit focused on creating a world free of illiteracy and gender inequality, Julie has always been driven by her passion. With her experience in leading MarCom functions, managing agency relationships, and developing strategic business plans, she thrives on overseeing the creation of compelling content that can change perceptions and deliver quantifiable results. Julie also has a deep passion for bringing out the best in people and shaping new leaders. Hear her story today – Enjoy the show!

Christine Taylor's journey has been filled with extraordinary adventures that have aligned perfectly with her personal passions and interests. It's the kind of dream we all secretly harbor. A true creative at heart, she has immersed herself in the realms of film, video, music, and theatre. For years, she has been an integral part of the TV and movie entertainment industry, specializing in licensing, consumer products, content development, and fan events. Her work revolves around some of the biggest and most beloved brands and properties in the world, such as Star Wars, Disney, The Simpsons, and Marvel, just to name a few. Brace yourself to meet a truly remarkable individual who cherishes and celebrates the wonders of popular culture in all its glory.

Debbie Millman is the creator and host of Design Matters, which is the world’s first podcast about design and is known for its wide-ranging conversations with designers, writers, artists, curators, musicians, and other prominent figures in contemporary thought. Additionally, Debbie is an author, teacher, and co-curator of the online Print Magazine. She is also an artist, speaker, and curator of creative conferences like the HOW Design Live Conference. Get ready to hear Debbie’s story, where we talk about her podcast and work, relationships, and the pain that has influenced our lives. Enjoy the show.