Design Better Podcast

by Eli Woolery

If theres one thing weve learned from the multitude of people weve interviewed for Design Better, its that the most innovative creators of our time share an unlikely trait: they refuse to stay in their lane. While conventional wisdom pushes specialization, these polymaths build careers by following curiosity across fieldsfrom nuclear engineering to footwear design, from video games to graphic novels.

In my own career, it took me many years to realize this, and in some ways my journey began the day after my son was born.

I remember that day as unseasonably hot. September 2015 on the Monterey Peninsulathe kind of clear, warm day that follows long stretches of coastal fog. After leaving the hospital where my wife Courtney was recovering with our newborn, I grabbed a quick (wife-sanctioned) surf. The clear horizon promised a month of record warmth ahead.

At home, I checked email before setting up my auto-responder for two weeks of paternity leave. Near the top of my inbox: a message from our startup's CEO. Not what I expected.

The gist: "We're sorry, but our co-founders had a fight, the company is splitting up, and we have to lay you off."

Panic. Losing my job right after our second child wasn't the plan, especially since we'd just moved to the Monterey Peninsula in an era before remote work was widespread.

I delivered the news to Courtney at the hospital along with her Starbucks coffee, and couldnt find anything comforting to say. She ended up reassuring mewe were going to be OK.

And we were. It became a rare chance for me to spend real time with our newborn son, young daughter, and Courtney. Time to reflect on what came next. And I had a secret weaponsomething I hadn't always considered a strength.

Continue reading this issue of The Brief on Substack at DesignBetter.com

This is a preview of a premium episode. To get access to the full episode, head to our Substack: https://designbetterpodcast.com/p/christopher-lyons

Some careers have clear through lines: pick a college major, get a job in that industry. Others take serendipitous turns. Christopher Lyons is the latter, but with some surprising twists.

Chris started his career as a music producer with Jermaine Dupri, founder of So So Def records in Atlanta, a role that honed his eye for recognizing talent and helping them reach their potential. Then, he joined renowned venture capital team Andresen Horowitz where he helped connect talent to business opportunities by creating the Cultural Leadership Fund. Eventually, he became a general partner at the firm.

We talk to Chris about why he thinks EQ is far more important than IQ in a successful career, how he connects creative thinkers to business opportunities, and the common threads he sees across all creative disciplines.

Bio

Christopher Lyons is a visionary leader and President of Web3 Media at a16z crypto. Since joining a16z in 2013 as chief of staff to Ben Horowitz, he has helped shape the firms strategic directionmost notably by launching the Cultural Leadership Fund (CLF) in 2018 and co-founding a16zs $400M Seed Fund in 2021. The CLF broke ground as Silicon Valleys first venture fund with an all-Black LP base, bridging cultural leaders from sports, music, and entertainment with the tech world while advancing opportunities for Black builders and creators.

Lyons began his career as a sound engineer, working with Grammy-winning producer Jermaine Dupri before founding PictureMenu, a mobile menu platform. He now serves on the boards of Yuga Labs, the James Beard Foundation, the Black Economic Alliance, and New Story Charity. A Kauffman Fellow and founder of Lyons Wine, he brings a spirit of craftsmanship and mentorship to everything he does, including his continued involvement with Kappa Alpha Psi Fraternity, Inc.

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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 the documentary Design Disruptors and our growing library of books. Youll 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.

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We are living through a Cambrian explosion of new tools, powered by generative AI. It can be tough to wade through the sea of options in front of us, and find platforms that actually help us in our workflow instead of being a distraction.

That’s why it was so refreshing to discover the tool Capsule a little over a year ago. We use it to create motion graphics and short videos for Design Better, and the experience is a thousand times easier and more rewarding that using arcane tools like After Effects.

Today we’re chatting with Champ Bennett, CEO and co-founder of Capsule. We talk with him about his entrepreneurial journey, what motion design systems are and how they fit into more general design systems, and how motion design fits into branding.

This is a sponsored bonus episode that we’re excited to share, as Capsule is a tool that we love. They believe that video storytelling should be easy and scalable, and if your team is hoping to create more video their platform is the place to go.

If you’re interested in open design roles or in building a motion design system for your enterprise team, you can learn more at capsule.video



Bio

Champ Bennett is the co-founder and CEO of Capsule—an AI-powered video editing tool that helps enterprise content and marketing teams create more videos while staying on brand.

His background is as a software engineer, designer and musician. After running a product agency for 4 years, Champ pursued a decade-long journey as a 3x startup founder focused on creative technology.

Fascinated by creative tools since he was a child, Champ believes there’s never been a better time to be building creative tools than now. Through Capsule, he is showing the world how AI can be practically applied to augment human ability rather than replace it — solving real world challenges in creative workflows. Capsule raised $7.75M after a product demo went viral on Twitter, recently raised a $12M Series A round, and is working with some of the world’s leading B2B brands to help democratize video creation in their organizations.

This is a preview of a premium episode. Visit our Substack to get access to the full episode: https://designbetterpodcast.com/p/cassie-mcdaniel

Cassie McDaniel, Medium’s head of design, is someone with a clear vision for how a design team should work. She believes team members should have a breadth of skills, craft should be the foundation of product design, and experimentation is important in both work and workflow.

To that end, Cassie and the leadership team at Medium recently made what some might see as a controversial decision: They eliminated product management. The result? They are moving faster than ever.

We chat with Cassie about what led to this decision—and why it might not work for all teams, how she thinks about balancing Medium’s legacy of thoughtful design while moving the product forward, and how writing can help you advance your design career.

Bio

Cassie McDaniel brings nearly 20 years of design leadership across agencies, her own studio, nonprofits, and high-growth startups. Currently the Head of Design at Medium, in her previous role as Product Design Director at Lattice, she led Insights & Analytics and Engagement, partnering with cross-functional teams to deliver humane, impactful digital experiences that drive business results.

Cassie excels at building and mentoring teams, championing customer-centric culture, and solving complex problems at scale. She combines curiosity, empathy, and kindness with a relentless focus on execution—especially on mission-driven initiatives in creativity, environmental advocacy, and ethical product design.

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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 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

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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.

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If you're interested in sponsoring the show, please contact us at: [email protected]

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BioPremium Episodes on Design Better

Find bonus content and more on our Substack: https://designbetterpodcast.com/p/the-roundup-ai-creative-workflow

Rarely do we get the chance to pause and reflect on the conversations we’ve been having—and to spot the red threads that run through them. But that’s exactly what we’re doing today.

We’re trying out a new format—we’re calling it The Roundup. Think of it as a prototype. We’d love your feedback.

In this episode, we’re revisiting past conversations through the lens of AI. It’s a fun new way to explore themes that have come up across episodes, highlight insights from our guests, and help you synthesize ideas you can apply in your own work.

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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, 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

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What you'll learn in this episode:



Changing Roles & Workflows

Scott Belsky (Adobe’ Chief Strategy Officer) discusses "boundaryless workflows" where AI collapses the steps between ideation and execution



The concept of "collapsed talent stacks" where individuals can now perform multiple functions that previously required separate specialists







Evolution of Design Jobs

Jenny Blackburn (design team lead for Google Gemini) shares how her team is "inventing the next version of UX jobs" as boundaries blur between roles



New UX jobs are emerging around defining great AI responses from a user perspective





AI as Creative Partner

Marcus Bell (music producer for artists like Snoop Dogg) explains how AI has transformed music production, enabling him to do what once required five people



Bell predicts AI will enable "hyper-personalization" of music based on individual needs and preferences







...and more!