Chris Piascik is an independent illustrator, author, and top Skillshare teacher best known for his 14-year public daily drawing project. His quirky, unmistakable work—rooted in punk, pop art, skate culture, and humor—has attracted major clients including Nike, Nickelodeon, Cartoon Network, and McDonald’s.

In this episode, we discuss Chris’s unlikely path from being laid off to building a thriving independent illustration and design career—and how the simple practice of making and sharing personal work every day opened doors to some of his dream clients.

Chris talks about the moments he nearly gave up, how he built an audience online long before “personal branding” became career advice, and what thousands of daily drawings taught him about developing a creative voice.

We also dig into what it takes to stay visible without letting the internet take over your life, and why Chris believes the story, meaning, and person behind the work matter more than technical perfection.

Find Chris on Instagram at @chrispiascik or visit his website for more at chrispiascik.com

Christian Watson is the founder of the boutique branding agency 1924us and the creator of the mega viral animated character Mr. Skelly.

Rooted in the craftsmanship of the 1920s, all his work is entirely hand-drawn, using vintage techniques to create modern brand systems.

Through 1924us, Watson has helped brand more than 200 companies — from independent coffee shops to Fortune 500 brands — while also building an audience of over 7 million followers across social media platforms.

In this episode, we discuss Christian’s rise to fame, how he approaches social media today, why he’s not using any AI in his design process at all, and his advice for how to unlock more opportunities as a working creative.

In this episode, we speak with Phil Garnham and Damien Collot, both Executive Creative Directors at Monotype, the global leader of fonts including Helvetica, Futura, Ariel, and Gotham. Their collaborative work involves exploring how typography, font, and graphic design reflect our shifting culture and how type serves as a brand’s essential visual voice in real-life contexts.

Phil and Damien share what makes font and design culturally relevant, how designers impact and reflect social perception, and the ways design can make the world better. We also discuss Monotypte's new Peace and Conflict project—an open-source collection of icons created to provide a universal code for communicating hope, empathy, and humanity in times of increasing conflict, which is available to the public domain at Noun Project. 

In this episode, we chat with Eric Wittman, CEO of VSCO, a platform that gives photographers the tools, community, and exposure they need to expand creatively and professionally. VSCO offers products to capture, edit, display, and share visual content with a global community of creatives and brands. Eric’s career has centered on building technology products that help people be more creative, and includes leadership roles at Adobe, Atlassian, and Figma.

Eric explains how AI is a paradigm shift that’s changing the entire creative process rather than simply introducing new tools like past photography disruptions. With AI capable of generating photorealistic imagery, we discuss the unique advantage of the human photographer and how soul, intention, and style cannot be replaced. Eric shares how photographers are using technology to speed up business tasks like invoicing, marketing, creative exploration, and post-production editing. He offers essential advice on the most valuable skillsets for photographers to double down on—storytelling, empathy, and relationship building.

In this episode, we chat with Khyati Trehan, an internationally awarded designer who currently works at Google Creative Lab developing visual systems and experimental tools. Khyati has built a career that illuminates the intersection of design, creativity, and technology. She's worked with major global brands, including Apple, Instagram, Snapchat, Adobe, Samsung, Vogue, and the Oscars.

Many creatives feel uncertain about the future of the industry, particularly concerning the impact of emerging technology like AI. Khyati shares an optimistic perspective on the bright side of these new tools, explaining that designers are essential for adding human value, empathy, and context to these systems. She explains how she is embracing new methods of creation, like vibe coding, which allows her design to become more malleable. Ultimately, Khyati reminds us that the key to preparing for the future is focusing on novelty over efficiency, and embracing play to make experiences that we couldn't before.

In this episode, we speak with professional illustrator and lettering artist Mary Kate McDevitt on how she's built a fulfilling career stemming from personal design projects that snowballed into dream clients. She’s worked with major brands like Target, Nike, Panera, New York Times, Johnson & Johnson, and AT&T (to name a few).

Many creatives feel like they struggle with getting a foot in the door in the industry, especially in an era ruled by the pressure of algorithms and chaotic news cycles. Mary Kate shares why returning to analog methods can reignite artistic joy that translates to paid work and how freelancers can confidently price their illustrations to win new business. From her Vermont barn studio, she reminds us that creativity thrives where curiosity and real-world making meet.

We’re chatting with Tom Froese, an Award-Winning Illustrator, Top Teacher on Skillshare who has led over 120,000 students, and the host of the podcast Thoughts on Illustration. Tom has illustrated for clients like Yahoo!, Airbnb, GQ, and The Wall Street Journal. He’s best known for his brightly colored maps and illustration work made with expressive shapes and printmaking-inspired textures.

In this episode, we cover finding a unique career path as an illustrator in a crowded space, how to develop a signature style, and ways to increase visibility towards getting more work. Tom shares how he deals with burnout, leans in on what comes naturally to maximize his talent, and shares ideas for young illustrators to get a foot in the door.

In this episode, we're talking with Evante Daniels about Cultural Physics and how to build resonance that's felt, remembered, and trusted through design and marketing. Evante is the founder and Chief Strategy Officer at SEEQER, a cultural intelligence firm. His professional background spans industrial design, brand strategy, and marketing leadership.

For many creatives, the concept of “culture” feels like something that moves independently of us, making it difficult to gauge its importance in strategic decision-making. But it’s not guesswork. Evante shares how we can define and work intentionally with the forces shaping collective perception. We cover what cultural physics is, why it matters to designers and marketers, and how to actually work with culture instead of trying to get lucky.

Grace Ling is the Founder of Design Buddies - a massive design community hosted both online and in-real-life events. She is a UX designer, product designer, illustrator, community builder, content creator, competitive runner, and a world traveler with visits to over 40 countries stamped on her passport.

She’s built a huge personal brand across various social media networks, spoken at over 100 events, and has been featured in New York Times Square and Wall Street Journal. Her career also includes several design roles at Electronic Arts (EA).

This episode features a live conversation with Grace where over 100 attendees joined to listen in. We cover how to get started with building a personal brand, what to focus on as you grow, and what to avoid as well. 

Frank Bach is a Staff Product Designer at Doordash, formerly Instagram and Headspace. He's interested in the relationship between mindfulness and creativity: how meditation can empower you to be a stronger designer and more engaged contributor. His work spans product, growth and brand design – and on the side, he also runs an online store and tours with his punk band, Monk.