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Cheers & Tiers: Cultivating Community with Bridge Builder Josh Silverman

Chatting with Josh was like stepping into a whirlwind of wit, wisdom, and a hefty dose of inspiration.

Author

Rachel Elnar
March 18, 2025 • Estimated Reading Time: 5 minutes

What happens when you combine over three decades of design expertise, a passion for community building, and a slight distaste for standing in lines? You get Josh Silverman, of course. Sitting down with our friend Josh for this podcast was like unraveling a treasure trove of insights, amusing anecdotes, and wisdom laced with equal parts humility and brilliance.

Leadership Lessons from the Design World

Josh’s career is the stuff of legends in the design community. Between founding PeopleWork Partners, running Schwadesign (a lean business so well respected even The Wall Street Journal took notice), and leading the MDES program at the California College of Arts, he’s done it all. And if that wasn’t enough, his work in coaching leaders and placing top-notch designers at companies like Netflix, Target, and OpenAI practically screams “overachiever”—in the best possible way. 💪🏼

But Josh’s approach isn’t just about connecting dots on a résumé. It’s about people. Or, as he put it during our conversation, “being the ancestors we need in the design community.” It’s clear he sees leadership not as a title but as a responsibility—to foster, inspire, and mentor the growth of others.

Design Leadership Runs Deep

Our conversation took us back to Josh’s roots with AIGA, where he’s practically a legend in his own right. A self-proclaimed “pretty good greeter,” he began as a Membership Chair for AIGA Boston but didn’t stop there. Oh no, Josh doesn’t “do” stopping. He went on to co-create a Community Membership Director position and then helped form several chapters, including Rhode Island, all while dragging the famed Best of New England (B.O.N.E.) Show across, well, New England.

Josh’s knack for community-building wasn’t limited to events and memberships. He sees leadership retreats as core to design’s backbone.

One of my favorite nuggets? Josh’s tale of critiquing AIGA’s slightly off typography during a leadership retreat. “Are we not designers?” he said, exasperated. But that moment—where he fearlessly spoke up in a room of peers—underscores his natural tendency to lead, challenge norms, and push for betterment (and better typography).

Why Designers Need Heroes (and Why You Should Be Someone’s)

Josh’s advocacy for creating community wasn’t just about networking—it was about mentorship and reciprocity. This ethos translated into countless opportunities to collaborate with heroes and newcomers alike. One serendipitous meeting with Stefan Sagmeister led to an unforgettable day of record shopping and conversations about music design. “You can’t pay to spend a day with your heroes,” Josh laughed, “but if you volunteer or get involved, doors you didn’t know existed open for you.” 🚪

It’s not just luck—it’s about showing up, raising your hand, and being present in spaces that allow creativity to flourish. Josh jokingly called himself “lucky,” but I’d argue it has more to do with courage, generosity, and ceaseless curiosity—a mix that creates truly limitless opportunities.

If there’s one takeaway from our chat, it’s this—whether you’re building pyramids at retreats or brainstorming the perfect UX flow, great design will always come back to relationships. And if that’s the case, the design community is in good hands when people like Josh are steering the conversation. Cheers to Josh Silverman, a true connector of dots, people, and ideas.

Want to hear more stories like Josh’s? Subscribe to Cheers & Tiers on Apple Podcasts, Spotify, or wherever you get your podcasts. We’ll have more episodes featuring your friends and favorite design leaders, sharing their journeys, challenges, and triumphs.

This episode is now available for listening. Please subscribe, rate, and review Cheers & Tiers: Design Leadership Tales Retold wherever you get your podcasts.

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