Design Matters with Debbie Millman – Brian Chesky

Episode Date: January 26, 2026

Overview

In this episode of Design Matters, Debbie Millman sits down with Brian Chesky, co-founder and CEO of Airbnb, to explore how art, design, entrepreneurship, and personal values can come together to create global change. Chesky reflects on his design-driven upbringing, his unconventional career path, and the ethos that powers Airbnb. The conversation is candid, inspiring, and rich with insight into creativity, risk, leading by design, and the future of human connection—both online and off.

Key Discussion Points & Insights

1. Early Creative Influences and the Power of Imagination

• Brian’s unique childhood involved redesigning toys and products rather than just using them.
  • Quote: “Artists and designers aren't just communicators. We can actually be change agents. We can actually build things.” — Brian Chesky [00:01]
• His parents, both social workers, modeled service to others and shaped his empathy for people’s needs.
• Chesky describes himself as intensely imaginative—even sleeping in hockey gear out of pure enthusiasm as a child.
  • Quote: “When I went into something, I went into something all the way. It was almost like becoming a method actor.” — Brian Chesky [31:47]

2. Discovering Design as a Calling

• Brian didn’t realize “design” was a discipline until much later; he initially saw himself as an artist, drawing inspiration from objects around him.
• A high school art teacher recognized and encouraged his talent, which gave both Brian and his parents hope that creativity could lead to a viable career.
  • Quote: “If you tell somebody they’re really great at something, you’ll reinforce that and they’ll become even better.” — Brian Chesky [11:17]
• Winning a national art competition and seeing work displayed in the US Capitol solidified the idea that art and design could be a life path.

3. Identity, Expectations, and the Choice to Pursue Joy

• Chesky recounts the tension between following his passion and parental expectations for security—a major theme for creative individuals.
  • Quote: “You can just decide to be happy… Just do what makes you happy and have faith you’ll figure out the rest.” — Brian Chesky [11:46]
• He reflects on the pressure for conformity in 1980s/90s America and how art school at RISD fostered a new mindset: individuality can build community.

4. Rhode Island School of Design (RISD): A Crucible for Creative Leadership

• RISD’s environment taught Chesky that design isn’t about conformity or finding the one “right answer,” but about changing the world through your own lens.
  • Quote: “There couldn’t possibly be infinite right answers… At RISD, it was your interpretation—and in fact it was celebrated to see it differently.” — Brian Chesky [21:53]
• Leadership experiences outside the classroom (running the hockey team and collaborating with MIT students) cultivated entrepreneurial skills.

5. From Design Jobs to Entrepreneurial Leap

• Early career: Chesky worked at a small LA design shop on rapid-fire projects (like the Pure Flush toilet seat) and reality TV. These fast-paced, scrappy assignments mirrored the startup environment.
• A moment of existential clarity led him to quit his steady job and move to San Francisco, betting on his happiness over safety.
  • Quote: “I looked in the rearview mirror and it was the same road that was my life. I didn’t want to see the rest of my life—I wanted to discover it.” — Brian Chesky [44:36]

6. The Birth and Growth of Airbnb

• The initial Airbnb prototype—air mattresses in Chesky and Joe Gebbia’s living room during a city-wide hotel shortage—taught them about necessity, hospitality, and trust.
• Early bookings came slowly; perseverance was built on the conviction that the positive experience could be scaled through design and storytelling.
  • Quote: “We realized the problem wasn’t a home rental problem, it was a trust problem. We had to design a system of trust.” — Brian Chesky [54:19]
• Investor skepticism was high; Chesky and team encountered resistance, bias against designer-founders, and countless rejections.
  • Quote: “One investor said, ‘I like everything about your company but you and your idea.’ … Those were not unreasonable conclusions.” — Brian Chesky [56:46]

7. Embracing Uncertainty and Persistence

• Chesky describes maxing out credit cards and living with daily anxiety during the early days—balancing determination with emotional resilience.
  • Quote: “You don’t need to know how to get to the top of the mountain, you just need to make some progress tonight.” — Brian Chesky [60:12]

8. Managing Scale, Staying Hands-On, and Personal Evolution

• Chesky discusses how his early philosophy—do everything by hand until it’s too painful—shaped Airbnb's culture but eventually had to evolve.
  • Quote: “For me, the doing it by hand is the act of designing, is the act of creating… Once we figure out the product, I work with a team to industrialize it.” — Brian Chesky [62:29]
• As the company matured, he shifted toward high-level direction and sought new creative challenges, especially with AI and experiences.

9. The Future: Airbnb, AI, and Human Connection

• Chesky is enthusiastic about AI but believes Airbnb’s value lies in the timelessness of real-world connections.
  • Quote: “Our business is not going to change as much as Instagram’s will, or Meta’s will, or Google’s will… I like that our business is so timeless.” — Brian Chesky [63:58]
• He envisions Airbnb moving beyond homes to become a holistic community based on trust, belonging, and understanding.

10. Success, Wealth, and Philanthropy

• Chesky reflects on becoming a billionaire, signing the Giving Pledge, and his belief in returning wealth to society.
  • Quote: “Warren Buffett had this great quote: ‘I’m going to give my kids enough money to do anything, but not so much money to do nothing.’… The utility of billions is capital allocation to do good.” — Brian Chesky [69:44]

11. Advice to the Next Generation

• Chesky encourages creatives to embrace their power as change agents—not just communicators—with the entire world as their canvas.
  • Quote: “Artists and designers aren't just communicators. We can actually be change agents. We can build things, we can run things, we can be in charge of things … The world can be our canvas.” — Brian Chesky [74:10]
• Importance of working backwards from the experience you want to create, not just the tool or product.

Notable Quotes & Memorable Moments

• On the birth of Airbnb:
  • “We called it Airbed and breakfast dot com. That’s where the name Airbnb comes from… I was an entrepreneur. And that’s when I realized the difference between unemployed and entrepreneur—starting is mostly in your head.” — Brian Chesky [49:54]
• On risk and nonconformity:
  • “Anyone can get on a rocket ship… If enough people start things, create things, then you can design the world you want to live in.” — Brian Chesky [75:55]
• On philanthropy and wealth:
  • “What actual burden it would be to give all that money to children? … Having billions of dollars, the utility of it is capital allocation, that I believe that I can do really good things to the world.” — Brian Chesky [72:05]
• On AI and technology:
  • “I think the future of AI is going to be much richer than text. It's going to be visual, it's going to be multimodal, it's going to be very much interactive.” — Brian Chesky [65:50]

Timestamps for Key Segments

• [04:37] — Childhood, artist origins, and early imagination
• [07:16] — Family background in social work and empathy
• [10:01] — Teachers who shaped his creative path
• [12:46] — Parental anxieties and career doubts
• [16:10] — Choosing RISD and design education philosophy
• [19:11] — The culture and impact of RISD
• [23:25] — Creativity in education: Assignments and lessons in improvisation
• [25:42] — Entrepreneurship lessons from leading RISD’s hockey team
• [29:53] — Early design internships and pushing boundaries
• [34:08] — Performing at graduation: The white tuxedo speech
• [35:38] — The challenge of finding work post-graduation
• [40:44] — Design firm in LA, reality TV, and “Pure Flush”
• [44:36] — Existential turning point: Quitting for the unknown
• [49:54] — The origin story of Airbnb
• [54:19] — Systemic trust: The real design challenge
• [56:40] — Investor rejection and perseverance
• [59:51] — Financial uncertainty and persistence
• [61:16] — “Do everything by hand until it's painful”
• [63:55] — AI’s place in Airbnb’s future
• [69:44] — Philanthropy, wealth, and the Giving Pledge
• [74:10] — Final advice to the next generation of innovators

Tone & Style

Chesky's tone is enthusiastic, introspective, occasionally humorous, and always candid. Millman guides the conversation with warmth and curiosity, drawing out both practical advice and philosophical insights.

Summary Takeaway

This episode is a masterclass in trusting creative instincts, challenging the status quo, and building systems that allow people to connect in new and deeper ways. Chesky’s story offers permission—and encouragement—for anyone with imagination and empathy to see the world as their canvas, designing and redesigning not just products, but possibilities for the future.