Squawk Pod – “Leaders Playbook: Inside Airbnb” (Jan 28, 2026)

Overview

This episode of “Leaders Playbook,” hosted by CNBC’s “Squawk Pod,” dives deep into the evolution of Airbnb, focusing on the leadership journey of co-founder and CEO Brian Chesky. Recorded at a luxury Airbnb listing in Beverly Hills, the episode traces Chesky's path from designer to CEO, unveiling pivotal moments that defined Airbnb—from an air mattress startup to a global hospitality disruptor. The discussion centers on leadership during crises, the power of optimism, and the unique impact of a designer’s mindset at the helm of a tech company.

Key Discussion Points and Insights

The Origin Story and Core Beliefs (01:02–04:36)

• Beginnings in San Francisco: Brian Chesky recalls quitting his job as a designer, moving to San Francisco with $40k–$45k/year, and brainstorming startup ideas with Joe Gebbia. Lack of rent money and a sold-out design conference sparked the idea of “Air Bed & Breakfast.”
• Serendipity and Friendship: Early guests became friends, not just customers. This shaped Chesky’s core belief that “people are basically good. They could trust one another” [01:24].
• Surviving the Financial Crisis & Early Growth: Entering Y Combinator in 2009, the team found a product that filled basic needs in hard times—helping people generate income by sharing their homes. Rapid growth followed, with Airbnb becoming a billion-dollar company before “unicorn” was a common term.

Brian Chesky [01:24]: “I just maybe had this core insight that people are basically good. They could trust one another.”

Finding Leadership in Crisis (04:36–07:27)

• The ‘RIP Airbnb’ Moment: In 2011, a host’s apartment was trashed, leading to public outrage and the #RIPAirbnb hashtag. Chesky describes this as his “moment of truth,” realizing that a leader’s job is to make courageous, principled decisions—not simply follow consensus.
• Transforming a Weakness into a Strength: Airbnb introduced a $50,000 property damage guarantee (now $3 million), using trust as a company pillar.
• Philosophy of Principle-led Decision Making: Chesky acted according to values over business calculation—betting on humanity’s goodness.

Brian Chesky [05:23]: “A leader steps up in times of crisis. They’re decisive. You’re not just seeking consensus. You have to have the courage to make a defining decision that’s going to chart your way forward.”

Navigating the COVID-19 Pandemic (09:03–13:35)

• 80% Revenue Collapse: In March 2020, Airbnb lost 80% of its business in eight weeks while preparing for an IPO.
• Immediate Actions: CFO Ellie Mertz describes deploying company capital to help guests and hosts, rapidly raising cash despite a strong balance sheet, and restructuring the organization to eliminate redundancy.
• ‘Founder Mode’ Leadership: Instead of becoming hands-off, Chesky doubled down on involvement—making swift, detailed decisions, and restructuring Airbnb to function more like its startup roots.

Ellie Mertz [10:07]: “A business that had been growing at approximately 30% was effectively down 80%... we took this horrible exogenous hit to the business as a forcing function to not only move quickly, but also to figure out things that we could do to make ourselves a better company.”

“Founder Mode” vs. Micromanagement (13:35–17:58)

• Defining Founder Mode: Chesky challenges common CEO advice—arguing the founder should stay deep in the details for product and strategy, coining “Founder Mode” (Paul Graham, Y Combinator).
• Not Micromanagement, but Partnership: Drawing on a conversation with Apple’s Jony Ive, Chesky distinguishes being detail-oriented from micromanaging, focusing on “making people better,” not disempowering them.
• Efficient Decision-Making: Structures meetings to include all relevant decision-makers, reducing delay and keeping teams focused and small.

Brian Chesky [16:30]: “Jony Ive said ... Steve Jobs didn’t micromanage me. He partnered with me ... If I’m in the details with somebody, am I making them better or am I disempowering them? And I hope that when people feel like I’m involved in projects ... I am helping them push to think bigger.”

Strategy, Budgeting, and Product Development (17:58–20:32)

• Decoupling Strategy from Budget: Instead of annual, bottom-up planning, Chesky implements a two-year strategy updated every six months, separate from the annual budget. This aims for agility and continuous alignment with the product vision.
• Product Before Finance: Both Chesky and Mertz describe focusing on customer-centered product ideation before financial modeling—seeing financial planning as supporting innovation, not restricting it.

Ellie Mertz [19:57]: “We spend a lot of time thinking about ... what are we trying to design, what are we trying to offer for the customer as opposed to starting with ... what is the incremental dollar you are going to generate. That comes after.”

Scaling a Two-Sided Marketplace (20:32–22:43)

• Trust and Behavior Change: Airbnb’s challenge was changing consumer behavior at scale—convincing people to trust strangers with their homes, and guests to choose homes over hotels.
• Global, High-Stakes, Regulated: Unlike city-based network apps (Uber, DoorDash), Airbnb required global supply and handling across cultures, regulations, and monetary systems.
• Relentless Problem-Solving: Chesky emphasizes tackling problems daily and relying on great people.

Brian Chesky [21:14]: “You have to get buyers and sellers [at] the same time ... these are 2, 3, 4, $500, even $1,000 purchases. So you need a global network effect that is two-sided marketplace that’s high trust, high consideration. It’s highly regulated in a lot of markets.”

The Designer’s Mindset in Leadership (22:43–25:09)

• Optimism as Superpower: Chesky attributes much of his success to imagination, optimism, and a core faith in humanity.
• Designer’s Approach to Leadership: He sees design as deeper than aesthetics; it’s about how things work, creativity, assembling elements, and problem-solving fundamentally.
• Complementary Leadership with CFO: Mertz and Chesky’s different backgrounds (business vs. design) strengthen their teamwork.

Brian Chesky [22:43]: “I have ... a huge imagination for what’s possible ... people are basically good. They could trust one another, and we could bring people together, and people are better when they’re together.”

Memorable Quotes with Timestamps

• On founding Airbnb:

  “It all started with an airbed.” — Brian Chesky [01:02]

• Core belief in humanity:

  “I just maybe had this core insight that people are basically good. They could trust one another.” — Brian Chesky [01:24]

• Responsibility during crisis:

  “A leader steps up in times of crisis. They’re decisive.” — Brian Chesky [05:23]

• Handling the COVID crisis:

  “A business that had been growing at approximately 30% was effectively down 80%.” — Ellie Mertz [10:07]

• On “Founder Mode”:

  “I was told to hire great people and trust them and get out of the way. I think that is terrible advice for the vast majority of founders.” — Brian Chesky [12:41]

• Partnering vs micromanaging:

  “Steve Jobs didn’t micromanage me. He partnered with me ... If I’m in the details with somebody, am I making them better or am I disempowering them?” — Brian Chesky (quoting Jony Ive) [16:30]

• On optimism and design:

  “One of my superpowers is maybe I’m just an optimist ... I have, like, a huge imagination for what’s possible in the world.” — Brian Chesky [22:43]

• Designer on the CEO path:

  “Very rarely in history have designers been given a bigger canvas than a company as big as Airbnb, and so I think I’m a bit of an experiment. What happens when a designer runs a tech company?” — Brian Chesky [25:09]

Segment Timestamps

| Segment Topic | Key Speaker | Timestamp | |----------------------------------------------|-------------------|------------| | Intro: Airbnb origin story | Chesky, Narrator | 01:00–04:36| | Leadership amid crises | Chesky | 04:36–07:27| | Surviving the 2020 pandemic | Chesky, Mertz | 09:03–13:35| | Founder Mode, leadership style debate | Chesky | 13:35–17:58| | Approach to strategy & budgeting | Chesky, Mertz | 17:58–20:32| | Scaling trust and disruption | Chesky | 20:32–22:43| | Designer mindset, optimism & collaboration | Chesky, Mertz | 22:43–25:09|

Conclusion

This “Leaders Playbook” episode offers a rare, candid look at the leadership philosophy and evolution of Brian Chesky and Airbnb. The discussion provides valuable insights for entrepreneurs, business leaders, and anyone interested in how design thinking and optimism can drive transformation, even in the face of crisis. Chesky's journey shows the power of principle-driven decisions, deep involvement from founders, and the value of designing both a product and a company for trust and creativity.