textlize - How Airbnb's Brian Chesky Rediscovered "Founder Mode" to Save the Company

The Drift from Founder-Led Culture

As Airbnb scaled, Brian Chesky experienced a profound leadership challenge: "You go on a rocket ship and you're alone in that rocket ship. It's lonely because your co-founders start working for you, and you hire executives who are more experienced." This transition eroded the company's original operating principles:

Well-intentioned advice like "hire great people and trust them to do their job" backfired when leaders weren't properly audited
Executives pushed for professional management styles conflicting with founder instincts
Decision-making became negotiation rather than clear direction
Multiple teams operated in conflicting directions without unified vision

Chesky admits: "The bigger we got, the more I lost my confidence. I was seeking advice when I should have listened to myself." This drift created what he now calls "manager mode" – where leaders become disconnected from core operations.

The Pandemic Catalyst

When COVID-19 devastated the travel industry in March 2020, Chesky received a pivotal call from board member Ken Chenault (former American Express CEO): "This pandemic is 10 of them [referring to 9/11-scale crises]. This is your defining moment as a leader."

The crisis created three critical conditions for transformation:

Permission to lead – Teams urgently sought direction rather than operating autonomously
Existential imperative – With predictions of Airbnb's demise, radical change became acceptable
Blueprint clarity – Chesky could finally implement the founder-led model he'd envisioned

"I made what felt like five years of decisions in three months," Chesky reflects. The crisis eliminated organizational resistance to fundamental change.

Founder Mode in Practice

Chesky defines founder mode as returning to first-principles leadership:

Management Philosophy

Leadership is presence, not absence. Reject conventional wisdom that CEOs should delegate vision. "The right way is one way – the founder's way."

Operational Rhythm

Operate like a giant startup: small teams, deep involvement in work details, and daily creative collaboration rather than hierarchical approvals.

Chesky implemented two structural changes:

Concentric circles management: Treating 40-50 key reports as direct collaborators rather than through layers
Multi-level skip meetings: Building relationships across all levels to maintain connection to actual work

"If you have infinite time, all employees would report to you. Since that's impossible, skip-leveling is essential to understand reality," he explains.

The Founder's Advantage

Chesky argues founder-led companies outperform because:

Founder Mode	Professional Management
Direction through daily vision-setting	Vision as periodic pronouncement
Hands-on problem solving	Delegation without oversight
Speed through alignment	Slowed by negotiation layers

This approach proved critical in the pandemic rebound: "We went from 'is this the end of Airbnb?' to a $100 billion IPO by rejecting professional management orthodoxy."

Why Founder Mode Matters in the AI Era

Chesky sees founder mode as essential for modern companies:

Speed advantage: "In the age of AI, velocity comes from small teams moving in unison"
Reinvention capacity: "AI forces constant reinvention – founder-led companies pivot faster"
Technical depth: Founders understand core work because "they did every job before hiring others"

He concludes: "Great companies are defined by crises. But you shouldn't need a once-in-a-generation pandemic to rediscover founder mode. The most valuable companies globally demonstrate this principle consistently – it's about maintaining founder instincts at scale."