This interview features Airbnb CEO Brian Chesky arguing that in the AI era, founders must dive deep into product details rather than relying on managers. He predicts a consumer AI renaissance in 12-24 months. Key holdings: Airbnb (boosted conversion rates via a small-team pilot called 'Project Hawaii'), Apple (Jobs' founder-mode comeback), and Disney (founder-led longevity). Chesky advises founders to spend 50% of time on 'pipeline hiring'—constantly meeting talent, not just using headhunters.
Brian Chesky (co-founder and CEO of Airbnb) discussed the core thesis of "AI Founder Mode" on the Invest Like the Best podcast: the AI era demands that founders engage more deeply in product details rather than relying on pure managers. He introduced the "11-star experience" approach, which involves
Brian Chesky (Co-founder and CEO of Airbnb) discussed the core thesis of "AI Founder Mode" on the Invest Like the Best podcast: the AI era demands that founders engage more deeply with product details, rather than relying on pure managers. He introduced the "Eleven-Star Experience" approach, which seeks to achieve product-market fit by envisioning the most extreme customer experience. Key conclusions include: founders are typically not good CEOs early on, but founder-led companies are more enduring; AI will eliminate the role of pure people managers and drive consumer-grade AI innovation. Chesky also shared the shift from seeking praise to creating for passion, and the importance of minimizing problems (as illustrated by the "Project Hawaii" case). He emphasized that hiring is the most important job for a founder, and noted that Airbnb treats "people" as the atomic unit, not technology.
Brian Chesky argues that the AI era demands founders engage more deeply with product details than ever before, rendering pure people managers obsolete.
Chesky distinguishes between "founder mode" and "CEO mode." He notes that founders are born with intuition, but the CEO role is entirely counterintuitive: "No one is born a good CEO. And the job of CEO is completely counterintuitive." The common mistake founders make is over-delegating to professional managers, causing the company to lose control. Reflecting on 2019, he recalls: "I had like 7,000 employees. I didn't know what anyone was doing. I felt like I was in a car without a steering wheel."
The pandemic became a turning point. Airbnb lost 80% of its business in eight weeks, and Chesky shifted from "peacetime" to "wartime," taking full control of the company. His approach included: holding only small group meetings (not one-on-ones), ensuring the full chain of command was present, speaking last but making the final decision. He advocates for "first controlling hands-on, then gradually delegating," rather than the opposite.
AI founder mode will be even more extreme: Chesky predicts that companies will reduce management layers ("The Catholic Church has been going on for 2,000 years and only have four layers of management") and shift toward asynchronous work rather than meeting-driven operations. He believes pure people managers will not survive; everyone must become a "hybrid people manager or manager IC," directly engaging with products or customers. He concludes: "The two types of people that will not survive the age of AI are pure people managers and people that are rigid and don't want to change."
Chesky believes the current AI market is dominated by enterprises, but the next 12 to 24 months will usher in a renaissance of consumer AI.
He notes that among the latest batch of 175 companies from Y Combinator, 159 are enterprise-focused, with almost no consumer-facing companies. He attributes this to three reasons: 1) entrepreneurs fear that ChatGPT will crush their businesses; 2) consumer AI lacks mature business models (subscriptions, advertising, and e-commerce all have their ceilings); and 3) enterprise AI is easier to get started with (due to internal referrals within YC). However, Chesky sees this as a trend rather than an inevitability: "My prediction is that we're living in the age of enterprise AI. And I think in the next 12 to 24 months, you're going to see the beginning of a consumer AI renaissance."
He specifically points out that the interface for consumer AI must be extremely simple: "The next wave of AI is going to be consumer AI. Consumer AI is going to be the big prize." Current AI tools (such as Claude and Copilot) are not intuitive enough for ordinary people, but economic incentives will drive them to become more intuitive. He criticizes Silicon Valley's "herd mentality": "I think it's very trend-based and vibe-based. I think there's a sense that everyone kind of does what everyone kind of does."
Chesky proposes a methodology of "making the problem as small as possible," achieving product-market fit through small teams and single-city pilots.
"Project Hawaii" was an internal experiment at Airbnb: a small team of 10-12 people (designers, engineers, data scientists) focused on improving the "search-to-booking" conversion rate. They adopted a "crawl-walk-run-fly" strategy: first fixing bugs, then developing features, then restructuring the process, and finally achieving full automation. The result was approximately $200 million in incremental revenue in the first year, about $400 million in the second year, and an eventual conversion rate improvement of over 600 basis points (based on $13 billion in revenue).
Chesky emphasizes that Airbnb, as a company with nearly $100 billion in annual sales, has had only one core business for 18 years. He reflects: "We're like a one-hit wonder. And for 18 years, I couldn't get a second hit out." The solution is to return to the early approach: first validate in a single city (e.g., New York), then expand to 10 cities, and finally industrialize. He quotes Peter Thiel: "It's better to have a monopoly of a tiny market than a small share of a big market."
Core Principle: Paul Graham's "It's better to have 100 people love you than a million people sort of like you." Chesky explains: "The smaller the problem, the more there's fewer abstraction layers. You're actually on the ground. You're talking to people." This aligns with the logic of prototyping in industrial design: first create a small-scale prototype, then mass-produce.
Chesky shared his journey from seeking external validation to being driven by intrinsic motivation, which he believes is key to building great products.
He admitted that his early entrepreneurial efforts were driven by "love and fun," but after achieving success, he fell into the "praise trap": "Adulation is like a cup with a hole at the bottom. And you keep filling it in, thinking it's love, except it just keeps coming out the bottom." The day after going public, he attended a Zoom meeting in sweatpants and found everything unchanged: "It became the saddest day of my life because I realized, OK, what now? I got all this adulation. And I don't feel any different."
The turning point was returning to "creating for passion." He cited Rick Rubin's view: "An artist is an artist when they make it for themselves." And Obama's advice: "Don't focus on who you want to be. Focus on what you want to do." He concluded: "Suddenly there's no way to fail if you're making what you love."
Specific changes: He reduced "ruminating" (obsessing over others' opinions) and focused his energy on two things: "making" and "spending time with people I care about." He referenced Bill Walsh's philosophy, "The Score Takes Care of Itself": "Don't focus on winning. Focus on getting all the inputs perfect."
Chesky believes founders should spend 50% of their time on hiring, and adopt "pipeline hiring" rather than "search hiring."
He criticizes the common practice: "I need to hire a blank. So they do a search. They hire a search firm. They give you like 50 profiles. You pick the best one you hire. And a year later, you realize like they're good or bad." The correct approach is to continuously build a talent pipeline: "You're constantly recruiting. You're constantly meeting people." The specific method: first identify outstanding results (e.g., an ad you like), then work backward to find the person who created that result; then ask them to recommend other top talent, forming a "talent mafia" (e.g., Uber's operations mafia, Apple's design mafia).
Key data: Chesky personally served as the co-hiring manager for the company's first 200 employees. His first and last calls of the day were both to the recruiting team, and he spent 2–3 hours per day on hiring. "The more time you spend on recruiting, the less time you spend on management because the really good people are self-managing." He advises founders that their first hire should be a recruiter, not an engineer.
| Position | Guest Stance | Key Data |
|---|---|---|
| Airbnb | Bullish (but needs self-disruption) | Annual sales near $100 billion; conversion rate improvement over 600 bps (based on $13 billion revenue); 40% free cash flow margin |
| Apple | Positive reference | Adopted founder mode after Jobs' return; iPhone is a model of industrial design |
| Disney | Positive reference | Founder mode creates lasting value; no real innovation since Walt's death in 1966 |
| Uber | Neutral (as analogy) | Operates a talent mafia |
| OpenAI | Neutral (as analogy) | Most efforts shifted to Codex |
| Neutral (as analogy) | Gemini primarily serves search, unwilling to self-disrupt | |
| Expedia | Negative (as contrast) | Uses outdated tools like Outlook |
| Polaroid | Positive reference | Founder Edwin Land tested equipment with Ansel Adams |
1. Founders are not born CEOs, but founder-led companies are more enduring (Brian Chesky): The CEO role is entirely counterintuitive, and founders must learn how to be CEOs; however, companies with deep founder involvement (e.g., Disney, Apple) can sustain their legacy for decades after the founder departs.
2. AI will eliminate pure people managers (Brian Chesky): In the future, everyone must become a "hybrid people manager or manager IC," meaning directly engaging with products or customers; pure managers (those who only hold meetings and conduct one-on-one coaching) will not survive.
3. Consumer AI will see a renaissance within 12–24 months (Brian Chesky): The current AI market is dominated by enterprise (159 out of 175 companies in YC's latest batch are enterprise-focused), but economic incentives will drive interfaces to become intuitive, making consumer AI the "big prize."
4. The "11-star experience" method: achieving product-market fit by envisioning the ultimate customer experience (Brian Chesky): Start from five stars (everything normal) and push to six stars (wine, handwritten cards), seven stars (airport pickup), eight stars (elephant parade), nine stars (Beatles-style welcome), ten stars (Elon Musk takes you to space); "Go beyond the edge of reality and work backwards."
5. The principle of "making the problem as small as possible": first get 100 people to love you, then 100 million to like you (Brian Chesky, citing Paul Graham): Airbnb's "Project Hawaii" used a small team of 10–12 people to pilot in a single city, generating $200 million in incremental revenue in the first year; Peter Thiel's "monopolizing a small market is better than capturing a small share of a large market."
6. The "praise trap": seeking external validation is like a cup with a hole in the bottom (Brian Chesky): The day after going public felt like "the saddest day"; the solution is to return to "creating for the love of it," quoting Rick Rubin: "An artist only becomes an artist when they create for themselves."
7. Hiring is the founder's most important job, and "pipeline hiring" should be used instead of "search hiring" (Brian Chesky): Spend 2–3 hours a day on hiring; first find excellent results, then work backward to find the people; the first employee should be a recruiter, not an engineer.
8. "People" are Airbnb's atomic unit, not "homes" (Brian Chesky): In the future, Airbnb will be built around people's identity, preferences, and social graph, not properties; the goal is to become the most trusted identity verification platform on the internet.