Inside Airbnb CEO Brian Chesky’s “Founder Mode” and the Influence of Steve Jobs

Brian Chesky, co-founder and CEO of Airbnb, sat down for an interview on *Decoder* for his third appearance, joining the ranks of only one other recurring guest, Mark Zuckerberg. Chesky shared excitement about being in the studio for the first time with host Nilay Patel, recalling their last conversation in New York, which was so engaging that it felt as if they’d been in the same room.

The interview covered Airbnb's recent Winter Release, which introduces several new features and enhancements aimed at reshaping the hosting experience. Chesky emphasized that Airbnb’s model relies on maintaining a high number of listings, as a wider variety of homes helps regulate prices on the platform. To this end, Airbnb recently launched the Co-Host Network. This feature allows experienced hosts to help manage other properties, supporting owners who find hosting too time-intensive. Chesky noted that the idea stemmed from listening to potential hosts who were hesitant to start due to concerns about workload. The Co-Host Network aims to match such homeowners with skilled co-hosts who manage a few properties, ensuring a more personalized service while avoiding the large-scale, impersonal approach of traditional property management companies.

The Co-Host Network is designed to provide trusted support, as co-hosts on the platform are vetted and typically manage just a handful of properties, offering a high-quality hosting experience. With 10,000 co-hosts in 10 countries, this system lets hosts who lack the time for daily management partner with skilled individuals who bring local knowledge and a commitment to the Airbnb ethos. This approach ensures that guests still get the localized, unique experiences that made Airbnb popular in its early days. Co-hosts work exclusively within the Airbnb ecosystem, helping ensure high standards and customer satisfaction.

Chesky further explained Airbnb’s approach to product development, comparing it to a hardware company. Instead of continuous, incremental software updates, Airbnb rolls out significant, twice-yearly updates: the Summer Release and Winter Release. This cycle has helped speed up development, with the Winter Release alone delivering more than 50 upgrades focused on personalizing the guest experience. These updates take into account individual preferences, past booking behaviors, and location. Over the past two years, Airbnb has implemented 430 upgrades through this release cycle, showing a commitment to innovation and user experience.

In addition to enhancing the user interface and personalizing the search experience, Chesky discussed Airbnb’s dedication to authenticity and quality assurance. One of the challenges of managing a platform like Airbnb is the diversity of its listings. Unlike traditional search engines, Airbnb needs to match guests with suitable homes from a vast inventory, which is a complex task given the variation in listings. Chesky emphasized that the company’s approach to quality is becoming more hands-on, moving beyond reviews and ratings to proactively certify and verify users and listings. He noted that while the early days of Airbnb mirrored the self-regulation seen on platforms like Craigslist, the expectations of modern users demand a more structured approach. The Co-Host Network reflects this evolution by providing a middle ground between fully independent hosting and third-party property management.

Airbnb's emphasis on quality is also a business imperative. Chesky explained that unlike social media platforms where user satisfaction may be more subjective, in the travel industry, a bad experience directly impacts customer loyalty. Users expect their Airbnb experience to be reliable and seamless, which has led the company to invest heavily in moderation and quality control.

Chesky addressed the broader challenges of platform management, especially with Airbnb's global footprint. He compared Airbnb's challenges to those of large-scale social media platforms, mentioning how challenging it is to maintain authenticity on such a vast network. Unlike video or social platforms, where engagement is often concentrated on a few top users or pieces of content, Airbnb's business depends on a long tail of individual hosts and unique listings. This diversity necessitates a nuanced approach to content moderation and user verification. Chesky noted that, unlike social media, Airbnb’s moderation is often welcomed by users who expect a level of trustworthiness from the platform. He suggested that platforms prioritizing authenticity and user trust will likely find more long-term success, pointing out that these values align well with Airbnb’s mission of connecting travelers with unique, authentic experiences.

Reflecting on the platform’s challenges, Chesky shared that Airbnb's growth and global presence present unique regulatory and operational hurdles. He highlighted the complexities of balancing supply and demand globally, managing billions of dollars in transactions, and dealing with safety concerns in diverse markets. Chesky recalled that Sequoia Capital partner Doug Leone once told him that Airbnb was one of the hardest companies to scale due to the intricate balance of local and global demands, high customer expectations, and regulatory scrutiny. These challenges, Chesky explained, are part of what makes Airbnb unique and motivate him to keep innovating within a complex industry.