Brian Chesky Manages 50 Direct Reports to Stay Connected in Founder Mode

Airbnb CEO Brian Chesky maintains a direct and hands-on leadership approach at the $79 billion travel platform, personally managing, hiring, and firing up to 50 employees, despite the company's substantial size and scale. During a recent appearance on the "Social Radars" podcast, Chesky emphasized the importance of staying closely connected to the people executing the work at the company. "I treat them all as my directs," he stated, noting that he participates in the hiring process and makes decisions about employee performance and retention. This approach, which Chesky calls "skip-level" management, allows him to maintain direct relationships with employees beyond immediate supervisors, bypassing traditional hierarchical structures [1].

Chesky's leadership style is rooted in what he describes as "founder mode," a concept he outlined during a Y Combinator event in 2024. This approach prioritizes close employee relationships and direct engagement in company operations, in contrast to the more conventional "manager mode," which emphasizes delegation and larger-scale oversight. According to Paul Graham, founder of Y Combinator, this method challenges traditional leadership advice and allows founders to retain control and adaptability, particularly in an AI-driven business environment [2]. Chesky believes that "founder mode" is essential for maintaining agility and innovation, especially as companies face increasing disruption from technological advancements and market shifts.

The shift toward "founder mode" came after a critical turning point for Airbnb in 2020, when the company faced a 72% revenue drop due to the pandemic’s impact on global travel. Chesky sought advice from Apple designer Jony Ive, who suggested that "you don’t manage people—you manage people through the work." Inspired by this insight, Chesky began removing layers of management, echoing the leadership style of Steve Jobs. This restructuring allowed Airbnb to remain nimble during uncertain times and adapt to the rapidly changing market [1]. Other business leaders, such as Jensen Huang of Nvidia, have similarly adopted a hands-on approach, with Huang reportedly reviewing payroll for all 42,000 employees at the end of each cycle [2].

Chesky’s commitment to "founder mode" is not without challenges. He acknowledged that managing 50 employees directly is "a lot of work," but he views it as necessary to maintain a deep connection to the company’s operations and culture. This approach has allowed him to ensure that Airbnb’s executive team remains aligned with the company’s long-term vision and that he can remain close to the day-to-day workings of the business. The philosophy has also influenced other leaders, with some adopting similar strategies to retain a startup-like agility at their organizations.

The broader implications of Chesky’s leadership model suggest a growing trend among tech founders to retain tighter control over their companies, even at scale. As AI and automation continue to reshape business landscapes, the ability to pivot quickly and maintain close employee relationships may become increasingly valuable. Chesky’s approach underscores the belief that in a rapidly evolving market, the traditional corporate hierarchy may not be as effective as a more direct, founder-driven leadership style [1].

Source: [1] Airbnb CEO Brian Chesky still in founder mode - hire, fire, promote, and manage (https://fortune.com/2025/08/26/airbnb-ceo-brian-chesky-still-in-founder-mode-hire-fire-promote-and-manage/) [2] Airbnb CEO Chesky Is a Hands-On Manager With 50 Employees (https://www.entrepreneur.com/business-news/airbnb-ceo-chesky-is-a-hands-on-manager-with-50-employees/496317)