Airbnb’s Brian Chesky breaks down the crucial differences between founders and managers

In a recent episode of The Diary of a CEO podcast, Airbnb co-founder and CEO Brian Chesky offered a candid look into the leadership dynamics that shape companies, drawing a sharp distinction between founders and managers—a topic especially relevant as companies wrestle with scale, identity, and innovation.

Chesky likened founders to "biological parents" of their ventures, underscoring the emotional depth and innate connection they have with what they create. "You can love something, but when you're the biological parent of something, it came from you—it is you," he said. This deep-rooted bond, he argues, gives founders a unique clarity of vision and purpose that’s hard to replicate.

1. Permission to Reinvent Founders, Chesky noted, possess a level of inherent authority that gives them “permission” to transform their businesses fundamentally. Unlike managers, who are typically brought in after a company's foundation is laid, founders can shift direction, rework strategy, or even dismantle what they’ve built without raising eyebrows—because they’ve earned that right through creation.

2. Intimate Knowledge of the Company Their granular understanding of every facet of the company—from product to culture—makes founders uniquely capable of rebuilding or reinventing when needed. That institutional memory, accumulated from the earliest days, is often absent in hired leadership.

3. Leadership as Presence Chesky challenged the notion that being a founder means sitting at the top and calling the shots from a distance. “Great leadership is presence, not absence,” he said, debunking the myth of the detached visionary. He described “founder mode” not as a charismatic persona but as an intense, hands-on commitment to the product and the people behind it.

Avoiding Managerial Bloat One of Chesky’s key critiques of modern corporate culture is the proliferation of management layers. “Managers managing managers” can dilute focus and stifle expertise, he warned. Instead, he advocates for a flatter, functional structure where leaders are specialists—not just generalists in charge of other generalists. At Airbnb, this philosophy shows up in the elimination of traditional one-on-one meetings. Chesky prefers group discussions that promote shared understanding and decision-making.

Learning from the Greats Chesky, who has long drawn inspiration from visionaries like Steve Jobs and Elon Musk, sees himself as Airbnb’s "chief editor"—meticulously involved in product development and strategy. He keeps tabs on multiple projects, carves out time for in-depth reviews, and ensures that the leadership team stays close to execution.

On the Challenges for Women Founders Touching on a crucial cultural barrier, Chesky also spoke about how women often face hurdles in embodying the “founder mode” due to outdated perceptions of leadership. While male founders are often praised for assertiveness and control, women in similar roles may be criticised for the same behaviour. Chesky called for a recalibration of how society views—and values—female leadership.

What’s Next for Airbnb? Looking ahead, Chesky hinted at Airbnb’s ambitions beyond home rentals. The company, which has spent the past few years doubling down on design and user experience, is now exploring ways to expand its travel ecosystem. New services that enhance the full journey—not just the stay—are in the pipeline, reflecting Chesky’s belief that Airbnb can evolve into something broader than a booking platform.

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