Brian Chesky: the sketchbook behind Airbnb and the discipline of daily drawing

Brian Chesky did not study business. He studied industrial design at the Rhode Island School of Design (RISD). He co-founded Airbnb in 2008 with his roommate Joe Gebbia, then Nathan Blecharczyk joined them. Fifteen years later, Airbnb is capitalized at more than $80 billion. What almost no one tells about Chesky is what he continues to draw: entire notebooks, every day, as the main product management tool. That daily sketchbook practice closely matches what Julia Cameron prescribes in The Artist's Way — only Chesky draws it instead of writing it.

Who is Brian Chesky?

Chesky was born in 1981 in Niskayuna, New York. Father and mother social workers. He studied industrial design at RISD from 1999 to 2004, where he met Joe Gebbia. After graduating he moved to San Francisco. In 2007 he and Gebbia couldn't pay the rent. They rented three air mattresses on the floor of their living room to three design conference attendees who needed a hotel. They charged 80 dollars each. That night the idea of ​​Airbnb (originally Air Bed & Breakfast) was born. They went out to find investors with a notebook full of product sketches. And Bill Gurley turned them down. And Fred Wilson. And the majority. Until Paul Graham invited them to Y Combinator in 2009. Today Airbnb is listed on Nasdaq with a market value of more than 80 billion. Chesky remains CEO. And keep drawing.

The practice: the daily sketchbook as a product and management tool

Chesky is famous among Silicon Valley founders for a practice that in many companies would be considered rare: he brings a sketchbook to all important product meetings. Not for taking notes. For draw. Screen sketches, user flows, spatial ideas, mind maps. The sketchbook is your thinking tool, not your documentation one. In episode 1 of Masters of Scale (Reid Hoffman, 2017), Chesky described how in the early days of Airbnb he and Gebbia They literally designed the guest experience frame by frame — as if it were a movie script or a comic. They drew every moment of the experience: when you receive the confirmation email, when you pack your suitcase, when you arrive at the neighborhood, when you open the door. That practice of thinking visually, rather than in spreadsheets, is what allowed Airbnb to build a differentiated experience when all competitors were listing generic rooms. Complementary practice is what Chesky calls 'product walks': 90-minute walks without a computer, only with a sketchbook. Once a week minimum. Usually with Joe Gebbia, before he left the company. During those walks they don't solve operational problems — they explore big questions about product direction.

The connection with Julia Cameron's The Artist's Way

Chesky's daily sketchbook is Julia Cameron's Morning Pages in visual version. The 'product walks' are the appointment with the artist of Cameron applied to product management. The interesting question is why so few non-designer founders do the same. The likely answer is that they lack the training to think visually — RISD gave it to Chesky. But the principle does not require being a designer. Any entrepreneur can start a notebook tomorrow where he draws flows, diagrams, spontaneous doodles. The difference between thinking only with words and also thinking with drawings is enormous — and it is orthogonal to artistic talent. Chesky's notebook does not contain 'good drawings'. Contains 'drawings that think'. Anyone can learn to do it. Julia Cameron implicitly recommends it in her chapter on 'recovering a sense of wholeness' — Chesky applies it as a management system.

How to apply it to your own case

Brian Chesky wasn't born with creative superpowers. He built a sustained practice over years, sometimes decades, that connects directly to the method he Julia Cameron encoded in The Artist's Path. If you have come to this post from reading about why Cameron's book is for entrepreneurs and ambitious people, you already know the framework. If you've come from another direction, we'll summarize it for you: Cameron's system trains the creative faculties that professional training ignores — lateral association, tolerance for ambiguity, discipline of the imagination, integration of intuition and analysis. The powers that separate the average founder from the exceptional founder, the competent manager from the memorable manager, the good professional from the indispensable professional.

The course Your Artist's Path It is the Spanish version of that system. 12 weeks, free, without spiritual choreography, designed for the ambitious profile who arrives skeptical and wants results. Brian Chesky's practice is living proof that the system works in the real world, with real stakes. The only thing missing to make it work for you is for you to get started.