Brian Chesky’s new playbook

Way too many founders apologize for how they wanna run the company. They find some midpoint between how they wanna run a company and how the people they lead wanna run the company. That's a good way to make everyone miserable because what everyone really wants is clarity, and what everyone really wants is be able to row in the same direction really quickly. And so I basically got involved in every single detail and I basically told leaders that leaders are in the details. And there's this negative term called micromanagement. I think there's a difference between micromanagement, which is like telling people exactly what to do, and being in the details. Being in the details is what every responsible company's board does to the CEO. It doesn't mean the board is telling them what to do, but if you don't know the details, how do you know people are doing a good job? People think that great leaders' job is to, like, hire people and, and just empower them to do a good job. Well, how do you know they're doing a good job if you're not in the details? And so I made sure I was in the details and we really drove the product.

(instrumental music) Today my guest is Brian Chesky. Brian is the CEO and co-founder of Airbnb, which he started in his apartment with his co-founders Joe and Nate, and has turned into an $80 billion global business with travelers and homes in 220 countries. I was very lucky to get to work with Brian for many years, and my sense is if you ask people who they consider the most inspiring tech or business leaders today, Brian would be right near the top of that list. In our conversation, Brian shares an in-depth explanation of what's happening with product management at Airbnb, which caused quite a stir in the product world when he talked about this previously. We also get deep into Brian's new approach of how he runs Airbnb, including shifting away from traditional growth channels like paid growth, and instead betting that if they just build the best possible product and tell people about it, growth will happen. Also, how the product team now operates, including having just one single roadmap across the entire company and Brian staying very close to every design and every feature. We also get a bit into his personal life, including how he finds balance and avoids burnout, how he continues to learn himself so that he can stay ahead of the business and its growth. This is a very special episode for me, and I'm thrilled to bring you Brian Chesky after a short word from our sponsors. This episode is brought to you by Sidebar. Are you looking to land your next big career move or start your own thing? One of the most effective ways to create a big leap in your career, and something that worked really well for me a few years ago, is to create a personal board of directors, a trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted private supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls, leading to more responsibility, faster promotions, and bigger impact. Guided by world-class programming and facilitation, Sidebar enables you to get focused tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you can meet them at Sidebar today? Jump the growing wait list of thousands of leaders from top tech companies by visiting sidebar.com/lenny to learn more. That's sidebar.com/lenny. You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers and crafting a strategy, you're drowning in spreadsheets and roadmap updates and you're spending your days basically putting out fires. A better way is possible. Introducing Jira Product Discovery, the new prioritization and road mapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds. And it's all built on Jira, where your engineering team's already working, so true collaboration is finally possible. Great products are built by great teams, not just engineers. Sales, support, leadership, even Greg from finance. Anyone that you want can contribute ideas, feedback, and insights in Jira Product Discovery for free. No catch. And it's only $10 a month for you. Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny. That's atlassian.com/lenny. Brian, thank you so much for being here. Welcome to the podcast.