5 Surprising Leadership Lessons from Airbnb

When things got bad during Covid, Airbnb CEO Brian Chesky did a surprising thing: he doubled down on design. In 2 years, he turned the ship around. How?

Airbnb went from the highest of highs to the lowest of lows in a matter of months. They were poised to be one of the largest IPOs in 2020, with their stock price soaring over 112% on the day of their debut. Then covid hit. Travel went to zero overnight. 

But then something remarkable happened. Not only did Airbnb not, it became more profitable than ever. It went from a company that was breakeven in 2020 to generating $4B in free cash flow yield last year (that’s more cash flow than ever dollar earned than Apple and Google). 

What did Airbnb CEO Brian Chesky do to turn the ship around? He doubled down on design. 

Here are the 5 most surprising things he did that made a difference: 

👍 Designed how decision-making happened

Instead of pushing decisions out, he decided to pull decision-making in. He saw the CEO role as an orchestra conductor, and created a shared consciousness of the top 30 to 40 people in the company, streamlining decision-making. 

“A designer can design a company to move with fewer parts. We found a way to save more money.” 

📈 Product Is not above marketing

Chesky replaced Product Managers with Product Marketing Managers. Apple famously didn’t have that role either. “You can’t develop a product unless you knew how to talk about it”. 

He says you can measure the health of an organization by the relationship between marketers and engineers. In most companies, marketers are like waiters, engineers are like chefs. And if the waiter goes into the restaurant, the chef yells at them. That’s not a great relationship.” 

💎 How to beat Shiny Object Syndrome 

We can’t do new things until we have permission. And we don’t have permission to work on new things until people love our core service. And if they are complaining on social media and customer service, then we need to fix the house first. 

💖 Businesses need more heart and more imagination

Heart: Ship something you’re proud of. 

Imagination: You know when you have two bad options and you can’t choose between two bad options? Sometimes you need a third path. And that third path requires creativity.

🤔 Why, Not What

When you do an A/B experiment, make sure it’s hypothesis-driven. If it works, you should be able to say why, not just what. 

#design #venturecapital #startups #leadership

Lots of great gems in there if you’d like to dive in deeper: