Brian Chesky, Curiosity & Learning from ‘Sources’

Airbnb and its growth over the past decade are legendary, scaling rapidly across countries to become an international brand. Leigh Gallagher documented its journey in her early 2017 book “The Airbnb Story: How to Disrupt an Industry, Make Billions of Dollars… and Plenty of Enemies”*, definitely a worthwhile read, both as an analysis of its evolution and challenges but also an inspiration to others who want to change the world too.

One of the interesting aspects is the extent to which Airbnb’s people scaled as the company itself grew rapidly, adapting and learning new skills at an incredibly fast pace. Brian Chesky, Airbnb’s CEO, is a shining example of this. In Leigh’s words: “One of the unique aspects of the Airbnb story has nothing to do with its weird, unthinkable idea for a business or its high-profile battles with lawmakers or even the rapid growth of its user base. Rather, it is the lack of traditional management experience of the company’s founding team – especially its CEO – and the speed with which they have had to learn how to become leaders of a very large company.”

It hasn’t always been a smooth road, but the way they managed to keep up and learnt to lead a company that had come to be Airbnb’s size with such little prior experience may offer a new playbook for leadership development.”
LEIGH GALLAGHER

​Read more to discover techniques that Brian used to learn and grow rapidly, innate skills he possesses, and our extrapolation to lessons applicable to all of us wanting to keep learning throughout our lifetimes.

​‘No time for the conventional’
Brian is the only one of Airbnb’s three founders who previously had no business experience at all. “It’s kind of like, what did I know?” he says. “Almost everything was brand new.” 

Yet, as Leigh describes, “there was no time for any of the conventional ways to learn how to become a CEO. Being groomed by a predecessor, running a key division of the business, spending a few years at the company’s overseas subsidiaries, acquiring an executive MBA – none of these strategies applied. Even the idea of getting any kind of formalised training would have been laughable; there was no time. The company was growing so fast, it was essentially shedding its skin every few months, crises were hitting left and right, and there was an entire culture to build, with everyone looking directly to Chesky for vision and direction. The company needed him to be a CEO immediately; it couldn’t wait for him to get there.” In Brian’s words: “There is basically no time for a learning curve”.

Insatiable curiosity and learning from ‘sources’
“Chesky possessed a couple of key skills that would become essential to his growth as a leader: a knack for ringleading dating back to his days at RISD [Rhode Island School of Design] and a near-pathological curiosity,” explains Leigh. “His solution to acquire the rest of the tools he’d need was to basically hack leadership by seeking out help from a series of expert mentors. But while any new CEO will seek out advice, Chesky’s process could best be described as obsessive, methodological, and interminable. He calls his practice ‘going to the source’: instead of talking to ten people about a particular topic and then synthesising all their advice, he reasons, spend half of your time learning who the definitive source is, identifying the one person who can tell you more about that one thing than anyone else – and then go only to that person. “If you pick the right source, then you can fast-forward”, he says.

Some of Brian’s earliest advisors & mentors were Michael Siebel, Paul Graham, and the venture capitalists who invested in Airbnb near the start: Greg McAdoo, Reid Hoffman, Marc Andreessen, Ben Horowitz… “all seen as gurus when it came to the art of building tech companies in Silicon Valley” in Leigh’s words.

She continues: “...As it began to get bigger, Chesky started seeking out sources for specific areas of study.” These included:

• Apple’s Jony Ive on design
• LinkedIn’s Jeff Weiner and Disney’s Bob Iger on management, including Jeff’s input on the importance of removing managers who weren’t performing
• Facebook’s Mark Zuckerberg on product
• Facebook’s Sheryl Sandberg on international expansion and on the importance of empowering women leaders
• eBay’s John Donahoe on scaling operations, managing a board, and other aspects of being the CEO of a large marketplace business
• Salesforce.com’s Marc Benioff on how to push your executive team

“A key principle of Chesky’s sourcing strategy was to become creative with identifying just who the experts were, and seeking out sources in unexpected disciplines.”

Leigh acknowledges that Brian is operating at “a level of highly privileged access; not everyone can call up Jony Ive or Mark Zuckerberg or Jeff Bezos. But Chesky insists there are always good mentors, regardless of someone’s level... ‘It’s a matter of picking people that are, at least, a couple of years in front of you’.”

“...As Chesky has evolved, so have his ‘sources’… [including] paid consultants”. For example:

• Stanley McChrystal, the former army general, advised on transparency and engagement between the company’s top and mid-level leaders
• Simon Sinek advised on purpose
• Geoffrey Moore helped Airbnb grow from a one-product company to a dual-product company

Leigh also explains that “‘sources’ need not be living: Chesky took some of his most valuable lessons from biographies of two of his biggest heroes, Walt Disney and Steve Jobs, as well as historical figures like General George S Patton, former secretary of defence Robert McNamara, and scores of others; management tomes by the dozens (his favourite is Andy Grove’s High Output Management*); and niche-industry sources like Cornell Hospital Quarterly.”

​Relentless focus on learning
“The most consistent observation from those who know Chesky is that he possesses this extreme level of curiosity, and what could be described as an obsession with constantly absorbing new information. ‘Brian’s biggest strength is that he is a learning machine,’ says Reid Hoffman. ‘It’s a skill set for all successful entrepreneurs – the phrase I use is infinite learner – and Brian is the canonical example of that.’… That relentless focus on learning, [Sequoia’s Alfred] Lin and others say, is the main reason Chesky has been able to scale with the company.”

Three Lessons for us
We conclude this post with three lessons for all of us wanting to keep learning throughout our lifetimes:
1) Support from others is invaluable, including mentors or coaches we can look up to – learning from others’ experiences can significantly shortcut the time it takes us to learn something new
2) Input from multiple sources can give us alternative perspectives, including specialists in different areas or assorted formats of information such as one-on-one engagement, books or videos/recordings
3) Applying the learning in practice is key: one of the reasons Brian grew so fast was that he applied his newfound knowledge and very quickly (and consciously) gathered feedback on whether his practical actions were effective and how he could improve further

* PROTAGION is a participant in the Amazon EU Associates Programme, an affiliate advertising programme designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.co.uk. The links with * participate in this programme. ​