Chesky
Airbnb CEO Brian Chesky [Credit: Airbnb]

Brian Chesky: What we learned from his Diary of a CEO podcast

Worldwide: Airbnb co-founder and CEO, Brian Chesky, joined entrepreneur and ‘Dragon’s Den star, Steven Bartlett, on his Diary of a CEO podcast to discuss his career and life this week.

Read our takeaways from the interview below:

  • Chesky discussed his early experience attending design school and creating his own “magical” world to “escape numerous challenges of childhood”

In his early days prior to Airbnb, Chesky discussed how he was immersed in the world of design, which led to him attending design school. There, he described how he designed his own “magical” world that was better than the one he was in and to which he could escape, while detailing the challenges he faced in the real world relating back to his childhood, from being “very sensitive and idealistic” to not fitting in at school due to being “hyperactive and impulsive” and considering getting a diagnosis for ADHD [Attention deficit hyperactivity disorder]. This ultimately spurred him on to found Airbnb and to create a sense of “belonging”.

  • Chesky explained how he had become “addicted to work” and described the “loneliness” of being a CEO while scaling Airbnb

The Airbnb CEO spoke in profound detail about the “loneliness” in his role and his desire to value things differently and prioritise relationships higher, despite calling it the “joy of a lifetime” to grow the company. In a candid discussion, he laid out how difficult it had been to adapt his role as Airbnb scaled to a corporation size, including having boundaries with colleagues but still maintaining the empathy and need to have different opinions around him to make decisions.

In particular, he wished that he made more time for his family [particularly his sister] and also explained how he had developed a close friendship with former US president Barack Obama, who had helped to change his perspective on his values and priorities in life.

  • Chesky’s “biggest regret” in life so far

Even after scaling Airbnb to the place it is now, at 42 years old, Chesky said he regretted not spending more time with the people he loved and not being able to create his own family yet. Referring back to his “addiction” to work, the CEO detailed how he did not necessarily have regrets about his career as he had already lived “multiple lifetimes” in his job and the things we regret in life are the things “we didn’t do”.

Pondering what he would do if he had ten years left to live, Chesky said that he would want to have more amazing life experiences to share with other people, given that “80 per cent of trips on Airbnb are with other people”.

  • Being “inspired” by Walt Disney and Steve Jobs

Chesky cites Walt Disney [the founder of Disney] and Steve Jobs [the founder of Apple] as his biggest inspirations in life after having built companies “that lived beyond them”. Like himself, he said that the two late founders were also “creative people leading tech companies” and had a desire to “design something better” – something that is becoming more difficult to find nowadays because “creativity is becoming compressed in corporations”.

  • Starting out with Airbnb and receiving a rejection letter while wanting to raise funding

Having first conceived the idea for Airbnb [formerly AirBed&Breakfast.com] with Joe Gebbia and Nate Blecharczyk in 2007, Chesky admitted that he never would have expected the platform to be getting three to four million users and that they would have taken it public. Initially, the platform was set up to keep solving problems for people who needed a place to stay [e.g. on airbeds] while other accommodation providers were already sold out, but the co-founders had bigger ambitions to get the word out and design something “bespoke” for everyone.

By August 2008, the co-founders were seeking to raise $150,000 at a $1.5 million post-money valuation but they were rejected by one potential investor who told them that the potential market opportunity for Airbnb “was not large enough”. Taking this into account, Chesky said that it takes certain types of people with “audacity” to overcome obstacles, and suggested that the world needs more entrepreneurs to build economies [especially female entrepreneurs].

  • Designing the company culture you want

During the interview, Chesky reads back an email that he had sent out the week prior to all 6000 Airbnb employees in which he underlined how culture is the most important thing you will ever design because it is what “creates the foundation for all future innovation”. His drive to instil a healthy, long-lasting culture is evident throughout the discussion, even saying that he wanted to feel like he was running “the world’s largest startup, based on minimal bureaucracy and communication layers”.

In order to create a company culture, Chesky outlined how it was necessary to lead by example, notably in times of adversity, and when choosing to hire, fire or promote employees.

  • Chesky’s darkest hour professionally: “Losing 80 per cent of our business in eight weeks” 

The Covid-19 pandemic and subsequent lockdowns from March 2020 had coincided with Airbnb preparing to go public via a long-awaited IPO [initial public offering] but led to the company losing 80 per cent of its business in the space of eight weeks, according to Chesky.

While admitting that his “darkest hour” professionally had come from reading online speculation about Airbnb’s potential demise, Chesky saw the crisis as an opportunity to “define” Airbnb and the company would “redefine” every part of the business over the following six months.

In the meantime, Chesky opened up about the pain of reducing Airbnb’s headcount by 25 per cent in the early days of the pandemic and explained how the company had looked after its departing employees with mental health and health care provision, as well as a public directory to increase their chances of being recruited elsewhere. Such a move later led to laid-off employees sending him “hundreds” of thank you letters as Airbnb was recovering its business, and Chesky believed that this highlighted the sense of “belonging” at the company.

  • His “pride” at Airbnb going public

As the business recovered from the nadir of the pandemic, Airbnb resurrected its IPO in December 2020, going public at a valuation of around $50 billion which shot up to more than $100 billion in the first hour of trading. During that year, Chesky said that he had “lived 20 years”, though the feeling while going public was around “70 per cent pride and sense of accomplishment and 30 per cent sadness” when the IPO valuation started to go down.

  • The personal “low” moment post-IPO

After the best part of a year working 16 hours a day, seven days a week, Chesky described the post-IPO period as his “personal low moment”, despite the initial euphoria. Referring back to his work “addiction”, he explained how he was no longer feeling the adrenaline of working towards the IPO and felt moments of “isolation” as he suddenly had spare time on the weekends, and he started reaching back out to friends he had not been connected with for some time.

  • Chesky’s “vision” for Airbnb

While most people may see Airbnb as a space for homes, according to Chesky, he said that he wanted to create more of a “global travel community” where everyone has their own robust profile with a rich identity and they can feel that the app really knows them and what they want, hence its push into artificial intelligence [AI].

The CEO also hinted at the potential for Airbnb to grow “beyond travel” in the future and push back against “the dark cloud of loneliness” that he had felt at times of adversity in his life and career. He believed that this message would resonate with everyone from teenagers to older generations who all had the same desire to feel “loved”, and this would be his clear vision for success at Airbnb.

Listen to Brian Chesky’s Diary of a CEO podcast here.

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