Airbnb CEO Skipped Business School for Obama's Mentorship — Here's the Life-Changing Advice He Got

In 2018, Airbnb CEO Brian Chesky made a bold choice rather than attend a traditional business school, he opted for weekly mentorship sessions with former US President Barack Obama. The sessions, which began with hour-long evening calls, took place as Chesky prepared to lead his company through one of its biggest transitions: going public.

The mentorship didn't take place in a classroom but over personal conversations that Chesky described as 'night school' with Obama. The setting may have been informal, but the impact was anything but. The advice he received would alter not only how he ran Airbnb, but also how he approached leadership and life itself.

The Making of a Mentor–CEO Bond

Chesky's relationship with Obama wasn't random. It began in 2015 when Obama appointed him a Presidential Ambassador for Global Entrepreneurship. Over time, that official role evolved into a genuine mentorship, solidified by Obama's curiosity about the future of Airbnb.

When Obama asked Chesky to write down what he truly wanted to achieve with the company, Chesky didn't just send a list, he drafted a full manifesto. That document sparked the start of a structured mentorship with weekly calls, including homework and feedback. Obama's first key piece of advice? Be intentional. 'So many leaders are like self-driving cars,' Obama reportedly told Chesky, according to Fortune. 'They're not intentional. They never put the destination in.'

From IPO to Identity: Lessons in Leadership

These weren't just theoretical discussions. Chesky credits Obama's mentorship with shaping how he led Airbnb through its 2020 initial public offering (IPO). The guidance helped him move from reactive decision-making to forward-thinking leadership, especially during one of the most uncertain periods in tech history.

According to a recent interview with Fortune, Chesky said the experience 'changed my life,' highlighting how Obama encouraged him to define his personal values, not just corporate ones. That push led to a more human-centred approach at Airbnb, which now includes commitments to accessibility, refugee housing, and sustainable travel.

Personal Advice That Hit Home

Obama's influence extended beyond the boardroom. In 2021, after Chesky experienced a painful breakup, he turned to Obama for guidance. Rather than offer relationship tips, Obama gave him unexpected advice: focus on friendship.'I don't think you need to be in another relationship,' Obama told him, as reported by Hindustan Times. 'I think what you need are friends.' For Chesky, the simplicity of that advice was powerful. It reshaped how he prioritised relationships outside of work and reinforced the importance of grounding himself in meaningful personal connections, a theme he later brought into his leadership ethos at Airbnb.

Giving Back: The Voyager Scholarship

Inspired by those sessions, Chesky took the lessons further. In 2022, he pledged £79 million ($100 million) to the Obama Foundation to create the Voyager Scholarship for Public Service. The fund supports university students pursuing careers in public service, a mission rooted in the values Obama encouraged Chesky to explore.

The scholarship not only highlights Chesky's commitment to purpose-driven leadership but also mirrors the transformational impact mentorship can have when combined with vision and resources.

A Modern Education Outside the Classroom

Chesky's story offers a radical rethink of what executive education can look like. Rather than case studies and classrooms, he found growth through personalised advice, life reflection, and accountability to someone who had led on the world stage.

In today's age of rapid disruption, Chesky's decision to skip business school in favour of intentional mentorship serves as a compelling case study in modern leadership. It also raises a broader question: could direct mentorship from seasoned leaders be more valuable than an MBA?

From political icon to entrepreneurial guide, Barack Obama helped shape the mindset of one of Silicon Valley's most influential CEOs. Chesky's story is more than a tale of guidance it's a reminder that sometimes the best education comes not from books, but from the right conversation at the right time.