Case Study #82: Letting Go — and Finding Purpose

For entrepreneur and former hotel magnate Chip Conley, the decision to sell the second-largest hotel chain (called Joie de Vivre) he built over 24 years marked a profound shift in his life. But, after a near-death experience, he realized he wanted out. He then went on to become Airbnb’s Head of Global Hospitality and Strategy, where he mentored the co-founder Brian Chesky. Today, he is the founder and CEO of the Modern Elder Academy (MEA), the world’s first school dedicated to career and life transitions.

Chip is an incredible entrepreneur and had an outstanding exit from Joie de Vivre. He has since gone on to reinvent himself after that sale. Chip has a lot of insight into selling, finding a new purpose, and the transformative power of owning wisdom.

The Exit

When Chip was 47 years old a broken ankle quickly deteriorated into a bad case of septic leg. He was taking antibiotics but they weren’t working well — he flatlined after giving a book talk and had to be rushed to a hospital. He says that this near-death experience caused him to question what he was doing with his life. Chip quickly came to the realization that he didn’t want to be in the hotel business anymore.

He knew he had to be strategic to make the most out of his exit, so he decided to sell the brand and management company but retain ownership of the real estate.

Although the market wasn’t at its peak during the sale, the proceeds were substantial enough to sustain him for a lifetime. The real game-changer was the appreciation in the value of the retained real estate over the following years.

The unique dual income streams, combining the upfront sale with an escalating buyout over time, sweetened the deal. Surprisingly, the 44% he retained eventually outpaced the 56% he initially sold. Additionally, owning a significant portion of the real estate, including nine of the 22 or 24 hotels, strengthened his financial portfolio even further.

The Next Steps

After selling, Chip found himself at a crossroads: what to do next?

A few years after the sale, he was approached by Brian Chesky, the 31-year-old CEO of a then-small tech startup called Airbnb. Brian’s reputation for humility and a deep desire to learn set him apart from the typical Silicon Valley tech CEOs, which interested Chip.

Despite his initial limited knowledge of Airbnb, a four-hour meeting with Brian left him intrigued. Brian’s proposition to “democratize hospitality” struck a chord with Chip, leading to a consultancy arrangement that soon evolved into a full-time commitment that was very lucrative.

For the next four years, Chip served as Airbnb’s in-house mentor, overseeing global hospitality and strategy. The founders affectionately called him the “modern elder,” a term he would go on to use when he created MEA.

As he navigated the unique world of tech startups, he realized that there was an enormous gap in the market: the need for midlife “wisdom” schools, a place where individuals in their 40s, 50s, and 60s could reimagine and repurpose their lives. And so MEA was born. At the time of writing, the academy has hosted over 4,000 participants from 44 countries, providing a platform for navigating life transitions.

Key Lessons

Chip’s story is full of valuable lessons for entrepreneurs who are navigating transitions and seeking purpose in their lives. Here are a few of note:

• Timing matters, but it’s not everything: Chip sold the Joie de Vivre brand and management company during a challenging market. Although the sale wasn’t as lucrative as it could have been, he notes that the sale set him up for a lifetime. Sometimes, a well-timed exit provides enough, and waiting longer might bring more significant returns…or it might not.
• Don’t be afraid to create empty space: Selling his hotel company allowed Chip the freedom and time to explore new opportunities like Airbnb. Recognizing when to step back and create room for unexpected possibilities can be a transformative strategy for entrepreneurs.
• Mentorship can be very fulfilling: Chip never knew how much becoming a mentor would add purpose to his life. Not only was he able to help a budding entrepreneur create his dream business, but he was also able to learn from his mentee.

From selling his hotel business to the surprising success at Airbnb, Chip’s experiences are proof that success often comes from creating space, taking smart risks, and embracing unexpected opportunities.

If you’re ready to create more space in your life, we can help you sell. Give us a call today.