This video features an in-depth conversation with Chip Conley, founder of Joie de Vivre Hotels and known as Airbnb's "Modern Elder." He shares his journey from joining Airbnb in his mid-50s to guiding young founders, and eventually founding the Modern Elder Academy (MEA) to spread the wisdom of midlife. He emphasizes that age and experience can be assets, and that midlife can serve as a launchpad for new purpose and impact.

1. Joining Airbnb and Collaborating with Brian Chesky

Chip Conley joined Airbnb at age 52. At the time, the average age of Airbnb employees was 26, and he had to report to CEO Brian Chesky, who was 21 years his junior. Initially planned as a 15-hour-per-week consulting role, within three weeks he was working 15 hours a day as a full-time employee, eventually taking on the role of Head of Global Hospitality and Strategy.

He initially struggled with unfamiliar tech jargon. He recalls:

"I was mentoring Brian, but he was also my boss. I was 52, and the average age was 26. I had to be wise yet curious, and I was often the dumbest person in the room."

The confusion over the definition of "product" was a particularly big challenge. It took him time to realize that in the tech industry, "product" meant the digital interface, not physical accommodations.

"When people talked about the product, and Joe (Gebbia) said he was the Chief Product Officer, I asked, 'Isn't the product homes and apartments?' Joe said, 'No, in tech, product means something different.'"

Through these experiences, he explains that he "had to be wise yet curious, and often had to be the dumbest person in the room." This shows his humility and his commitment to constantly learning. While Airbnb's hosts and guests differed in age demographics, Chip Conley specifically pointed out that older hosts had lower understanding of mobile usage and advocated on their behalf.

1.1. Working with Brian Chesky

Working with CEO Brian Chesky was clearly challenging. Chip Conley candidly discusses the advantages and disadvantages of Brian's founder mode.

"Being in founder mode is great, but working under someone in founder mode is not so great."

Chip Conley mentions Brian's three biggest challenges:

1. Expecting the same pace and stamina: Brian assumed everyone would work at the same speed and hours as he did. He would even call meetings at 10 PM. Brian himself acknowledged his workaholism, but this approach put significant stress on team members.
2. Admiration for Steve Jobs and a sense of superiority: Brian greatly admired Steve Jobs, and as a design school graduate, tended to think he knew everything best. As a result, the product team often pulled all-nighters before meetings with Brian.
3. Setting unrealistic goals: Brian sometimes set unrealistic goals with difficult-to-achieve deadlines. This may have carried an implicit message that "people won't work hard enough on their own." Chip Conley pointed out that this approach placed excessive stress on team members.

Despite this, Chip Conley praises Brian Chesky as "the defining leader of the millennial generation" and acknowledges that his leadership was instrumental to Airbnb's success. Chip Conley highly valued Brian's growth mindset. He emphasizes that Brian showed curiosity in acknowledging his shortcomings and learning from experts, noting this as what differentiates Brian from Steve Jobs.

1.2. Tactics for Working Effectively in Founder Mode

To work effectively with a leader in founder mode, Chip Conley emphasizes the importance of building trust and setting clear goals.

"At the start of a meeting, you need to say, 'Brian, let's talk about what we're trying to achieve here. What is the intent of this product improvement, what are the criteria for success, and what do you want to accomplish in this meeting?'"

He advises establishing alignment at the beginning of meetings to create a reference point for returning to the original objectives when discussions go off track or unexpected critiques arise. He also says that trust built on firsthand experience from customer touchpoints is crucial. His experience traveling the world and meeting hosts directly became a major asset in his relationship with Brian.

"Be careful about over-relying on PowerPoint or other tools. Especially when you have a fiery founder, your presentation can go in a completely different direction from the original intent."

Chip Conley recommends not depending too heavily on slides so you can maintain flexibility in uncertain situations.

2. The Value of Intergenerational Collaboration and the Benefits of Aging

Through his Airbnb experience, Chip Conley deeply realized the value of intergenerational collaboration and wrote a book about it called Wisdom@Work: The Making of a Modern Elder. He explains the differences between young and older brains and argues how they can play complementary roles.

• Young brains: Excel at fluid intelligence, are fast and focused, and are skilled at problem-solving and linear thinking.
• Older brains: Have developed crystallized intelligence, move more easily between left and right brain, and are superior at holistic, systemic thinking -- the ability to connect the dots.

When these characteristics are combined, teams can achieve remarkable synergy.

"The combination of an older brain connecting the dots and thinking broadly, with younger team members working fast, focused, and linearly, is truly excellent."

Chip Conley says his role was sometimes to identify the team's blind spots. For example, he pointed out that Airbnb hadn't developed a long-term strategy for tax issues and regulations, something younger team members could miss while focused on short-term growth.

He offers generous advice for older employees seeking to succeed at tech companies:

"As you get older (45+), show curiosity and passionate engagement in what you do. People will notice your energy more than your wrinkles."

Energy means not just physical vitality but a positive attitude. Being approachable and bringing a positive atmosphere to meetings -- these efforts made Chip Conley a "timeless" presence at Airbnb. He further emphasizes maintaining a mentor-and-intern mindset -- having the humility to recognize that you have things to teach while also having much to learn from younger generations.

"Wisdom is gained through experience and, when consciously shared, becomes something for the common good."

2.1. Ageism in the Tech Industry

Chip Conley acknowledges that ageism clearly exists in the tech industry. There is a perception that older people are technologically behind, expensive, and slow. However, he believes this perception could change in the AI era.

"In the AI era, new rules of the game will emerge. What AI cannot do is provide human wisdom. We may see an era where artificial intelligence and human wisdom find balance."

The faster AI solves technical problems, the more valuable broadly-thinking generalists with pattern recognition and high emotional intelligence -- older managers -- could become. He also suggests that older professionals could contribute to companies on a part-time basis, sharing institutional wisdom or process knowledge.

2.2. Advice for Hiring Managers

He advises hiring managers to focus on finding generalists. In the AI era, the ability to solve problems with a broad perspective becomes more important than expertise in a specific skill.

"We are moving from the age of specialists to the age of generalists, and AI is accelerating this."

He also proposes building mutual mentoring systems where young employees teach technical skills and older employees teach management skills like running meetings and conducting employee evaluations. He says interviews should go beyond simply reviewing resumes and encourage candidates to talk about difficult problems they've faced and how they solved them.

"On a resume, rather than roles, I'd like to see a paragraph explaining what you learned -- when faced with a thorny problem, what skills you used, how you solved it, and what the outcome was."

3. Founding Joie de Vivre Hotels and Life's Turning Points

After graduating from Stanford Business School at age 26, Chip Conley was working at a commercial real estate development firm when he felt bored and sought a new challenge. Taking advice from famous concert promoter Bill Graham, he started a business with the unique idea of a rock and roll hotel. He bought a rundown motel in San Francisco's Tenderloin district and transformed it into a hotel called Phoenix, which he has owned for 39 years. From there, he grew Joie de Vivre into the second-largest boutique hotel chain in the United States, operating 52 hotels, 25 restaurants, and 4 spas across California.

However, in his late 40s, he confesses that he "came to dislike what he used to love." He went through significant hardship during the Great Recession, describing it as a "midlife crisis." During this period, he wanted to change everything.

3.1. Insights Gained at Death's Door

One of the biggest turning points in Chip Conley's life was a near-death experience (NDE). During a book tour, an allergic reaction to antibiotics taken for an ankle injury caused his heart to stop 9 times in 90 minutes. Through this experience, he realized that "every day is a gift and a bonus."

"I saw birds. I saw all the beautiful things. I was wearing slippers from the Vitale Hotel I had created in San Francisco, floating in the air in a 40-foot-high living room in the Alps. I was surrounded by birds chirping at me. I understood the birds. They kept telling me, 'Slow down and you will see beauty and awe.' Then the birds said, 'It's time to go,' and flew out through a large window. I tried to follow them, and just as I was about to reach the window, I came back to life."

This experience gave him the message that "when you slow down, you see beauty and awe," and ultimately led him to sell his company during the Great Recession and open a new chapter by joining Airbnb.

3.2. The Importance of Company Culture

While running Joie de Vivre, Chip Conley placed great emphasis on company culture. He defines culture as "what happens around you when the boss isn't there" and emphasizes that culture is even more important in distributed organizations. Culture helps employees make decisions and acts like a magnet that attracts the right talent.

He uses examples from Amazon and Apple to explain how different corporate cultures can be. Airbnb was a better fit for employees coming from Apple rather than Amazon. He recommends adopting a "culture add" perspective rather than "culture fit" when hiring, embracing diversity and encouraging candidates to judge for themselves whether the company's culture aligns with their values.

"When you're interviewing, you're also interviewing them. It's not just about you proving yourself -- the company should also prove itself."

During interviews, he advises probing company culture with questions like, "What are three to five adjectives that characterize this culture?" and "What is the biggest problem in this culture, and is there a possibility of improvement?"

3.3. Maslow's Hierarchy of Needs and the Peak Model

In his book Peak, Chip Conley uses Maslow's hierarchy of needs to present the Peak Model, which explains the needs of employees, customers, and investors.

• Employee Pyramid:

  1. Money/Compensation: Basic need
  2. Recognition: Mid-level need
  3. Meaning: Highest need (often the most important differentiator)

     "Despair equals suffering minus meaning. If suffering is constant, the more meaning you have, the less despair."

• Customer Pyramid:

  1. Meeting expectations: Basic need
  2. Meeting desires: Mid-level need
  3. Meeting unrecognized needs: Highest need In Airbnb's case, expanding beyond simple accommodation sharing to making people "belong anywhere" was an example of meeting this "unrecognized need."

4. The Modern Elder Academy (MEA) and Rediscovering Midlife

After earning the nickname "Modern Elder" at Airbnb, Chip Conley moved part-time to Baja, Mexico at age 56, where he learned Spanish, started surfing, and took on new challenges. Drawing on his experience, he founded the Modern Elder Academy (MEA). MEA is the world's first midlife wisdom school, with campuses in Baja and Santa Fe, helping people navigate transitions, reinvent themselves, and find new purpose during midlife.

"Think of the caterpillar's journey to becoming a butterfly -- midlife is the chrysalis stage. Midlife is not a crisis; it's a chrysalis."

MEA likens the period from age 35 to 75 to a "chrysalis," emphasizing that this can be a transformative time. He says it's important to shift perceptions of aging in a positive direction. Citing research from Yale professor Becca Levy, he emphasizes that a positive mindset about aging contributes to longer life.

"Becca Levy at Yale showed that shifting your mindset about aging from negative to positive can give you seven and a half additional years of life. That's more life span than any biohacking currently being done."

MEA highlights the upside of aging and helps people adopt a pro-aging rather than anti-aging perspective.

"Ten years from now, what will you regret not having learned or done? This is a really important question as we age."

He says "anticipated regret" can be a form of wisdom and a catalyst for action. He also mentions the happiness U-curve theory, noting that happiness typically reaches its lowest point between ages 45 and 50, but then rises again, with people becoming progressively happier in their 50s, 60s, 70s, and even 80s for women. This is because midlife is a time for "midlife unraveling" -- dismantling expectations and gaining freedom.

MEA primarily serves people averaging age 54 who are going through significant life changes such as career transitions, divorce, children leaving home, caring for aging parents, or health issues. It's also popular among tech industry professionals, with over 7,000 graduates and 56 regional chapters worldwide, becoming a movement.

5. Using AI and Personal Insights

Chip Conley actively uses AI in his daily life. He writes a daily blog called "Wisdom Well," and when ideas don't come easily, he uses ChatGPT to help draft initial versions.

"ChatGPT gives me inspiration. It essentially gives me a rough draft. And that alone is enough."

He explains that ChatGPT understands and replicates his writing style and unique sense of humor well. He asks ChatGPT to write blog posts of about 250 words, and recently wrote about "shifting perspectives on the soul -- what if instead of me having a soul, the soul has me?"

6. Lightning Round and Wrap-Up

The interview concludes with a lightning round offering a glimpse into Chip Conley's personal tastes and philosophy.

• Most recommended book: Viktor Frankl's Man's Search for Meaning. He says it teaches how to find meaning and maintain hope even in suffering.
• Emotional Equations: Chip Conley mentions his book Emotional Equations and shares two important formulas:
  • Despair = Suffering - Meaning: Suffering is always present in life, but finding meaning in life can reduce despair.
  • Anxiety = Uncertainty x Powerlessness: He explains that 98% of anxiety comes from what we cannot know and cannot control, and advises creating an "anxiety balance sheet" to identify the sources of anxiety and bring them within manageable range.
• Recent favorite movie/TV show: He enjoyed Ted Lasso, a drama with a positive message. The movie he's most looking forward to is I'll Push You, about two friends who push a physically challenged friend in a wheelchair for 500 miles along the Camino de Santiago.
• Recently discovered favorite product: He recommends Vuori shorts for their comfort and breathability.
• Life motto:

  "Your painful life lessons are the raw material for your future wisdom." He believes that when going through difficult times, those experiences will gift valuable wisdom in the future.

• Burning Man: As a founding member of the Burning Man board, he introduces a little-known place called Fly Ranch. Located 10 miles from the Burning Man event site, this 3,400-acre property is a desert but has hot springs and wildlife, making it a beautiful place.

Conclusion

Drawing on his unique life experiences and deep insights, Chip Conley exemplifies the "Modern Elder" who continues to learn, grow, and collaborate with younger generations even in midlife. He emphasizes that aging should not be viewed negatively but rather as an opportunity for wisdom and growth, and that this positively impacts not only personal life but also organizational success. His story reminds us how important it is to maintain curiosity, passion, and positive energy regardless of age.