Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Key Concepts:

• Intergenerational collaboration
• Founder mode
• Crystallized vs. Fluid Intelligence
• Agism in tech
• Modern Elder
• Midlife Chrysalis
• Wisdom at Work
• Maslow's Hierarchy of Needs (adapted for employees, customers)
• Culture (Culture Fit vs. Culture Add)
• Emotional Intelligence
• Transitional Intelligence (TQ)
• U-Curve of Happiness
• Anticipated Regret
• Despair Equation (Despair = Suffering - Meaning)
• Anxiety Equation (Anxiety = Uncertainty x Powerlessness)

Joining Airbnb in Your 50s:

• Chip Connelly joined Airbnb at 52, where the average age was 26. He was mentoring Brian Chesky (CEO) but also reported to him.
• He initially struggled with tech lingo and the concept of "product" in the tech industry. Jobot (Chief Product Officer) clarified that "product" in tech is different from the physical homes and apartments.
• Connelly had to be "wise and curious" and often felt like the "dumbest person in the room," requiring humility.
• He became the head of global hospitality and strategy, initially focusing on hosts worldwide.
• Example: When there was a discussion about making Airbnb mobile-only, Connelly advocated for including older hosts in the testing process, as they might not be as comfortable managing listings solely on mobile devices.

Working for Brian Chesky (Founder Mode):

• Connelly emphasizes the importance of believing in the founder. He believed in Brian's curiosity and appetite for learning.
• Challenges:
  • Brian assumed everyone would work at the same pace and duration, scheduling meetings late into the night.
  • Brian's admiration for Steve Jobs led to a belief that he knew best, especially in product matters, which could be demotivating for the product team.
  • Brian often set unreasonable goals, believing it would push people to "kick ass," but this created stress when goals were missed.
• Connelly built credibility by going on a world tour to understand hosts' psychology, which gave him a unique perspective.
• Tactics for working with founders in "founder mode":
  • Start meetings by clearly defining the intention and goals of the iteration.
  • Ensure alignment on these goals upfront.
  • Limit reliance on PowerPoint presentations to avoid getting sidetracked.

Intergenerational Collaboration:

• Younger brains have fluid intelligence (fast, focused, problem-solving, linear thinking).
• Older brains have crystallized intelligence (holistic, systemic thinking, connecting the dots).
• Combining these strengths can be "brilliant."
• Example: Laura Hughes Modi (CEO of Bobby) valued Connelly's ability to reframe the concept of "product" to include hosts and experiences.
• Older employees can identify blind spots and offer process knowledge.
• Invisible productivity: Elevating the talent of those around you.
• Example: John Q. Smith, an engineer at Airbnb, became a great manager by bringing out the best in younger, more technically skilled coders.

Agism in Tech:

• Agism is a real problem in tech, although less so than a decade ago.
• Older employees may be perceived as expensive and slow.
• The rise of AI raises questions about whether it will disproportionately impact older workers.
• Older individuals may need to be willing to take pay cuts to work part-time.
• Key to thriving in tech as you age:
  • Be a mentor and an intern (mutual mentorship).
  • Show up with curiosity and passionate engagement.
  • Exhibit energy (both physical and positive).
  • Be approachable.

Advice for Hiring Managers:

• Focus on generalists who can think broadly.
• Look for passion, curiosity, and a learning mindset.
• Create intergenerational collaboration through mutual mentorships.
• Resume advice: Focus on thorny problems you faced, the skills you used to solve them, and the results you achieved.

Building Jadviv (Boutique Hotel Chain):

• Connelly started Jadviv at 26 after being inspired to create a "rock and roll hotel."
• The company grew to 52 hotels and became the second-largest boutique hotel chain.
• He hated it in his late 40s due to the Great Recession and a desire for change.

Near-Death Experience (NDE):

• Connelly had an allergic reaction to an antibiotic and flatlined multiple times.
• He experienced visions of a 40-foot tall living room in the Alps, surrounded by birds.
• The birds told him, "If you slow down, you will see beauty and you will see awe."
• This experience led to a significant life change, including selling his company.

Culture:

• Culture is "what happens around here when the boss is not around."
• It's especially important in distributed companies.
• Culture guides decision-making and attracts the right people.
• Culture Fit vs. Culture Add: Culture add suggests that diversity is helpful.
• Interview advice:
  • Ask for 3-5 adjectives that define the culture.
  • Ask about the biggest problem in the culture.

Maslow's Hierarchy of Needs (Adapted):

• For employees:
  • Base: Money/Compensation
  • Middle: Recognition
  • Top: Meaning
• For customers:
  • Base: Meeting Expectations
  • Middle: Meeting Desires
  • Top: Meeting Unrecognized Needs (e.g., Airbnb's "belong anywhere" concept)

Modern Elder Academy (MEA):

• A midlife wisdom school focused on reimagining and repurposing oneself.
• Offers workshops in Baja and Santa Fe.
• Helps people navigate transitions, build wisdom, and reframe their relationship with aging.
• Becca Levy's research shows that a positive mindset on aging can add 7.5 years of life.
• The "midlife chrysalis" is a period of transformation, not just crisis.
• MEA is for people in the midst of a transition (e.g., selling a company, divorce, health diagnosis).
• Tagline: "Four Seasons meets Blue Zones meets Esalen Institute."

Upsides of Aging:

• Emotional intelligence grows.
• Wisdom can grow (metabolized experience mindfully shared for the common good).
• You learn how to edit and have fewer "Fs" to give.
• You become more spiritually curious.
• You become more whole (alchemizing different aspects of yourself).

AI Corner:

• Connelly uses ChatGPT for inspiration for his daily blog, Wisdom Well.
• He asks it to write a 250-word post on a specific topic.
• ChatGPT knows his writing style well enough to "ape" him.

Lightning Round:

• Recommended books:
  • Man's Search for Meaning by Victor Frankl
  • Emotional Equations by Chip Connelly
  • Big Magic by Liz Gilbert
• Despair Equation: Despair = Suffering - Meaning
• Anxiety Equation: Anxiety = Uncertainty x Powerlessness
• Recent movie/TV show: Ted Lasso, I'll Push You
• Favorite product: Vuori shorts
• Life motto: "Your painful life lessons are the raw material for your future wisdom."
• Burning Man: Fly Ranch (a beautiful, life-filled area near Burning Man)

Conclusion:

Chip Connelly's journey highlights the value of intergenerational collaboration, the importance of curiosity and continuous learning, and the potential for growth and reinvention at any age. His experiences at Airbnb and the creation of the Modern Elder Academy demonstrate a commitment to fostering wisdom, navigating transitions, and challenging societal narratives around aging. The insights shared offer actionable advice for individuals and organizations seeking to thrive in a rapidly changing world.