Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Joining Airbnb in Midlife & Intergenerational Dynamics 00:00
Chip Conley joined Airbnb in his early 50s, while the average age at the company was 26, bringing hospitality experience to a young tech environment.
Initially hired as an advisor, he quickly shifted from consulting part-time to working full-time with expanding responsibilities.
Faced challenges adapting to tech lingo and company culture, often feeling both wise and the least technically knowledgeable in the room.
Added value by questioning definitions (e.g., "what is the product?") and advocating for the needs and perspectives of older hosts.
Emphasized the benefit of intergenerational teamwork: younger employees offer speed and technical focus while older ones contribute holistic and systemic thinking.
Acted as a voice for older hosts during significant product transitions, such as the move to mobile-only management.
Conley only joined Airbnb because he believed in Brian Chesky's potential as a leader, despite initial reservations about the business model.
Chesky displayed both hubris and humility, showing a willingness to learn from experts, including Conley for hospitality advice.
Working with Chesky presented challenges: expectations to match his intense work pace, high (sometimes unreasonable) goal setting, and an inclination toward a "founder knows best" mindset.
Advised building credibility with founders by bringing real customer insights and aligning on meeting intentions and desired outcomes.
Warned against overreliance on structured presentations when dealing with unpredictable founders.
Conley’s experience highlighted the strengths of age diversity, including "invisible productivity"—helping others excel through mentorship.
Created opportunities for mutual mentorship within Airbnb, where older employees help with "soft" skills and receive technical help in return.
Age diversity helped organizations spot blind spots, such as regulatory challenges (e.g., anticipating occupancy tax regulations).
Described the transition from individual contributor to manager as an opportunity for older employees to leverage wisdom and elevate teams.
Addressing Ageism and Career Advice for Older Workers 27:04
Acknowledged that ageism is real in tech but has become less of a blind spot due to resource groups and changing awareness.
Stressed that older employees might be seen as more expensive and less up-to-date technically, but their process knowledge is critical for effective operations in large organizations.
Encouraged older employees to consider part-time or flexible roles that make the most of their institutional wisdom.
Highlighted curiosity and "age fluidity"—showing up with positive energy and an adaptable mindset—as key to maintaining relevance and success in tech.
Advised companies to look for generalists with broad problem-solving skills, as AI accelerates the value of these profiles over narrow specialists.
Building Company Culture and Leadership Frameworks 48:05
Defined culture as "what happens when the boss isn't around," especially impactful in distributed or remote organizations.
Company culture serves as both a decision-making guide and a magnet for attracting aligned talent.
Emphasized the importance of understanding and assessing culture during the interview process, not just seeking "culture fit" but also "culture add."
Discussed using Maslow’s hierarchy as a model for organizational needs: employee pyramid of compensation, recognition, and meaning; customer pyramid of expectations, desires, and unrecognized needs.
Airbnb's shift toward "belong anywhere" emerged as identifying and serving the top of the customer needs pyramid (belonging).
The Modern Elder Academy and Reframing Aging 57:21
After Airbnb, Conley founded the Modern Elder Academy (MEA), focused on purposeful transitions in midlife (defined as ages 35–75).
MEA offers workshops and programs to help people reframe aging and embrace midlife transitions, emphasizing wisdom development and positive mindset shifts.
Shared research showing that adopting a positive view on aging can add more than seven years to life expectancy.
Described emotional and psychological benefits of aging, such as increased emotional intelligence, ability to synthesize experiences, and personal wholeness.
Advocates for "the midlife chrysalis"—seeing midlife as a time of transformation, not crisis.
Encourages self-reflection, anticipation of regret (what will you regret not learning or doing in 10 years?), and continuous learning at all ages.
Outlined frameworks for emotional well-being: "Despair = Suffering – Meaning" and "Anxiety = Uncertainty x Powerlessness," with practical exercises to reduce anxiety.
Recommends focusing on developing both energy and approachability to remain influential and integrated within organizations.
Book, Product, and Lifestyle Recommendations 70:31
Highly recommends Viktor Frankl’s "Man’s Search for Meaning" and Elizabeth Gilbert’s "Big Magic."
Favorite product discovery: Vuori shorts for comfort.
Shares the motto, "Your painful life lessons are the raw material for your future wisdom."
Mentioned "Ted Lasso" as a favorite TV show for its optimistic spirit.
Reflections on Burning Man & Online Presence 75:32
Shared insights about Burning Man’s Fly Ranch, emphasizing its contrast with the main event as a restorative, nature-filled space.
Conley can be found at chipconley.com and meawisdom.com, and is active on LinkedIn, regularly posting resources about wisdom and transition management.