Founder, Modern Elder Academy; mentor to Brian Chesky; Burning Man co-chair
AUG 3 2025
The Origin
An Older Mentor in a Young Founder's World
"Brian Chesky called me when Airbnb had 40 employees. He wanted a mentor who had scaled a hospitality company. I had. What happened next changed both our lives."
The Modern Elder: wisdom-holder who is also a curious learner — not a lecturer
Brian Chesky and Chip Conley: the most unusual mentor relationship in tech
The Burning Man lesson: culture at scale requires intentional architecture, not just rules
Dying 9 times: Chip's heart surgeries taught him what actually matters
Framework
The Modern Elder Academy
55+
average MEA student age
40%
report career transformation
2
generations learning from each other
MEA's thesis: midlife is not a crisis — it's a second adulthood waiting to happen
The modern elder is not a know-it-all but a "learn-it-all" with more context
Intergenerational mentorship: tech learns speed and tools from youth; youth learns wisdom and patience from elders
Burning Man board: Chip brings hospitality design thinking to the event that shaped Silicon Valley culture
Chip's gift to AirbnbChip brought hospitality wisdom (guest experience, host culture, brand as feeling) that no 28-year-old VC could provide.
What Mentorship Taught
The Airbnb Years
The scale lesson: Culture doesn't scale automatically. It must be deliberately designed at every stage.
The hospitality principle: Every Airbnb interaction should feel like being welcomed by a friend, not a hotel chain
The crisis playbook: COVID almost killed Airbnb. The response (laying off 25%, preserving culture, going public) was a case study in leadership
The Chesky-Conley dynamic: Brian brought speed; Chip brought depth. Together: velocity with wisdom
The culture design lesson
Airbnb's "belong anywhere" is not a tagline — it's a design specification for every product decision.
The 11-star experience
Brian Chesky's famous "11-star experience" framework came from Chip's hospitality background: what would a literally perfect stay feel like?
Playbook
Mentorship and Wisdom
Find a modern elder: someone 15-20 years ahead of you who is still learning, not just teaching
Be a modern elder: you have wisdom from your experiences that younger colleagues desperately need
Design culture intentionally: what stories, rituals, and heroes define your culture? Create them deliberately.
Accept help from different generations: the best innovation happens in intergenerational teams
The MEA missionModern Elder Academy exists because Silicon Valley worships youth and wastes wisdom. The best companies blend both.
Contrarian
Mentorship and Culture Myths
✗Mentors should just give adviceINSTEAD →✓ The best mentors ask questions. Advice directs; questions develop.
✗Young companies don't need culture workINSTEAD →✓ Young companies need MORE culture work. Culture is easiest to shape when the company is small.
✗Tech needs young energyINSTEAD →✓ Tech needs young energy AND elder wisdom. The combination is where breakthrough innovation happens.
✗Midlife is too late to transform a careerINSTEAD →✓ Midlife is the ideal time to transform a career. You have wisdom, relationships, and resources. The Modern Elder Academy exists to prove it.