Chip Conley on Mentoring Airbnb and Midlife

TL;DR

Experienced professionals can thrive in younger technology companies by combining hard-earned wisdom with beginner-level curiosity and humility. Chip Conley brought hospitality expertise to Airbnb at age 52, mentored leaders including Brian Chesky, represented older hosts in product discussions, and learned unfamiliar technology concepts while reporting to a boss 21 years younger.

Transcript

Let's paint a picture of just what it was like to  join Airbnb in your 50s. I was mentoring Brian, but he was also my boss. I was 52. The average  age was 26. I had to be both wise and curious and often the dumbest person in the room. So, it's  great to be in founder mode. It's not as great   to be working for someone in founder mode. Brian  assume... Read More

Key Insights

• A modern elder is both a mentor and an intern, contributing accumulated wisdom while remaining curious enough to learn unfamiliar ideas. Conley practiced this balance at Airbnb by advising its founders and simultaneously learning the language, methods, and assumptions of a technology company.
• Age diversity is valuable because older and younger minds can contribute complementary abilities. Conley describes older colleagues as skilled at connecting dots, while younger team members can be fast and focused, creating a stronger combination than either group working without the other.
• Airbnb's product extended beyond its digital interface to the homes, hosts, experiences, and trips that customers encountered. Conley's hospitality background challenged teams that focused primarily on buttons and conversion, broadening internal discussion about what the company was actually creating and improving.
• Older customers need representation during product development because their habits may differ from those of younger designers and engineers. Conley encouraged Airbnb to involve older hosts when considering a mobile-only experience, testing whether they could comfortably manage listings without the original non-mobile option.
• Humility is essential when experienced leaders enter unfamiliar industries. Although Conley had built a large boutique hotel company, he had never worked in technology and initially misunderstood the industry's use of the word product, so he accepted being the least informed participant in some discussions.
• Founder mode can create demanding expectations for employees because a founder may assume that everyone will match the founder's pace and working hours. Conley recalls Brian Chesky expecting late meetings, including gatherings at 10:00 at night, illustrating the strain behind intense organizational focus.
• Energy can matter more than visible age when an older professional joins a younger organization. Conley argues that colleagues are less likely to focus on wrinkles when they see curiosity, engagement, and useful contributions, making personal vitality an important part of remaining effective.
• Midlife is a transition rather than inherently a crisis, according to Conley's caterpillar-to-butterfly metaphor. He compares it to a chrysalis and says he was happier at age 64 than at 47, when he experienced what he calls a flatline period.

Questions & Answers

Q: How did Chip Conley become Brian Chesky's mentor at Airbnb?

Chip Conley was invited to Airbnb near the end of 2012 after Natalie Tucci and Brian Chesky discussed having him give a talk about innovation and hospitality. The positive response led Chesky to invite Conley to work 15 hours a week as an in-house mentor to Brian, Joe, and Nate. The commitment quickly expanded, and Conley eventually joined full time as Head of Global Hospitality and Strategy.

Q: What does it mean to be a modern elder at work?

A modern elder combines the roles of mentor and learner. The person contributes pattern recognition, leadership experience, and wisdom accumulated over a career, but also remains willing to ask basic questions and learn from younger colleagues. Conley demonstrated this approach at Airbnb by mentoring its founders while admitting that he did not understand some technology terminology and was sometimes the least knowledgeable person in the room.

Q: How can older professionals succeed in a young technology company?

Older professionals can succeed by pairing relevant experience with humility, curiosity, and visible energy. Conley entered Airbnb at age 52, when the average employee age was 26, and had no previous technology-company experience. He learned unfamiliar concepts, accepted guidance from younger colleagues, and applied his hospitality knowledge where it mattered, especially in leadership, culture, host relationships, and understanding older users.

Q: Why did Chip Conley question Airbnb's definition of product?

Conley came from the hotel industry, so he naturally viewed Airbnb's product as its homes, apartments, hosts, experiences, and trips. Technology colleagues used product to mean the digital service and its features, including interface elements and conversion improvements. His confusion exposed a useful strategic distinction and encouraged the company to consider the complete hospitality experience, not only the software through which customers accessed it.

Q: Why is age diversity useful in product development?

Age diversity helps teams identify needs that may be invisible to people whose experiences resemble one another. At Airbnb, younger engineers, designers, and product managers considered making the service mobile-only. Conley suggested involving older hosts to determine whether they could manage listings entirely on mobile. Their perspective mattered because hosts tended to be older than guests, and Airbnb was increasingly reaching boomers and Gen Xers as hosts.

Q: What are the challenges of working for a founder in founder mode?

Working for a founder in founder mode can involve an unusually intense pace, long hours, and expectations that employees will share the founder's personal level of commitment. Conley describes Brian Chesky expecting people to attend meetings at the office as late as 10:00 at night. He acknowledges the value of founder focus while noting that experiencing it as an employee can be stressful and demanding.

Q: How did Chip Conley balance mentoring Brian Chesky while reporting to him?

Conley separated the value he offered as an experienced hospitality leader from the authority Chesky held as his boss. He mentored Chesky on leadership while reporting to someone 21 years younger and managing global hospitality and strategy. The arrangement required humility because Conley could be wise in areas such as culture and hospitality while still depending on younger colleagues to teach him technology concepts and company practices.

Q: How does Chip Conley describe midlife and renewed purpose?

Conley describes midlife as a chrysalis in the caterpillar-to-butterfly journey, framing it as a period of transformation rather than an inevitable crisis. He says he was happier at age 64 than at 47, when he experienced a flatline period. His Modern Elder Academy, now called MEA, applies this view by helping people approach midlife through wisdom, transition, meaning, renewed purpose, and continued impact.

Summary & Key Takeaways

• Chip Conley joined Airbnb at age 52 after building Joie de Vivre into a major boutique hotel chain. Initially invited to give a hospitality talk, he became a consultant and then Head of Global Hospitality and Strategy, advising Airbnb's founders while helping the company develop its hospitality operations, leadership, and culture.

• Working at Airbnb required Conley to become both a mentor and a beginner. He advised Brian Chesky on leadership but also reported to him, learned unfamiliar technology terminology, and sometimes considered himself the least knowledgeable person in the room. Humility and curiosity helped him adapt without discarding his experience.

• Conley argues that older and younger colleagues offer complementary strengths. Older workers can connect ideas, understand mature customers, and provide accumulated wisdom, while younger colleagues can contribute speed and concentrated focus. His later work with the Modern Elder Academy reframes midlife as a period of transition, renewed purpose, and potential growth.