Wise and Curious: Chip Conley on Mentoring Brian Chesky, Dying Nine Times and Learning to Love Midlife

Conley says he never planned to work at Airbnb. He was invited to give a talk on innovation and hospitality, which he later realized was a dress rehearsal for Brian Chesky to see how a young crowd, with an average age of 26, would react to a 52-year-old with a bricks-and-mortar boutique hotel background. The audience liked him, and Chesky asked him to work 15 hours a week as an in-house mentor to Chesky and his co-founders. Within three weeks it was 15 hours a day, and he eventually went full-time as head of global hospitality and strategy.

The early months were hard because he didn't know the tech lingo and had never worked at a tech company. He recalls asking the chief product officer whether the product wasn't the homes and apartments, only to learn that "product" means something different in tech. He says he had to be wise, curious and often the dumbest person in the room, while reporting to someone 21 years younger. Lenny notes that former colleague Laura Hughes remembered precisely this kind of question from him.

Conley found ways to add value as a voice for older users. When Airbnb discussed going mobile-only, he suggested testing whether older hosts could manage listings entirely on mobile. His advice for working in a young environment is simple: don't pretend to know what you don't, bring humor and humility, and show respect in the hope of getting it back. He also notes that younger managers sometimes expect older colleagues to know as much as they do, just as older managers can expect the same of younger ones' emotional intelligence.

Conley says he would never have joined without believing in Chesky, whose appetite for learning stood out: after a 2011 incident in which a guest trashed a host's apartment, Chesky went to find experts, and he came to Conley saying he didn't know what he was doing in hospitality. Conley sees that growth mindset as the best part of Chesky, who also has "a lot of hubris."

He lists three hard things. Chesky assumed everyone would work at the same pace and duration, such as a 10 p.m. office meeting. Chesky also admired Steve Jobs so much that he believed he knew better than anyone, and Conley says a product meeting with him could keep people up the night before. Third, Chesky added a zero to expectations and set unreasonable deadlines, believing that hitting even half would be encouraging, which Conley says sets people up for stress. He credits Chesky as a generational leader and says he hopes he had some influence on applying emotional intelligence.

Conley's tips for dealing with a founder in founder mode: build credibility by getting close to the customer, as he did by visiting hosts in 20 cities, and set alignment at the start of a meeting. Start by stating the intention and what success looks like, and if there is no alignment, spend the meeting on that. Keep decks short, because a combustible founder may take the discussion off the planned order.

After Airbnb, Conley wrote Wisdom at Work and spoke with neuroscientists. He explains that a younger brain has fluid intelligence, tending to be fast, focused and linear, while an older brain has crystallized intelligence and thinks more holistically and systemically. When both are on a team, he says, the result can be brilliant, and he calls this brain diversity a benefit that is less noticeable in other forms of diversity.

One of his jobs was to find blind spots. Early on he told Chesky that the company's strategy depended on avoiding regulation and occupancy taxes, and that if Airbnb grew as planned it would be regulated, so it should build a proactive strategy. Regulation in municipal markets has since been Airbnb's biggest challenge, and he thinks starting earlier might have avoided some of the toxicity in New York.

He also talks about "invisible productivity," which means making everyone around you better, as an engineer he knew did when he became a manager. A young HR head with a French accent once called Conley her "confidant" and explained that in her part of France it means someone who gives you confidence. Conley takes that as a good definition of a mentor.

Conley agrees that ageism in tech is a problem, though less of a blind spot than a dozen years ago. Airbnb had an employee resource group called Wisdom at Airbnb for people 40 and older, and it pushed for a program that brought "senior nomads" in to act as the voice of the customer for 10 weeks. He acknowledges the challenge: older workers can be expensive and perceived as slow when new hires arrive with fresh technical skills.

On AI, he says it is a whole new ballgame, and the question is whether human wisdom, emotional intelligence and pattern recognition can balance artificial intelligence. The jury is out, he says, and the answer to whether AI will wipe out older or younger workers' jobs is probably both. Lenny adds that AI makes it easier for people less connected to cutting-edge building methods, since you can just talk to it.

For older professionals who are financially secure, Conley suggests being open to reduced hours. In his fourth year at Airbnb he cut his time to 40 or 50 percent, with matching salary and options. He argues that institutional wisdom and process knowledge, such as knowing how to get things done in a particular organization, can be valuable even at 60 or 80 percent time.

Conley says the people who thrive in tech as they age are both mentor and intern, with a voracious appetite for curiosity. His advice is to show up with curiosity and passionate engagement, because "people won't notice your wrinkles as much as they'll notice your energy." That energy has a physical part, so you aren't resting on your laurels, and a positive part that draws people to you. He was approachable, worked 60 to 70 hours a week and traveled, and Chesky called him the "secretary of state" of the company.

For hiring managers, Conley points to David Epstein's book Range and says AI is accelerating the shift from specialists to generalists. He suggests screening for passion, curiosity, learning, good energy and problem-solving range. He also recommends mutual mentorships: people at Airbnb taught him his iPhone and Google Docs, and he taught them how to run a great meeting or give an employee review, like an apprenticeship in the field.

Conley acknowledges his own privilege, since he was recruited. For others, he stresses getting a foot in the door through networking and being able to articulate accomplishments in a new way. He would love to see a resume that, in place of role bullet points, describes a thorny problem, the skills used and the result, and he likes the interview question of asking what the biggest problem is and how you can help.

Conley started his hotel company at 26, a couple of years after Stanford Business School, when concert promoter Bill Graham told him San Francisco needed a rock and roll hotel. He turned a run-down Tenderloin motel into the Phoenix, which he has owned for 39 years, and grew the company to 52 hotels, the second-largest boutique hotel company in the world. He loved it until he hated it in his late 40s, when the Great Recession hit and he went through what he calls a midlife crisis.

While on a book tour with a broken ankle, a cut on his leg became septic, and he had an allergic reaction to the antibiotic. He flatlined nine times over 90 minutes. In the experience he saw himself flying in a living room in the Alps wearing slippers marked "slow" and "down," surrounded by birds he understood, who told him that if he slowed down he would see beauty and awe.

He says he came away believing every day is a gift and bonus. Within two years he sold his company at the bottom of the recession, which created the space to join Airbnb. Lenny observes that people often need a jolt like this, or momentum just keeps carrying them forward.

Conley defines culture as what happens around here when the boss isn't around, and it matters more the more distributed a company is. At his own company, with 52 hotels, 25 restaurants and four spas, he couldn't be everywhere, and the same was true at Airbnb. Culture guides decisions and acts as a magnet for the right people: he notes that Apple people did well at Airbnb while Amazon people less so. He prefers "culture add" to "culture fit," since fit can be negative for anyone who is the aberration.

For candidates, he recommends interviewing the company: ask for three to five adjectives that define the culture, what the biggest endemic problem is and whether it will ever be fixed. Ask several people, and see whether you hear the same answers, because a department can have a culture different from the company as a whole.

His Peak model applies Maslow's hierarchy to employees, customers and investors. For employees the layers are money at the base, recognition in the middle and meaning at the top. For customers they are meeting expectations, meeting desires and meeting unrecognized needs. At Airbnb, asking whether it was in home sharing or something bigger led to the idea of the "belong anywhere" business, which gave hosts and marketing an organizing principle.

The nickname "modern elder" came to Conley at Airbnb, where it meant someone as curious as they are wise, and led to the Modern Elder Academy, now called MEA. It offers five-day workshops on a beach in Baja and on a ranch in Santa Fe, and also online programs, to help people navigate transitions. Conley defines midlife as 35 to 75, says the average attendee is 54, and reports 7,000 graduates from 60 countries and 56 regional chapters.

He cites research by Becca Levy at Yale showing that a positive mindset about aging adds seven and a half years of life. A favorite MEA question is what you will regret in 10 years if you don't learn or do it now, which got him to learn Spanish and surfing in Baja at 56. He calls anticipated regret a form of wisdom and a catalyst for action.

He also describes the U-curve of happiness: life satisfaction declines from the early 20s and bottoms between 45 and 50, then rises, though he notes that young adults are unhappier than ever. He says he is happier at 64 than at 47. Midlife is the chrysalis, the cocoon in which life seems to liquefy before a metamorphosis, and he defines wisdom as "metabolized experience mindfully shared for the common good."

In an AI corner segment, Conley says he writes a daily blog and uses ChatGPT for a first draft when he lacks inspiration, since it knows his humor and can produce 250 words in 30 seconds that he then adapts. In the lightning round he recommends Viktor Frankl's Man's Search for Meaning and Elizabeth Gilbert's Big Magic. He links Frankl to an equation from his own book Emotional Equations: despair equals suffering minus meaning.

His other equation is that anxiety equals uncertainty times powerlessness. He says 98 percent of anxiety comes from what you don't know and what you can't control or influence, and recommends an anxiety balance sheet with four columns: what you know, what you don't know, what you can control or influence, and what you can't. Putting free-floating anxiety into that structure makes it more tangible and often less intense.

His favorite recent show is Ted Lasso, and he mentions the film I'll Push You. His motto is that painful life lessons are the raw material for future wisdom. He also points listeners to free resources on the MEA website, including one on why successful leaders value wisdom and one called the Anatomy of a Transition.