I’ve always liked doing hard things. My first hotel had “failure” written all over it — a bankrupt pay-by-the-hour motel in a sketchy neighborhood, run by a guy with zero hospitality experience. Yet, 39 years later, next week we’ll celebrate the retirement of The Phoenix, San Francisco’s legendary rock ’n’ roll hotel. That “little engine that could” became a company with 52 boutique hotels with 3,500 talented, joyful humans. I didn’t know my limits until I blew past them — and hit my wake-up call during the Great Recession when I sold the business at the bottom of the market.
Then came another hard thing: joining Airbnb as the “modern elder.” Reporting to my mentee, CEO Brian Chesky, required me to right-size my ego and supersize my curiosity. My hotel friends laughed — until they realized this so-called ridiculous startup was real competition. I often quoted Gandhi to my Millennial colleagues: “First they ignore you, then they ridicule you, then they fight you, then you win.” Brian called me the Secretary of State because I was constantly putting out fires globally. It was exhilarating and exhausting.
And then I founded the “world’s first midlife wisdom school.” What the hell is that? Who wants to be a “modern elder”? COVID, cancer, leadership transitions, and running two campuses (one of them a four-square-mile horse ranch that tripled our capacity) made it feel like I was standing on my surfboard before the wave had even arrived. It’s hard to balance when the swell is still forming.
When I’m teaching, though, I feel an unmistakable calling. This is my ministry now — my ROI: Ripple of Impact. Yet, the other ROI — Return on Investment — hasn’t been as kind. Maybe we grew too fast (going from one to three retreat centers overnight has been a stretch), gave too much away (half of our 7,500 alums have received financial aid from MEA), or led with too much heart and hope.
Fortunately I’m still the sole investor and not answerable to some private equity firm, and I do see the wave coming especially since our alums love the MEA experience so deeply. The world is finally waking up to longevity and purpose and our trend line for revenues is strong. Time doesn’t just heal wounds; it yields wins. And, maybe, it’ll someday yield me a salary. LOL. Patience is a virtue, right?
Traditional investors chase money. I chase meaning. MEA’s real dividends live in our alumni across 60 countries and 56 regional chapters — a global circle of wisdom-keepers who remind me that success and failure can, in fact, coexist. It all depends upon how you define success.
I may not have made a fortune…yet. But I’ve made a difference — and maybe, in the long run, that’s the richer return.
-Chip