Open Letter to Brian Chesky

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Open Letter to Brian Chesky
(May 14 2025)

Dear Brian,

First, immense respect. Very few founders have re-architected a consumer habit as completely as you did when you turned spare sofas into the world’s largest lodging network, changing global real estate prices in the process. That accomplishment is why this note is both appreciative and direct.

1. The Frame: Top-Down vs. Bottom-Up

  • Top-Down companies start with a grand vision and bend reality toward it.
  • Bottom-Up companies spot an emergent behavior in the wild, wrap software around it, then let the crowd carry it uphill.

Both can build iconic businesses—but only when they act in accordance with their “genotype.”

2. Airbnb’s DNA Is Bottom-Up

Your founding story wasn’t a master plan; it was two designers renting air-beds to pay rent. Every major unlock since—instant book, Superhost, category browsing—came from observing how millions of hosts and guests actually behave, then institutionalizing those patterns. That is bottom-up to the core.

3. Experiences Is a Top-Down Import

Experiences reverses that playbook:

  • Central Curation. A small internal team decides which experiences qualify, which violates the crowd-sourced logic that made homes scale.
  • Labor-Heavy Supply. A spare bedroom can earn money while the host sleeps; a three-hour pasta-making class cannot. The yield curve is inverted.
  • Repeated Relaunches. The product was paused in 2023, reopened to new hosts only last September, and is being “relaunched” again this month. These resets are signals that the market, not the mechanics, is rejecting the idea.

4. Why the Mismatch Will Persist

Bottom-Up Strength

Experiences Reality

Passive, scalable inventory

Active, thinly-traded inventory

Host economics driven by idle assets

Host economics driven by personal time

Guest intent: “place to stay”

Guest intent: “thing to do,” a separate decision tree

Algorithm learns from hundreds of nights

Sparse, noisy data—few reviews per listing

No amount of integration polish can force-fit a top-down concept into a bottom-up engine. The gears simply don’t mesh.

5. The Blind Spot

Your very success may tempt you to believe you can will new verticals into existence. But the genius of Airbnb was never a grand narrative, it was tinkering plus perfect timing and a perpetual sensitivity to what hosts were already hacking together. Acting like a top-down visionary risks turning your super-power (pattern recognition) into a kryptonite (requiring pattern invention). Lean into the product-driven pattern match and be aggressive on M&A to expand the product footprint–this is the way many other Bottom-Up companies scale (e.g. Google + YouTube, Facebook + Instagram).

6. Stay Bottom-Up, or Let It Go

If you must pursue the adjacency, flip the polarity: open the floodgates, let hosts bundle whatever local magic they already provide to distinguish themselves (airport pickup, fridge-stocking, neighborhood walks) and algorithmically surface the ones guests actually buy. Otherwise, Experiences (and whatever comes next) will keep absorbing leadership bandwidth for diminishing returns, and the platform’s focus—your most precious commodity—will drift and ultimately decay.

Respectfully,

Chris Paik
Partner, Pace Capital

(Written as a friendly outside-in memo from a bottom-up investor who has admired Airbnb since the air-bed days.)