Founder Appeasement

So, I'm a tad late to this article about Airbnb and their big launch a few months ago. The gist is that Airbnb, as its core vacation and remote work rental business saturates the market, has been looking for new products and offerings. They landed on creating an adjacent marketplace around travel-related services and experiences, something the company has tried to break into for the past decade^[1] without much traction.

I'm skeptical about how well this initiative will perform. The CEO addresses this by claiming that the company lacked the scale to generate enough supply and demand to kickstart a marketplace, but Airbnb in 2025 has grown to that size where network effects start to take hold. That may well be true, but the problem is that it rests on a conflicted business model.

Airbnb works in part because it represents trust absent established relationships: most people go on vacations once, maybe twice a year, in new and unfamiliar locales. An Airbnb listing assures the vacationer some baseline level of reliability in their accommodations; its brand and ratings serve the same function as a reputable, established hotel chain. To expand to services used more frequently—plumbers, barbers, etc.—works the first few times, but once the user establishes a steady relationship with the service provider, there's no reason to continue going through the marketplace and funding its commissions. Much like when you discover a good restaurant via Uber Eats or DoorDash, if you frequent enough to become a repeat customer, there's a good chance the restaurant would ask you to order directly and save both you and the restaurateur some fees.

Product launch aside, the other part of the article that piqued my interest was how it weaved in a profile of Airbnb's founder-CEO, Brian Chesky, and how he acted as the driving force for this reinvention of his company. The context here is that last year, one of his interviews inspired the "Founder Mode" essay by Paul Graham; he was the one complaining that companies get bogged down by professional managers and lose their ability to innovate and disrupt, and his solution was to leverage his authority as the company founder to drive projects, make decisions, and yes, micromanage teams and people to get results. My reflections at the time were that it's too easy, and often tempting, to justify bad behaviors and shoddy strategies under the guise of founder mode execution and privilege^[2].

The example given about how founder mode worked, from the source , was…weekly design reviews. Now, Chesky's background is in design, and Airbnb is famous for its design-led culture, so getting input from the founder-CEO on this area of product development makes total sense. What struck me was how superficial his feedback was: drop shadows, misaligned iconography, copy edits. Granted, even the article's author realized that this type of critical review is pretty minor and nitpicky.

The charitable read from this interaction would be that this particular design review was set up to be a dumbed-down version of the real CEO feedback sessions, simple enough for a tech journalist to write about and for readers lacking context to get a gist of how a founder can uniquely shape their vision. The less charitable read is that Airbnb's product and design teams don't find the reviews useful, so they're purposefully adding snafus to placate the CEO and his sense of being in control. The latter explanation would be far-fetched—except I've seen it happen, multiple times, across different companies and teams. There's even a term of art for it: the sacrificial duck.

All of this comes back to the Great Man mythology, the belief that history is shaped by singular geniuses altering its course. In tech, we're in a bit of a lull; many of the founder-CEOs of the biggest tech companies have moved on and brought in professional successors, and the next generation of founders seems less eager to chase the same spotlights. They have good reason to avoid chasing the same level of publicity; the techlash is still ongoing with antitrust lawsuits, while a notable number of founder-CEOs—Sam Bankman-Fried, Elizabeth Holmes, Adam Neumann, etc.—led companies that proved to be more hype than substance. I suspect this is why the same names keep showing up in tech journalism: Elon Musk, Sam Altman, and, to a lesser degree, Mark Zuckerberg.

So, color me more skeptical of the entire notion of "founder mode." In light of how this term came about, what Chesky was driving towards at Airbnb and its product pivot, it's almost a callback to an earlier era when CEOs like him were revered—as was Airbnb during its growth phase—as forces that changed the world for the better. I'd love to return to that environment that celebrated our industry with optimism, though encouraging powerful people to go back to running roughshod over their teams would seem a counterintuitive strategy.