Photo by Allan Franca Carmo.
A 24-hour news cycle is an awful lot to fill. And whether an idea is good or bad, the fact that a famous and wealthy person said it is enough to make it newsworthy. This means someone can spout total nonsense and Forbes will gladly slap a masthead on it so they can monetize the clicks. And, to be clear, the more chaotic or unhinged the take, the better. Because while the high engagement metrics on the post could mean, “let us reflect thoughtfully on this contribution to modern workplace discourse.” It is far more likely they mean, “getaloaddathisshit.”
So forgive us for being cynical when Forbes posted a two-year-old social clip with Airbnb’s CEO, Brian Chesky. The fact that it was old should be your first clue. Any time something shows up in your feed, it’s worth taking a beat to wonder, why is this making the rounds again? Why now? The answer is that it performed well the first time around and so either a real human or an LLM thought you might wanna see it again. In order to make it timely, the social team (bot?) tied the clip to Chesky’s birthday. Not because it has anything to do with his birthday. And not because it was the birthday of the clip. No, no. The entire post is just “Check out this thing yer boy the Virgo said that one time a long time back! Happy bday, Bri-man!”
Chesky doesn’t do 1:1s. Tobi doesn’t do meetings. Zuck doesn’t do morale. It’s hard to argue with billionaires on business topics. Not because they are always correct. But because all the mainstream storytelling about them includes the same two caveats. The first goes, “Sure, it may be a bit unorthodox but clearly it’s working for him. Just look at all those yachts/race cars/dinosaur bones.” By this math, any decision made by a person with vast personal wealth is a good decision. And the second goes, “He’s run a bigger social network than I have, the man must know a little something about how to manage teams. Maybe if I take his advice, my business will also grow to be ginormous.”
These are magic beans, not thought leadership.
So here we are. In 2026. All doing another round of “Shit Billionaires Say” and having to wade through it together. If you’re new here. A few things. Being a billionaire means you’ve successfully made a billion dollars. This is an enormous feat. A billion is a very big number. That narrow thing really can stand-alone as a mind-blowing milestone. We don’t need to extrapolate to other topics.
Specifically, being a billionaire…doesn’t mean you’re a good boss. It doesn’t mean you’re more clueful than the average non-billionaire manager. In fact, you’re often less clueful cause your people have a billion reasons not to tell you when you’re screwing up. It doesn’t mean your team likes you or even that your team enjoys their work.
Ask Travis who didn’t believe in HR. Or Larry & Sergey who didn’t believe in managers. Or Gates who, well, there’s actually rather a lot. Anyway, no shortage of wealthy people with lukewarm takes. But the wonderfully good news is that you don’t have to take our word for it and you definitely don’t need to take theirs.
My house my rules
Look, the most literal read here — the one they’ll fall back on, if challenged — is that these guys are just telling us their preference. This is how they run their company. We, the audience, presumably asked, and they are answering. It’s not advice, and no they haven’t done a bunch of research or whatever, it’s just them talking about their own cute little quirks and preferences. Like we’re reading the profile of a new and terrible boyband. Brian likes travel, beaches, and meeting as a group. Mark likes creamy coleslaw and yelling at his employees. David likes fast cars, self-determined priorities, and ethnic cleansing.
That’s obviously not what they intend, though. Chesky goes into a whole song and dance — he sets up a straw man definition of a 1:1, describes running it poorly, and then leaves it there as evidence that the very concept of a 1:1 is at fault. He’s not just describing, he’s making an argument. He’s trying to persuade you of a thing. They may not care what kind of coleslaw you like, but they want you to agree with their arguments on management. It’s not enough to be a wealthy CEO of a large and well-known company, they also desperately need you to think of them as luminary leaders. And one thing you should know about the weird little group chats they inhabit is that, in those rooms, the most luminous way to be luminary, the coolest way to be cool, is to be heterodox.
And so we find ourselves awash in billionaires-and-wannabes who have seemingly each picked an organizational noun phrase as their enemy. 1:1s. Meetings. Goals. Org charts. Morale. HR. Remote work. Weekends. We’d make a joke about how no one has come out against keyboards yet, except obviously also that.
It’s hard to blame people for listening (except to the keyboard guy, who is pretty clearly doing a bit). These are obviously very successful people. They’re saying something counter-intuitive. If you found out that your favourite member of the CEO boyband liked creamy coleslaw maybe you’d start eating more of it, or maybe you’d write that off as unrelated to their success in the role. But management stuff feels pretty CEO-ish? If they have management things to say, maybe they’ve cracked the code? Maybe those are the keys to the kingdom, right? Maybe we should all follow suit?
Is this competence? 🫴 🦋
Maybe not. Imagine that you had listened to that 2024 interview with Brian and thought, “There’s a guy who’s cracked the code. His arguments are appealing to me. Blech, talking to my team one on one! Who needs that?” Imagine that you’re swayed by his arguments, and tempted to do the same with your own team. But, unlike some of these luminaries, imagine that you have even a whiff of intellectual honesty and curiosity about your own fallibility. How would you assess it?
Well you could look at stock charts or other public indicators of success. It’s sort of tricky, looking at historicals, to judge whether a company’s rise was brilliant leadership or brilliant timing. Did Jensen Huang’s distaste for 1:1s drive NVDA to the moon or was there, maybe, some exogenous increase in market demand for GPUs for some reason? Within 12 months of Brian giving that interview, two C-suite executives had quit and the stock dropped 10%. Maybe those things were exogenous, too? Maybe SEC 10-Qs aren’t a great proxy for leadership luminosity?
So what else? We could look for counterexamples. Tim Cook is a famously intent and intentional listener in 1:1 conversations. Andy Grove writes about 1:1s extensively in High Output Management as a central tool of effective management, and is broadly recognized as one of the greatest managers of his generation. Are they actually just a couple of thoughtless chumps wasting their time, tragically missing out on Brian’s heterodox wisdom? Are you a chump for still doing 1:1s with your own team, or your own boss?
Speaking of books, one option might be to look at whether anyone’s ever done any research on this stuff. As luck would have it, it’s been extensively studied in a variety of contexts for decades! In papers, in books, in industry research. Because of course it has. Of course the tools and techniques and practices of organizational health and psychology have been studied extensively. Like, that’s obvious, right? That we haven’t all just been sitting around hoping that Brian, or Tobi, or David, or some other chucklehead would some day crack the code?
It’s not obvious to everyone. The interviewer could have saved Chesky by stopping him after the first bit to say, “Wait, though. You’re describing very badly run 1:1s? You’re either setting up a strawman, or else you actually think that’s what 1:1s are, in which case it feels like you’re probably too incompetent to speak on this topic? Maybe we should talk about real estate or travel or bylaw evasion or some topic you actually know something about?” But it isn’t anyone’s job to save him there and I’m not sure he’d have let them anyhow. Some folks are desperate to show their whole ass — sorry, heterodoxy — and call it thought leadership.
The moment someone’s novel take removes a key component of leadership or management that’s present for nearly every organized group of humans working toward a common aim, that’s a great time to get skeptical. Not because every dish needs every ingredient. But because a chef who just doesn’t do tomatoes is maybe making a brilliant statement about the over-reliance of nightshades in North American cooking. Or is maybe shooting from the hip and hoping no one will notice that they are making it up as they go along.
Management is a hard job. You need every available tool in the toolbox. When someone tells you to throw out a tool without stopping to ask what you’re trying to get done or how, it’s a safe bet that they don’t know how to use it. You can assume that person has a team of folks behind them who clean up their messes and hide their own tools in the shed.
— Melissa & Johnathan
