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The Customer Who Almost Killed Slack, Stripe, and Airbnb

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21–30 of 33 posts

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#21
> Stewart Butterfield has talked about the pressure Slack faced from large organizations in its early days wanting features that would have fundamentally changed what Slack was. The requests were reasonable on their face: more administrative controls, different permission structures, audit logging. Each one seemed like a logical extension. Taken together, they were a blueprint for a different product aimed at a different user. Butterfield’s team had to repeatedly decide what they were actually building.

I'm pretty sure Slack has those things by now. So the question is, what did the team actually end up building? What features were prioritized over the enterprise compliance features? Would Slack have less revenue had they gone with the enterprise stuff first?

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#22
post #6

Remember that there is an alternate universe in which AirBnB is the way that 70% of all corporate short-term housing gets booked, and they are telling the story of how they nearly didn't pivot correctly. And a zillion alternate universes in which they never got big. Survivor bias is real, and everyone has just-so stories. The ones they choose to tell are partially an artifact of organizational culture, and partially…

On the other hand, what's the appeal of Airbnb in 2026? I'm genuinely confused at what is it better at than Booking, which also has hosts. Booking is also significantly cheaper at all offerings ranges and has a much wider catalogue including hotels. Airbnb was cool and interesting when it was genuinely cheaper and offering authentic experiences. Every vacation or place I go I check Airbnb and bar for one apartment in…

I’m the opposite and never use Booking but part of that is I’m put off by the experience of using the site. Also noticing it heavily skews towards getting you into a hotel in “touristy” locations. Feels like these are slightly different use cases and are optimized thusly.

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#23

Earlier quoted context omitted.

On the other hand, what's the appeal of Airbnb in 2026? I'm genuinely confused at what is it better at than Booking, which also has hosts. Booking is also significantly cheaper at all offerings ranges and has a much wider catalogue including hotels. Airbnb was cool and interesting when it was genuinely cheaper and offering authentic experiences. Every vacation or place I go I check Airbnb and bar for one apartment in…

I’m the opposite and never use Booking but part of that is I’m put off by the experience of using the site. Also noticing it heavily skews towards getting you into a hotel in “touristy” locations. Feels like these are slightly different use cases and are optimized thusly.

There's no shenanigans.

Both prioritize putting at the top places that are likelier to sell and hotels in more touristic areas draw more people.

What are those off putting experiences on booking?

Both apps and websites do essentially the same, it's not a sketchy dark pattern filled Ryanair check in.

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#24

Earlier quoted context omitted.

I get it. When AI writing tropes show up day after day, post after post, it’s hard to keep your sanity. It’s not just slop—it’s turbo slop . (Embrace the suck I guess, won’t last too much longer)

> (Embrace the suck I guess, won’t last too much longer) I'll take "Things I've heard every single day for the past 3.5 years" for $200, Alex.

Looking at the markets, either we all get turned into paperclips soon, or what goes up finally does the inevitable.

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#25
post #15
post #5

> Chesky said no. Not politely declined. No. Gaaaah please stop

Does anyone use a decent "ai detection" algo/service/on device model that they are happy with?

here is a product idea: a public service where you can submit urls for public content which will then be analyzed. the result can then be shared. the platform can allow a number of free submissions, but importantly if the same url is submitted multiple times, the analysis does not need to be redone. the free plan only allows a few submissions per day/month, whereas paid plans can offer bulk submission, more submissions, private results, etc...

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#26

Earlier quoted context omitted.

> (Embrace the suck I guess, won’t last too much longer) I'll take "Things I've heard every single day for the past 3.5 years" for $200, Alex.

Looking at the markets, either we all get turned into paperclips soon, or what goes up finally does the inevitable.

https://www.decisionproblem.com/paperclips/index2.html

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#28

Earlier quoted context omitted.

> (Embrace the suck I guess, won’t last too much longer) I'll take "Things I've heard every single day for the past 3.5 years" for $200, Alex.

Looking at the markets, either we all get turned into paperclips soon, or what goes up finally does the inevitable.

Even if the bubble pops, the spambots will be here for the rest of our lives. Indeed the inference will only get cheaper as hardware prices plummet and get repurposed by third parties running DeepSeek etc. Just like the dotcom burst didn't wipe out the internet, only the people who lost touch with reality.

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#29
post #25
post #15

Earlier quoted context omitted.

Does anyone use a decent "ai detection" algo/service/on device model that they are happy with?

here is a product idea: a public service where you can submit urls for public content which will then be analyzed. the result can then be shared. the platform can allow a number of free submissions, but importantly if the same url is submitted multiple times, the analysis does not need to be redone. the free plan only allows a few submissions per day/month, whereas paid plans can offer bulk submission, more submissio…

[deleted]

Re: The Customer Who Almost Killed Slack, Stripe, and Airbnb

#30
post #6

Remember that there is an alternate universe in which AirBnB is the way that 70% of all corporate short-term housing gets booked, and they are telling the story of how they nearly didn't pivot correctly. And a zillion alternate universes in which they never got big. Survivor bias is real, and everyone has just-so stories. The ones they choose to tell are partially an artifact of organizational culture, and partially…

This line of argument proves too much. As it would apply to a lot of things throughout history. e.g. “Remember that there is an alternate universe in which ancient Anatolian farmers defeated the Yamnaya steppe raiders in Europe, and they are telling the story of how they nearly didn't make it.” Which would mean even the concept of “European” as known in this universe… is just a bundle of survivor bias, just-so storie…

On the contrary, this line of argument proves nothing. Rather, it is a caution that people telling you stories tells you a lot about what they want to portray, not so much about whether what they did was a generally good decision.

As to your second point: "European" is an arbitrary social concept. Cartographers could have decided that Eurasia is obviously a single landmass, or that nothing is more important than river systems, or that the most important directionality is the path of the sun. Thousands of years later, the decisions made have consequences, but there is nothing divinely ordained about what those decisions were.

I suppose if a hundred years from now the common, generic word for "hotel" is "airbean", that might be a significant effect. But it's a little more likely to be "marriott" or "hilton", I think.

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