I feel like this is a common trajectory for a lot of companies (Airbnb, Uber, etc.)

It starts off with cool intentions. Let's create a place where people can stay with other people - and chip in a little money. Instead of paying $150 for a hotel room, they get an air mattress for $20. It's a cool, couch-surfing kinda deal between people who want a cool experience.

Some time passes and someone starts thinking. What if we let them rent a whole place while the owner is away. The owner is going on vacation and it would be great to rent the place for a week and make $500 rather than letting it go to waste, right? That way you can go on vacation and a bit of it is paid for by renting out the place you won't be!

More time passes and more "good" ideas come. Travelers want a more professional experience with services like someone who has keys if they get locked out, someone to call if something goes wrong with the house and they need maintenance, etc. Likewise, the people offering space want cleaning fees because it's no longer a quirky site catering to people looking to have a cool experience, but also to every traveler who is looking for a bargain hotel - and is going to treat the property like a bargain hotel, not like a guest in someone else's home. It becomes a way for landlords or other property companies to make more money than they can with a long-term lease. Why rent an apartment for $2,500/mo when you can get $200/night ($6,000/mo potential) on Airbnb?

Well, you placate people by throwing cash at them. A host cancels? Your staff rebooks them at an amazing hotel in the area. A guest is messy? Throw some extra cash at the hosts. It's not your money. Nice Uncle VC is picking up the tab.

But then you're supposed to be getting to the stage where you can make money. The honeymoon is over. If you keep rebooking people in nice hotels at 2-3x what they're paying you, if you keep believing every sob story someone tells you about a place not being as advertised or a guest creating a mess, you're just going to keep bleeding money. You start instructing your support staff to be more skeptical of claims. Previously, it was always "we're so sorry, we'll deal with that immediately!" Now it becomes, "the host says that you checked in and until we hear back from them, there's nothing we can do."

It's not just Airbnb. The problem is that you start looking at the amount of money you're losing to various things and you want to tighten that up. How many customers do you think are just complaining about a cold food delivery or a room that doesn't live up to their expectations just so that they can get a discount?

In the beginning, you were something new and different. In the beginning, there weren't huge expectations. You were making something cool that could be really useful to people. Once the expectations became so high along with other people's money banking on those expectations, it becomes kinda difficult because the original, more limited scope isn't going to get those people the money they're expecting. Worse, even if you want to create a small and sustainable business, someone else will undoubtedly take the idea to its conclusion. Even if Airbnb didn't go this route, someone else would have and Airbnb might fade away.

And this happens with lots of things. Addictive social media? Well, if you don't do it, someone else will and then they'll stop using your site. Not only that risk, but your addictive competitor will now have so much more money so they can hire away your engineers and hire so many more engineers until you really can't keep up.

Even things like moderation policies end up here. Yep, you've worked hard to deal with things fairly and reasonably, but you can't spend an hour on every report and you've suspended someone that shouldn't have been. It starts out small with people who have reasonably similar expectations. Over time, a larger group might have more disparate and even competing expectations. Some even want to do things that benefit them at your expense - I bet I could grow my follower base if I got suspended for something innocent showing that the platform is biased against me! At the same time, there's pressure from advertisers to have a brand-safe environment while some users are trying to figure out exactly where the line is and maybe even push the line a bit. And all that was initially intended was a cool way to post messages to friends!

> But PG says, the best startups are the ones who solve intense immediate pain for a small number of people.

Not to nitpick a word in there, but it does say "startups", not "companies". I don't know if PG said startups, but you've paraphrased it as such. Startups might live and die by their reputation. People hear about how awesome Airbnb is in 2009 and it creates this great word of mouth - even problems are handled swiftly to everyone's satisfaction. It's the future. However, at some point their reputation is reasonably solidified and they're reasonably entrenched. Now they can act differently. Back in 2009, other startups might have fought for Airbnb's crown. Today, it's their market.

I think a big part of it is money - and not just on the company's end. Now property owners are looking how to maximize their money too. Can they work the Airbnb system to milk a few thousand more a year out of it? What might have started as happy guests having a cool experience are now guests looking to maximize as well - in part because they're now paying hotel-like prices with similar expectations. Not only that, if you get a reputation for being too easy, unscrupulous guests will try and figure out how to work the system to get more than they've paid for. And every industry has these problems, but with something like Airbnb, they're supposed to be a low-touch tech firm just taking a percentage for running some software, not a big company employing a lot of boots on the ground making sure things are what people are claiming. They're not looking to be Marriott with an army of workers.

Things can go from something somewhat nice and new to something where everyone starts looking closely at the bottom line. "Why am I renting out my spare bedroom so cheap?" "Why am I paying X when I'm not getting Y?" "Why am I accepting this report of a bad room with no evidence?"

I think this is why the Batman/Harvey Dent quote has so much sticking power: you either die a hero or live long enough to see yourself become the villain. And I'm not even saying it's the company's fault or anything. It's more just to note that at some point you start having to deal with the mess of reality. What starts with a lot of trust, hope, and optimism starts becoming a bit more actuarial. In some way, it has to become that way. If it doesn't, it's simply a target for bad actors. Or maybe this is just a cynical comment at the end of a long day and I'll feel silly for having written it tomorrow, but I do think there's something real about moving from the optimism stage to a more actuarial stage in a company's growth. At some point, you've gotten hit on the head and you create a rule and some people aren't going to like what that rule means. I remember AWS's S3 not charging for requests - and then someone created FUSE-mountable volumes backed by S3 generating incredible numbers of requests. At some point, any "unlimited" service gets limits - even if you just want the limit there so that a customer will email you why they need more and what they're doing. And I'm not calling companies evil or villains, but I do think that they do start looking at things a bit more like an insurance company would - with a bit more skepticism and a bit more of an eye toward the bottom line. That isn't necessarily a bad thing because businesses do have to make some hard decisions, but it certainly does change the feeling.

I'm really sorry that you had a bad experience. I hope that you're safe, healthy, and that Airbnb makes things right by you. I hope the rest of your vacation goes well.