With hosts in 34k cities (from article), airbnb probably has more employees if we classified hosts as such. Also, many hosts hire of cleaners. It's quite possible that ~500k people are earning income (directly or indirectly) related to airbnb bookings.
Question: why didn't any of these issues prevent the web from taking over the desktop during the years between 1995-2005? Native has always been faster and more feature rich, on every platform and at every point in time.
Really? If you use Windows, you should be familiar with Windows Explorer. Since Win95 with Internet Explorer 4 desktop refresh (shipped also with Win98) you have a trident (IE) web engine in Explorer. The side bar with the metadata and info is DHTML in Win95(IE4), 98, ME, 2000. And a fork of trident code is used in XP and newer. Also WinXP "Software" application to uninstall programs is basically DHTML based. The newer control panel pages, the newer dialogs, etc. The EU demanded that Microsoft has to document the new UI-engine, used in IE "addons" dialog, Vista/7/8/10 Explorer bars & shell dialogs and Office 2007+, so that there no completive advantage. One has yet to find that in MSDN.
1) Microsoft made Windows too damn fragile. Installing the app means that setup.exe will write all over the hard drive, and uninstall was never easy. Web didn't required install/uninstall.
2) Windows programs, with a few notable exceptions, were/are butt ugly. Web started as an ugly abomination, but designers catched up quickly. Web applications, even then, on slow connections, often provided more pleasant experience.
Web app on mobile today doesn't have the same luxury - native app install/uninstall is painless; native applications are better integrated and most of the time handle unstable connections better; good native apps are beautiful and often have superior usability compared to web apps.
I think its because the bar for native apps wasn't that high back then. Also the interactions required for desktop apps are much simpler than mobile apps, where gestures are key part of interactions. Gesture-based animations is actually part of using the app, instead of on desktop where they just make things look pretty.
Most desktops are far overpowered for the (relatively) trivial computing tasks they are used for. As a result the relatively poorer performance of the webapps most people use desktops for is masked to a large degree, where it's even relevant.
In the context of this article, a big portion of the risks and costs are supported by national health care (Obamacare). If these gig workers had to acquire health care via the old means (i.e. benefits from a corporation, or hoping an insurance co will accept you), they would not have the luxury to work as contractors.
ACA/Obamacare is not national health care - it's national health insurance, and despite it being better than before (i.e., no pre-existing condition rescissions), the plans offered by carriers even with subsidies are still too pricey for many.
The mistakes you listed make it sound like you're trying to move too fast. Moving fast is good when it comes to product development. But not on the business side. Just focus on these two things:
1) Find a few users who love the product
2) Improve it to the point where they start telling people about it
Forget about analytics, pricing pages, press, etc etc. If you can't get some family and friends to rave about it, you won't get the masses.
Realistically, it will probably take years to really nail 1) and 2) above. But once it happens, you'll very quickly become the next big thing. Read up on the history of Pinterest for a great example of this.