It's definitely one of my favorite stories, and really serves as a great testament to the idea that staying alive so you can keep working on your product is easily one of the most important things for (early stage) companies.
The cereal box story serves as a reminder that sometimes it takes the most unlikely, left-field, crazy-seeming idea to get yourself out of the hole.
The one my company pulled was very different to this, but it worked, and the company is now thriving, albeit on a much smaller scale to Airbnb.
Had we not been in the same YC batch as Airbnb and seen up close just what it takes to survive hardship and get to sustainability, it's unlikely we'd have made it.
There are way more reproducible methods of keeping your company above water, such as reducing burn or spending your time wisely and focusing on your core product (as opposed to adding more and more features no one really wants).
I've heard the Airbnb founders tell their story many times and even they acknowledge this was a last-ditch effort. They ate ramen and cereal for all their meals to extend their bank account and tracked it to the penny. I think that is the point that should be taken from the story; when it comes down to the end of the wire, you should be willing to do whatever you can to stay alive. All cliches aside, startups are hard.
Though it does make for an awesome 'hustle' story (on that, I agree; same with startups being hard). It sounds like they were just having fun, and happened to earn some scratch along the way.
They really were doing this because they were out of money. And this is like a Hail Mary for them.
The sensible advice YC partners will always give you is to avoid running out of money.
If you've run out of money, there's not much advice the YC partners can give you, and the only options are to (a) shut down immediately, or (b) throw a Hail Mary.
The lesson here is that if you're the kind of founder who, in a do-or-die situation, can figure out a Hail Mary that actually hits the mark - and if you believe in your idea enough to be willing to try anything to survive, even when nobody else in the world believes in your idea - you're more likely to be the kind of founder who will accomplish huge success in the long term - due to the determination and inspiration you've shown yourself to possess.
Of course, nobody should fetishize getting in a situation where you have to throw a Hail Mary - but as Jessica explains, in the 2008 climate, it was hard to imagine how they could have avoided it.
But offering this story as a perfect example of how determination and inspiration can lead to massive success continues to be entirely appropriate.
It was a good move, probably only works once, and anyone running a startup about to die should think up something as effective. Lesson learned.
EDIT: Interesting our replies came at almost exactly the same time.
Whether its making personal sacrifices, cutting all unnecessary costs, selling "on boarding" you would do anyway for free - whatever it takes to keep the company alive (lots of things that don't scale) end up being significant in the early (and middle-year) history of startups.
Maybe its played, but I still think its a pretty great example of just getting it done by whatever means necessary.
I don't look at it as a random side business because it provided marketing and helped them raise money when they were broke.