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Comment by pbreit | Hacker News Reader

I'm not sure there's immense danger. VRBO/ADP/PayPal/UPS/Xdrive 2.0 aren't super risky. Basically going in to huge categories and "doing it right". Again, easier said than done. I get that. But with 100 startups per year, an incredibly smart group evaluating, a priceless 3+ months, etc, I'd like to see even better stuff. Sure, maybe slugging percentage is the better number.

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If AirBnb was such an obvious win, why didn't anyone want to invest? https://medium.com/@bchesky/7-rejections-7d894cbaa084

One of the challenges with this business is that our decisions look foolish at the time, and then obvious and easy with hindsight :)

Maybe because AirBnB found success in commercial property rental, not renting out your couch to someone, the original pitch. But I still don't think it's clear why AirBnB succeeded.

(Although parent didn't mention AirBnB?)

Even very early on though the plan revolved around there being no real natural barrier between couches and commercial property no? It's in the email exchange released by PG to show how people can miss the idea. If someones plan involves starting with X because it's a good stepping point to Y, I don't think it's fair to say "oh but they were only found success with Y".

It's not clear couch rentals was a good stepping stone to whole unit rental; why not list whole units directly? And I'm wary of claims that grand strategies existed from the beginning, those strategies are usually post-hoc inventions.

In retrospect AirBnB could have been more accurately pitched as a better VRBO but there still isn't an obvious reason why that would have been a good investment.

Exactly. Also noting that there is a similar theme that has gone around in business calling companies stupid for, say, not green lighting computer or idea that "a Wozniak" (he wasn't probably the only one just the one that we know about because of what happened next) showed them and didn't recognize the potential. Could have been the pitch could have been 1000 other reasons. (And of course sure maybe they did miss the opportunity possibly..)

VRBO 2.0 -> Airbnb

Photography. Make your landlords properties look better than the same property on another site and you are on the way to being a unicorn.

Oh, it was far from an obvious win. At that stage, it was going to take a relentlessly resourceful team making a series of good decisions. Further, going to complete strangers for an initial $150k raise doesn't make a ton of sense. This is friends and family territory or you would need to get to know some (semi-)professional investors. I don't think there's a whole lot to be learned from that story except that it's not a great approach to seed raising.

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