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Comment by pbreit | Hacker News Reader

Nope. It really isn't. The hardest thing by far is to get lots of usage. Once you have lots of usage, it's really easy to make money whether it's advertising, fees or whatever.

Can you name 2 or 3 "idiots" that have done what you suggest?

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I don't think any of them are idiots. But here's a small sample of companies, off the top of my head, who have had serious problems in terms of monetization / revenue and needed to use investors / host company's money to run:

Pinterest. Groupon. Reddit. Snapchat. Instagram. Youtube (for many years). Twitter took a long time to make money. Most news sites have a hard time, which is why WSJ is paywalled (as mentioned in the article). On the "smaller valuation side", we could say FriendFeed, Zite, Hot Potato, Beluga, GroupMe, TweetDeck, Dodgeball.

It's much harder to than you may realize to monetize.

It's very hard to monetize, but it's orders of magnitude harder to get big in the first place.

Groupon and YouTube are printing money now that they are public. Pinterest, Snapchat & Instagram haven't even tried to make money (ie, they are doing what I explained). Most or all of those small ones never grew fast enough to matter.

Digg? Everpix? Myspace (though the original owners managed to cash out before it crashed)? Metafilter (not a VC-funded startup AFAIK, but having to shrink because they can't profit despite their popularity)? Twitter, though they haven't quite crashed yet?

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