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Examples like this makes me scratch wonder about the sky-high valuations for Dropbox and Airbnb.

Kudos to Dropbox and Airbnb for executing on great ideas and building awesome companies.

Kudos to YC and other early investors for finding a diamond in the rough.

They'll all make tons of money :)

But those lofty valuations come with lofty expectations. Groupon has over $1B in revenue and a $2B marketcap but is perceived as a failure.

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$1B in rev but $3 mm in losses without profitability in sight.

You can create a pretty "massive" company pretty quickly if you basically sell $10.00 for $9.97

Their size actually works against them. Lots of companies lose money in the early days, but are able to justify / demonstrate why and when they'll be profitable. If you already have $1 B in sales and are still operationally unprofitable ... how much more will it take?

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