Making money along the way: Did Dropbox and Evernote heed the lessons of Flip?
DHH
49813

For almost all VC funded tech companies, included the ones you mention, the game is rigged against your sensible advice.

It has become accepted wisdom bordering on an article of faith that successful investors will see the entirety of their returns concentrated in a few companies that achieve massive valuations through hyper-growth.

Almost all well known players in the startup funding ecosystem have espoused some variation of this view, partially because it matches their own experience.

But it does so primarily because the very same investors extend term sheets during successive funding rounds that all but require massive, unsustainable and unprofitable growth.

This in turn compels many otherwise promising startups that might have extracted sizable free cash to fail under the weight of cumulative unsustainable decisions before ever having seen a dime.

Worse, the suggestion from a founder that investors themselves might be better served in some circumstances by concentrating on extracting free cash from the business would not only be greeted with derision and condecension, but would probably result in serious questions as to whether the founder could be trusted at all in further management decisions.