As somebody who disagrees with much of what "Silicon Valley" accepts as common sense (you can read my past comments if you care), I'd suggest that startups have

As somebody who disagrees with much of what "Silicon Valley" accepts as common sense (you can read my past comments if you care), I'd suggest that startups have to be just as careful about unrealistic long-term expectations as they are about unrealistic short-term expectations. It's just as easy to fall for "If you build it they will come" as it is to convince yourself that your lack of traction will miraculously address itself if you can stay afloat long enough. As burritofanatic noted in his comment, the fundamental question for Casetext is "What is the incentive for a user to annotate case law?" If the incentive or incentives were compelling, you would not expect a statement like "The cases are mostly barren, and the ones with annotations aren’t particularly insightful like the earlier ones from when Casetext was first announced" nearly two years in. You'd see evidence of increasing traction. Casetext is trying to attack a very difficult market. Bloomberg invested over a billion dollars trying to do the same thing and had very limited success. Casetext has raised less than $10 million.