It is the opposite of the truth that high-end customers start at the cheapest plan and move up. High-end customers start at the most expensive plan and stay forever. They will frequently not downgrade even if they have a multi-month dry spell in using the software because e.g. $250 a month is not a meaningful amount of money for them.
Free accounts upgrade to premium accounts essentially never. (1% ~ 2% is quite common.) Cheapo-plans upgrade to higher plans very, very rarely. For Appointment Reminder, I've had one person ever transition from Personal ($9) to something higher and then actually pay for a month of it.
Yeah, but that is because of deliberate choices on their part.
An alternative product model for Dropbox would be to partition the product on one or more features. Something like the ability to share files is an obvious choice, as is things like selective sync.
In retrospect it seems obvious to give all the features to everyone, give away a base level of storage and sell storage upgrades.
Before anyone says who'd be stupid enough to sell backup software any other way look at things like Norton Backup[1], where the license is limited on both the number of computers you can install it on and the size of online storage available.
Free accounts upgrade to premium accounts essentially never. (1% ~ 2% is quite common.) Cheapo-plans upgrade to higher plans very, very rarely. For Appointment Reminder, I've had one person ever transition from Personal ($9) to something higher and then actually pay for a month of it.