> A strategy could have been "start with a $700 offering at the top of the market and work down," but that's not something they tell you on the way in

This is absolutely the kind of thing you should be asking about and they should be telling you on the way in. As an early stage startup employee you are basically an investor. You should deeply understand how the businesses you are joining are going to work, and if they wont tell you you should consider it a red flag.

I have been lied to on the way in. You hear about all this incredible stuff coming down the pipe that just needs a little more work. After a few months you figure out that that cashflow was 1/10th of what was implied and the pipe is dry.

Whether you want to call it an offering or a strategy, Ben doesn't claim that the failure was due to any aspect of the business model other than a) price, and b) competitive risk. Both of these were risks that existed (I assume) at the time he joined the company. So he can't blame management for failing to assess these risks any more than he can blame himself.