The only red flag is that he has waited around when he lost creativity, and even that is not red - at least he had the courage to quit.
It is a job of the employee to be creative (talking about design, of course). But it is the job of employer and investors to make an environment that challenges the employer. If they are unable to do that then any really creative employer will (or at least should) leave.
@OP: good luck!!! I wish you well on your path, wherever it takes you.
> It is a job of the employee to be creative (talking about design, of course). But it is the job of employer and investors to make an environment that challenges the employer. If they are unable to do that then any really creative employer will (or at least should) leave.
Well, that sort of goes back to a common theme in software companies: Are the people being hired as creatives or are they being hired to implement someone else's vision?
My experience is that in most roles you're likely to be being hired for the latter - and having intelligence outside of the ability to do your assigned task efficiently is strongly discouraged in them.
It is a job of the employee to be creative (talking about design, of course). But it is the job of employer and investors to make an environment that challenges the employer. If they are unable to do that then any really creative employer will (or at least should) leave.
@OP: good luck!!! I wish you well on your path, wherever it takes you.