Why does it need to be the Internet Archive that takes big risks?
In the startup space it's common for a founder to, after a successful launch, hand off control of the organization to someone else who's better equipped to drive the company in slow and steady mode. If the people in charge of the Internet Archive feel like they're best equipped to be revolutionaries rather than maintaining the ground they won in the past, maybe it's time for them to transition into a new organization and hand off the IA to people who are able to run it in maintenance mode.
In the startup space it's common for a founder to, after a successful launch, hand off control of the organization to someone else who's better equipped to drive the company in slow and steady mode. If the people in charge of the Internet Archive feel like they're best equipped to be revolutionaries rather than maintaining the ground they won in the past, maybe it's time for them to transition into a new organization and hand off the IA to people who are able to run it in maintenance mode.