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Why Did Ben Gilbert Doubt Disney Plus?
David Rosenthal quotes Ben Gilbert from the end of Acquired's 2019 Disney Plus episode, where Gilbert's one reason to doubt Disney Plus was that he thought Disney may be underestimating how much content people need to stay satiated. The back catalog of storied franchises is beautiful, but $7 a month is not worth paying just to keep the option available. To rewatch a Star Wars movie, the subscription can be reactivated later. Disney has to aggressively turn on a fire hose of content.
A fire hose of content is completely orthogonal to the flywheel of only the best content, very infrequently: a theatrical release, a cultural moment, then quiet while Disney harvests the one movie. Streaming runs the other way. On Disney Plus, something new and fresh has to be waiting whenever Disney Plus opens. Disney had two things to lose, including an existing content library that was highly differentiated, and bolting new stories onto the universe makes the original less valuable. The Obi-Wan show on Disney Plus made Obi-Wan seem less cool and risked destroying the competitive advantage.
Every sequel is a big risk in top-tier stories and characters, which is why Disney did not make sequels before the 90s. Pixar proved sequels can be great with the same care, effort, and time. Pixar does one every seven years.