Bill Oakley on 5% Asks, ‘Predictions,’ and Room Morale
The 5% ask that changes careers.
I just sat down with Bill Oakley.
Former Simpsons showrunner, multi‑Emmy writer, and Steamed Hams creator turned food enthusiast.
In this episode you’ll learn
An ask‑playbook that beats 95% rejection and lands dream rooms (05:39).
Room rules that ship: morale > hours, pitch alternatives, protect vibe (11:22–18:56).
Why “Simpsons predictions” happen and how to use the pattern for trend‑spotting (19:34–33:06).
We dive into the details later in the conversation.
Timestamps
00:00 Intro
02:28 The Journey to The Simpsons
05:39 Asking for Opportunities
08:15 Navigating Hollywood’s Challenges
11:22 The Writer’s Room Dynamics
14:02 Maintaining Morale in Creative Spaces
16:38 The Evolution of The Simpsons
19:34 Cultural Commentary and Predictions
22:02 The Steamed Hams Phenomenon
24:47 Transitioning to Food Enthusiasm
27:46 The State of Fast Food Innovation
30:26 The Steamy Awards Explained
33:04 Philosophical Reflections on Creativity
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