O'Leary didn't just read his lines; he inhabited his character. He successfully pushed back on the script, including the ending, by convincingly arguing how his character would realistically think and behave. This collaborative approach allowed him to embody the character rather than just act.
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Before committing to his movie role, O'Leary's interest was cemented when a guest, knowing nothing about the project, found a printed copy of the script and couldn't put it down. This raw, unbiased reaction from a neutral party validated the story's power more than any formal pitch could have.
O'Leary's agent advised against the role, fearing it would damage his brand. However, O'Leary believes pushing beyond one's comfort zone is like exercising a muscle, essential for staying sharp. He saw the acting opportunity as a way to avoid professional stagnation.
A coherent picture of a person is built from heterogeneous, often contradictory, elements. Readers find this more convincing because it mirrors real life; everyone we know is contradictory. Instead of forcing a simple narrative, revealing inconsistencies makes a character feel more authentic and human.
The "99% Invisible" podcast subjects every script to a live table read where the entire staff provides hundreds of written comments in a shared document. This process is intensely rigorous but culturally gentle, focusing on elevating the story without personal criticism.
Early in his post-exit career, O'Leary's private equity partners advised him to keep a low profile, as is typical in the industry. He rejected this, choosing instead to build a media presence to ensure he was "in the narrative," which he later leveraged for business and political influence.
We often think of freedom as the absence of rules. Matthew McConaughey argues the opposite: taking responsibility—like rigorously preparing for a role—is what creates the freedom to improvise and perform at your best. Lacking preparation leads to anxiety and constraint, not liberty.
While many creatives dread repetitive takes, Helms sees each one as a new opportunity to explore and refine a performance. He actively asks for more takes to experiment with nuances, transforming a potentially tedious process into a "thrill" of pursuing unattainable perfection.
Instead of seeking feedback on a finished manuscript, authors can use a "writer's room" mid-process. Assembling a group to brainstorm and challenge plot points leads to a better final product because the author is less attached to the material and more open to fundamental changes.
O'Leary's famous "Mr. Wonderful" persona wasn't accidental. Shark Tank creator Mark Burnett recruited him explicitly for his reputation as a "dick" in other shows. Burnett believed the show's dynamic needed that confrontational, truth-telling character to succeed.
To write authentically for someone else, you must go beyond mimicking their language and stylistic quirks. The key is to understand their fundamental worldview—how they see the world and their core beliefs. This deeper understanding is what prevents the writing from feeling inauthentic.
