O'Leary distinguishes between celebrity and politics. As a celebrity, 50% of people may dislike you. As a politician, 50% hate you, and a "lunatic fringe" of 2.5% poses a physical threat to you and your family. He found this reality untenable, even in Canada.
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.
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.
O'Leary demonstrates how media power translates into political influence. He used his reputation as a job creator to gain access to congressional staffers writing legislation, successfully negotiating changes to paragraphs he deemed harmful to small businesses, like shortening an IRS audit period.
O'Leary doesn't care if people think he's an asshole. He learned from working with an unpleasant Steve Jobs that execution is what earns respect, which is more valuable than likability. This philosophy allows him to make tough, unpopular decisions focused on results.
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.
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.
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.
While many assume Mark Cuban left Shark Tank due to fatigue, O'Leary suggests the real reason is a "contractual issue" related to content distribution. Cuban, with his media background, likely wants the show to have wider streaming availability, clashing with the show's many production partners.