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Issa Rae Says a 2014 Gamble Nearly Wiped Out Her Savings in New Essay Collection

She recounts self-financing three pilots following a collapsed investment, presenting the loss as a lesson that shaped ColorCreative.

Overview

  • Rae released a six-essay collection, I Should Be Smarter By Now, on Aug. 26 through Amazon Original Stories.
  • She writes that she needed about $150,000 for three pilots and had roughly half, largely from a book advance for her first memoir.
  • A promised contribution from a “rich ex” fell through a week before shooting, prompting her to fund the projects herself.
  • Her business manager warned that the costs would drain her savings, and Rae says the pilots were completed but not picked up.
  • Rae frames the experience as foundational to ColorCreative’s mission, and she begins a six-city book tour on Sept. 8 in Philadelphia.