Episode 1915 • • 2:08 - 5:04
1915: Off The Rails
Jason Calacanis Early Career and Hot Tapes Bootlegging Story
Jason Calacanis recounts his early entrepreneurial roots in Brooklyn, including a story about selling bootleg VHS copies of The Empire Strikes Back. He describes using two VCRs to duplicate tapes and selling them at school for $20 each under the business name Jason's Hot Tapes. The venture ended when a math teacher caught him, only to buy a copy for himself at a discounted price.