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Caleb's foray into YouTube began in 2016 when his father lost his corporate job of 15 years, instilling a sense of urgency and responsibility in Caleb to support his family. At the mere age of 16, he invested his meager earnings from a fast food job into purchasing equipment for YouTube, which became his avenue to financial independence. He took a bold step, donating $200—almost all the money he had—to a popular YouTuber in exchange for guidance. This act led to mentorship opportunities and the eventual launch of his first successful YouTube channels.