They say every “overnight success” takes 10 years, and that’s something reality TV tycoon Brent Montgomery knows all too well. In 2014, Brent sold an 80% stake of his production group Leftfield Entertainment for $360 million—the most lucrative nonfiction television deal ever made in North America. But if you rewind ten years, you’d find Brent producing wedding videos in New York City. He was working 80-100 hour work weeks with minimal pay, hustling to land a ticket into the entertainment business.

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