Trump Reveals How He Once Had Less Money Than A Homeless Man

WATCH:

He was $900M in debt but he believed in himself; pic.twitter.com/P02jfM0cID

— Naruto (@NarutoNolimits) January 10, 2026

In this memorable interview moment with Ellen DeGeneres, Donald Trump candidly discussed a low point in his business career, revealing that he was once more than $900 million in debt. Trump recounts walking down the street with a woman when they passed a homeless man, explaining to her—somewhat shockingly—that at that moment, the man actually had more money than he did, a story he used to illustrate perspective, resilience, and how financial setbacks don’t define long-term success.