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I Tried to Sneak Into The Masters as a Caddie

April 7, 2026

Josh sits down with University of Tennessee golfer Jackson Herrington, who casually qualified for the Masters after finishing runner-up at the U.S. Amateur. No big deal. Just one of the biggest stages in golf.
Naturally, Josh decides the best way to contribute is by becoming Jackson’s caddie… despite having zero qualifications, the wrong clubs, and a strong preference for getting paid.
Inside this episode:
• Josh negotiates a completely unreasonable caddie deal (50/50 split sounds fair, right?)
• Learns that winning the Masters pays exactly zero dollars… which he absolutely cannot wrap his head around
• Tries to simplify golf down to three clubs like a true innovator
• Asks the hard-hitting questions like “Where do you keep your beer?”
• And attempts to mentally prepare for Augusta by saying “nine” over and over again
Meanwhile, Jackson somehow stays composed while preparing for the biggest tournament of his life.
It’s part interview, part practice round, and part “this is why Josh should never be allowed near Augusta National.”
Watch now before Josh prints his own caddie bib.