My Cup Is Full Podcast

From Waiting Tables to a Comedy Career | My Cup is Full Ep 4

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In this episode of My Cup is Full, host Sydney Castillo takes us through his incredible journey from the hustle of waiting tables to making it big in the comedy scene. Sydney dives into his early experiences, including his first stand-up gig discovered via Myspace, performing on HBO’s Bad Boys of Comedy, and balancing day jobs while pursuing his dreams. Listen in as he recounts working with legendary comedians like Ian Edwards, his time on BET shows, and his big win on TBS’s Funniest Wins. This episode is packed with humor, perseverance, and invaluable insights into the world of comedy.

Show Highlights:

  • Sydney's transition from modeling to stand-up comedy
  • The bittersweet reality of post-TV fame and waiting tables
  • Learning the craft of comedy writing from industry veterans
  • The emotional highs and lows of working on major award shows
  • The pivotal moment of winning a major comedy competition
  • Adventures in international travel and career milestones
    • ...more
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