The Side Hustle Show

From $17/hr to 6-Figure Side Hustle (Greatest Hits)

27 snips
Mar 6, 2025
In this episode, Jeff DiOrio, founder of EliteChess.net and former summer camp instructor, shares his inspiring journey from earning $17/hr to making six figures through his online chess academy. He discusses how he built a thriving community by organizing charity events and offering free lessons, emphasizing the power of organic growth. Jeff also reveals strategies for adapting to challenges, creating a recurring revenue model, and the importance of student engagement, all while nurturing a passion for chess.
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ANECDOTE

Charity Tournament Beginnings

  • Jeff DiOrio, initially earning $17/hour teaching chess, wanted to serve his community.
  • He organized a charity chess tournament, donating his skills and giving the proceeds to local charities.
ADVICE

Piggyback on Existing Audiences

  • Leverage existing audiences by partnering with organizations.
  • Offer value to their members, like free events, to gain exposure and build your own following.
ANECDOTE

Free Game Analysis

  • DiOrio offered free game analysis at chess tournaments, comforting upset children and impressing parents.
  • This grassroots approach, combined with paper sign-up sheets, helped build his initial email list.
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