The Side Hustle Show cover image

The Side Hustle Show

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

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.
50:54

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

  • Jeff DiOrio successfully transformed his passion for chess into a lucrative side hustle by leveraging community-building and charity events.
  • The shift to online classes during the pandemic not only preserved his business but significantly increased student enrollment through wider accessibility.

Deep dives

Leveraging Airbnb's Co-Host Network

Airbnb offers a unique opportunity to generate income when homes are vacant, but it doesn't require hosts to manage every detail personally. Utilizing Airbnb's co-host network allows hosts to delegate tasks to local professionals who can help with listing creation, guest communication, and on-site support. This enables hosts to focus on their primary commitments, whether traveling for work or enjoying vacation time, while still earning money from their property. It presents a streamlined approach for those seeking additional income without the burden of constant oversight.

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