From $17/hr to 6-Figure Side Hustle (Greatest Hits)
Mar 6, 2025
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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.
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.
Building a Chess Teaching Side Hustle
A high school dean successfully turned his passion for teaching chess into a profitable side hustle that now outpaces his day job income. Starting from summer camps, he realized that he could create his brand by hosting charity chess tournaments in collaboration with local organizations. These events built a community of engaged participants and allowed him to raise funds while promoting his teaching skills in a supportive environment. He employed grassroots strategies to build a following, eventually leading to the establishment of EliteChess.net.
Using Feedback to Enhance Offerings
The dean adopted a strategy of seeking input from his initial students and their parents to tailor his offerings effectively. By asking what they wanted, he was able to expand services, creating new classes and tournaments that reflected their interests. This responsive approach helped to develop strong relationships and retain students as they progressed through various skill levels. The focus on community building and satisfaction played a crucial role in the growth of his chess academy.
Navigating the Impact of the Pandemic
The COVID-19 pandemic drastically shifted his teaching model, prompting a swift transition to online classes due to venue restrictions. This change not only maintained enrollment but facilitated an unexpected surge in student numbers, as families across different locations registered for remote lessons. Enhanced visibility and a wider reach also resulted from the cultural upswing in chess interest, partly due to popular media influences like 'The Queen's Gambit.' The ability to adapt to changing circumstances proved vital for sustainability and growth during challenging times.
"Changing the world with chess" and making $100,000 per year on the side.
That’s the story of today’s guest, Jeff DiOrio from EliteChess.net.
Jeff went from earning $17/hr working in summer camp chess programs teaching kids how to play chess, to running his own camps and earning five times as much.
He then transitioned to an online recurring membership model, in part due to the pandemic, while also keeping the in-person coaching side of his business alive.
Jeff’s approach to growing his student numbers so rapidly?
Organic growth through giving to charities and delivering a value-driven service, all while doing something he loves—teaching chess.
Tune in to The Side Hustle Show interview to hear:
how Jeff built his minimum viable audience
the methods he used to set up the business for recurring revenue
how you can borrow some of these same tactics in your business