The Side Hustle Show: From $17/hr to 6-Figure Side Hustle (Greatest Hits) Hosted by Nick Loper of Side Hustle Nation | YAP Media
Release Date: March 6, 2025

Introduction

In this episode of The Side Hustle Show, Nick Loper welcomes Jeff di Iorio, a high school dean who transformed his passion for chess into a thriving side hustle that now generates a six-figure income, surpassing his day job. This in-depth conversation explores Jeff's journey, strategies for building a loyal customer base, effective pricing models, and the challenges of scaling his business both online and offline.

Jeff's Journey: From Salary to Side Hustle

Starting Point and Initial Challenges

Jeff di Iorio began his side hustle while earning $17 an hour as a summer camp counselor teaching chess. Recognizing the potential to earn more and better serve his local community, Jeff contemplated turning his part-time role into a self-sustaining business.

Jeff di Iorio [02:05]:
"Was making $17 an hour and started thinking, wow, maybe I could do this for myself and give myself a little bit of a raise."

However, Jeff faced the common hurdle of getting started. Procrastination and fear of failure held him back until he decided to host a charity chess tournament to catalyze his initiative.

Jeff di Iorio [02:37]:
"I didn't really move on it. I sometimes have a little trouble getting started... but I decided to just host a charity event."

Building the Foundation: Charity and Community Engagement

Jeff's strategy hinged on leveraging charity events to gain visibility and build trust within his community. By partnering with local charities and schools, he utilized their existing audiences to attract his initial clientele.

Jeff di Iorio [04:24]:
"We're just saying that we're going to serve their audience."

These grassroots efforts paid off when his first summer camp attracted 12 kids, earning him five times his previous income from teaching at a summer camp.

Jeff di Iorio [08:19]:
"Making five times the amount of money that I made teaching summer camps for somebody else, just with 12 kids."

Effective Pricing Strategies

One of the pivotal aspects of Jeff's success was his approach to pricing. Initially hesitant to charge more than the prevailing rates for babysitting, Jeff set his first group class at $8 an hour. This modest pricing strategy proved effective, especially when coupled with the value he provided through teaching chess.

Jeff di Iorio [16:12]:
"We charged $8 an hour. And that was, like I said, lots of things that I've kind of grown as an entrepreneur and charging..."

As his reputation grew, Jeff incrementally increased his rates, ensuring that each price raise was accompanied by added value, such as tournaments, seminars, and individual assessments. This approach not only justified higher prices but also enhanced customer satisfaction and loyalty.

Jeff di Iorio [19:05]:
"Our pricing for in-person classes is about $25 an hour, and online is about $17 an hour... every time we raised our prices, we gave something more."

Pivoting to Online During the Pandemic

The COVID-19 pandemic posed significant challenges, forcing Jeff to transition his in-person classes to an online format. This pivot was crucial in maintaining and even expanding his business during uncertain times.

Jeff di Iorio [20:22]:
"They said, you no longer can host in-person chess classes because of the pandemic. And that was a huge wake-up call for me."

To adapt, Jeff halved his prices and moved his operations online, which surprisingly resulted in an increase in enrollment from 90 to 200 students per week by the end of the pandemic. This shift also allowed him to reach a broader, non-local audience, facilitated by word-of-mouth and minimal online marketing.

Jeff di Iorio [22:35]:
"Now, suddenly all those people now had access to us."

Scaling the Business: Systems and Team Building

As demand grew, Jeff recognized the need to systematize his operations to sustain and further scale his business. He implemented recurring monthly memberships through Stripe and used tools like Jotform and Zoom webinars to manage registrations and class sizes effectively.

Jeff di Iorio [27:07]:
"We use Jotform to take people's information and then we use Stripe to manage our monthly memberships."

To maintain the quality of instruction, Jeff built a team of coaches from within his community and beyond. By training former students and hiring passionate individuals globally, Jeff ensured personalized attention for each student while expanding his reach.

Jeff di Iorio [34:17]:
"Kids who took our classes are now coaches for us... we're able to hire them and pay them back for all they've done."

Overcoming Challenges: Online Retention and Customer Churn

While in-person classes boasted a low churn rate of under 3%, Jeff faced higher retention challenges online, with monthly churn rates around 9-10%. To combat this, he focused on building habits among students and demonstrating tangible progress through electronic charts and regular assessments.

Jeff di Iorio [39:36]:
"If you can build habits for these people to keep showing up every week and you serve them well, that's a big deal."

Future Plans and Expansion

Looking ahead, Jeff aims to balance both online and offline growth. He recently opened a physical chess center in his community, providing a stable home base for in-person classes. Concurrently, he plans to enhance his online presence through platforms like YouTube and Twitch, ensuring continued accessibility and engagement with a diverse audience.

Jeff di Iorio [45:55]:
"Our business never was that. It was always about making a few extra bucks, but now we're starting to think about maybe moving full time into chess."

Key Takeaways and Insights

1. Partner Marketing and Community Engagement

• Leveraging existing audiences through partnerships with charities, schools, and libraries can rapidly build a loyal customer base.
• Hosting free or charity events not only serves the community but also establishes credibility and trust.

2. Demonstrating Progress

• Showing tangible progress to customers enhances satisfaction and reduces churn.
• Implementing systems like progress charts and regular evaluations keeps customers engaged and motivated.

3. Strategic Pricing and Value Addition

• Incremental price increases paired with added value services ensure customers perceive continued worth.
• Starting with modest pricing can lower barriers to entry and attract initial clients, paving the way for future growth.

4. Adaptability and Systemization

• Pivoting to online operations during unforeseen circumstances like a pandemic ensures business continuity.
• Implementing robust systems and leveraging technology tools streamline operations and support scaling efforts.

5. Building a Sustainable Team

• Hiring and training passionate individuals, including former students, fosters a strong, dedicated team.
• Maintaining personalized attention through a well-structured team enhances customer experience.

Conclusion

Jeff di Iorio's journey from a $17/hr job to a six-figure side hustle underscores the power of community engagement, strategic pricing, adaptability, and relentless focus on delivering value. His story serves as an inspiring blueprint for aspiring side hustlers aiming to transform their passions into profitable ventures.

For more insights and actionable tips, visit Side Hustle Nation and explore Jeff’s work at elitechess.net.

Notable Quotes:

• Jeff di Iorio [02:05]:
  "Was making $17 an hour and started thinking, wow, maybe I could do this for myself and give myself a little bit of a raise."

• Jeff di Iorio [08:19]:
  "Making five times the amount of money that I made teaching summer camps for somebody else, just with 12 kids."

• Jeff di Iorio [16:12]:
  "We charged $8 an hour. And that was... I've kind of grown as an entrepreneur and charging..."

• Jeff di Iorio [19:05]:
  "Our pricing for in-person classes is about $25 an hour, and online is about $17 an hour... every time we raised our prices, we gave something more."

• Jeff di Iorio [22:35]:
  "Now, suddenly all those people now had access to us."

• Jeff di Iorio [39:36]:
  "If you can build habits for these people to keep showing up every week and you serve them well, that's a big deal."

• Jeff di Iorio [45:55]:
  "Our business never was that. It was always about making a few extra bucks, but now we're starting to think about maybe moving full time into chess."

Resources Mentioned:

• Side Hustle Nation - Chess
• Elitechess.net

Listener Bonus:

Download a free list of 20 hobby-related niches where you can apply Jeff's business model at sidehustlenation.com/Chess.

Final Thoughts from Nick Loper:

Jeff’s story highlights the importance of leveraging partner marketing, demonstrating progress, and maintaining strong customer relationships. Whether you're just starting out or looking to scale your side hustle, these strategies can help you build a sustainable and impactful business.

Thank you for tuning in to The Side Hustle Show. Until next time, let's go out there and make something happen. Hustle on!