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

Summary

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!

Transcript

[Nick Loper]

You probably already know that Airbnb can help you earn some extra cash when you're not using your home. Maybe you're traveling for work, you're taking an extended vacation, or you're just snowboarding someplace warmer. But here's where it gets interesting. You don't have to do all the work yourself. You can tap into Airbnb's co host network. This is a team of local pros who handle the nitty gritty so you can focus on what matters most. Think of it like outsourcing for your side hustle. These professional co hosts help with everything from creating a killer listing that stands out to to guest communication and even on the ground support. You provide the space, they handle the details, and you get paid. Personally, I'm a fan of income streams that don't require constant oversight. When I'm traveling for work, I'm at a conference or a mastermind, or if I'm on vacation, I'm trying to be present with my family. Here's a way to add an extra income stream without having to be glued to my phone the whole time. When you're ready to get started, see how much your space could be worth and get connected with an awesome co [e-mail] host here's an oldie but a goodie from the archives from the Side Hustle show greatest hits collection. What's up, what's up? Nick Loper here. Welcome to the Side Hustle show because your 9 to 5 may make you a living, but your 5 to 9 makes you alive. This week you'll meet a high school dean who's built his side Hustle to the point where it now makes more than the day job. And he's done it. Teaching chess. Stick around to hear how Jeff di Iorio from elitechess.net built his minimum viable audience, how we set up the business for recurring revenue, and how you can borrow some of these same tactics in your own business as a listener bonus this week I put together a free list of 20 more hobby niches where you could apply the same general business model to. You'll find that along with the full show notes for this [e-mail] Chess or through the link in the episode description of your podcast app. The story starts with Jeff teaching chess at a neighboring school's summer camp.

[Jeff di Iorio]

Ready? Let's do it.

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. Plus I was, you know, making all these kids really strong in chess in the neighboring cities, and then not really focusing on my own community that I was working with.

You're helping out the competition for your own chess team.

Yeah. And while I believe strongly in just kind of helping anyone, I thought I should at least serve the people nearest to me, too.

Okay.

So that was the idea, but I didn't really move on it. I sometimes have a little trouble getting started. I have these ideas, and then I kind of think about them quite too long. And it wasn't until I was about to begin my fourth year of summer camp, where I said, I've got to give this a try, but I was scared to do it. And so I decided that, you know, what's going to get me off of get me moving, would be to just host a charity event. I thought that if I made it about someone else, then it would make it a little bit easier for me to handle if, you know, it didn't go well or if my idea wasn't as strong as I thought. And so then I reached out to some local charities and asked them if they would be willing to let me run a charity chess tournament in their name and give them all the money, basically. So they were very supportive. Sometimes when you knock on doors and ask people, can I give you money? They very rarely turn you down.

I found they're not, like, skeptical. What's the catch? What's this guy's angle?

Yeah, I mean, I didn't get a lot of that angle. Maybe just inherently being in education, people kind of, for whatever reason, I think they approach you with a little bit of a sense that you are giving yourself to the community in general. So I think that helped. The charities were all on board, and they said, well, what can we do to help? I really didn't need much, but I said, if you want it to go better, you could always send it out to your audience. And so that's what they did.

Okay. You're piggybacking on the audience that they already have or the lists that they already have.

Yeah. And we're just saying that we're going to serve their audience. And we did that, and it went well. And so then we did it at some local schools, and that really went well. And so we started to get sort of this little following that joined from it. From there, I basically then just started. I said, you know what? I'm just going to donate my skills and chess knowledge and teaching abilities to anybody in the area. And so from there, I reached out to local tournaments, and I would show up at their tournament. And I would go over games with kids. So when a kid plays a chess game, they take record of the moves and after their game they come out and I would go through the games and kind of guide the kids. And if anyone here who has children, you know that when you play board games with kids, when they lose, it can be pretty traumatic.

Yes, we're, we're in that stage for sure.

Yeah, we had to put Monopoly on hold in our house for about a year. And so that definitely happens with chess because it's a one on one thing and kids would lose and be really upset. And I would show up at these local tournaments and I would just scan the room for crying kids and I would just show up and I'd say, hey bud. Or you know, to a little boy or girl and you know, parents and say, hey, can I go over that game with you? And then my goal was just to really, just to try to make those kids feel really big and 10ft tall when they left and show them, you know, all the great things they did.

This would be the equivalent of a basketball or football player, like watching game film after the fact, trying to figure out what, what went well, what didn't go so well.

100%. 100%. In chess you often find that you make, you know, in a 30 move game you might have made 28 really good moves and two bad ones. And unfortunately that causes you to lose. But the essence of what you did is still really positive. And so I can tell you if you get a bunch of crying kids to stop crying, parents are very, very thankful. They think you're a magician. And we started to get little crowds at these tournaments and started to build a following.

Okay, does elite chess exist at this point or just kind of like you're building your own reputation in the community?

Does not really exist. It's doesn't even have a website or anything. The name exists, but I don't really have a platform. I'm just building my name in the community. And I had literal sign in lists of people's emails. You know, I said, hey, if they asked, do you continue? Do you do this on the side or where can we get more of what you're doing? And I would say, well, this summer we're going to try some summer camps. So if you're interested, just write your email down on this sheet of paper. And we started to build a list.

Okay, from the charity organizations inviting their existing audience of people, their existing email list for the local school. Like, hey, we're Going to host a charity tournament at your school or we're going to host a free tournament at your school. And they're inviting their students, their parents. And so you're kind of like very grassroots, trying to build up this initial audience of people. And I like the paper sign up sheet. Oh, I don't have to have any fancy tech involved. Just put your name and email down here and we'll be in touch.

Yep, that's exactly what we did. And we did that for a few months and I think we had around maybe 50 emails on there. But as with most of the stuff we've done, you know, they're really, they're usually really strong leads, really strong emails and contacts. And so we then held our first summer camp and we ended up having 12 kids show up our first week. And I remember just in that first camp, you know, making five times the amount of money that I made teaching summer camps for somebody else, just with 12 kids.

Wow, that's really cool. Kind of just grassroots validation. Hey, I didn't have a huge database to advertise this to, but the people who were on this list were interested. We had 12 people show up and you're kind of off to the races from there. Were you able to secure a church basement or a community center? I'm just trying to think of logistics of having 12 kids show up. Where do they go and how does this work?

Yeah, that's exactly what we did. We went out and rented space from local churches and local schools. A lot of schools will rent their spaces as well. Some people don't really know that, but schools often will rent, especially if you're community based organizations. And in my case I did have some relationships in education. Not that they don't do it to anyone, but yeah, especially well in the summer.

They're not using the place, you know. Makes sense.

Exactly. They've got these buildings sitting empty. And so we did that with churches and schools all summer. And then, you know, that's where we kind of grew elite chess. And then once the summer was over, our families were like, well, you can't stop now. Like, can you keep teaching our kids? And so I basically just asked them what they would want and they said that they wanted once a week chess instruction during the weekdays, you know, at a night. And so that's. That was the start of our first weekly chess academy.

Did you find that from those first 12 kids, was there some stickiness factor where they would come back the following week or they would come back later in the summer? You get This a lot with, you know, online marketing. Well, I had, you know, I built up this audience and I launched my thing and I made all the sales. And then the next week, the next month, it's kind of like back to the drawing board. Well, now I gotta go find more people. How does this work?

Yeah, we. I'm very blessed. We built some really amazing relationships. And sometimes, you know, when I think back to those times, you know, they're just really great times because when you have a small audience, you know, so much of the time we have this small audience sitting in front of us and we think like, wow, I wish it was bigger or where's the next person? Where's the next person? But even if you just have 15 people in front of you basically showing up saying that they like you and support you and want to be around you and what you're doing, you can leverage it into just amazing situations and impact. And that's kind of what we did. We built such strong relationships with those first 12 to 30 kids. And I remember us going to tournaments together, sitting in hallways and stairwells, going over games, and they ended up being huge champions for us and really spreading the word. And we went to their birthday parties and graduation parties.

Oh, nice.

And when you get bigger, you lose a lot of that. And so there's obviously a balance. But those original people that are with you on your journey are really special and if you treat them well, it can really start you off on the right page.

Yeah, there's some advantages of being small and scrappy that the big players can't necessarily afford to do. And it's like, well, you can know everybody by name and you can spend time with them versus somebody with a huge audience. Just, it just isn't feasible.

[Nick Loper]

More with Jeff in just a moment, including how he initially priced his group classes and how he pivoted to online instruction to keep the business afloat. Years ago, I was sitting in a conference in Santa Barbara and the presenter asked this question, are you working on your business or are you working in your business? And at that point I'd already quit my job. I saw myself as a full time entrepreneur. But it was this moment of clarity that, no, I'm still very much working in the business. So when I got back home, that's when I made my first full time hire. It was the first in a long series of steps of learning to truly take control by being okay, of letting go of certain tasks. Now when you find yourself in that position of needing to hire like yesterday, you need indeed with a sponsored job on Indeed, your post jumps to the top of the page for your relevant candidates so you can stand out and reach the right people faster. Plus, there's no monthly subscriptions, no long term contracts, and you only pay for results. That's why for my next hire, I'm using Indeed. There's no need to wait any longer. Speed up your hiring right now with Indeed side Hustle show listeners get a $75 sponsored job credit. To get your jobs More visibility at indeed.comsidehustleshow just go to indeed.com/ and support our show by saying you heard about Indeed on this podcast. Indeed.com Sidehustleshow terms and conditions apply. Hiring Indeed is all you need. On the side Hustle show. We spend a lot of time on generating ideas and the marketing tactics that drive traffic and make sales, and intentionally less time on the behind the scenes mechanics of how those sales actually happen. And the reason for that is for tons of side Hustle show guests like Randall Pulfer, Mike Ettenberg, Becky Beach, Lou Rice and more, the business behind the business is all the same. It's Shopify. Nobody does selling better than Shopify, and that's why it's the number one checkout on the planet. Plus, when you use Shopify, you'll be giving your customers access to Shop Pay, which boosts conversions up to 50%, meaning a lot less abandoned carts and a whole lot more sales going. Shopify is the commerce platform that helps you sell wherever your customers are scrolling or strolling online, in person, in their feed, and everywhere in between. Upgrade your business and get the same checkout used by dozens of successful side Hustle show guests. Sign up for your $1 per month trial period at shopify.comsidehustle all lowercase go to shopify.comsidehustleen to upgrade your selling today. Shopify.comsidehustle.

[Jeff di Iorio]

Give an example of how things started to spider out from those first dozen or two dozen customers, honestly.

So everything we've ever done to kind of continue to grow has been just asking these people that, you know, show up for us what they need and what they want, how can we serve them? And so we did that and we started to run our classes in seven week blocks, kind of like selling a class. And every time our seven week blocks were over, we'd have to go out and try to do another launch and get more kids and we would grow. But then they started to say, hey, we want to do this more regularly. Can you offer tournaments and can you offer seminars and so we just started to continue to do that. All the while, charity and giving to local organizations was a big part of our mission. And so just through word of mouth, charity, and listening to our people, we just slowly grew. And then it just sort of picked up momentum to the point where we are today.

I like that call too. Just, well, what is the audience asking for help with? This is straight out of John Lee Dumas book and all his advice over the years. Well, I got a little bit of people paying attention to me. What do they want help with? Okay, they want help with podcasting or webinars or, you know, whatever, and okay, I can do that. And then on to the next thing. Well, what else are they asking for help with? How can we structure that in a way that makes sense for them? They want, you know, once a week, chess classes, they want tournaments, they want this other stuff. And then, you know, continuing to build that out and go from there.

[Nick Loper]

Was there anybody else doing this in.

[Jeff di Iorio]

The community or you? I just from a sense of, like, competitive pricing, like it was there. Like, how do I know what to charge for this? Just throw a number out and see what kind of reaction it gets.

Yeah, there was not anybody doing that I knew of that was doing these, like, night classes. There was definitely organizations out there doing tournaments because that's kind of where I started gathering some of my people. But really the model that was out there was more of an after school model where organizations would partner with a school and they'd have a chess coach show up to the school and run an after school program. Yeah, and that's a great model. And we do a little bit of that today too. The only difference is that sometimes parents put kids into there and their goal isn't always because their kid loves chess and they want to grow them in chess or challenge them or inspire their intellectual abilities. A lot of times we would find that parents would put kids into there because it would work out for their work schedules and those kind of things, which is fine. But nobody was really focusing on chess for chess sake. And then basically, once we started doing it, the pricing, as you mentioned, was a challenge. And me just some of my own limiting beliefs and just being scared to charge. I remember the thought of, well, what are we going to charge per hour? My thought was, well, babysitters are getting paid $8 an hour. So at the very least, we can charge $8 an hour. And people would be like, oh, it's babysitting, but our kids are learning chess.

Okay.

And so our first program, 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 and kind of diving into this part of the world when I was in education prior has been a great transition. And hopping over those hurdles has been part of my journey, too.

Well, if it's a group program, I'm trying to do the math on this. Well, If I got ten kids showing up and I can teach them at eight, now all of a sudden I'm at 80 bucks an hour. That's not. That's not bad at all. Is that how this was structured?

Yeah, that's exactly it. That first group that had, I think 12 kids show up at $8 an hour was $96 an hour. And to me, that was five times what I was making as a summer camp counselor. And you start to realize the power of these small groups and community around chess.

Yeah. Going from one to one to one to many. What's the pricing look like today?

So now our pricing has come a long way. I would say our pricing for in person classes is about $25 an hour, and online is about $17 an hour. And for me to get there was a journey. And so I've always just kind of re. You know, went back to this idea of giving. And so anytime I would raise prices, I would always say, okay, I have to give them something more. And so I would give a little bit. And so we started doing things like giving tournaments as part of our program or giving seminars as part of our programs, or providing individual assessments as part of our program. And so the more we gave, it made it easier for me to kind of increase and justify pricing to a point where we are today. And. And frankly, I don't know where our pricing could go because we've never raised prices and lost people, which is kind of interesting, you know.

Okay, so you're saying, well, we're going to make it this price. We're going to charge 25 bucks an hour. But when you join this cohort or when you join this, you know, weekly class session, you also get this personal evaluation and you get access to our tournament calendar. So there's other reasons than just show up at this time at this place.

Yeah. And for me, that's always just been a way that I could, with integrity, look at my people and say, hey, we're going to raise the prices, but here's why, and here's what's additional coming down for you.

Talk to me about the pandemic impact of doing in person classes Here. And I don't know if there's a transition. It sounds like you're doing online stuff today. You're doing both today. And was that always the case or was that born out of necessity?

Definitely born out of necessity. One day we got an email from our school and church that we were currently renting from, and 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. Just kind of realizing that no matter what you do, if you can kind of insulate yourself from having outside forces kind of impact your business. But I think just as a rule for me, that was something I said. From this point forward, we're really going to try to make sure that we're in charge of our people and kind of what we do. And so we switched over to online and I basically cut all everyone's prices in half and said, okay, stick with us, we're going to try to do this online thing. And they really all did and everyone stuck with us. And then a very interesting thing happened. We don't really do much marketing, which is kind of crazy, but the word of mouth that hit through online was incredible. And so our people started going out and telling their friends and cousins who they'd been talking to about chess and us for so long, but they weren't able to physically get there. And suddenly all those people now had access to us.

Right, because prior to this point, it's all. It's all been local, all local.

And we'd have parents driving from really far to come to us. And all of a sudden now we had this bigger market open up. And so we, I think at the start of the pandemic, we had about 90 kids coming every week to class. And then within, you know, by the end of the pandemic, we were all the way to like 200.

Wow.

That. And then on top of that, you know, the, the Queen's gambit.

Right. I was just gonna say.

Yeah. And it did, it did positively impact our business. Not massively, but just, you know, we found that we started getting more inquiries from like, little girls to play chess, which was really cool. And so we were able to kind of then maximize the online learning environment. It helped that my background is education and we were able to kind of create a product that could really help kids and families even when they were locked in their houses.

Yeah, that's really cool. So, yeah, being in the right place at the right time to capitalize on an increase in interest in chess through some Pop culture stuff and just broader trends, but also just being able to serve a broader community of. Well, it's not just local anymore. We can do this for anybody, you know, as long as it's a reasonable time zone for you. Come hang out and we'll do this. Is there a cap to the size of the classes that you can reasonably host and allow for proper instruction and Q and A and everything?

We try to keep our class sizes to around eight kids, if we can. With that amount, we feel like we can give kids pretty good individual attention and still keep those relationships with our students. I have other coaches that are working with me now and as I say now with a little bit of a broader audience, my personal relationships with each of our students is definitely different than it was, but they still have really strong relationships with their direct coaches.

Okay. And right now it's show up at this time and we'll do live instruction. Is there or are there any plans to create the Chess for Kids, you know, beginner intermediate advanced online course or like the Chess for Parents online course? There's, I have to imagine there's some sort of product out there or there's some YouTube content around there.

Yeah, that, that what I would say is, is one of our, you know, next steps. We are looking to get into the online space a little bit more. It's been positive for us, but we don't haven't had any presence on YouTube or Twitch. There's a lot of streaming that goes on with chess. And so that is the next step for us is trying to serve people without it being time sensitive and live. But then also we are continuing to expand in person as well. We just opened a physical retail chess center in our community. So we are starting to grow in that direction too.

Okay, side note, do you know if this is true or not? I read somewhere that a chess grandmaster can burn thousands of calories during a match just due to the brain processing power that they're using. Or is it just like a total.

Myth that is true? I don't know the science of it, but I will tell you that I personally have found I've played in three day chess tournaments where you're playing sometimes up to 12 hours a day and you will actually lose weight. I've lost like four or five pounds in a weekend and all I did was sit at a chessboard and play chess.

Wow.

It is kind of crazy to think about. And so when we compete with, when I was competing with our high school team and coaching them, I mean our food intake and how we manage that, we were pretty extreme, I would say, just because we were at a higher level trying to win state titles. But that would be a big part of our, of our process.

That's awesome. Now, now there's a new product for you is, you know, Chess as a, as a weight loss tool. That's crazy.

Yeah.

I'm curious about the like, tools and tech that you're using to manage the database of customers and process payments and, you know, host these online classes and separate that from the in person stuff. Can you give me a sense of what's helping you stay organized and run this whole thing?

We use Jotform to kind of take people's information and then we use Stripe. Integrate Stripe into that and that manages our monthly memberships. As I said, we used to do seven week blocks, but now it's just recurring month over month charges automatically through Stripe. That's really helped our churn rates.

Okay. So it's like for a monthly membership and it's 80 bucks or 100 bucks, you get one class a week and it's at this time slot and it's just recurring until you cancel.

Yep, yep, that's exactly right.

Okay.

And so those are most of the tech that we use. And then we deliver our classes through. We use Zoom webinars because it allows us to. It allows kids and families to register for their classes. So we post our class schedules and then families can register for those classes and we can set class size limits based off those registrations. So that allows us to kind of manage how many kids are in each class and then it allows our coaches to access this too. Because just been kind of a really fun. Part of our growth is, you know, we have coaches right now. We have fantastic coaches in India. We have a coach in Bosnia. We have coaches all over the country. And because of this system, we're able to kind of allow all these people from across the country and world to connect through chess.

Yeah. Do they rotate through the weeks or. If I sign up as a student, I'm going to get the same coach week after week.

You get the same coach week after week. We did do some switching in the past, but we just. Once again, we're very relationship based. And we think that coaches building relationships with their kids allows them to give individualized instruction, allows them to guide those kids. And so if you sign up, you will have the same coach week after week.

[Nick Loper]

More with Jeff in just a moment, including his rule for when it's time to systemize and how he's grown his team. So it's not just him selling his chess expertise anymore. Right after this.

[Jeff di Iorio]

You hear that?

[Nick Loper]

That's the sound of your marketing working. And as an entrepreneur, you know that every call is an opportunity. But if you miss it, potential customers don't wait. They just call the next business on their list. With our sponsor, OpenPhone, you'll never let another customer's call go unanswered. OpenPhone is the number one modern business phone system that helps you separate your personal life from your growing business. For just 15 bucks a month you get complete transparency and visibility into everything happening with your business. Ph number. OpenPhone works through an app on your phone or computer and integrates with HubSpot and hundreds of other systems. One of my favorite features is their AI powered call transcripts and summaries so you can streamline client communication and get a summary of every phone call with action items right when you hang up. That means no more note taking, no more forgotten to DOS. And right now Openphone is offering side hustle show listeners 20% off your first six months of when you go to openphone.com sidehustle that's O-P-E-N-P-H-O-N-E.com sidehustle for 20% off six months openphone.com sidehustlez and if you have existing numbers with another service, Openphone will port them over at no extra charge. Some businesses are quite adept at helping you part with your money. With their crazy high bills, bogus fees and quote unquote free perks that actually cost you more in the long run. I would lump traditional wireless carriers into this category and that's why I made the switch to mint mobile in 2019 and haven't looked back. With our sponsor Mint Mobile, you get premium wireless plans starting at 15 bucks a month. All plans come with high speed data and unlimited talk and text on the nation's largest 5G network. You can bring your own phone with any Mint Mobile plan and even bring over your existing phone number and all your existing contacts. So join me in ditching overpriced wireless and get three months of premium wireless service from Mint Mobile for 15 bucks a month. If you like your money, Mint Mobile is for you. Shop [e-mail] Sidehustle that's mintmobile.com Sidehustle upfront payment of $45 for 3 month 5 gigabyte plan required equivalent to $15 per month new customer offer for first 3 months only, then full price plan options available, taxes and fees extra. See Mint Mobile for details.

[Jeff di Iorio]

This might be a silly question, but I'm curious about coming up with curriculum that is changing or different sub games or drills to do Just the body of content that you have to come up with. To teach these classes on a weekly basis has got to be, at least from an outsider looking in, kind of a daunting thing.

Oh yes, incredibly daunting. Most of our business has grown just me being a full time dean and having this on the side. I would, as soon as something got unmanageable to where I'm staying up all night doing something, I generally think, okay, I need to get a system. And so for this I was creating all the curriculum on my own, but now I license it. So I bought a package curriculum which basically gives what we have is we have five different levels of class. There are 30 topics in each level. And so as the kids progress through those 30 topics, once they master them all, then they can just move up to the next level. So there's a very nice path for them and we don't have to create any more curriculum. And our magic, I think is really not necessarily in the X's and O's, it's more of how we deliver it. And so how we structure our classes and work with kids. And so we use that curriculum with our style and community to kind of make our product.

Okay. No, that's helpful to say, well, somebody, somebody else has already solved this problem. And I like this message that whenever I'm up, you know, if I'm staying up too late working on this, there's got to be a better way. There's got to be a system for this. And then going out and finding that and then I didn't even think about that too. But yeah, everybody's coming in at different levels. Kind of like swim lessons. You know, I go from minnows to sharks or something. I forget what it was when I was a kid. But yeah, yeah, not everybody's going to be jumping off the deep end. Right, right at the beginning.

Yeah. So that point now allows me for anybody who comes into our system, they sit down and they play me in chess for 10 minutes and I give them like a little mini lesson and it allows me to kind of set the stage for, you know, what kids and families will expect. And so after they play me and I give them some guidance just like I did back in the day, then we'll place them in a class level and then they're off and running.

Okay. On the instructor side, how do you end up connecting with These instructors really all over the world to come and work for you, teach classes for you.

That mostly started with just the local chess community. We had people who were volunteering for our chess team that I was coaching at the high school for years. And so those were just the easiest ones because they had donated so much time to our programs in the past that they kind of knew my style and what I wanted, and I was able to hire them on and try to pay them back for all they've done. And then from there, really just people started reaching out to us, and we would just vet them and train them. And now, actually, we've been doing it for so long. Not crazy long, but 10 years now. Kids who took our classes are now coaches for us, which is really.

Oh, that's awesome.

Yeah. I mean, we have. In fact, one of the kids in our first. Out of that first 12, you know, is basically one of our strongest coaches, and he's a junior in college, but he's perfect for our online coaching, and hopefully he'll have a future with us after he graduates, too.

Okay. Yeah. That's really cool. A way to employ people, Hire from within, in a way. We went and looked at a preschool the other day where it had been around long enough, where some of the student TAs that would come and help. It started there when they were four or five years old. Okay. It comes full circle.

Yeah. And that's a really fabulous endorsement, I would say, of that preschool. Right. Where people feel the connection to kind of return, much like we see in some of our private schools in our area. There's just this strong connection and returning to kind of give back what you were given.

Did you ever get the pushback that I wanted? Jeff, you're the guy with the credentials, and you're the face of this thing. I don't want some other random instructor. I want my kid to have you.

Yeah. Still, to this day, I would say when I do the assessments with people, that they say that they would want me. I think this is not uncommon in anyone who runs a business, whether it's a bakery or an online, you know, consulting or. You name it originally, there's this feeling that it's like a personal brand and it's all tied to you. And while that makes you feel good, you know that if you truly want to impact more people, you're gonna have to find ways to kind of step away, at least enough to kind of expand impact. And so we still do get that. But I've trained and worked with our coaches so much that they're just incredible people and incredible coaches, that I've never without a second had any doubts that once we put a kid with one of our coaches that they don't get top notch service.

Yeah, you're right. This is the challenge amongst freelancers and tutors, experts of any kind, where it's like, do you get stuck selling your own expertise and trading time for money? Even if it's great money, there's still a limit to that. Well, here's a way to scale it. I connected with a guy in the Bay Area who was doing coding tutoring or computer science tutoring. And it was the same thing, kind of like starting out doing it himself. But pretty quickly had branched out to hiring computer science majors from the local area colleges to go out and do this kind of act as his proxy. Like, hey, look, they know what they're doing, they're trained on the stuff. They can help you just as well or better than I can. And that was his way of kind of removing himself from that time for money, driving to kids houses and doing all that stuff. So that's pretty cool that you're able to get that set up with any recurring revenue side. It becomes this kind of math equation of managing the churn versus managing the growth and hopefully find net positive one.

[Nick Loper]

Extra person a day.

[Jeff di Iorio]

I just gave myself a raise to borrow from Shane Sams. Give me a sense of how you're thinking of that in terms of a monthly recurring revenue number or the metrics that matter most to you.

It is definitely something that I think about now. It's not something I thought about before only because, well, I guess I thought about it a little bit when we had this kind of class model where we were selling these groups of seven weeks of class. Then I was always relaunching and trying to figure out why so and so didn't, you know, return or. But once we got to the monthly recurring model, then churn became more of something that I focused on. I would say that there's a few ways that we really believe to kind of decrease churn number one is habits. You know, I think we are such creatures of habits and habits probably lead to more of the large, you know, growth in our life than anything else. And so if you can build habits for these people to keep showing up every, you know, at the same time every week and you serve them well, that's a big deal because they will just start to say, ah, Wednesday is chess day. So we can't go to, you know, we can't have Soccer that day or whatever else.

Okay.

So we build habits. And then of course, you know, providing value is always a great way to reduce churn. But I think more than anything, what we've started to notice is finding ways to show progress to kids is really powerful and to anyone, we're addicted psychologically to progress. And so no matter who you, what kind of business you offer or service you offer, if you can show people, hey, this is where you were when you came to us, and here's where you are now. And you can regularly show that to people, you have a really strong chance of making them stay. And so what we do is we have these progress charts where kids are working through those 30 topics in their level, and they kind of put stickers on every time they master a topic. And every five topics they master, we give them a different chess piece, keychain, and then those kind of things just keep them looking forward. And then they, of course, over time, can graduate to the next level.

Okay, this would be like in martial arts. Okay, you got your yellow belt, your brown belt, you're working your way up.

Exactly right.

And they're. And they're sharing this with the parents or you're sharing this with the parents. Like, hey, look, look at where your. Your kid was. And look where they are today.

Yep, they have access to the charts. And the kids always love to show their parents their charts every day at class. So our in person churn rates are really, really low. Like they're under 3%. And so that's, you know, really good. Online, though, now is our next kind of challenge. And in our last coaches meeting, this is one thing that we've been talking about is, you know, how do we decrease our churn online? Because it's much higher. Our churn rate online is, you know, like 9% to 10.

And meaning every month, 10% of the people drop off.

Okay, yeah, I don't really like that. I don't like feeling like I'm on a hamster wheel, but I also just don't. I don't want kids to kind of stop getting the benefits of chess if it's something on our end that we can kind of fix. Of course, kids try many different things, so that's normal. But online, we are having trouble with showing them that same progress. We can't give them the keychain. We can't really have. The chart is kind of a difficult thing for them to show their parents. And we don't get to touch base with the parents always at the end of class. So so right now we are working through that and kind of showing. Creating electronic charts and how we can go about showing that regular progress so that maybe kids will stick around longer.

Okay, yeah, that's the life of the entrepreneur is like, there's always another challenge, like a game of whack a mole. In a way, it's like, okay, well, what's the next thing to try and work on improving. But I appreciate that you got things going on. I like this figuring out ways to show progress. I think that's probably something that anybody who's in an instructional role or even a client facing role can be helpful with to say, like, well, here, here's the impact that we're having and cultivating positive habits there. Jeff, you mentioned you don't do a lot of marketing, but new people are finding you somehow. Are you incentivizing word of mouth? Are you still going out into the community doing these pro bono events? What's. There's got to be something else that keeps Replacing that 10% a week?

It is a little weird to say, but we've really never done any marketing. Just in about the last four months, we've started running Facebook ads, but at a very low rate, like under $10 a day. Like nothing really small. So it continues to be word of mouth and definitely, I would say charity events. So that is our marketing. It's just the way that our company, we just view, like we want to change the world with chess. And so we always are doing charity events of some sort. Just this week, for instance, I, you know, I donated to two, like, fundraisers. So lots of people reach out to us and say, hey, we're going to have a fundraiser for our school or our program or whatever it might be, community event. And so we always donate to those no matter what. We always, if any school reaches out to us and says, hey, we want to start a chess club, we will always donate all the boards to their chess clubs. So we donate. We've donated probably thousands of boards. We know that if we serve those people, generally speaking, you know, someone asks or they want to know about chess, they send them to us. And then even in the pandemic, you know, one of the first things we did is once we got the online piece figured out, we just reached out to libraries in the area and all over really, and just said, hey, we know all your people are stuck at home. Can we offer free chess classes for them? And they said, yes. And so the library would reach out to all their people and we would show up once a Month and teach a chess class for the kids. And those kind of things just always seem to bring people back to us.

Yeah, well, on the library thing, it doesn't have to be just the local library system anymore. I mean, you could lather, rinse, repeat across the country.

Yeah, without a doubt. And it's become such a part of kind of what we do that I don't even think about it anymore. Like in a transactional way. I just sort of know that. I just know that it's going to happen and that people will come back to us. And often people ask like, what can.

We do for you?

That question we get a lot. And I often say nothing. And I think that does maybe impact people even more because I just really. We're not interested in that kind of transactional giving, but we know that in the end it seems to have served us.

So.

Yeah. And at this point I basically get a new student. A day is where we're at right now, you know, joining our programs or at least taking an assessment with me. So I've got all the people I can handle right now.

Yeah, super cool. What's next for you? Do you foresee this becoming a full time thing? Where do you want to take it?

Yeah, our business never was that. It was always. It started being something where make a few extra bucks and then, oh, maybe my wife can stay home and raise our kids. And then it's like, oh, maybe we can actually save for someone's college. And so it's kind of progressed, but. But now my wife's been amazing kind of raising the kids, but our kids are getting older and so now my time is certainly something I'm even more conscious of. And the fact that my side hustle now makes more money than my main hustle. We are starting to think about maybe moving full time into chess. And so, yeah, we'll see. We just opened a physical location in our community last month. So that's been an incredible dream realized. And so we're going to work with that and then hopefully do a little bit more online chess. Basically building a YouTube physical location.

This would be a home base for the local in person classes. So you don't have to keep shuffling around to different schools and church basements.

Yeah, yeah, exactly. And we're able to kind of have a home. And you know, we've been running local events here for high school and middle school kids where they're showing up on Friday nights at a very like safe, positive place for kids. And so we're trying to be a pillar of the community and then online and see what we can do online too.

Well, I'm excited for you. I mean, that's anytime you get a side hustle to outpace the day job salary is incredible. So really inspired by what you've [e-mail] you can check Jeff out over there. Really appreciate you joining me. Let's wrap this thing up with your number one tip for side Hustle Nation.

My number one tip is to give whenever your business stagnates. I would say give. If you're scared of starting your business, don't make it about you. Give. And I think businesses were really designed to solve problems and make the world a better place. And if we just go back to that when you're kind of banging your head against the wall or afraid or suffering from a limiting belief, if, if you just reach out to a local charity or find, you know, the community that you live in and find a way to give to them or give to the online community, I just think that in the end there's going to be some magic that'll happen both in you and the people you serve.

Absolutely. I can hear it throughout this story. This spirit of giving and being a good steward of the community reminds me in one of Gary Vaynerchuk's books. It's like this one word chapter on how to win in marketing. Like the chapter title is longer than the entire chapter. And it was just care. And I was like, that's it, next chapter. I was like, okay, if you can care, if you can give, you're going to be in a in a good position to have people start paying attention to you. So Jeff, really appreciate you joining me and sharing all this stuff. We will catch up with you soon. You can find [e-mail] and appreciate you joining me.

Thank you so much, Nick. This was really fun.

[Nick Loper]

All right, I hope you enjoy enjoyed that chat with Jeff. Definitely a really cool story. A couple takeaways I wanted to highlight were. First, the power of partner marketing. If you don't have an audience, go find someone or some organization that does and figure out how to be of service to them in some way. In Jeff's case it was these charities and schools and libraries teaching free classes, hosting these charity benefit tournaments, all while establishing himself and tapping into those pre existing audiences. Dustin Lean on the podcast took the same approach for his online marketing agency. Reaching out to e commerce software brands to host these free educational workshops or webinars for their customer base. This is definitely a fast track power move. To build an audience quickly and important note here. It doesn't have to be a big audience to get the ball rolling. If you're selling a higher ticket service, maybe just three or four clients is enough for a pretty serious side hustle. In just case 50 emails, you can find 50 people and you can know them by name and you can find out their problems and you can build their solution. That's something that a company with 50,000 prospects can't really do beyond just generic surveys and heat map software. Personal Example for the first two and a half years of side Hustle Nation, I would send a personal welcome message to everyone who joined the email list. I probably sent 10,000 of these things from 2013 to 2015 trying to get a response, trying to start a conversation, trying to figure out what people were struggling with. So I could either point them in the right direction or map out future content that would help the second takeaway that I want to highlight is figuring out a way to show progress for your customers, your readers, your listeners. I think we all strive for a sense of progress, to be better, smarter, faster, richer than we were yesterday, and I want to challenge you to think of ways to highlight that progress for your own audience. Maybe it's tracking their website traffic or their social media following, or how much weight they've lost, or their practice test scores. I'm thinking about this in terms of.

[Jeff di Iorio]

My own email efforts and I'm not.

[Nick Loper]

Sure the best way to measure it outside of trying to collect like benchmark survey data. In my case, if I could capture someone's side hustle income on day one when they joined the list and then recapture that every three to six months, I think that would be a cool way to illustrate over time how that number is hopefully growing and keep people sticking around. If you have any sort of membership.

[Jeff di Iorio]

Or recurring revenue business, I think Jeff's.

[Nick Loper]

Call to show positive progress can really.

[Jeff di Iorio]

Help address the you know, why are.

[Nick Loper]

We paying for this again Question. You will find the full text summary of this episode, links to all the resources mentioned, and that free listener bonus of 20 more hobby related niches that you can probably apply the same general business model to to at sidehustlenation. Com Chess. Once again, that's sidehustlenation. Com Chess. To download that free bonus and get your creative juices flowing. That is it for me. Thank you so much for tuning in. Until next time, let's go out there and make something happen and I'll catch you in the next edition of the Side Hustle Show. I'll see you, then hustle on.