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

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1:17What's up, what's up, Nick Loper here. Welcome to the Side Hustle Show because your nine to five may make you a living, but your five to nine 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 DiOrio from Elite Chess.net built his minimum viable audience, how he 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 2.

1:53You'll find that along with the full show notes for this episode at sidehustlenation.com slash 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. Ready? Let's do it.

2:12I 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, and then, uh, not really focusing on my own community that I was working with. You're, you're helping out the competition for your, uh, your own chess team. Yeah. And, and while I, 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.

2:53I 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 like 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.

3:46So 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, well, 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.

4:29And so that's what they did. Okay. You know, you're piggybacking on the audience that they already have or the list 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 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.

5:14So 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 has children, you know that when you play board games with kids and when they lose, it can be pretty traumatic. Yes, 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.

5:49And I would just show up and I'd say, hey, bud, or, you know, to a little boy or girl and 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 10 feet 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 went well, what didn't go so well. A hundred percent, a hundred percent. 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.

6:24And 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? It does not really exist. It 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.

7:00And I had literal sign-in lists of people's emails. You know, I said, hey, if they asked, 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 schools. 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.

7:34And 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.

8:13and 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 told people show up and you're kind of off to the races from there. were you able to like secure a church basement or a community center? I'm just trying to think of like logistics of having 12 kids show up. Where do they go and how does this work? Yeah, that's exactly what we did.

8:57We 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're, you know, that they don't do it to all anyone, but. Yeah, especially in the summer, they're not using the place. You know, it 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 kind of grew elite chess.

9:34And 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.

10:15And then the next week, the next month, it's kind of like back to the drawing board. Well, now I got to go find more people. How does this work? Yeah, we, I'm very blessed. We, we built some really amazing relationships. And sometimes, you know, when I think back to those times, I, 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, where's the next person? Where's the next person? But, you know, 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, you know, be around you and what you're doing, you can leverage it into just amazing situations and impact.

11:02And that's kind of what we did. You know, we built such strong relationships with those first 12 to 30 kids. And I remember, you know, us going to tournaments together, sitting, you know, in hallways and stairwells going over games. And, you know, they ended up being huge champions for us and really spreading the word. And we went to their birthday parties and graduation parties. parties. 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.

11:41Yeah, 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. It just isn't feasible. 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. A lot of side hustlers suffer from what-if-itis. What if it doesn't work? What if I don't have the skills? What if I pick the wrong path? But one thing 100 % of our amazing guests have in common is they took their shot.

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14:16Terms and conditions apply. Hiring Indeed is all you need. 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, you know, 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.

15:02Can 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, you know, it just sort of picked up momentum to the point where, you know, we are today. okay i like that call too just well what is the audience asking for help with this is straight out of john lee dumas's book and all his advice over the years like 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 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 continuing to build that out and go from there.

16:05Was there anybody else doing this in the community or just from a sense of competitive pricing? 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 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.

16:47And 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, you know, intellectual abilities. A lot of times we would find that parents would put kids into there because it would work out for their, you know, work schedules and those kinds of things, which is fine, but nobody was really focusing on chess for chess sake. And then basically once we started, you know, doing it, yeah, the pricing, as you mentioned, was a challenge.

17:27And 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. um okay and and so we our first program we we charged eight dollars an hour you know and and that was like i said lots of things that i've kind of grown as a as an entrepreneur and and charging and kind of diving into this uh part of the world when i was in education prior has been a great transition and hopping over those hurdles has been a part of my journey too well if it's a group program, I'm trying to do the math on this.

18:18Well, if I got 10 kids showing up and I can teach them at eight, you know, now all of a sudden I'm at 80 bucks an hour. Like that's not, that's not bad at all. But is, 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, you know,$96 an hour. And to me, and 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.

19:01Our 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.

19:47And 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 an hour. But when you join this cohort or when you join this 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.

20:33Talk 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, you know, if you can kind of insulate yourself from having outside forces kind of impact your business.

21:24But 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, you know, 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.

22:18And 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 that. And then on top of that, you know, the, the Queens gambit, right. I was just going to 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.

23:08And so we were able to kind of then maximize the online learning environment. I helped that my background is education and we were able to kind of create a product that was, that could really help kids and families, you know, even when they were locked in, in their houses. Yeah, that's really cool. So yeah, you know, being in the right place at the right time to capitalize on an interest, an increase in interest in chess through some pop culture stuff and just broader trends, but also just, you know, being able to serve a broader community of, well, it's not just local anymore. We can do this for, for anybody at, you know, as long as it's a reasonable time zone for you.

23:47Come 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 &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 pretty good individual attention and still keep those relationships with our students. I have you know other coaches that are working with me now and and as I say you know now with a little bit of a broader our audience You know 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 the Chess for Kids, you know, beginner, intermediate, advanced online course or like the Chess for Parents online course.

24:48I have to imagine there's some sort of product out there or there's some YouTube content around there. Yeah, that what I would say 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, you know, 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.

25:28So we are starting to grow in that direction too. Okay. Side note, do you know if this is true or I read somewhere that a chess grandmaster can burn like 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, you know, 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.

26:10It 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 process. That's awesome. Now there's a new product for you, chess as a weight loss tool. That's crazy. Yeah. I'm curious about the tools and tech that you're using to manage the database of customers and process payments and host these online classes and separate that from the in-person stuff.

26:54Can 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 a hundred bucks, like 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.

27:37Okay. 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 or 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 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.