English Teacher Writes His Way Into All-Star Tutoring

This transcript was generated from the episode audio and may contain minor errors.

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When you say you specialize in everything, people know you specialize in nothing. Wise words from today's featured story, a New York City English teacher in need of extra money to support his family. What was the trick he used to go from being just another tutor to suddenly becoming the number one writing tutor in New York, according to his glowing Yelp reviews? That's what we're gonna look at in this story. It is short yet packed with lessons on authority, qualifications and the importance of specialization in a crowded market.

Now, by the way, when a market is crowded, often it's crowded because there's opportunity there. It's crowded because it's a good market. So don't write it off. We are talking about writing after all. Don't write it off.

Ask if there's a way you can edit your idea to earn a higher test score. English teacher writes his way into all-star tutoring. That is today's story. That story is coming right up. [Music]

John Castellano was working as an English teacher in New York City.

As much as he loved his job, he needed more money to support his family. So a few years ago, John started doing odd work around the school to get paid overtime. He taught night school, summer school, and started coaching basketball and volleyball. One night, he even went back to help the IT technician update the school's antivirus software. The most he could possibly make from overtime was $42 an hour, which might sound like a good rate to some of our listeners, but remember, this is New York City.

He had a family to support, and he was already working a lot. What John needed was to find a way to make more. As he thought about his options, he realized there might be some advantages to working as an independent tutor. He could set his prices based on the market and shift them easily in response to supply and demand. There would be no fixed ceiling.

But what kind of tutoring would he do? He hit the books and found out that SAT tutors made the most money. There was, you know, as there always is, just one problem. John hadn't done very well on the SAT. Back in high school, in fact, he had scored in the 50th percentile.

And even though it had been years since then, and he had a lot of experience as a teacher since then, he knew that without a good score himself, he'd have a credibility gap. John also knew what he had to do next. As a 32-year-old, he signed up to take the SAT again. This time, he scored in the 90th percentile. From there, he spent $3,000 in magazine ads to start getting clients.

But was this a good idea? No, it was not. He actually got zero in return. It was an expensive lesson to learn. He decided to switch his technique and spent $150 on a Squarespace website and another $50 on SAT books.

That was the right move. And with those credentials, John scored a job, yes, another job, at a different school to tutor for the SAT. It was a great way to get some experience there. And a year later, he was let go due to low enrollment. But over the course of that year, he'd become even more knowledgeable about the test.

So he decided to spend another $70 to take it one more time. On that attempt, he scored in the 99th percentile of test takers in the writing section. From there, he decided to specialize in writing and market his business as MrWritingTutor.com instead of just as a general SAT tutor. By niching down, he gained a lot more clients. As John says, when you say you specialize in everything, people know you specialize in nothing.

As soon as parents could see how much John was impacting their kids, they would start to ask if he also tutored for English for other tests, including the ACT. He was able to hook his clients because he specialized in writing, but if they needed any help with standardized testing at all, he was totally prepared. Word of mouth spread quickly among parents, and his client base grew rapidly. These positive experiences also meant that he was getting glowing Yelp reviews. John soon became the number one ranked writing tutor in the area, a fact he trumpeted on his website.

In his first year, he charged $60 an hour for general homework help and $120 an hour for standardized test prep. Between these two formats, John now takes home thousands of dollars in extra earnings per month. In his best months, he earns anywhere from $2,000 to $4,000 just from the tutoring. Not only that, but he says the side hustle has helped him get better at his career. He is constantly sharpening his teaching skills.

He now has experience with marketing, advertising, branding, sales, and finance, skills he incorporates into his lessons at school. He says that sometimes kids find it even more valuable than the actual curriculum. John loves teaching and has no desire to stop, but now he can breathe easier about the money, thanks to his curiosity, initiative, and hard work. [Music]

All right, what can you learn from this story? What can all of us learn?

'Cause I am learning along with you. First of all, don't spend any money on magazine ads. I have sadly heard that story multiple times, many multiples of times. Magazine ads are the worst, don't waste your money. In fact, any kind of advertising, you wanna start with a much lower investment than $3,000 and do some tests as you go along.

If you've been listening for a while, you probably know that the majority of our stories actually grow apart from advertising. They grow because they're providing something useful and there's this word of mouth thing, or in John's case, those Yelp reviews helped a ton. So I imagine that he encouraged people to leave those reviews, especially once he started noticing that it was a good source of intake of referral. And then just the branding that he's done, on his website, I went to check it out, it looks great. Right at the top, it's like the number one writing tutor in New York City is Mr. Castellano,

which is kind of how he brands himself. And that's a bold claim, but he backs it up with the Yelp reviews and such. And so I think it's really smart that he chose to focus on writing. And as we see sometimes, when you specialize in something that is really tightly focused, then people trust you with other things. Obviously he is qualified to be an SAT tutor, but there are a lot of, if you just Google SAT tutor in New York City, you're gonna find a lot of people.

So by positioning himself this way, he's been able to do very well. Congratulations, Mr. Castellano, and thank you for letting us share your story. Listeners, inspiration is good, but inspiration with action is better. What can you do that's different?

How can you improve? How can you tweak? How can you create more freedom for yourself so you can do more of what's important to you? Today's show notes. All right, sidehustleschool.com/1226.

If you have a comment or question for the show, just come to sidehustleschool.com/questions. Thank you so much for listening. Do come back tomorrow. My name is Chris Guillebeau. This is, well, I already said it, Side Hustle School.

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From the Onward Project.