9 min 5 sec

English Teacher Writes His Way Into All-Star Tutoring

An English teacher becomes New York City’s #1 writing tutor, as judged by Yelp reviews. How does he thrive in this crowded market?
Service Tutoring Writing

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What It's About

How an English teacher became NYC's best writing tutor according to Yelp.

Business Model
Skills Required
Writing & Marketing
Profit Potential

Words of Wisdom

Although John was able to tutor many different subjects, he found the best success when he niche’d down and marketed himself as Mr. WritingTutor. As John says, “When you say you specialize in everything, people know you specialize in nothing.”

Fun Fact

Although John is an English teacher, he isn’t naturally good at grammar. After being reprimanded by his administrators, he dove into grammar. He learned so much that he even published a book about it, called 50 Grammar Rules Everyone Should Know.

Notes from Chris

Episode 1226

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.

As he thought about his options, he realized there might be some advantages to working as an independent tutor. For example, 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 that SAT tutors made the most money. There was only one problem - John didn’t do very well on the SAT.

Back in high school, John had scored in the 50th percentile on his SAT. And even though it had been years since then, and he had a lot of experience as a teacher, 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 invested $3,000 in magazine advertisements in order to start getting clients - but he got zero in return. Unfortunately, this ended up being an expensive lesson to learn. He decided to switch his technique, and invested $150 into a Squarespace website and another $50 into SAT books.

This time, 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 an SAT tutor. By niche’ing down, he gained a lot more clients. As John says, “When you say you specialize in everything, people know you specialize in nothing.”

In his first year, he charged $60 an hour for general homework help and $120 an hour for standardized test prep. A year later, he raised his homework prices to $70 an hour. Eventually, he tried to raise it to $80 an hour, but he found that many new clients would not call him back with those prices. Through testing it over time, John found his threshold.

Now, John takes home thousands of dollars in extra earnings per month. In his best months, he earns anywhere between $2,000 to $4,000 just from tutoring. Not only that, but this side hustle has helped John get better at his career. He is constantly sharpening his teaching skills.



Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"When you say you specialize in everything, people know you specialize in nothing."
—John Castellano #SideHustleSchool

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