I recently sat down with Ruben Stephen, a mechanical engineering and computer science student at MIT, for an episode of his LearnWell podcast. Ruben runs his own tutoring operation on the other side of the continent, and he reached out because we’re working on similar things at different stages.
What was supposed to be a quick chat turned into almost an hour and a half covering how Heywood Academies got started, what I’ve learned about tutoring, and the business behind it all.
You can watch the full episode here:
If you don’t have 90 minutes, here are some of the things we talked about.
How a Mechanical Engineer Ended Up Running a Tutoring Company
I didn’t plan any of this. I went into mechanical engineering because I was good at math and physics in high school and liked building things with my hands. After graduating I worked in technical sales for a company supplying pumps to mines across BC and the Yukon.
About a year into that job, the learning curve flattened out and I started looking around. One of my old instructors had a setup I admired: he ran his own engineering consulting firm and taught at the college on the side. I wanted to find out if I’d enjoy teaching, so I started tutoring first year engineering students a few hours a week on the side of my full time job.
It turned out I liked it a lot. Around the same time, my landlord decided to move back into the place we were renting, so my fiancee and I sold most of our stuff, quit our jobs, and moved to Australia for a year. I ran the tutoring business online from there while we travelled a lap of the country.
When we came back to Victoria, that’s when things really took off. I hired my first tutor shortly after getting home, and the company has been growing ever since.
What We Talked About on the Podcast
Finding the gaps. A big part of the conversation was about how tutoring actually works. My main mission in the first couple of sessions with any student is figuring out exactly what they know and what they don’t. You can’t get there by asking how the course is going. You have to work through problems together and watch where things break down. Once you find a gap, you drill that one specific skill until it sticks, then get back to the bigger problem.
Sales lessons that carried over. My technical sales job taught me two things that apply directly to tutoring: get back to people fast, and solve their problems for them. When a parent reaches out about tutoring, they’re usually contacting several companies at once. If you’re the last to respond, it’s too late. And instead of asking them a dozen questions, tell them what usually works. They might not know how many hours a week their kid needs. That’s our job to figure out.
Hiring tutors. Half the evaluation is already done before the interview because I have their transcript. Good grades prove they can solve the problems. The interview is about the other half: can they communicate clearly, are they patient, and do they have some humility about what they can and can’t teach. Someone who says they can tutor every course at the university is a red flag. Someone who says they could handle a course with a bit of preparation usually understands what tutoring actually requires.
The gap between knowing and teaching. One thing that surprised me when I started: getting an A+ in a course and being able to tutor that course well are two very different levels. There’s a real jump between doing well on the exam and being able to walk someone else through the material at their pace.
Why we built our systems the way we did. We also got into the operational side: why students book their own sessions, why payment happens at registration, and why I handle all the admin so our tutors can just focus on tutoring. The short version is that I talked to a lot of student tutors who were spending hours every week on scheduling, invoicing, and chasing payments. Take that away and the job gets a lot better.
Why I Did the Episode
Conversations like this are rare. Not many people run tutoring companies, and even fewer are willing to talk openly about pricing, hiring, capacity, and the things that didn’t work. Ruben asked sharp questions and it ended up being as useful for me as I hope it was for him.
If you’re a student thinking about tutoring on the side, someone curious about starting a service business, or a parent who wants to know more about the person behind Heywood Academies, the full episode is worth a listen.
And if you’re looking for a tutor in Victoria, BC for high school or university math and science, that’s what we do.