This Side Hustle Spotlight Q&A features Carter Osborn, who started tutoring students needing help with college application essays in 2017. Today, Osborne’s business brings in about $110,000 a year—more than her full-time job as a director at a global PR firm. ,Thank you for reading this post, don't forget to subscribe!
Image credit: Courtesy of Carter Osborne
When did you start your side and where did you get the inspiration from?
Tuition was my basic motivation. I started graduate school in 2017, and my tutoring business was originally a temporary, small-scale operation to profit from tutoring.
I was inspired by two people who ran their own tutoring practices at the time, both of whom mentored me during the weeks leading up to launch. One of them was a test prep tutor in New York who helped me understand the methodology behind starting my own business. The second was a Seattle-based college advisor who had previously supported me during my application process at Stanford. I only met him once, but he had such a profound impact on my college search that I was inspired to reconnect, emulate his work, and start teaching college essays.
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What were the first steps you took to get your cause off the ground?
Consultation was key. I reached out to local college advisors and asked for informational meetings to understand their business models and offer myself as a potential resource. It worked out – one of them recommended several clients from her waiting list to help me get started, and the other hired me as a part-time writing coach. These were small steps by my standards today, but at the time, they were exactly what I needed to get off the ground.
From there, client referrals became the core of my growth. I had three customers in the first year, 14 customers in the second year, 23 customers in the third year and so on. This year, I worked with over 50 clients and referred many families to other tutors after reaching capacity. It was a nice full-circle experience – I got my start with referrals from established tutors, and this year, I’ve had the chance to provide those referrals to others.
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What were the biggest challenges you faced while building your team and how did you overcome them?
I quickly discovered that there were hundreds of qualified tutors in urban centers like Seattle, many of whom worked in my core business of college applications. This posed a huge challenge: How could I create a unique service that was different from all the rest?
Two answers emerged. At first, I distanced myself from academic tutoring and test preparation and focused solely on the niche market of college essays. It was a calculated risk – the market for college essays is relatively small, but that’s exactly what made it easier to distinguish yourself as an expert.
Second, I took my competitors as partners. College admissions counselors usually provide advice on the entire application process, but many do not enjoy working on essays. As an essay specialist, I offered this as an opportunity for consultants in the Seattle area – they could take on new clients, outsource the essay portion to me, and then handle all other aspects of the application on their own. Can continue working with customers. The result was a win for everyone: college consultants got work they didn’t like, students got special essay support, and I got a surge in business from people who otherwise would have been my competitors.
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How long did it take you to start seeing consistent monthly revenue? Did revenue ever exceed your full-time income, and if so, when?
I started seeing monthly revenues immediately. It started small: a few thousand dollars in my first year and about $10,000 in my second. However, by my fourth year, I earned more than $113,000, which was more than my full-time income as a director at a public relations firm.
You have turned your business into a successful one. Now what is the average monthly or annual revenue generated from this?
In 2023, my business generated approximately $115,000 in revenue. Almost all of this comes during the six-month period from June to December when college applications are at their peak. I take time off from tutoring from January to May, allowing me to reset and think critically about ways to improve my service for the next application cycle.
What advice do you have for other side-hustlers who hope to turn their venture into a successful business?
First, develop something unique about your product or service. How can you make your work different from the competition? This may mean pursuing a niche market within your field (such as the field of college essay tutoring) or building diversity into your product. It doesn’t need to be revolutionary – I’m always amazed by customers’ enthusiasm for products that are a little different from the mainstream.
Second, be patient as you grow. There are plenty of stories about people overcoming adversity to strike it rich in the first year, but for most of us, success takes time. If you have a multi-year time frame and the tenacity to stick to it, your investment will be more likely to pay off.
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Finally, remember that there are no prerequisites for starting a successful side hustle. I hardly picture a business owner: I studied public policy in college and never dreamed of starting a business. There’s no such thing as one “type” of person to be a successful business owner, so run with your ideas and see what happens.