This Side Hustle Spotlight Q&A features Carter Osborne, who started tutoring students in need of help with college application essays in 2017. Today, Osborne’s business brings in about $110,000 per year — more than his full-time job as a director at a global PR firm.
Image Credit: Courtesy of Carter Osborne
When did you start your side hustle, and where did you find the inspiration for it?
Tuition was my original motivation. I started graduate school in 2017, and my tutoring business was originally meant to be a temporary, small-scale operation to take the edge off tuition.
I was inspired by two people who ran their own tutoring practices at the time, both of whom advised me during the weeks after I launched. One was a test prep tutor in New York who helped me understand the logistics behind starting my own business. The other was a Seattle-based college consultant who had previously supported me during my application process to Stanford. I only met with her once, but she had such a profound impact on my college search that I was inspired to reconnect, emulate her work and start tutoring college essays.
What were some of the first steps you took to get your side hustle off the ground?
Mentorship was key. I reached out to local college consultants and asked for informational meetings, both to understand their business models and to pitch myself as a potential resource. It worked — one of them recommended several clients from her waitlist to help me get started, and another hired me as a part-time writing coach. These were small steps by my standards today, but at the time, they were just what I needed to get off the ground.
From there, client referrals became the core of my growth. I had three clients in my first year, 14 clients in my second year, 23 clients in my third year and so on. This year, I worked with over 50 clients and referred several families to other tutors after reaching capacity. It was a nice full-circle experience — I owe my start to referrals from established tutors, and this year, I got to provide those referrals to others.
What were some of the biggest challenges you faced while building your side hustle, and how did you navigate them?
I quickly discovered that there are hundreds of qualified tutors in urban hubs like Seattle, including many who work in my core business of college applications. This created a major challenge: How could I build a unique service that stands out from everyone else’s?
There turned out to be two answers. First, I pivoted away from academic tutoring and test prep and focused entirely 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 differentiate myself as a specialist.
Second, I turned my competitors into partners. College admissions consultants typically advise on the full application process, but many don’t enjoy working on essays. As an essay specialist, I pitched this as an opportunity to consultants in the Seattle area — they could onboard new clients, outsource the essay portion to me, and then continue working with their clients on all other aspects of the application. The result was a win for everyone: College consults got to offload work they didn’t like, students got specialized essay support, and I got a bump in business from people who otherwise would have been my competition.
How long did it take you to begin seeing consistent monthly revenue? Did revenue ever surpass that of your full-time income, and if so, when?
I began seeing monthly revenue right away. It started small: a few thousand dollars in my first year and about $10,000 in my second year. However, by my fourth year, I earned over $113,000, which exceeded my full-time income as a director at a public relations firm.
You’ve turned your side hustle into a successful business. How much average monthly or annual revenue does it bring in now?
In 2023, my business generated roughly $115,000 in revenue. Almost all of this comes during the six-month stretch from June to December when college applications are at their peak. I take time off from tutoring from January to May, which allows me to reset and think critically about ways to improve my service for the next application cycle.
What’s your advice for other side-hustlers who hope to turn their ventures into successful businesses?
First, develop something unique about your product or service. How can you make your work stand out from the competition? This might mean pursuing a niche market within your field (like college essays within the field of tutoring) or building a variation on your product. It doesn’t need to be revolutionary — I’m always surprised by customer enthusiasm for products that are marginally different from the mainstream.
Second, stay patient as you grow. There are plenty of stories about side hustles that struck it rich in year one, but for most of us, success takes time. If you have a multi-year time horizon and the persistence to keep at it, your investment will be much more likely to pay off.
Finally, remember that there are no prerequisites to starting a successful side hustle. I am hardly the stereotype of a business owner: I studied public policy in college and never dreamed of starting a business. There’s no such thing as a “type” of person who becomes a successful business owner, so go pursue your ideas and see what happens.
Amanda Breen
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