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Conversations with Terri O’Brien

Today we’d like to introduce you to Terri O’Brien.

Hi Terri, thanks for joining us today. We’d love for you to start by introducing yourself.
I’ve been an educator since 1987, and education has always been at the heart of who I am. After years of working in schools, I saw a real need in our community for personalized, one-on-one academic support that could meet students where they were. That need inspired me to open Alphabet Soup Tutoring in 2005, originally as a combination educational resource store and tutoring center.

In 2010, following the 2008 recession, I made the decision to close the retail side of the business and focus solely on tutoring. It was a leap of faith, but one that allowed me to fully invest in the part of the business that was making the greatest impact.

The early years were exhausting—I had to learn how to be a “business” person while still being an educator—but I was fortunate to have a supportive community that believed in what we were doing. As the business grew, so did my confidence. Over time, we became a well-known and trusted part of the community, and I’m proud that we’ve been able to support so many students and families.

My identity as an educator and my deep roots in this community have shaped everything about how I run the business. We don’t just offer tutoring—we offer encouragement, mentorship, and a belief in every student’s potential.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It definitely hasn’t been a smooth road. When I first opened my business, I’ll admit—I didn’t know anything about running one. I’m a teacher, not a businessperson, so suddenly having to learn about things like taxes, payroll, human resources, and marketing was overwhelming. I had no background in any of it and was figuring things out as I went, often through trial and error.

Then the 2008 recession hit, and that made it incredibly hard to keep the business afloat. Every month felt uncertain, and I had to be creative just to stay open.

And just when I thought I’d made it through the toughest part, COVID arrived. Overnight, everything changed. I had to pivot to online operations, decide when it was safe to return in person, and constantly adjust—figuring out how to sanitize, when to wear masks, when to stop—all while trying to make sure people felt safe and comfortable.

It’s been a journey full of challenges, but each obstacle pushed me to adapt, persevere, and learn more than I ever imagined about both business and resilience.

Thanks – so what else should our readers know about your work and what you’re currently focused on?
Throughout my professional career, I have dedicated myself to supporting both students and educators through strong instructional leadership, data-driven decision-making, and a deep commitment to student growth. I began as a classroom teacher and instructional resource leader, where I designed and implemented professional development, coordinated testing, and helped guide school improvement initiatives. Over the years, I transitioned into roles focused on academic intervention and coaching, where I collaborated with teachers and administrators to strengthen instruction, increase student engagement, and support struggling learners through targeted interventions and data analysis. In my current leadership role, I coordinate intervention programs, manage school-wide assessment systems, and organize events that connect families and the school community.

In addition to my work in education, I have owned and operated a successful tutoring business for two decades, managing a team of tutors and supporting hundreds of students across grade levels. Running a business while working in education has expanded my skills far beyond the classroom—teaching me how to handle everything from payroll and human resources to customer service and financial management. Together, these experiences have shaped me into a well-rounded educator and leader who values growth, collaboration, and creating opportunities for all learners to succeed.

What were you like growing up?
Growing up, I was deeply influenced by my grandmother, who was an educator and one of my earliest role models. Watching her make a difference in students’ lives inspired me, even as I faced my own challenges in school. Learning didn’t always come easily to me, and those struggles shaped my desire to become a teacher who could help students understand content more clearly, learn effective study habits, and become better organized. Even as a child, I was naturally a leader—someone who liked to take initiative, stay organized, and work hard to achieve my goals. That combination of perseverance, empathy, and determination has stayed with me throughout my life and continues to guide me in everything I do as an educator and leader.

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