We caught up with the brilliant and insightful Cynthia Kemper a few weeks ago and have shared our conversation below.
Alright, Cynthia thanks for taking the time to share your stories and insights with us today. How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? The world needs to hear more realistic, actionable stories about this critical part of the business building journey. Tell us your scaling up story – bring us along so we can understand what it was like making the decisions you had, implementing the strategies/tactics etc.
I started Insight Tutoring when I was a junior in college. It began through word of mouth, especially in my sorority, which let me speak at chapter meetings each semester about my business. Soon, friends and classmates started texting me nonstop to book sessions, it became overwhelming fast. That Thanksgiving break, I talked with my cousin, who had just started a career in web design. He helped me create a simple booking website, and that’s when Insight Tutoring was officially born.
During my first finals season as a business owner, I was tutoring at least ten students while studying for five of my own exams. I couldn’t say no to anyone because they told me they would fail without my help. Balancing tutoring and my classes was hard, but every single one of my students passed. The next semester, things really took off, I was tutoring around 30 students, skipping classes just to keep up. I spent six hours tutoring in Walker Hall and the library every day, then went home to do my own schoolwork late into the night. I never stopped moving, but I loved it. That semester, I realized I wanted to keep running Insight Tutoring after graduation.
At the start of my senior year, one of my students suggested I hire someone and gave me Shea Welling’s number. At first, I hesitated. Then I woke up in the middle of the night with this sudden gut feeling that I needed to call her. I set up an interview, and we met in Walker Hall. Shea was incredibly smart, and it felt amazing to finally have help. Finals that semester were brutal; Shea had difficult exams herself, but she still helped me with seven appointments. I did 29 sessions the week before finals and 25 during finals week while taking four of my own exams. I ended up with a B in one class simply because I had no time to study.
My last semester, I hired my second tutor, Rachel Walden. That was one of the hardest semesters of all. It was my senior year, and I was trying to balance a full-time business with soaking up my last months of college. We ended up helping more than 60 clients that semester.
After graduation, I moved into my first office space. It was completely empty, and I had to order and build all the furniture myself along with my friend’s help. It took two months to get Wi-Fi installed which made running a tutoring company pretty interesting. For weeks, we used my dining room chairs for sessions. My friends and tutors helped me every step of the way. I worked 12-hour days, often late into the night, carrying furniture between rooms and tutoring up to ten students a day. I was exhausted, but I loved every second because I knew I was building something meaningful for my students and for myself.
That first year taught me so much. I was getting hundreds of texts a day on my personal number. Referrals and word of mouth fueled our growth, and by the next semester of 2024, we expanded into two more office spaces. Our revenue doubled for the third year in a row. During finals that winter, I worked 144 hours in 12 days. I developed wrist tendonitis from all the writing and ended up having surgery that August after wearing a brace for eight months. Despite that, when I saw how much we’d grown, I was so happy I literally ran around the parking lot celebrating.
In February of this year, Shea and I realized we needed even more space. An office opened right next door, and we jumped on it. We moved in on July 31st just one day before my wrist surgery on August 1st. Now we’re in midterm season in the new office, and things are going great. Insight Tutoring has come such a long way from that first semester in college, and I’m hopeful we can continue to help even more students.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
My name is Cynthia Kemper, and I am the founder and owner of Insight Tutoring, a tutoring company based in Fayetteville, Arkansas. We help students succeed in their most challenging courses. I started Insight Tutoring when I was a junior at the University of Arkansas when I was 20 years old. At first, I was simply helping students with finite mathematics, survey of calculus, and data analysis. What began as a few study sessions quickly grew into something much bigger.
Insight Tutoring specializes in college-level subjects and supports high school students preparing for the ACT. Our goal is to make difficult material understandable and to build students’ confidence in subjects that often feel overwhelming. We offer one-on-one tutoring, study guides, group review sessions, and ACT prep programs. Every resource we design focuses on meeting students where they are and helping them make meaningful progress quickly.
What truly sets Insight apart is the personal connection we build with every student. Our culture is built on kindness, accountability, and genuine care for each student’s success. Much of our growth has come through word of mouth, with students enthusiastically recommending us to their friends. Another unique aspect of our approach is our use of iPads in every session. We currently have eight iPads that tutors use to take personalized notes, which are then uploaded to a shared database. This allows students to review notes anytime and enables tutors to study and prepare for sessions outside of work. With four years of organized digital notes, the system has become an incredibly valuable resource.
One of the things I am most proud of is how much we have grown while staying true to our mission. In just four years, we have gone from tutoring a handful of students on campus to supporting hundreds of college students each semester in our own office spaces. Our sales have doubled every year since launching, and we have built a team of tutors who are passionate about helping others learn.
What means the most to me, though, are the stories from students who tell us they passed a class they once thought was impossible, or that our tutors made them feel confident for the first time in their academic journey. That is what Insight Tutoring is all about, helping students realize they are capable of far more than they believe.
For anyone learning about us for the first time, I want them to know that Insight Tutoring is more than a place to get help. It is a community that believes in students, celebrates their progress, and is deeply invested in their success both inside and outside the classroom.
Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
The book that has had the biggest impact on my entrepreneurial thinking is Shoe Dog by Phil Knight. Reading about how he built Nike from the ground up completely changed my perspective on what it means to be an entrepreneur. What stood out to me wasn’t just his success but his mindset. He wasn’t driven by money; he was driven by purpose and a relentless desire to bring his vision to life. He took out loan after loan, doubled his revenue year after year, and kept pushing forward even when things seemed impossible. That level of resilience and belief in his mission really resonated with me. I read it last August, and it has been a constant reminder that building something meaningful requires persistence, risk, and a deep sense of purpose.
Let’s talk about resilience next – do you have a story you can share with us?
One experience that truly tested my resilience happened during finals week about a year ago. I worked 144 hours in just 12 days, helping students prepare for their exams. It was one of the most demanding but rewarding times of my career. I was so focused on making sure every student felt prepared that I didn’t even have time to see a doctor, even though my wrist had started to hurt from writing constantly. By the end of the week, I developed ECU tendonitis from overuse, which eventually required me to wear a brace for ten months and later undergo surgery the day after I moved into our new office.
Even with the injury, I was determined not to slow down the momentum of Insight Tutoring. I had other tutors’ step in to write notes for me during sessions, and I learned how to teach without relying so heavily on writing. In an unexpected way, that challenge made our sessions even more effective. Since the students were now the ones doing the writing, I noticed they were retaining the material better. It shifted the dynamic of our tutoring sessions and reinforced the importance of active learning, something we still emphasize today.
I’m still managing the effects of that injury, but it taught me a lot about resilience, adaptability, and teamwork. What could have been a major setback became a lesson in growth and creativity. It reminded me that resilience isn’t just about pushing through difficult moments, it’s about finding new ways to move forward, trusting your team, and turning challenges into opportunities to improve.
Contact Info:
- Website: https://www.insighttutoring.online/
- Instagram: @insighttutoringuark
- Facebook: https://www.facebook.com/insighttutoringuark/
- Linkedin: Personal: https://www.linkedin.com/in/cynthia-kemper/ Business: https://www.linkedin.com/company/103754516/admin/dashboard/
