Mountain Mule Media features a conversation with Callie Kazakoff, founder of Big Sky Tutoring, a Bozeman-based tutoring and academic mentorship company that has grown from a one-person side hustle into a team of 14 tutors supporting students across a wide range of subjects and grade levels.

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Callie started Big Sky Tutoring before she even moved to Montana State University. After visiting Bozeman for the first time and immediately feeling connected to the area, she realized there wasn’t a centralized tutoring service in town and decided to build one herself. At just 17 years old, she filed the paperwork and launched the business before beginning college.

Today, Big Sky Tutoring offers academic support and mentorship for K-12 and college students, with tutors specializing in everything from early literacy and reading to advanced chemistry, physics, and engineering coursework. Callie explained that one of the company’s biggest strengths is the diversity of academic backgrounds within the team, allowing them to match students with tutors who fit both their educational needs and personality.

More Than Just Grades

One of the biggest themes throughout the conversation was that tutoring is not only about improving grades. For Callie, mentorship and relationship-building are just as important.

When hiring tutors, she explained that personality matters just as much as academic performance. She looks for people who can genuinely connect with students, build trust, and create an environment where kids feel comfortable asking questions and admitting where they’re struggling.

The conversation also explored how many students are still dealing with the educational and social effects of COVID, particularly those who missed critical developmental years during sixth and seventh grade when schools shifted online. Callie shared that many students today still carry gaps in foundational math and reading skills because of those disruptions.

Rather than pushing every student toward the same outcome, Callie emphasized that success looks different for different kids. Some students are preparing for highly competitive colleges, while others are working toward trades, firefighting, welding, or alternative career paths. Her goal is to help students find the direction that fits them best, not simply pressure everyone into a traditional college route.

Supporting Rural Montana Students

One of the most exciting parts of the conversation focused on Big Sky Tutoring’s developing partnership with Montana Digital Academy.

Through the partnership, students in rural Montana communities who may not have access to specialized teachers or advanced coursework will be able to receive tutoring support remotely. Callie explained that many small schools across Montana simply do not have the staffing or resources to offer subjects like chemistry or advanced math. This program aims to bridge that gap and give students throughout the state better educational opportunities regardless of where they live.

The discussion also touched on homeschooling, Montessori-style learning, mentorship programs, and how hands-on learning and meaningful relationships can shape the way young people develop confidence and critical thinking skills.

AI, Technology, and the Future of Education

Tim and Callie also discussed how AI is rapidly changing education. Callie shared that she uses AI as a tool for generating practice problems, organizing resources, and improving efficiency, but she also expressed concern about students relying too heavily on AI-generated work instead of developing critical thinking and communication skills themselves.

The conversation highlighted both the opportunities and challenges that technology brings into classrooms, especially as schools, teachers, and students continue adapting to new tools and changing expectations.

Building a Business Around Values

Toward the end of the episode, Callie discussed the realities of scaling a service-based business while still prioritizing ethics, accessibility, and employee well-being. She shared that Big Sky Tutoring now offers healthcare benefits to employees working more than 20 hours per week and emphasized the importance of paying tutors a livable wage.

She also spoke about future plans to create scholarship and nonprofit-supported tutoring opportunities to help students who otherwise might not be able to afford private academic support.

You can learn more about Big Sky Tutoring at:

• bigskytutoring.info
• Instagram: @bigskytutoring

Mountain Mule Media is a production of Mountain Mule Transportation, connecting listeners with Montana businesses, entrepreneurs, and community leaders through long-form conversations and storytelling. Whether you’re visiting Montana, planning transportation for an event, or exploring Yellowstone National Park, Mountain Mule Transportation provides private transportation and guided experiences throughout Southwest Montana.