Matt & Andy.

These guys are not your average teachers. They're adventurers and educators who know how to make studying fun and effective. Kids love them because they get it — learning doesn't have to be boring. They've been out living life (skiing, traveling, going to concerts, aka...having fun) just as much as in classrooms, so they know how to connect with students in a genuine way.

MATT HOLLOWAY

Matt has been in education for over 20 years, beginning as an English teacher at Whitefish High School before shifting into college admissions consulting and standardized test prep. He has helped hundreds of students improve their SAT and ACT scores, craft standout essays, and navigate the complex world of college applications.

Matt is a highly respected educator and college admissions expert known in our community for his approachable and supportive style. He excels in SAT and ACT prep, delivers engaging presentations, and crafts personalized study plans. He guides students across the country through every step of the college application process—from building college lists to perfecting essays and interviews. With deep knowledge of testing changes—whether it’s the HiSET, SAT/ACT, or SSAT—Matt’s expertise and genuine dedication have helped countless students achieve their goals.

Credentials

Independent Educational Consultants Association – Associate Member since 2012.

Independent Educational Consultant Certification – University of California-Irvine. Winner of distinguished UCI Student Achievement Award.

Fiction EditorWhitefish Review; 2004 – present.

M.F.A. Creative Writing – 2010, Pacific Lutheran University.

B.A. English; minors in biology, art history, and philosophy. – 1995, Millsaps College.

Click through to learn more about Matt.

1980

Matt has always loved learning.

As a child, books mesmerized Matt, and there was nothing better than reading. He devoured every book he could find, always curious and full of questions. Perhaps more importantly, he enjoyed the process of learning—it was fun. (Image—Matt reading to his younger cousin.)

1991

Connecticut.

When Matt moved from Mississippi to Connecticut in fifth grade, he found himself at a college prep school that pushed him both academically and personally. He thrived in the challenge—even spending senior year diving into a seminar on his favorite author, William Faulkner—while also discovering his love for skateboarding and skiing. Those years shaped both his curiosity as a learner and his passion for adventure.

1995

College is awesome.

After high school, Matt headed back to the South for college, where he took a cross-section of pre-med, art history, philosophy, and English classes, and eventually settled on an English major. He never wanted college to end! There is a certain palpable energy that exists on college campuses, one that nourishes and celebrates the idea that anything is possible, and Matt fell in love with this energy.

2000

Montana!

But then he chased another dream, which was to live in one of the last wild places in the Lower 48—Montana. Matt worked as a backcountry ranger in Glacier National Park, getting paid to explore wild landscapes. Matt then earned a Montana Secondary Teacher’s License and taught high school English. After six years with the public schools, he opened a business for general academic tutoring, standardized test prep, and college admissions.

2011

College Consulting, SAT/ACT Prep, and tutoring.

Over the years, Matt has tutored most every high school subject—from AP Calculus to American History—while also focusing on college admissions.

Matt completed an intensive “College Admissions Consulting” certification program at UC Irvine, earning top honors in his class.

Matt Holloway Columbia Falls Skatepark

2025

Whitefish Review, Skateparks, and more!

When he’s not guiding students through college admissions and test prep, Matt is the Fiction Editor for the Whitefish Review. He has also helped design and build several skateparks across northwest Montana, and finds peace exploring the state’s wild landscapes. Closer to home, you’ll often spot him on the sidelines, cheering on his kids at the soccer fields.

ANDY CONNELLY

Andy has dedicated his professional life to education, with experience as a coach, counselor, outdoor educator, and teacher. For the past decade, he has run his own tutoring, homeschooling, and private teaching company in Whitefish, Montana. He prefers alternative settings and a holistic approach, working with students in a variety of environments to help them become curious, confident learners who understand how they learn best.

With over ten years of experience teaching standardized tests, Andy brings both deep subject knowledge and a keen understanding of individual learning styles to his work. He blends academic expertise with emotional intelligence, creating personalized strategies that help students feel prepared and capable. His calm, supportive presence reassures students, builds confidence, and turns test preparation into a process of growth rather than stress.

Credentials:

B.S. History; minor in Political Science - 2009 Montana State University.

Social Studies Broadfield Teaching Degree.

Boarding School/Outdoor Education Counselor and Teacher 2009 - 2022.

Private homeschooling, tutoring, and teaching 2016 - present.

Click Through To Learn More about Andy

1986

Growing up...

During his elementary school years, Andy lived in the Middle East with his family, and from there was able to travel to other countries. Spending time overseas and in interesting places filled him with an inherent wonder about the world. While marveling at the sights and soaking up the sounds and smells of various countries, Andy developed a deep appreciation for all the people, cultures, animals, geography, and the history of the world. 

2000

Teenage Years

In the awkward middle and high-school years, Andy lived in close proximity to the vast and mountainous wilderness. The time in the woods perpetuated his desire to learn about and explore his surroundings, all while learning new skills and things about himself. The seemingly infinite wilderness was the perfect outlet for Andy’s physical and mental energy, and his natural curiosity made him go see what’s on the other side of that next ridge or around the next river bend.

2005

College Years

This combination of worldly curiosity and a passion for the outdoors came to a confluence at Montana State University. While in Bozeman, Andy studied History, Political science, and Education/Teaching, while skiing and fishing as often as possible. Montana State was rated Top 10 in Powder Magazine and nicknamed “Trout University” by the fly-fishing community. Chasing academics and extracurriculars, Andy left Bozeman with diplomas and a more invigorated desire to learn.

2010

The Work Life

Since then, Andy has been a teacher, tutor, ski coach, outdoor educator, counselor, and a life coach. Working with so many kids, in so many different settings, has led to developing a more comprehensive view of students and intentionally using that to form a mindful approach to working with each individual. 

For the last decade, Andy has been running his own tutoring, homeschooling and private teaching company in Whitefish, Montana.

2025

Work Life Balance?

Depending on the weather and time of year, you will find Andy hiking around the backcountry, searching for fresh snow to ski, or waist deep in a cold river trying to figure out what the trout are eating. Regardless, he’ll be looking for the quiet of the woods, where the animals outnumber the people. When not in the mountains and rivers, he is still driven by adventures, and his many intellectual interests lead him to frequently explore local used bookstores for esoteric books.

“Matt and Andy were a huge reason I felt confident walking into the ACT. Every session was focused, effective, and actually kind of enjoyable!”

— Charlie (student)