Ryan Max Riley
Founder & CEO
I have always been fascinated by learning—by wisdom, knowledge, and above all by teachers and the educational institutions that foster them. For centuries, schools and colleges have been places where we go to cultivate our minds and abilities, and I created The Shires Tutoring Company in the hope of contributing, in a small but meaningful way, to that enduring pursuit of knowledge.
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My goal is to help both students and tutors ignite their passion for learning and develop versatile skills and talents through personalized, meaningful educational experiences tailored to each individual’s needs and aspirations.
In traditional school settings, this level of personalization is often overlooked or simply impossible. But by supplementing formal, collective education with one-on-one tutoring, both student and teacher can gain far more from—and contribute far more to—our great academic institutions, whether they are our beloved local elementary and secondary schools or our esteemed colleges and universities.
Over more than a decade as a private tutor and coach, and half that time as an instructor at a liberal arts college, I have gained deep insight into education, learning, and the many ways knowledge can be shared. In fact, the two courses I am currently teaching at my local college explore the history of learning itself—so fascinating has this area become to me.
As a former professional athlete who went on to study literature and later developed interests in entrepreneurship, mathematics, and finance, I have also seen firsthand how enriching it is to cultivate the mind, body, and creativity in harmony. With this philosophy in mind, I designed The Shires Tutoring Company to embrace not just the academic, but also the athletic and the artistic. I know of no other tutoring company that takes this multifaceted approach—though I believe they all should. It reflects the very ethos of the finest schools and universities, where intellectual, physical, and creative growth are treated as essential parts of a full education.
Education
Harvard College
Bachelor of Arts, Literature, 2007
University of Oxford
Master of Studies, Medieval and Modern Languages, 2011
Yale University
Master of Arts, French Literature, 2013
Work Experience
2025-present
2019-present
2014-present
2002-2013
1998-2005
In the current phase of my entrepreneurship, I started a New England tutoring company, and I'm working on a project in finance.
In winter term, I often teach at Williams College, lately, courses on mind control and the ways Arab science transformed Europe.
The first phase of my entrepreneurship: a craft distillery and cocktail bar in the Berkshires using locally gathered ingredients.
After earning my bachelor's at Harvard, where I was a member of the Harvard Lampoon, I earned master's from both Oxford and Yale.
I was an athlete on the U.S. Ski Team and competed on the World Cup tour in the freesytle discipline of moguls.