TIGERWAY / THE EXPERIENCE CAME FIRST
Tigerway did not begin as software. Classrooms, difficult questions and years of direct student work created the educational judgment behind the company. StudentOS is becoming the intelligence layer that carries that judgment across Tigerway: priorities, learning evidence and a clearer next decision.
Years of working directly with students shaped the Tigerway method: understand the difficulty, explain the idea and look for evidence that the learning holds. StudentOS is the emerging codification of that accumulated teaching judgment: keeping evidence, purposeful work and the next decision connected.
Larry Cheung leads the methodology and StudentOS direction. Calvin Cheung, Co-Founder & Academic Director, leads instructional quality, coach supervision and the educational conversations that need accountable judgment.
Larry began Tigerway with a study group at Boston Public Library in 2013. His teaching philosophy connects critical thinking, care for the student and the responsibility to make the next decision well. He leads the platform, curriculum and methodology that carry that purpose forward.
Photo & history sources
Calvin leads academic standards, coach supervision and the educational conversations that need accountable judgment. Program arrangements determine who teaches and who reviews; this is not a promise of routine personal access.
Photo & history sourcesLarry leads educational methodology, StudentOS product direction, curriculum and research. Years of direct student work inform his Founder judgment about the system and the next chapter of Tigerway.
Calvin leads instructional quality: setting standards, supervising teaching, handling difficult educational situations and leading parent conversations. Workshops, group sessions and selective StudentOS demonstrations connect that academic leadership to families.
At Tigerway Boston, in-person Group Coaching, workshops and educational events follow those standards. Sessions, instructors and registration are confirmed individually. Private Coaching is a separate, 100% online 1:1 service.
A student’s next decision rarely belongs to one test or one class. Schoolwork, available time, a difficult concept and the choices ahead all matter.
Private Coaching puts the Tigerway method to work today through high-touch 1:1 online instruction. The student works; the coach teaches and checks; a Tigerway Manager adds judgment where warranted. StudentOS carries those operating lessons into a connected learning record; Family Intelligence brings the useful signal into view. Boston remains the physical community behind that wider direction.
Know what deserves attention now—and see how it connects to the week, the month and the bigger picture. StudentOS keeps school context, recorded work and the next decision together.
Experience StudentOS
The plan remembers the work. The next decision starts with more context. Screen sources & learning context
Our physical community at 50 Milk Street brings people together for in-person Group Coaching, periodic Sunday workshops, StudentOS demonstrations and parent conversations.
Come with a question.
Leave with a clearer direction.
In-person group learning, with a clear purpose and an agreed instructor. Confirm the session and registration before visiting.
Explore StudentOS in a scheduled demonstration or bring an academic question to a parent conversation.
Periodic Sunday workshops and educational events connect families around useful questions. Registration opens when dates are confirmed.
Calvin Cheung · Co-Founder & Academic Director
Calvin leads instructional standards and coach supervision. At Tigerway Boston, a scheduled parent conversation, StudentOS demonstration or workshop brings that academic judgment into the room.
Meet Calvin at 50 Milk StreetAppointments and the person attending are confirmed directly with Tigerway.
SAT methodology, mathematical reasoning, reading and writing, and useful parent conversations. Explore the planned topics and take a practical framework into your week.
Explore the workshop portfolioTurn a recurring error pattern into focused work and a useful later check.
Join workshop interestBring competing priorities into view, make room for the right work and show the family what matters.
Join workshop interestSeparate completed work from evidence of understanding, then decide when human help would add value.
Join workshop interestPeriodic Sunday topics at 50 Milk Street. Dates and registration are announced when confirmed; these are planned formats, not a published event calendar.
Sarah’s story extends into helping other students. Durga’s continues across Boston and online learning. Adithi’s connects preparation with the demands of junior year.
Sarah Yang
Starting context: 1440 PSAT
Sarah’s story followed the work from junior-year PSAT to senior-year SAT.
Score report insideRead the story
↗ Interview / audioDurga Raja
Durga traveled from New Hampshire to Boston for weekend learning.
Score report insideRead the story
↗ Interview / audioAdithi Katikhaneni
Mock exams and repeated practice were not producing the result Adithi wanted.
Read the storyTigerway grew through the work of a broader community of teachers and mentors. Their different disciplines helped shape a shared ambition: understand the student, teach the reasoning, and make the next step count.
Selected educators from Tigerway’s coaching history. University backgrounds describe these coaches’ academic experience; current program leadership remains with Larry and Calvin.
Brown University
Philosophy and Law
Princeton University
International Affairs
Stanford University
Science, Tech, and Society
University of Southern California
Biology Pre-Med
Northeastern University
Software Engineering
University of San Diego
Data Science
The Founder’s account begins with a 2013 Boston Public Library study group. Students, questions and the shared work of learning came first; the program grew around critical thinking and care for the person.
Larry began with a study group: students, questions and the shared work of learning. That human beginning remains the center of Tigerway.
Group teaching grew into a coaching community. The public history records the effort, setbacks and individual breakthroughs that gave Tigerway its identity.
Sarah, Dusu, Zoey and many others shared stories that extended beyond a final score: confidence, planning, language and persistence.
Tigerway’s published account describes alumni returning to coach. Sarah’s case records one-to-one coaching during her first college semester: a student’s experience becoming part of another student’s learning.
Durga traveled from New Hampshire to Boston, then continued online. Adithi’s Pennsylvania story adds another perspective on coaching beyond the local classroom.
The methodology existed first. StudentOS makes it persistent: the student’s work, reasoning, focused work and later check can remain connected as the journey continues.
Historical student outcomes and teaching settings retain their original source context. They do not establish StudentOS-caused results or the availability of a current class.
Start with 100% online Private Coaching, explore the StudentOS learning system, or meet the physical Tigerway community through confirmed Boston programs. The goal is the same: stronger thinking and increasing independence.