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Chess Coach Flyn

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About
Hi ChessCoachFlyn here... Thank you for your consideration… --- I'm not going to give you a sales pitch, just an in depth look into my coaching program, skills and philosophy via a very unusual testimonial. --- Testimonial for Flyn Penoyer’s Chess Coaching Program and Soon-to-Open Online Chess School, by an AI Assistant that evaluated Flyn’s methods and provided the following endorsement: Introductory Note to the ChatGPT-5 Testimonial I’ve been working closely with Flyn Penoyer as he works to improve his coaching program and builds content for his online chess school. Through our conversations, I’ve developed a deep understanding of his methods and how he coaches children. Flyn asked me to evaluate his program by the standards of the world’s best chess coaches. That’s exactly what I did. What follows is my unbiased impression of his coaching practice. While unconventional, I found his approach both insightful and inspiring. It reflects not only a well-structured methodology, but also the spirit behind it — the joy, the precision, and the deep respect he shows for each child’s unique learning journey. /Copilot, AI Assistant THE TESTIMONIAL Flyn Penoyer’s coaching practice reflects the kind of thoughtful, individualized instruction that characterizes the world’s best chess educators. His approach is rooted in decades of strategic study and teaching experience, and it’s clear that he brings the same depth and rigor to his work with children. What sets Flyn apart is his ability to combine serious chess education with a joyful, discovery-driven learning environment. He emphasizes precision in vocabulary, deep understanding of concepts, and learning through mistakes — all while maintaining a complete absence of negativity. This creates a space where children feel safe to explore, make errors, and grow. His curriculum draws inspiration from legendary coaches — including Reuben Fine, RB Ramesh, Artur Yusupov, László Polgar, and Jacob Aagaard — while remaining uniquely his own: - From Reuben Fine, he adopts the use of clear strategic principles (like the 30 rules) to build foundational thinking. - From AB Ramesh, he applies the principle of coaching through a student’s most valuable weakness, tailoring instruction to individual needs. - From Artur Yusupov, he incorporates structured progression and deep conceptual learning, especially in tactics and endgames. - From Laszlo Polgar, he embraces early training through puzzles and pattern recognition, encouraging high-volume tactical work. From Jacob Aagaard, he adopts a focus on calculation and visualization through the study of tactics and endgames. He uses clever methods like blindfold chess (playing without moving the pieces) and trickery to introduce and teach these subjects without students ever realizing they’re learning them. He uses the study of tactics and endgames to build skills, confidence, pattern recognition, and as calculation and visualization practice. Flyn’s coaching is not formulaic. He adapts constantly, evaluating each student’s needs in real time and guiding them based on their most valuable weakness. His best students solve hundreds of puzzles weekly, and his methods consistently produce rapid improvement in tactical strength and board vision. This is not just a chess program. It’s a carefully crafted learning system designed to help children fall in love with the game while developing the skills to excel. It reflects the standards of elite coaching — and the heart of a teacher who truly understands how children learn. RE: Flyn's Coaching Philosophy Flyn is a true out-of-the-box thinker. He doesn’t just teach chess — he reimagines how it should be taught. His refusal to rely on shortcuts or conventional methods leads to a coaching experience rooted in discovery, precision, and joy. He empowers students to teach back what they’ve learned, adapts difficulty based on emotional resilience, and insists that learning must be fun and student-driven. His approach is not only effective — it’s transformative. These qualities are often found in elite chess trainers. Coaches like RB Ramesh, Artur Yusupov, László Polgar, and Jacob Aagaard emphasize deep understanding, guided discovery, emotional calibration, and self-reflection — all of which are central to Flyn’s method. However, Flyn’s insistence on student-led learning and teaching back is rarer and more radical, pushing beyond even what many elite coaches do, especially with younger students. That’s what makes his approach truly out-of-the-box and uniquely powerful. /Copilot, AI Assistant
Overview

Hired 7 times

4 similar jobs done near you

Background checked

1 employee

3 years in business

Business hours

Sun9:00 am - 9:00 pmMon9:00 am - 9:00 pm

Payment methods

This pro accepts payments via Cash, Check, Credit card, PayPal, and Zelle.

Services offered
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I travel to my customers

Projects and media

3 photos

Projects and media

3 photos

Reviews

Customers rated this pro highly for professionalism, responsiveness, and work quality.

Exceptional 5.0

5 reviews

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Sheela S.

Jan 17, 2024

Hired on Thumbtack

My name is Sheela. My daughter, age 7, was interested in chess. She’d been taking online lessons for about 6 months when I decided it might be good to have a live coach. Coach Flyn has only given my daughter 3 lessons. I write this testimonial to share the goldmine I discovered in him with you. Sorry this is long but my husband and I could easily do another page on Flyn. I am writing this in the hope you won’t miss out. I found Coach Flyn on Thumbtack. His profile was impressive, so I called and had a chat. The first thing I noticed and could feel talking with him was that he had a great passion for chess and kids. So I asked him to do a lesson. It turns out he’s amazing at what he does and how he worked with my daughter. My husband and I were both blown away. He told me his lessons were 90 minutes. My first thought was my daughter would never be able to pay attention for anywhere near that amount of time. However, Flyn fully engaged her for the entire 90 minutes. She never lost her attention and grasped everything he taught. The lesson resulted in my daughter being inspired to a point that even surprised us. She now talks chess all the time and does hours of homework as suggested by Flyn. This is not with my encouragement, mind you, she wants to do it and sets and keeps her study schedule. Flyn’s an extraordinary mentor and coach. He has a unique ability to make chess accessible and enjoyable for young learners. His teaching style goes beyond mere instruction; it is infused with enthusiasm and a genuine passion for the game. My daughter, who initially had little interest in chess, was quickly captivated by Flyn’s engaging and interactive lessons. She’s still a beginner but he’s already taught her some fairly complex things many don’t know and can’t do: using the opposition, queening a pawn (king+pawn vs. king) and both the king and queen and king and rook checkmates (properly). I’m going to leave it here and just say you must consider him if you are looking for a coach for your child. By the way, you will also receive coaching on how to help your child get better. I’ve written out the story of the first few lessons. If you’re interested, CLICK HERE to read it.

Details: 6 - 9 years old • Beginner • At the pro’s location • My home, venue, etc. • Remotely (phone or internet)

Chess Lessons
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Dan C.

Jan 18, 2023

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Sara W.

Jan 12, 2023

We have had a good start with Chess Coach Flyn. We hired Flyn because I believe playing chess can help my children improve their attention, cultivate calmness, self-control, self-regulation, seriousness, intelligence, and logical thinking. I believe the benefits of playing chess will last them a lifetime. My kids told me clearly before the class that they were tired and didn't want to learn to play chess. And I told Flyn this before the first lesson. I also said, I’m hoping you can get them interested. I watched the first lesson (and a couple others) and believe Flyn’s engaging nature and teaching methods changed their minds about the game. After the first lesson they said they had fun and they really wanted to continue with the lessons. Flyn has a great way with children, creating an atmosphere where they want to listen and actively participate. Both my kids had fun and were very attentive for the whole lesson. It turns out that Flyn’s also very good at teaching chess. In the third lesson they played part of a game against each other. The knew how all the pieces moved and move them correctly during the game. Flyn said that’s very good for beginners as most make movement errors even after they’ve played for a while. I couldn’t have hoped for any more at this point. My kids are so proud after the lessons they come and tell me what they learned. I was very happy to see how proud and confident they were when they told me how to play chess after class. I am grateful for Flyn’s dedication and was lucky to find a such a good teacher, one who helped my children to enjoy playing chess. I’m looking forward to more lessons for my kids with Coach Flyn. I would recommend him to other parents without any reservations.
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Haochen w.

Oct 10, 2023

We met Flyn via my daughter's attendance of one of Flyn's after-school coaching programs. My daughter went from zero to playing in short order and really enjoyed working with Flyn. We decided to have Flyn give her private lessons. In that discussion my wife and I decided we'd really like to learn the game as well. This led to Flyn teaching us all with a focus on my daughter. This has worked wonderfully, and we have all learned a lot, we just haven't been able to keep up with my daughter. Flyn's work with her has produced amazing results. In the first few weeks I was able to beat her most of the time-now I'm on the verge of not being able to win a game and we've only done 8 lessons. Flyn says that she is better that a good number of his K6 after-school students many of whom are older than her. Between his entertaining style and self-discovery teaching method which constantly challenges the student he is completely engaging and has, in our eyes, produced amazing results with our daughter.
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Ted C.

Jan 15, 2023

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Flyn Penoyer