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Across the sports industry, time is a coach's most valuable asset. From NBA directors of operations managing complex travel grids and Division 1 compliance officers mapping eligibility charts, to varsity high school coaches and youth academy directors writing parent newsletters, sports professionals are facing an unprecedented mountain of desk work. To combat administrative fatigue, thousands of coaches have turned to Sidekick™ (by...

If you’ve noticed that your favorite apps are getting harder to use, your search results are cluttered with ads, and the platforms you once relied on are now "nickel-and-diming" you for basic features, you aren’t imagining it. There’s actually a term for this: Enshittification. It describes a predictable cycle in the tech world. A platform starts out great for users to build a following. Then, it pivots to favor big advertisers or...

DOWNLOAD PDF FOR IMMEDIATE RELEASE MyCoaching Tree Launches Sidekick: The AI Specialized for Sports Professionals AUSTIN, TX - April 7, 2026 MyCoaching Tree, the premier platform for coach career and professional development, today announced Sidekick™ . This advanced AI assistant is dedicated exclusively to providing detailed, confidential counsel to coaches across all sports and competitive levels. Unlike general-purpose AI,...

December 23, 2025 New Report: Texas Coaching Stability on the Rise as "Retention Gap" Identified As 2025 draws to a close, MyCoachingTree is proud to share the results of our latest comprehensive analysis: the Annual Report on Coaching Stability and Retention (2021-2025) . Prepared by Phillip Engle using our specialized AI, Sidekick™ , for the Texas High School Coaches Association (THSCA) and the University Interscholastic League...

Why Your AI Assistant Gets Confused: The "Lost in Conversation" Problem Dated: June 6, 2025 Have you ever noticed that a conversation with an AI starts out great, but as it goes on, the AI seems to lose its way? It might start giving you long, rambling answers, making weird assumptions, or completely forgetting what you asked for three messages ago. A May 2025 study from researchers at Microsoft and Salesforce has finally put a name...

January 1, 2025 Celebrating a Milestone: 40,000 Coaches and the Future of MyCoachingTree As we kick off 2025, MyCoachingTree is proud to announce a major milestone in our journey to empower the coaching profession: our community has officially grown to more than 40,000 registered sports professionals . What started as a vision to provide better career tools for coaches has evolved into a thriving global network. Growth Beyond...

Why I Invested in MyCoachingTree So I first invested in MyCoachingTree back in 2021, the reasons were twofold. Number one is the deep respect I have for Coach Rutledge and the impact he has had on coaching on coaches all throughout the state and throughout the country. And at the same time when I first learned about the mission of MyCoachingTree it just made total sense to me. I think about my players as they go out into the business...