Rick Massel (Richard Massel) | Author & Strategist

Coming Soon

The Rear Guard

Letters to a Recruit: The Art of Holding On Through Basic Training and Finding Purpose in the In-Between

Two battlefields. Two reinventions. One lifeline.

When a recent college grad trades her freedom for the yellow footprints of Marine Corps Basic Training, a burnt-out school principal walking away from his career finds himself adrift in the New York City job market. Separated by 800 miles, he assigns himself a new mission: to be her Anchor by writing one letter every single day.

The Rear Guard is a dual-memoir that captures the hilarious, painful, and profound art of holding on when the world tries to wear you down. It is a story for anyone currently stuck in the hallway between two doors.

Release Date Pending Read Strategic Parables

About Rick Massel

Rick Massel (Richard Massel) operates at the intersection of human systems and digital change. A former New York City High School Principal turned SaaS operator, Rick has spent two decades bridging the gap between institutional reality and high-growth technology.

He believes the best way to understand the future of AI is to analyze the worlds we have already imagined. Through his writing in Data Driven Investor and Towards AI, he uses fiction to teach the "mechanics" of thinking, helping leaders navigate the complex transition from legacy systems to a generative future.

His perspective is shaped by a career that spans continents—from leading educational initiatives in India, China, and Angola to managing Customer Success strategy in the US. When he isn't decoding the latest AI models, he is an avid cyclist and endurance athlete who has trekked the Himalayas and visited over 60 countries.

View Executive Bio & Operational History →

Author Rick Massel climbing Mount Kilimanjaro

"Strategy is endurance."

Latest Insights

From Medium, Data Driven Investor, Towards AI, Illumination, and Activated Thinker

Loading latest articles...