About Josh Massey
Your Partner in Anchoring Growth

My Pathway to Being Your Coach

The "Drop Your Anchor" Moment & Understanding
My Own Wiring

My understanding of resilience and the power of a growth mindset wasn't initially learned in a boardroom; it was forged in a hospital bed.

At thirteen, a severe infection nearly took my life. I was told, "You will never walk again, and if you walk, you'll never run." The next two years were a battle - surgeries, hospital stays, and grueling rehabilitation - to reclaim my life. I had to learn to walk again, twice.

This experience, while challenging, became a cornerstone, teaching me invaluable lessons about mindset, the necessity of adapting systems (even personal ones), and the profound impact of dedicated coaching when facing what feels insurmountable. Though I still make some alterations in how I do things, that early fight instilled in me a drive that rarely lets anything stop me when I want to move forward.

In my early twenties, this drive led me to martial arts. I earned a third-degree black belt and, for the next decade, took over the daily operations of the school. This was my first deep dive into operational leadership. I learned firsthand about system building for startups and sustainable growth as we expanded from 70 students to nearly 300, tripling our monthly recurring revenue (MRR).

Life has a funny way of presenting new paths. Despite two associate degrees, the opportunity to earn my Bachelor's at 32 was a call I couldn't ignore. I resigned from the martial arts school and enrolled full-time in an Interdisciplinary Studies program, a "build your own major" perfect for an entrepreneurial mindset.

The sheer number of choices, however, led to decision paralysis. After my eighth revision, my typically calm and patient mentor, Gib Mason, bluntly snapped, "F*** you Josh! Drop your anchor!" That pivotal moment cut through my startup overwhelm and indecision, becoming a core philosophy for me and now, for "Anchored For Growth". I went on to finalize my degree in Social Entrepreneurship and Leadership Development and then earned my Master's in Entrepreneurship, Leadership, and Innovation, guided by that same mentor.

The entrepreneurial bug bit hard again early during my Bachelor's. Six months in, I co-founded and launched Banana Bones, a mobile app with fellow students, aiming to revolutionize the college tour experience. Nine months later, we sold the company, and I stepped in as a project manager for the acquiring company for the next year, learning about integration and growth from a different vantage point.

In 2014, my journey into financial literacy began when a friend and I launched Ortus Academy, a company to teach students and young adults how to make better financial decisions. We understood that this skill could fundamentally shift a person's life trajectory. We even created an interactive game simulating five years of financial decisions, getting students actively engaged with the consequences and wins of their choices.

When COVID hit, our contracts vanished, forcing a critical "pivot or die" moment. We restructured our business model, secured venture funding, and were granted access to Baltimore's Conscious Venture Lab, now known as the Novella Center for Entrepreneurship, and began to thrive. We launched online courses, hired 15 new team members, and expanded our offerings to include wealth generation and real estate investing with the assistance of an investor. As Co-Founder & COO, navigating this rapid shift and scaling operationally was an intense, invaluable period of growth.

It was also during this time that my passion for leadership coaching began to take shape, albeit informally. Friends and team members consistently sought me out to work through challenges or to brainstorm how to launch their own ideas into the world.

A desire for more time with my young family led me to a dream job in many ways: becoming a professor at a local community college. For three years, I loved being in the classroom, sharing my stories and experiences to help develop young entrepreneurs. I had transitioned my role in the Financial Intelligence company to part-time, but the pull to return to my own business was strong, and I did so when my daughter started pre-school.

The ADHD Revelation: A New Lens on Overwhelm and Opportunity

Then came another life-altering shift a few years later. Two weeks after earning my Master's degree, my family and I moved to India for my wife's job. My business partner and I decided to wind down our business, ensuring our team found new roles.

India is vibrant and beautiful, but for me, it was also unbelievably overwhelming. It was there, in my mid-forties, that I received my most profound "aha!" moment: an ADHD diagnosis.

Suddenly, many patterns in my thinking, approach to challenges, startup overwhelm, and even my leadership style made sense. This new lens wasn't just about understanding myself; it illuminated the dynamic, often ADHD-driven, entrepreneurs and visionary CEOs I'd always been drawn to work with and coach. I realized that the "idea tornado" energy, the rapid innovation, and sometimes the challenges with focus, were often part of this neurotype.

Since that diagnosis, I've been ferociously learning about ADHD—how to harness its creative "superpowers," enhance problem-solving, lead others effectively, and transform overwhelm into operational efficiencies. My personal experience navigating ADHD while leading and coaching others, many of whom have (diagnosed or undiagnosed) ADHD, has equipped me with unique empathy and practical strategies tailored for neurodivergent leaders and their teams.

Now, back in the Central Timezone, I'm more committed than ever to changing lives by helping operational leaders like you build amazing companies.

My journey - from physical adversity and martial arts discipline to entrepreneurial ventures, an ADHD diagnosis, and a deep love for coaching - has uniquely prepared me to help you become the anchor your company, your CEO, and you need to thrive.