Release Point Education - Darryl G. Cathcart

Can you share your transition story from the military to entrepreneurship? What inspired you to start your own business?

My transition story began the day I was diagnosed with Type 1 Diabetes. With the confirmation of a chronic illness, I knew I had breached universality of service and could no longer serve in uniform. At that moment, I started exploring what might come next. My final role in the Canadian Army was as a Directing Staff at the Canadian Army Command and Staff College, so it was natural to gravitate toward education and training, considering where that path might lead.

Upon retirement, I pursued a Master of Education at Queen’s University and a Doctorate of Educational Leadership at Western University. I focused on how training and education could better support those still in uniform, transitioning service members, military families, and, ultimately, Veterans. Through this research, I recognized that Canadian post-secondary institutions—colleges, polytechnics, and universities—could do more to enhance their programs, social supports, and student services for military-connected learners.

My military career was bookended by a lack of formal education at the outset and the completion of advanced degrees as a civilian. I enlisted in the Infantry as a teenager fresh out of high school, commissioned from the ranks as a senior non-commissioned member, and eventually left the service as a senior officer. Throughout my career, education remained a constant and unifying theme.

This experience laid the foundation for Release Point Education (RPE) through the development of tailored support systems for Canadian institutions. I firmly believe that training and education provide a meaningful post-military pathway to employment. However, it is essential to recognize that education takes many forms, and post-military growth is often enhanced through civilian certification and professional development opportunities.

The key takeaway is that Release Point Education was not a pre-planned destination but an idea I stumbled upon through academic research that eventually evolved into a small business.

What were the biggest frictions or obstacles you faced when leaving the military and starting your business?

One of my biggest challenges was realizing that entrepreneurship requires mastering far more than your subject area. You do not just become an expert in your field—you also have to become your own salesperson, marketing specialist, social media manager, administrator, accountant, planner, outreach coordinator, cheerleader, and motivational speaker, all while deepening your expertise in the area you are researching.

For Veteran entrepreneurs, breaking into a new industry is a hurdle. Release Point Education was entering uncharted territory—no other company was doing what we were attempting. This was both liberating and daunting. On one hand, we had the freedom to manoeuvre and engage with any potential client; on the other, there was no established roadmap, support system, or ready-made network to tap into.

To navigate this, I leaned on the operational mindset harnessed during service in the Canadian Army. We provided guidance (mission), created a strategy (concept of operations), and then executed. This structured approach helped us push forward despite the uncertainties.

Transitioning from military service to entrepreneurship also comes with many competing priorities. Achieving organizational alignment—ensuring that your vision, operations, and resources are in sync—is an ongoing challenge. It is not something you achieve once and forget about; it requires constant adjustment and recalibration. In Army speak – Has the situation changed?

Were there any aspects of your military experience that helped you as an entrepreneur? Skills, mindset, leadership, discipline?

The Canadian Armed Forces does not have a monopoly on discipline, skill proficiency, or leadership. Still, my military experience reinforced the importance of maintaining an unwavering focus on the task and a constant state of preparedness. Plans rarely unfold precisely as envisioned, so you must be ready to adapt. A deliberate mindset—directing efforts toward a desired outcome—is ingrained in military service, and that focus translates directly into entrepreneurship. Need more awareness? Invest in marketing. Don’t have a connection within an organization? Network and reach out.

Some core military skills—problem-solving, creative thinking, communication, and adaptability— are the foundation of a winning entrepreneurial mindset and must be retained in transition. That said, military structure emphasizes order and hierarchy, while entrepreneurship often requires a different approach. It is critical to remain flexible, willing to challenge norms, and open to unconventional solutions. In short, do not be afraid to step off the beaten path—this is your company.

One skill carried over seamlessly from military service was planning—thinking in branch, sequels, and contingencies. Entrepreneurship, like life, is rarely a linear path. A critical advantage is the ability to anticipate challenges, identify gaps, seek opportunities, and understand market needs. Beyond that, entrepreneurs must fully appreciate the competitive landscape. I am not confident that the marketplace cares if you are a Veteran—competing organizations will look to outmaneuver and displace your efforts. Success requires vigilance, adaptability, and the ability to execute with precision.

Looking back, what do you wish you had known before starting your business? What resources or support would have made the transition easier?

Looking back on the early days of Release Point Education, the primary focus was establishing a strong academic foundation and developing frameworks for implementation. In a more traditional business sense, this translates to market research, building a business plan, and ensuring a well defined value proposition.

The top priorities were the scholarship and rigor required to create credible, adaptable, and sustainable approaches in my field. However, I underestimated (or, more accurately, knowingly overlooked) the business side of things. These elements required just as much attention, from accounting and marketing to tax implications and HR considerations. While these gaps were eventually addressed, I wish I had recognized sooner the value of leveraging contracted services to offload some of these responsibilities, allowing me to focus more effectively on growing the business. Access to tailored entrepreneurial resources and mentorship early on would have made the transition much smoother.

What are the biggest lessons you’ve learned as a veteran entrepreneur? What advice would you give to veterans considering starting their own business?

One of the biggest lessons I have learned as a Veteran entrepreneur is the importance of understanding and defining your relationship with the identity of “Veteran.” Finding the balance between your business goals and how (or if) your military service factors into them is a personal and unique journey. Some lean fully into the Veteran identity, while others choose not to highlight it. Spoiler alert: Wherever you land on that spectrum, it is completely fine. Military service is part of your story, but it does not have to define your post-military objectives.

I encourage Veteran entrepreneurs to reflect on what is most essential to them and how they want to be perceived by their new client base. Canadian society holds a mix of real and perceived notions about what it means to be a Veteran. As a result, being a “Veteran entrepreneur” may not always align with what others expect. You must determine how much of that identity you want to incorporate into your business.

That said, most former service members are well-equipped to handle the uncertainty and unpredictability of entrepreneurship. The ability to adapt, problem-solve, and operate in ambiguous environments is ingrained in military training. Whether you served as a Corporal or a Colonel, your experiences have provided you with transferable skills that can enhance your business. The key is to think critically about the market you are entering, the product or service you are offering, and how (if at all) that connects to your time in uniform. Ultimately, success comes from building something that aligns with your goals—not just your past experiences.

What do you think needs to change to better support veterans in business? What initiatives or programs do you think would make the biggest difference?

When individuals enroll in the military, they forgo many civilian opportunities. As an all-volunteer force, the Canadian Armed Forces depend on a steady influx of young Canadians to fill its ranks, often resulting in missed educational and business opportunities, buttressed by a unique, non traditional quality of life. Canadian Armed Forces Veterans should be seen as assets, not liabilities. Any government, not-for-profit, or specialized transition program that helps bridge those missed opportunities is a step in the right direction.

That said, one of the most significant factors in a Veteran’s success in business is not just external support—it is a mindset. Veterans must recognize the value of their military experience and leverage it for their post-service growth. The key is complete immersion in their new direction. No transition program, grant, or mentorship initiative can replace the importance of taking ownership of your next move. Success in business, like in service, comes down to preparation, adaptability, and execution.