Mile Two

The Fellowship of Entrepreneurship

Jeff Graley // Nov 12,

Answering the Call

Many of you are aware of the Lord of The Rings series. In this epic story, the main protagonist, Frodo Baggins, in spite of great danger and uncertainty, accepted the quest of delivering the ring to safety.

In late summer 2015 I finally answered a similar quest: the call of entrepreneurship. It was something that had been stirring inside of me for longer than I was aware of. The Department of Defense (DoD) and the Air Force Research Laboratory (AFRL) had launched recent initiatives to spur innovation and entrepreneurship, which were the final catalysts for me to transition from civil servant to business owner. While the analogy of an entrepreneur answering the call doesn’t involve the danger of Frodo’s mission, it does come with endless uncertainty and the pursuit of building a company from the ground up.

Accepting Help Along the Way

Before Frodo set out on his journey to deliver the ring safely to Rivendell - and later to destroy the ring in Mount Doom - he built his team. At first Frodo’s team was one of friends (Merry, Pippin and Sam), but along the way he brought additions to the team. The Ranger of the North, Strider, guided them to Rivendell. Elrond used his magic to heal a wounded Frodo.

Much like Frodo, several years before I made the decision to become an entrepreneur, I too, began to build a team. I started to surround myself with likeminded individuals whom I believed would be both critical and supportive of the changes I wanted to make. The most significant of these changes being the need to quit the security of my current job. I also began shifting my network from nearly 100% DoD to a mix that better represented an entrepreneurial ecosystem. I met small business owners, incubators, venture capitalists, and others who were feeling the call to start their own businesses. By adding new peers to my network, I began building a circle of mentors to improve my chances of being a successful entrepreneur.

Build Your Entrepreneurial Fellowship

The Fellowship of the Ring included Frodo’s mentor, Gandolf, an elf, a dwarf, Ranger Strider, the three trusty, original friends as well as a member of the team that was not as supportive, Boromir. This new Fellowship was a mix of old and new, those strongly aligned and those with reservations. Yet all had something distinct to contribute to the journey. Along the way, parts of the team were lost due to distrust, injury, and even unexpected deaths.

My journey started with my trusty small team of likeminded supporters as well. But, while I found that my call to entrepreneurship was one that I could no longer ignore, my cohorts’ calls weren’t as strong. I struggled with the decision to go at it alone. I struggled with doubt, what my “product” would be, and how to stand out in the crowd. Oddly it was also along a trip (just to California) with a mentor of mine that my path to entrepreneurship was revealed. My mentor suggested I form a partnership with two of my long-time Air Force colleagues who were strong software developers. Why hadn’t I thought of that? It was like a bolt of lightening and made so much sense!

When I returned from California, I spoke with these colleagues and we agreed to launch Mile Two as a trio. Each of us brings something unique and complimentary to the table, and we continue to merge and prune our fellowship of entrepreneurship as roles and needs change during our journey. To be successful you must surround yourself with strong mentors, business partners, and colleagues. It is equally important to be willing to expand and prune that team as necessary. Roles change, needs change, and people change. Don’t be afraid to constantly reevaluate your team to make certain you have the best team for your journey.

The Trip Will Be Longer and More Difficult Than Expected

Frodo thought the journey was over once he arrived at Rivendell, only to realize they still had to go to Mount Doom. They experienced more attacks, a blinding storm, and dissension amongst the team. Then they encountered Gollum, whose intentions were murky and uncertain. Frodo thought his team was finalized for the next leg, only to realize the final journey would include just one of his original friends, Sam.

Every time you think you have a contract sealed or a new partnership formed, new obstacles appear. In our short few months of existence, deals have fallen apart at the last second and people and projects we desperately wanted have disappeared. In hindsight, we are fortunate some of those fell through. Entrepreneurship is not for the weak of heart. It will challenge you every single day. It is thus imperative to build a strong team, be open minded to new directions, and have a drive to weather the storms. No matter how difficult you think it will be, it will be more difficult. Build a fellowship that will help you emerge stronger at every phase of the journey.

I want to end this with a huge thanks to my “Fellowship of Mile Two”, including the ones who have helped us get to where we are today and those that we haven’t even met. I encourage everyone to step into the roles of founder, colleague, partner, and mentor. Remember that it is also acceptable to embrace the role of former founder, colleague, partner, and mentor. You will grow in and out of those roles over time. Embrace everyone every step of the way. (Y)Our story is still writing itself and I expect it to be epic!