From GI Bill to founding your own company

Vets in Business: An interview with Joshua Holley

Chris Zeitz
Point of Decision
5 min readJan 6, 2016

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Joshua Holley deployed to Afghanistan.

Joshua Holley is a veteran of the US Marine Corps. He was enlisted from 2002 to 2006 and deployed with the 22nd and 26th Marine Expeditionary Units. After completing his service, he obtained his Bachelor’s degree in Business Administration from the University of Tennessee and his Masters of Accountancy from Vanderbilt University. He started his career in the New York office of Ernst & Young before founding The Tripoli Group to support high-growth startups. You can follow Joshua at, @afonok, or The Tripoli Group at, @TripoliGroup.

This is the first in a series of Point of Decision interviews with veterans who have transitioned into business.

What were the first days, weeks, and months like as you left the USMC? Did you know what you wanted to do?

I was very fortunate coming out to be starting school at the University of Tennessee while on terminal leave for the first five weeks. I did not have a solid plan, but I had been accepted to major in Business Administration and had worked out all my GI Bill paperwork much earlier in the summer. So I knew what I would be doing during the weekdays and where I was getting money. Those are probably the two biggest obstacles coming out of the service for most veterans.

Not that it was an easy transition. My very first class was Philosophy 110 and on day one I realized I was closer in age to the graduate student teaching the class than to my fellow classmates. I had some serious jealousy of their ignorant bliss.

What were some of the challenges you encountered as you transitioned?

It sounds silly to say, but after the Marine Corps the civilian world was a lonely place. I did not know any other veterans until my senior year. Between the age gap I mentioned and just a totally different life experience I had a difficult time relating to my classmates.

The biggest challenge for me was transitioning from school to the workforce. I think the majority of service members are altruistic people. We ignore the politics and know military service provides a way to impact our communities for the better. When I was in, I knew my daily activities had a purpose. When I got to school my purpose was to better educate myself and use that knowledge to impact my community. Once I stepped into the corporate world, I struggled with finding a purpose. It took sometime but I began to find some outlets which provided the purpose; the Veteran Entrepreneur Academy being one.

As you transitioned from school to the workforce, were there other vets that you were in regular contact with or were you more on your own?

Josh in Business

When I first started at EY I did not know any veterans. However, there was a small group who had just started the EY Veterans Network, an internal professional group. Luckily I met one of them and was able to get involved in the group. Even though we met only every other month it was a great time to network with fellow veterans. As I mentioned, the transition from school to the workforce is where I really struggled and having this group really helped me.

Please discuss some of your experiences with EY’s Veteran Entrepreneur Academy? What were you seeing from veteran entrepreneurs that were positive? What were some of the challenges they were encountering?

The Veteran Entrepreneur Academy (VEA) was me putting my education and day job to use for the veteran community. In speaking to entrepreneurs and community members, I found there were great programs for people with an idea in their first year of business; however, if you had found some traction and made it to years two through five you were caught in a gap. The VEA was started to help those companies scale up through introducing them to business knowledge and a network of supporters.

The biggest positive in veteran entrepreneurship is a growing sense of starting your own business is a real option for veterans. At the end of my enlistment in 2006, the discussion was skilled labor or school. No one mentioned starting your own business as an option. Now the Small Business Administration’s Boots to Business is part of the transition curriculum.

I think the biggest negative is the idea that veteran entrepreneurship is a charity project for businesses. I want to see the mindset change from a mentality of these poor veterans need help, to these are the future business leaders who will grow our economy and be a positive impact on our community.

What made you decide to start the Tripoli Group? Why did you pick the name, beyond the Marine Corps allusion?

The Tripoli Group started because I saw a market opportunity in the startup community as a whole and in my network of veteran entrepreneurs. For high-growth startups there is a choice of working with a finance and accounting professional who you will quickly outgrow or pay too much for someone who is billing for services you do not yet need. Additionally, when talking with the leadership of young companies, I found they were having the same issues as my Fortune 500 clients. I wanted to build a practice to bridge the gap between the small bookkeeper and the multi-national firm. I can talk with entrepreneurs in their early days and help set a solid foundation; while keeping an eye to the future and where the company is headed from a finance perspective.

The Tripoli Group offers finance and accounting services to high-growth startups

For the name, I wanted to pay homage to my Marine Corps experience without excluding any potential clients with something that was over the top military. I also did not want to use my own name or something that was too descriptive of the business. The veterans I work with immediately know where the name originates and the civilians I work with think it is just an unusual name. As some advice to those who are still reading this far, I also wanted a name that could grow with the company. Similar to the Netflix case study, where they decided not to call the company DVDs By Mail. If I called the company whatever accounting services, I would be caught in one service. With this name the group can grow into other service lines as the opportunity arises.

What advice do you have for veterans who are just starting out, or who have hit setbacks?

I really like the question “How do you eat an elephant? One bite at a time.” I repeat it to myself on a daily basis. It keeps obstacles in perspective and reminds me to keep going.

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Chris Zeitz
Point of Decision

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