Ten Questions With Ryan Guina

Ryan Guina

Ryan Guina from Cash Money Life & The Military Wallet

This interview is with Ryan Guina, of Cash Money Life and The Military Wallet.  Ryan was the first person I met online when I started writing articles, after finding Military Wallet on a Google search of “top military personal finance blogs.”  Ryan has done some amazing things as he transition from active duty to being a civilian, then rejoining as member of the Air National Guard.  Read more to learn what Ryan Guina has to say!

  1. What’s your military background? Career, family, etc.

My military background is a little different from most of the people you have interviewed so far—I served one tour on active duty, had a very long break in service, and then later joined the Air National Guard. I initially joined the Air Force after completing my freshman year of college. I had always done well in school, but I needed a new challenge. I was seeking an adventure and I found it in the Air Force. I had an amazing 6½-year run on active duty, but I hit burn out and needed to try something else. My enlistment included an overseas assignment, 5 deployments, and a one-year special duty tour in which I traveled around the world and lived out of a suitcase. This doesn’t include other TDYs or training assignments. I was gone much more often than I was home and I was seeking more stability.

So I left active duty and moved across the US to be with the woman who is now my wife. I was lucky enough to find a job as a contractor on a military installation, so I remained close to the military community. Several years later, I started a business running several websites and offering consulting services. This eventually turned into my full-time job, and I left my job as a military contractor. My business was a blessing as it offered us location independence and the ability to make my own schedule. So my wife and I relocated to Illinois to be closer to her family. This was wonderful on a personal level, but it took me away from the military community that I had been a part of for my entire adult life.

It wasn’t long after we relocated that I realized I needed to get back into the military community. So 8½ years after leaving active duty, I joined the Air National Guard. Being an entrepreneur is great, but I missed being around the military community and being part of something that is bigger than myself. Being back in uniform after such a long break in service is an amazing feeling!

  1. What is it that you wanted to do after you left active duty?

This is a great question. My transition was a leap into the unknown. I earned my degree while serving on active duty and I wanted to use my degree and experience in a new way. I was an aircraft mechanic on active duty, but I didn’t want to go back to shift work and turning wrenches. I was lucky to find a job at HQ Air Force Material Command at Wright-Patterson AFB, in Dayton, OH (the Air Force logistics command). My new job was doing logistics analysis and data mining to identify constraints in the supply system. This was an excellent opportunity, as I was able to leverage my military experience while learning new skills. As a hobby, I started some websites while I was working there. Those websites started bringing in revenue, and I later transitioned into being a full-timer entrepreneur. I had never started a website before then, much less had designs on earning money online. I couldn’t have predicted any of this. But the entire process has been tremendously rewarding experience on many levels. I couldn’t have written the playbook to get where I am today, but I wouldn’t change a thing, either.

  1. What is it about your service experience do you think has best prepared you for your transition?

Preparation. I worked hard and played hard during my active duty years. But I was also strategic in giving myself options so I could make the best decision for me–not be forced to make a decision due to a lack of options.

My preparation actually started before I joined the military. My older brother joined the Marine Corps right after high school. He wasn’t prepared to leave the Marines after his 4-year commitment, so he made the default choice of reenlisting for 4 more years. Unfortunately, his MOS was full, so he had to cross-train into a new career field in order to remain in the Marines. His hand was forced and he had to make a decision he wasn’t prepared to make. It worked out for him in the end, as he retired last year after 20 years on active duty.

I learned from my brother’s experience. I wanted to be prepared at the end of my enlistment, so I signed a 6-year contract to give myself the extra time needed to make the decision. This was absolutely the right decision. Those extra two years gave me the time to earn my degree while I was on active duty. My degree gave me career options, both in or out of the military (if you are on active duty, you should absolutely take advantage of military Tuition Assistance benefits, it can super-charge your career!). When my enlistment was over I had a promotion waiting for me, I could use my degree to apply for a commission, or I could take my degree and experience and try my hand in the civilian world. Those were three very good options to have at that stage in my life and career.

Finally, I was smart with my money. I had the financial means to take the leap into the unknown without worrying about not being able to house and feed myself during the transition (5 deployments and several TDYs in 6 years made it easy to save a lot of money!).

Preparing for your separation is essential for everyone. Most of us don’t know when we will leave the military. The military is contracting and many service members face involuntary separations. Like me, some people decide they need a change of scenery. Others may have to leave for medical reasons or family reasons. The best thing you can do is be prepared for your transition before it happens.

There are many ways you can prepare for your transition—whether that transition is in a year, or in 15 years. Some examples include education, certifications, work experience, increased savings, paying off debt, understanding your benefits, and more. I recorded a podcast with another veteran, Mark Deal, in which we discuss preparing for your military separation, even when you don’t know when it will happen.

Start planning your exit strategy before you need it. Adjust as you go. You’ll be glad you did!

  1. Think of the most challenging part of your life to this point. What is it that you’ve done that helped you through it?

By reading my responses so far, it may seem like I had the perfect transition from the military. Nothing could be further from the truth. Transitioning out of the military was the most difficult time of my life.

My struggle was in finding my identity after leaving the military. I was unemployed for 6 months. I had enough money to pay for rent and food. But I didn’t have Purpose. I left a career where I was able to see tangible results from my work and I had managerial responsibility over several people on my shift. Then I had nothing. No job. No real responsibilities. I had moved across the country and only knew two people. It was extremely difficult for me. Every day I searched for jobs online. I went to job fairs. I networked. I sent out my resume. But it still took a long time to find work. It took just as long to get involved in the local community.

I would do many things differently if I were to go through a similar transition again, including working on getting plugged into the community more quickly. I would also have considered joining the Guard or Reserves sooner. Joining a military unit can work wonders for your morale and also open the doors to work opportunities through your new network.

In the following podcast, I discuss my struggles after leaving the military and offer some tips on the military transition. My hope is others can learn from my story and avoid some of the struggles I went through.

  1. On a scale of 1 to 10, how confident were you in your financial situation as you transition?

Overall, I would say my financial confidence level was an 8. I had some advantages—namely I was single and I had minimal fixed expenses (my only bills were a cell phone bill and a small car payment). As previously mentioned, I had deployed numerous times, so I had a lot of money saved. On top of this, I was able to draw unemployment benefits*, which helped with the transition.

That said, it also took me 6 months to find a meaningful job. I did draw down my savings, but this was planned and I never got into the danger zone. It worked out well, and I didn’t have to rely on credit cards or loans to make ends meet.

*For those who aren’t aware, many veterans are eligible for unemployment benefits after leaving the military after they complete their service contract. However, retirees and those who receive involuntary separation pay are usually not eligible for this benefit due to state laws and how they view these forms of compensation.

  1. What was your biggest fear about your transition?

The unknown. I didn’t have a well-defined description for the type of job I was seeking. All I knew was that I didn’t want to go directly into aircraft maintenance, which was my military career. I wanted to avoid shift work and my preference was doing something in more of a white-collar, 9-5 office environment. The end result worked out well, but as I mentioned, the transition was difficult on an emotional level, and it took 6 months to find a job.

  1. If you had one question that someone could have answered for you (not doing something for you, but a question that they could answer), what would it be?

“What can I do to get better integrated into the local community on both a personal and professional level?”

This ties in with my response to Question 4. Unfortunately, I didn’t know this was the question I needed answered until well after the fact. Hindsight is 20-20 in this case!

  1. What would you like to see “out there” that doesn’t exist, but if it did, it would solve a big problem for you, and other people like you?

I left active duty in early 2006. Many things have changed for the better in the decade since I left active duty. Ten years ago, there weren’t as many websites or communities for veterans. Those that were available often weren’t as comprehensive as today’s websites. Podcasts weren’t common, and there was no real platform for them. Social media was very different. MySpace was the big social media community and sites such as FaceBook, Twitter, LinkedIn, and Rally Point were either in their infancy, or hadn’t even started yet.

If you wanted to be in a community or find meaningful information on the military to civilian transition, you had to find a mentor or join a local veteran’s community (neither of which were always easy to do).

I started my websites, Cash Money Life & The Military Wallet, shortly after leaving active duty. They started as a way for me to document everything I was learning about my personal transition. Later, I started getting a lot of traffic to those sites and I started writing with a focus on reaching a wider audience. So in a way, I created a resource that I needed.

Today, there are many more resources available. Sites such as yours are invaluable to veterans who are gathering information on making the leap back into the civilian world. There are multiple military and veterans podcasts, groups on LinkedIn, FaceBook, and Rally Point, forums, websites, ebooks, and other resources that simply didn’t exist five or ten years ago.

The best advice I have is to not try and be a hero and solve every problem on your own. Get out there and seek answers and join communities. You will learn a ton, and just as important, you will help others by sharing your personal knowledge and experiences.

  1. What person has helped you through your military career and/or transition the most?

I have had two military transitions to date. One was leaving active duty, and the other was joining the Air National Guard. I’ll have a third transition one day, but I hope that one is for retirement!

My wife helped me the most during my transition from active duty. We were married several months after I left active duty and she was with me through it all. I would have had a much more difficult transition without her love and support.

She was also very supportive of me joining the Air National Guard. She too is a military veteran, so she understands what it means to serve. I have been in the Guard for two years now. It hasn’t always been easy, but she understands how important it is for me to be able to wear the uniform again and be a part of the military community and mission. I wouldn’t be able to serve today without her support.

I also have to add Doug Nordman, whose book, The Military Guide to Financial Independence and Retirement inspired me to begin looking at the Guard or Reserves as an option after being out of the military for so long. Doug has become a good friend and mentor. I’ve learned a lot from him, his book, and his website, The Military Guide.

  1. Do you want to be contacted by people who think you might be able to help them? If so, how do people get in touch with you?

I am always happy to help. People can find me through the contact page on my website. I also have a podcast on iTunes where I do some deep dives into related topics. I don’t update the podcast as much as I would like to, but there are over 20 episodes so far, with a wide range of topics that are all applicable to the military audience. My website also has hundreds of articles on a wide range of military and veterans topics. So I would recommend people search my site for the topic to see if it has been covered. If not, please send me a note!

I hope you enjoyed reading this interview as much as Ryan and I enjoyed conducting it!  Please feel free to leave any feedback in the Comments section below.  Also, if you’d like to be featured in an upcoming Ten Questions article, please feel free to email me or PM me through our Facebook Group!


About Forrest Baumhover

Forrest Baumhover is a Certified Financial Planner™ and tax professional. His firm, Westchase Financial Planning, focuses on the unique financial planning needs of servicemembers and families looking to separate or retire from active duty.If you’d like to learn more about Forrest or his services, please check out the About Forrest page at the top of this article.
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3 Responses to Ten Questions With Ryan Guina

  1. M. Potter says:

    I think this was the best “Ten Questions” interviews so far! In-depth and thoughtful answers as well as a unique perspective on various methods of military service and the transition experience.

    • Forrest Baumhover says:

      Thank you very much! However, I definitely can’t take the credit here…Ryan wrote these answers himself. As a professional blogger, he has a little more experience in sharing his story and crafting his message. Almost an unfair advantage, you might say…

    • Ryan says:

      Thanks for the kind words, M. Potter! I’m glad you found this helpful. The transition from the military was a major turning point in my life, as was deciding to join the Air National Guard after such a long break in service. My goal is to share my experiences and help others with making similar decisions in their lives. I hope this is a step in the right direction.

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