How This Veteran’s Transition to Civilian Life Led to a Successful Business

How This Veteran’s Transition to Civilian Life Led to a Successful Business

How This Veteran’s Transition to Civilian Life Led to a Successful Business

Ryan Guina transitioned into the civilian sector after six years of active duty in the Air Force. The transition was difficult for him, and throughout the process he documented what he learned so that other veterans didn’t have to reinvent the wheel. He is now the owner of The Military Wallet, a personal finance website, newsletter, and podcast for military members, veterans, and their families. He’s also a current member of the Air National Guard. Here’s his story, as told to Nav.

From Active Duty to Business Ownership

I left active duty in 2006 and moved to Ohio to be with the woman who is now my wife. The transition was difficult—when you’re in the military, you have a lot of responsibility, you’re taking a lot of action, and you often see very tangible results from those actions. But for about six months, I was unemployed and looking for work. I was fine financially because I had saved for the transition, but going from having been part of something that’s bigger than yourself and seeing tangible results from your efforts, to slamming on the breaks and having no real sense of accomplishment was a big struggle.

During that time I had to learn a lot about civilian life, so I started reading everything I could. I came across some personal finance websites run by individuals, and loved the fact that individual people were doing this, so I started a website called to document what I learned and also keep an online journal.

Later on, I started another site to help military members called, where I focus primarily on the financial aspects of the transition, the current military life, and military benefits.

Taking the Business Full-Time

About six-and-a-half years ago, my wife and I had our first child. We decided that either the day job or the business had to go. We thought, prayed, and talked a lot about it, and we decided to make that leap into full-time entrepreneurship. Since then there have been no regrets.

Funding the Business

We were able to bootstrap the business from the beginning. It grew slowly and organically, and because my wife and I both had day jobs, we were able to set aside the income from the sites that we were bringing in.

Thankfully, it worked out very well. We didn’t have to take on any kind of business loans or financing from investors.

The Smartest Decision

My business was a part-time hobby that grew into a full-time business. So I had a long runway before it became my sole source of income. When I transitioned the business to full-time, my income from both sites was roughly that of my day job. So I kind of grew into my business.

The first year I was full-time, I was very diligent about watching our expenses and our income, and made sure that I did everything I could to pull the right triggers for growth.

The Biggest Mistake

I actually carried that “this is fun” mentality for too long, even after I went full-time. I continued at times to treat it like a hobby and not be as serious with it as I should. I treated it seriously, but not seriously enough.

The Biggest Reward

The most rewarding part is being able to set my own schedule. I have two young children, and I can take time off in the middle of the day to go see a school presentation or a show they’re doing. Or if we need to take a vacation, I can rearrange my schedule. I don’t have to clear it with a different boss.

Now I do have very clear lines between work, play and family time, and I try not to work nights or on the weekends. And when you work from home, that’s extremely important. But my wife knows that if I’m taking time off during the day, I might need to give up an evening to finish work. So there are challenges there that come with that freedom, but it’s tremendously rewarding to have that time with my family.

The Most Challenging Aspect

The most challenging thing is that I’m kind of a bottleneck for everything. I have a lot of contractors, but it’s pretty much all run by me. Hiring other people is something I’ve struggled with in the past. I realized that most of my hiring mistakes weren’t because I hired the wrong person; they were because I didn’t set the expectations correctly from the get-go. And that often comes down to processes—without those systems and processes in place, then hiring someone who doesn’t meet expectations isn’t necessarily their fault, it’s the fault of whoever does the hiring.

So what I’ve been doing over the past few months is documenting my processes and standardizing things, so that if somebody comes into the organization, there’s going to be a clear set of expectations for them—they’re not wondering if their work is being done correctly, and I’m not frustrated that they haven’t done something exactly the way I wanted it to be done. It’s really the only way to set somebody up for success.

Future Plans

I’m very excited about the future for both websites. Right now, I’m redesigning each of the sites to make it more user-friendly on all platforms. I’m also in the process of hiring somebody to help me manage the site.

Because the ultimate goal is to be able to help more people. We’ve been able to help tens of thousands if not hundreds of thousands of veterans to receive proper benefits and make sure that they find the information they need. So I’m really excited about bringing on some new people to increase our reach.

Best Advice for Someone Starting a Business

The biggest thing is to make sure you have a very defined business plan. Know what your goals are, know your mission statement, and stay true to that. It’s okay if it changes, but really try to narrow in on that from the get-go. This will help you better serve your target customer.

Another is maintaining integrity. I have a rule that I will not publish anything or recommend any product or service that is not something I believe in or would recommend to a close family member or friend. I see that too often on the internet, people will recommend products or services just because they can make some money. I have turned away thousands of dollars in advertising opportunities, direct sales and those kind of things because my integrity says this is a product that isn’t appropriate for our audience or for our customers.

And I think that if you can do that, if you can keep that integrity and you can really be aware of who your target audience is, then you’re well on your way to being successful.

This article was originally written on November 11, 2016 and updated on November 14, 2016.

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