Smart Moves

What I Did Right, and What You Can Do Better

May 06, 20257 min read

Let’s skip the sugarcoating.

I could’ve done a lot better. I made some smart decisions early on, but I also left a lot of opportunities on the table. Still, there are a few key moves I got right that every young Soldier can learn from.

🚫 I Avoided the Credit Card Trap

I watched it happen to too many of my peers: high interest, minimum payments, and a cycle that eats your paycheck faster than you can say "statement due."¹

I didn’t map out some perfect plan, I just looked at the payments and thought, “That’s way too high.” Whether it was credit cards or car loans, the monthly hit wasn’t worth it to me. I made a simple choice to be frugal.

I’d rather have money in the bank and be comfortable than be flat broke and stuck with a flashy ride or a pile of gadgets I don’t need. That mindset helped me avoid debt when so many others fell into it.

I saw too many Soldiers locked into 20% interest loans for vehicles they could barely afford to maintain² just to roll up in something shiny at the barracks. They were stuck before they even realized it. I wasn’t perfect, but I avoided that trap early, and it gave me breathing room when others were drowning in payments.

🌱 I Bought a House

While others were dropping money on car mods and bar tabs, I was hunting for something that would hold value. I bought a house. And while it didn’t pay off overnight, it gave me something most service members never consider: a physical asset that doesn’t depreciate the moment you drive it off the lot.

And don’t get me wrong, I still went to the bar. I just wasn’t racking up massive tabs trying to impress anyone with money I didn’t have. I knew my limits. I knew what I could afford. That alone put me ahead of the game.

Buying a home also taught me patience. Unlike a new phone or a pair of Jordans, property doesn’t give you instant gratification. But overtime? That roof over your head becomes equity. That equity becomes leverage.

🚀 I Took Risks, Smart Ones

I didn’t throw money into slot machines. But I did start investing in startups and digital currency in 2016. Small amounts at first, nothing crazy. But enough to learn, to watch, and to grow. Those early plays opened my eyes to the power of having some of your money in high-risk, high-reward spaces. More importantly, they taught me to research before I buy a habit that’s paid dividends beyond crypto.

But the smartest risks I took weren’t just about markets. They were about investing in myself. I earned my FCC license with radar endorsement, got my life and health insurance license, and completed my Master’s degree. Every one of those moves added tools to my toolkit and opened new doors beyond the military.

Later, with my wife we launched a side hustle in the insurance world. That wasn’t easy. But it gave me ownership over my income and a mission beyond the uniform. Not every risk pays off overnight. But the right ones change the game over time.


🛻 What I Wish I’d Skipped

We’ve all made a purchase we thought we’d love. For me, it was a high-end car. I didn’t buy it to show off. I bought it because I wanted it. I liked the idea of it. The look, the feel, the status. But after about a year, I realized it just wasn’t me. It wasn’t practical. I couldn’t load it up with car parts like I used to when working on other builds. It wasn’t a workhorse it was a showroom piece. And that’s when it hit me:

Sometimes, we buy things for the version of ourselves we think we want to be, not the life we’re actually living. There’s no shame in trying something. But there’s wisdom in admitting when it doesn’t fit and walking away before it drags you down financially.


💳 What I Saw in the Ranks

I’ve seen it firsthand, Soldiers stuck in payday loan cycles³, others maxing out credit cards just to keep up appearances. Flashy cars parked outside the barracks. Amazon packages showing up daily. Most of it wasn’t about needs, it was about image.

Sure, some expenses were non-negotiable. Monthly fades were a requirement. Even I had to shell out to keep it clean and in regs. But a lot of the other stuff? It was just financial noise.

Designer nails, expensive hair appointments, every streaming service under the sun it all added up. And it wasn’t just the big purchases that caused the damage. It was the steady drip of little decisions made without a plan.

I’ve even been on TDY and had to cover a Soldier’s meals not because they were irresponsible that day, but because they’d mismanaged their money for months.

Financial maturity isn’t about your rank or paycheck it’s about how well you handle what you’ve got. ⁴ If this hits close to home, good. That means it’s time to make a change.

💡 What I’m Proud Of

Early in my career, I had a great financial advisor, someone who helped shape the way I thought about money. But in 2013, I moved to Michigan and lost nearly everything I had ever saved or invested due to poor financial management.

That setback taught me a few of the most painful lessons of my life. First, never assume your money is safe just because it's with a professional you have to stay engaged and ask questions. Second, I learned that not having a backup plan or even understanding my own investments was a risk I could never afford again.

But in 2016, everything changed. I met my current advisor, and together we started rebuilding. Around the same time, I began investing in digital currency small amounts at first, but enough to get skin in the game.

It wasn’t just about the money; it was about taking control again.

Even now, investing isn’t my strong suit. I prefer tangible assets, something I can see and touch. But I’ve learned the value of balance. And most importantly, I’ve learned the value of having a team.


⚖️ What I’ve Learned About Balance

Here’s the most important lesson of all:

Nice things don’t mean you’re doing well.

There’s no pride in being house poor, car rich, or vice versa. Life isn’t about having the best gear in the barracks it’s about having the freedom to walk away from bad situations because you made good choices when it counted.

There were times I wanted to splurge. And sometimes, I did. But I always came back to the same principle:

"Find your balance. Live below your means. And don’t mistake noise for success."

That’s how you build real freedom. You don’t need to be perfect. Just intentional. And if I could go back and give my younger self one message, it would be this: Keep doing the right things. Do them earlier. Do them better. And stay consistent.

That’s the edge you need and the one you can start building right now.

📅 Want help getting started?

Book a call with me. I’ll help you figure out the smartest next steps, whether it’s building your TSP, funding a Roth IRA, or setting up a protected-growth strategy like an IUL.

You don’t have to figure it out alone.


📚 Footnotes

  1. "Average Credit Card Interest Rate in May 2025," WalletHub, accessed May 5, 2025, https://wallethub.com/edu/cc/average-credit-card-interest-rate/50841.

  2. "Average Auto Loan Interest Rates by Credit Score," LendingTree, accessed May 5, 2025, https://www.lendingtree.com/auto/.

  3. "DOD is Misinformed on Rate Caps," American Financial Services Association, July 22, 2021, https://afsaonline.org/2021/07/22/dod-is-misinformed-on-rate-caps/.

  4. David Duebner, "Fixing the Military’s Financial Literacy Deficit," Military Review, Army University Press, 2022, https://www.armyupress.army.mil/Portals/7/military-review/Archives/English/Online-Exclusive/2022/Duebner/Duebner-v1.pdf.

 

Guy Bester is the co-founder of DarkHorse Insurance Solutions, a veteran owned agency committed to empowering families with smart, lasting protection. With a strong background in financial services and legacy planning, Guy specializes in helping clients build wealth while protecting what matters most through tools like Mortgage Protection, Indexed Universal Life (IUL), and tax-free retirement strategies. When he's not educating homeowners or business owners about their options, he’s focused on helping fellow veterans and families create financial legacies that last generations.
#GetInsuredWithGuy

Guy Bester

Guy Bester is the co-founder of DarkHorse Insurance Solutions, a veteran owned agency committed to empowering families with smart, lasting protection. With a strong background in financial services and legacy planning, Guy specializes in helping clients build wealth while protecting what matters most through tools like Mortgage Protection, Indexed Universal Life (IUL), and tax-free retirement strategies. When he's not educating homeowners or business owners about their options, he’s focused on helping fellow veterans and families create financial legacies that last generations. #GetInsuredWithGuy

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