Lessons from the Military That Made Me a Better Real Estate Investor

[David Litt]

Hey BP family,

Figured it was time I shared a bit of my journey—not just as a real estate investor, but as a veteran trying to make sense of the civilian world, wealth-building, and the strange beast that is real estate.

I did 12 years in the Army. Infantry. Saw a few countries, made a few lifelong friends, and picked up a set of skills I didn’t realize would transfer into property investing. But as it turns out, discipline, risk assessment, and adaptability are some of the best traits you can have in this game.

How It Started: From VA Loan to First Duplex

I bought my first duplex in 2017 using a VA loan. At the time, I didn't know jack about cap rates, BRRRR, or even what BiggerPockets was. I just wanted to stop throwing money into rent and get a little breathing room on my bills.

Lived in one side, rented out the other to a fellow vet I knew from my unit. That one move changed everything. It didn’t feel like investing at the time—it felt like survival. But six months in, I noticed the rent was covering the mortgage. A year later, I realized I had cash flow.

That’s when I started reading, watching, and asking questions. And eventually, I realized: I could build something here.

5 Military Mindsets That Helped Me Succeed in Real Estate

1. Mission Focus

In the military, you don’t move without knowing the objective. In real estate, if you don’t know your strategy (cash flow? appreciation? house hack?), you’re gonna waste time and money.

Every deal I’ve done since has started with a mission statement. Not a vision board—just a clear objective.

2. Risk Assessment

Combat teaches you to evaluate threats fast. In real estate, it’s not IEDs—it’s bad neighborhoods, inflated ARVs, or unknown repair issues.

I don’t panic when a deal has some hair on it. I ask: What’s the worst-case scenario? Can I survive it? If the answer is yes, I proceed cautiously.

3. Team Cohesion

Real estate isn’t solo. You need contractors, brokers, lenders, agents. I treat my team like my squad. Loyalty matters. So does clear communication.

I’ve passed on “cheaper” plumbers to keep the one who shows up, cleans up, and doesn't overpromise.

4. Training and Drills

In the Army, we trained endlessly for situations that might happen. In real estate, I study markets I haven’t entered yet. I run cash flow analyses on deals I don’t plan to buy. It’s not wasted time—it’s reps.

5. Adapt and Overcome

I had a flip go sideways in 2022—permits delayed, contractor walked. I took a hit. But I didn’t fold. I rented it out, refinanced, and walked away with a lesson instead of a loss.

Mistakes I’ve Made (So You Don’t Have To)

Let’s not sugarcoat it—I’ve fumbled plenty.

• Trusted the wrong property manager. They stopped doing inspections, let units fall apart, and stopped answering my calls. Had to fire them and do damage control.

• Skipped due diligence on a “hot” deal. Bought a fourplex in a city I’d never even driven through. Turns out the area had high vacancy for a reason.

• Over-renovated a rental. Military attention to detail can backfire. I spent way too much making things “perfect.” Tenants don’t pay extra for crown molding.

Advice for Fellow Veterans (and Anyone Starting Out)

• Use your VA loan wisely. House hacking is a game-changer. If I could do it over, I’d buy a fourplex instead of a duplex.

• Don’t let analysis paralysis stop you. Military life is structured. Civilian life isn’t. That uncertainty kept me on the sidelines too long after my first win.

• Find community. BiggerPockets was like finding a new unit. Ask questions. Share wins. Share failures. You’ll grow faster.

Where I’m At Now

I’m five properties in—three duplexes and two single-family homes. One is a mid-term rental for travel nurses. Another is a long-term hold I plan to pass down to my daughter.

I’m not rich. I still drive a ‘14 Tacoma. But I’m free. I’ve got control over my time, my income, and my future. That’s something no deployment ever gave me.

Final Thought

For anyone who’s served—or still serving—and thinking about real estate: you’ve already done harder things. You’ve shown up when it mattered, followed orders when it counted, and survived chaos most people will never understand.

This game is learnable. Just like boot camp, the first few weeks suck. But if you stick with it, lean on your training, and keep moving forward, you’ll win more battles than you lose.

Stay sharp. Stay humble. Keep learning.

—Ray