How I Got Started in Real Estate

In 2006, when I graduated from college, I knew I wanted to start planning for my financial future, and I wound up working with a traditional financial advisor to invest in the stock market. When I asked her for material to help improve my financial education, she recommended this obscure book, that I'm sure no one on BiggerPockets has heard of, titled "Rich Dad, Poor Dad," by Robert Kiyosaki.

I was hooked.

I knew I wanted to start generating passive income, and real estate seemed like a great way to start. But while I was all-in on the mindset from RDPD, I couldn't figure out the actual blocking-and-tackling of how to start buying properties, especially without a war chest of cash to deploy. I read three more Rich Dad books, plus a book on buying real estate without cash or credit, but it just never clicked.

In the meantime, I started flying for the Navy which involved moving around the country every 6-12 months. It just seemed too "risky" to be buying properties when I'd be in the location for such a short period of time. When I finished flight school, I was stationed in Japan for over three years, where I couldn't purchase property, and at the time the idea of buying in the U.S. from halfway around the world seemed insane.

When I finally got back to the states in March of 2016, I was going to spend about a year in Test Pilot School (TPS) in southern Maryland. I knew that: 1) I wanted to invest in real estate, and 2) I wanted to spend my weekends in DC rather than near our base down in Maryland. So, taking inspiration from a bunch of my buddies in Japan, I reached out to my TPS class to see if anyone wanted to team up, renting a place for weeknights near the base, and renting a place (from me) for the weekends in DC.

Two guys were in, so I started house hunting. After looking at MANY places in the very hot DC market where homes were typically selling above asking in less than a week, I came across a home in a ~B-C neighborhood that seemed to be on the rise. It met my basic requirements of 3 beds and 3 baths, with a PITI payment that worked within our budget. The first time I looked I actually passed on it, but after a few more days without any real options, I went back and decided it could work.

Unlike every other house on the market, it had been listed for over 30 days which made me a little nervous - what was wrong with it I hadn't seen yet? (6+ years later I still haven't found out!) Eventually I put in an offer slightly under asking, negotiated a bit, and wound up under contract. Inspection found a few things, and the sellers agreed to fix all the major issues. Appraisal came in above my purchase price, and after all the time you have to wait with a VA loan, I closed on May 31, 2013.

The property was just in my name, but we pooled my PITI payment and the rent payment on our house near base, and split it three ways. So I say I sorta house hacked before I knew what that was. The house worked perfectly for our purposes, and my roommates and I worked hard every week to be able to come up to DC on the weekends and completely unplug. I had a great time during my year in training, and even met my wife through living in DC on the weekends.

This post already got longer than I expected, so I'll save the rest of the story of this deal for the next one!