How a 31-Year-Old Veteran Owns 74 Rental Units

  • Shelby Osborne left the military in 2018 and went full force into real-estate investing. 
  • She has used lines of credit, private, VA, and hard money loans to invest.
  • But she highly recommends only one type of loan because it has the most advantages. 

Shelby Osborne started her career off in the army as a second lieutenant in 2012.

“I was becoming increasingly frustrated with my day-to-day life in the army,” Osborne told Insider. “It has so many pros for sure, but there are frustrations involved just probably like with any job. And I could easily see what my future looked like for the next five, 10,15 years in the military because of the job progression — and it was not something that I wanted to do for that long.”

Osborne, aged 31, served for six years before deciding to shift to real estate full-time as both an investor and agent. She now owns 74 rental units, according to property and LLC records viewed by Insider. They are a mix of single- and multi-family homes, along with some commercial properties. She’s also the founder of Five Pillars Realty, a firm that helps real-estate agents connect with investors. It’s comprised primarily of veterans who invest in real estate.

The first property she purchased was a condo in DuPont, Washington. She intended to live there while she was in the military. But after residing there for more than three years, she had to relocate and decided to keep the property and rent it out. After the mortgage was covered, she had an extra $150 a month that she could tuck away. 

“It was cash flowing, even though I hadn’t run numbers. I was like, ‘wow, if I just keep buying properties that bring in more than my mortgage payment, maybe I can stop trading my time for money’,” Osborne said. 

The second property was a duplex she purchased at the end of 2017. It was her first intentional investment. At that time, she wasn’t well-versed in real estate and didn’t know how to optimize money. So she bought it with cash she had saved up and used a conventional mortgage for the balance. The property was $75,000, she said.

The upside was that it already had two tenants when she purchased it. Therefore, it cash flowed about $1,000 immediately upon purchase after covering its mortgage. This encouraged her to keep going, no matter what it took to get there.  

“I wanted to live a life where I didn’t have to ask permission to travel outside of a 250-mile radius,” Osborne said. “I wanted to live a life where I wasn’t living for the weekends, where I was happy every single day of my life and not just living for the couple hours that I had off.”

How she scaled 

The only issue with these aspirations was that she had limited funds. She had been able to put 0% down on the first property using a VA loan. But the second property required a 25% down payment. 

“I quickly realized that I could not do that time and time again, or else I would need a lot of money quickly for that,” Osborne said. “So I dug into research and learned about the BRRRR strategy.”

This is a method where an investor buys, rehabs, and rents the property. Then, they turn to a bank and request a refinance. The money pulled from that is then used to repeat the process for the next investment. 

Osborne noted that this process of accessing funds wasn’t easy. That’s especially true now that home prices are near record highs and inventory is low.

“In real estate, in life, in entrepreneurship and all of these things, you’re going to hear ‘no’ time and time again,” Osborne said. “But the fact is that you have to find a way to make it happen if you really want it.”

She continued, “I’ve used every possible means to acquire properties and get these BRRRR projects done. Including private money. I’ve used hard money. I’ve used partnerships. I’ve done lines of credit with a local bank. You name it, it’s probably happened in order to get the money.”

Osborne recommended aiming for private money, if that’s an option, because the agreement can be customized. When it comes to hard money loans and lines of credit from banks, you get into high-interest rates and hard deadlines for repayments. 

As for picking a property, Osborne notes that the most important aspect is the home inspection. You’ll want to be sure there won’t be any major fixes that would require thousands of dollars out of pocket. 

That means using a contractor who will walk to the property and identify any potential issues upfront including structural damage, roof issues, a busted HVAC, and even checking if there are termites. 

“Make sure that you are tied in closely with someone who’s done it before, or is really familiar with the market,” Osborne said. “So for instance, it was super helpful that I was a real estate agent because I understood what a projected value would be after repair.”

Christin Hakim

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