December 31, 2021
Best Ever CRE Team

Creating a Life Fit for the Cover of a Magazine with Jason Schilling


When Jason Schilling began working at the United States Postal Service in 1997, he had no idea it would change his life in more ways than one. Jason met his wife of 21 years at the USPS, where they both still work today. Oddly enough, the post office also delivered the first step in Jason’s real estate investing journey. It all started when Jason noticed that none of his coworkers seemed to be in the financial position he had hoped to be in. 

“Most of my coworkers were maxing out their thrift savings plan or only putting $5,000 a year into a Roth IRA. I saw that and thought to myself, ‘Okay, I don’t want to be where they are when I retire,’” Jason explained. “I realized none of that was going to give me the financial freedom or lifestyle that I had dreamed about. You always see covers of money magazines with a husband and wife on a sailboat, and they’re doing all this traveling. I couldn’t envision myself doing that with the path I was on.”

Jason Schilling knew something needed to change if he wanted to achieve true financial freedom; he just didn’t know how to make it happen. In the summer of 2012, Jason spoke with a friend who happened to be a property manager. When the conversation turned to purchasing apartment complexes, Jason’s interest was piqued. It seemed the process of buying and renting out apartments was a lot simpler — and potentially more lucrative — than he had assumed. 

Their conversation got the wheels turning in Jason’s mind. He began watching YouTube videos and reading articles online to educate himself on how to buy his first apartment complex. But to raise the capital needed to purchase a multifamily unit, Jason and his wife had to get creative.

“We had stock in big companies like McDonald’s and Google. So we decided to sell all of them. We cashed out our IRAs, remortgaged our house, and even borrowed a little bit of money from my family to purchase our first apartment complex,” Jason said. 

Within a few months of their initial purchase, Jason Schilling and his wife had generated enough funds to purchase a second apartment complex. With two properties under their belts, the couple began saving up any amount of cash flow they earned to put toward buying more complexes. 

“We stopped contributing to our thrift savings plans and IRAs. That way, we could save up all the money we possibly could and put it into the next apartment complex. We thought, why should we put money into our IRAs, making 5%, 7%, or 8%, when we knew we could get more of a return on our investments by doing something else?” Jason said.

Today, they own seven apartment complexes consisting of 188 units total, each producing cash flow. Yet Jason Schilling was ready to take on more in the world of real estate. 

“I was continuing to educate myself, reading books, listening to audiobooks, listening to podcasts, just learning through a lot of other people’s experiences, when I heard about syndications,” Jason said. “Real estate syndications became very attractive to me because they offered a chance to invest in properties in other parts of the country, which would diversify my geographical and political risks.” 

The Schillings decided to pull the trigger and invested in multiple syndications. It wasn’t long before they started seeing significant returns on their investments. Syndication investments allowed the Schillings to look at their earnings through a different lens — actually being able to comfortably save and attain the elevated financial position they wanted in their early days at the USPS. 

“The monthly cash flow from the syndications has been a life-changer for us. It really has given us peace of mind and a sense of security in knowing that these monthly distribution checks just keep coming in, month after month after month, no matter what happens with our jobs or our own real estate portfolio,” Jason said. 

For Jason and his wife, the financial freedom awarded by syndicated investments has truly been life-changing. They’re in a place now where they can quit their jobs if they want to, retire comfortably, and even travel the world — just like those couples on the magazine covers.

“With our jobs now, we don’t really have to be there. Which makes going to work a lot easier,” Jason said. “We always wanted to travel, but now that we’ve got more money coming in, and more freedom, it’s opening even more doors for us. Back in the day, traveling for us would have been going somewhere for a week. Now, we can go do an Airbnb somewhere for a month if we want to and not have to worry that it’s X amount of dollars per night. We never would have been able to afford that before.” 

About the Author:

Leslie Chunta is a marketing consultant with nearly 15 years of experience in creating dynamic marketing programs and building brands for startups to enterprise organizations. She has worked agency- and client-side with high-growth companies that include Silicon Valley Bank, JPMorgan Chase, SailPoint, EMC, Spanning Cloud Apps, Ashcroft Capital, Netspend, and Universal Studios.


Disclaimer: The views and opinions expressed in this blog post are provided for informational purposes only, and should not be construed as an offer to buy or sell any securities or to make or consider any investment or course of action.

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