You Already Have the Skills for Real Estate Investing: An Interview with Matt Shedd

by | Mar 22, 2023 | Investment, Multifamily, Retirement

Regardless of where you are in your career as a Foreign Service member, you have most likely thought about what your life could look like after retirement. If you want to maximize your earning potential, you need to look beyond traditional pathways to retirement towards more robust options like real estate investing, which may help you find greater wealth and financial freedom once you are ready to retire.

But how do you know if you have what it takes to be successful in the real estate game?

Matt Shedd, retired Foreign Service Special Agent, experienced real estate investor, and administrator of the “FS Real Estate Investors” Facebook group, sat down with the Passport REI team to talk about just that.

In this article, Matt tells us that Foreign Service members already have all the skills needed to make exceptional investments for your family’s financial future. The scariest part is taking the first step.

From Foreign Service to Real Estate Investing: Matt Shedd Knows What it Takes

Matt is no stranger to the Foreign Service lifestyle. Born and raised in a Foreign Service family, Matt spent much of his childhood living abroad. He eventually went on to serve in the U.S. Army, where he spent 16 years learning and growing.

In 2000, Matt and his wife made the transition to new careers in Foreign Service and spent the first few years of their service stateside. Prior to embarking on an overseas assignment in 2003, the Shedds realized they needed to find a way to offset their increased tax burden when they went overseas. “We had to look at somehow trying to minimize our tax burden, and one way was real estate. So we bought a single family home,” he explains.

While their first real estate purchase turned out to be a solid yet conservative decision, Matt soon realized he had been bitten by the real estate bug, and he was thirsty for more information on how to make this new venture work for their future.

Not wanting to make any egregious mistakes out of the gate, Matt started reading anything he could get his hands on in order to educate himself on the basics of real estate investing. “I had only read one book at that point, Real Estate Investing for Dummies. It wasn’t really about how to invest in real estate. I just wanted to avoid making a major mistake in the transaction when buying our first home.”

Feeling good about their first investment, Matt and his wife went on to purchase two more single family homes in Florida before their retirement in 2015. Each investment provided an opportunity to learn something new and boost their real estate knowledge.

As very conservative investors, the Shedds felt wary of having a large amount of debt, so they were aggressive in paying down their loans. Because of this, they owned their homes outright by the time they retired.

Wanting better cash flow, Matt and his wife started to explore small multi-family units as an option. They sold two of their single family homes and made the switch to multi-family properties. While each of these opportunities provided cash flow and invaluable lessons, the Shedds are now cashing out in favor of joining real estate syndications as passive investors. Without the headache of direct ownership, they find value in enjoying the benefits with less risk and work/oversight.

Reflecting on his experiences in real estate investing, Matt is grateful for the many lessons it taught him and the confidence he developed over time. As he and his wife continue to evolve in how they invest in real estate, he wants to make it clear to other people in Foreign Service just how attainable real estate investing is. He also wants others to know that many of the skills they already have translate directly to real estate investing.

How Your Skills May Translate to Successful Real Estate Investing

As a member of the Foreign Service, you already have many of the soft skills and hard skills needed to be a successful real estate investor. Think of all the skills your job requires you to use in a day to day setting. Many of these skills can be translated to how you might manage your investments.

Soft Skills Hard Skills
Critical thinking skills
Negotiation skills
Cross–cultural communication skills 
Problem solving skillsInterpersonal skills
Organization skillsForeign language skills
Research capabilities
Project/program management
Computer/IT skills
Analytical skills
Contracting Budget formulation, oversight, and management


Matt was able to recognize quickly that both he and his wife possessed unique skills which were strengthened during their time in the Foreign Service. A solid background in banking coupled with strong personal organization skills made Matt’s wife the perfect defensive coordinator to his offensive coordinator (to use a football analogy).

While Matt excelled in researching and moving the ball down the field, his wife kept a close eye on the finances – protecting the investments they made and making sure it all came together in their favor. As a team, each of them brought their own skills to the table, allowing them to enjoy much success in their real estate venture.
While their initial leap into the game of real estate investing was a means to lessen their tax burden, decades of experience sharpened their skills as direct owners of their investment properties. With everything they learned along the way, the Shedds see clear value in syndications, which is why they have decided to cash out in favor of investing in multi-family, self-storage, and other commercial real estate syndications.

Matt’s Top Real Estate Investing Resources and Tips?

  1. Read a Book…Or Two…Or Three

Matt’s first piece of advice for Foreign Service members at the beginning of their real estate journey is to read as many books as they can. “For the past twenty years, I have continued to read books on real estate investing. The information we have now is better than it was twenty years ago.” While there are many titles he has since forgotten, Matt acknowledges that there is a wealth of information available online today, which can be accessed from anywhere in the world for free. Simply type a question into your web browser, and you will be fed a list of resources.

Matt’s short-list of book recommendations include:

The Millionaire Next Door, by Thomas J. Stanley Ph.D. and William D. Danko Ph.D.

Rich Dad, Poor Dad, by Robert Kiyosaki.

The Complete Guide to Buying and Selling Apartment Buildings, by Steve Berges.

Investing in Duplexes, Triplexes and Quads, by Larry Loftis.

2. Listen and Learn

In addition to reading up on books related to real estate investing, Matt also recommends listening to podcasts in the genre. Bigger Pockets has proven to be a helpful tool for Matt in his journey to gain deeper knowledge about real estate investing.

You can also learn a lot by talking to others who are already in the real estate game. Finding a mentor or joining an online group, where you can tap into people for questions is a great source for both knowledge and inspiration. “I was blown away when I started seeing what other people were doing…You name it, they’re out there doing it. We’re a smaller community and that is good because it inspires other people, and they don’t feel like they are alone.”

With a small amount of effort, you can find a wide range of free resources online to help you arm yourself with accurate information.

3. Calculate Your Expenses

Matt recommends a free online calculator to help map out your expenses should you choose the path of direct ownership. Knowing what your payments will look like over time helps you make an informed decision based on an honest understanding of your financial obligation.

Stay True to Yourself and Your Personal Goals

According to Matt, “the greatest barrier to entry” in real estate investing is taking the very first step. The key to overcoming this is education which leads to empowerment.

Matt is also a proponent of honest self-reflection and setting personal goals. “Everybody has different goals. You may have a goal of getting a certain ROI and you are willing to take more risk with it, but I’m not. I’m willing to accept a lower ROI with less risk… In my opinion, if you make an informed decision in real estate, it’s a great investment,” he asserts.

For Matt and his wife, they took the path that was the most logical for them. From new construction single-family homes, to small multi-family units, and finally on to real estate syndications, they always made the move that felt the best to them. Now, they are more than ready to settle into the far less stressful role of passive investors in syndications. To Matt, he sees it as an opportunity to enjoy the benefits without having to deal with the headaches.

In conclusion…

Reflecting on his own journey in real estate investing, Matt always tells people to figure out why they want to do this. “I think being honest with yourself and doing a personal inventory to say, ‘I don’t want to manage a property or I don’t like risk.’ Maybe they decide to invest in a syndication via a crowd-funding platform that doesn’t require you to be an accredited investor. You can invest a much smaller amount in relatively conservative investments on these platforms. You simply put in the money and you don’t have to worry about it.”
Ultimately, the process starts and ends by being honest with yourself and knowing what your individual needs are. Matt has seen many fallout of real estate investing because of a bad experience, which may have been avoided by doing some research and self-reflection beforehand.

Are you ready to learn more about multifamily syndication and Passport REI? 

Reach out today and we will start answering your questions about investing in a multi-family real estate syndication. 

Our experience in foreign service and real estate investing will help you make the most of your future legacy.