How to Successfully Invest in Real Estate While Working a Full Time Job

In my Investor Profile Series, I use a question & answer format to share the stories of actual real estate investors at different stages of their investing careers.

Today’s investor profile is with Jay Medina, a successful investor who has managed to buy properties while working a full-time job as an air traffic controller! He also has a popular Instagram channel at instagram.com/beingdetermined/ where he shares all the details of his wealth building and real estate investing. 

In the rest of this written interview you’ll learn why Jay’s goal is financial abundance (vs financial independence), how he approaches saving and investing, where he invests (and why), and who helps him to make real estate investing possible while he works a full-time job.




Jay Medina

Age (and your spouse/partner’s age, if applicable)

Both my wife and I are 42 years old.

Do you have kids? (if so, how old are they?)

Yes, we have two boys. 5 years and 2 years old, respectively.

What area of the country do you live in (& urban or rural)?

We live in the Jacksonville, FL area.

Career/Source of regular income (and non-income producing careers like stay at home parents or volunteers count just as much or more around here!)

I’m an Air Traffic Controller and my wife works in the healthcare industry.

What hobbies do you enjoy? What do you do for fun?

I’m a simple guy. I like to: learn, read, exercise, invest time with my family, enjoy nature and have meaningful relationships/conversations.

[Chad: My kind of simple! And I love the way you put it “invest time with family.”  I can’t thing of a better investment. ] 

A fun/interesting/little known fact about you?

I have done some cool/interesting things in my career. From talking to John Travolta in the frequency while he was flying his airplane to working Air Force One.

[Chad: You didn’t mention clearing the flying lanes for returning space capsules!! That’s about as cool as it gets!] 

Wealth Stage

How long ago did you begin investing in real estate?

I started investing in Real Estate back in 2006.

What was your wealth stage when you began investing in real estate? (I define wealth stages as 1. Survival 2. Stability 3. Saver 4. Growth 5. Income/Withdrawal.  See this article for further explanation. It’s ok to make a rough guess here.)

My wealth stage back then was Stability/Saver.

Has your wealth stage changed since starting investing in real estate? If so, what is it now?

Today, we are in the Growth stage.

Jay’s first deal!

Real Estate Investing Strategy

What was the primary real estate investing strategy that you used to get started?

Back then I did the Live-In Flip combined with House Hacking.

[Chad: SOOO many people start this way. It’s why I’m a house hacking evangelist!] 

Has your strategy changed since then? If so, what is it now?

Today, our strategy is: Long-Term buy and hold and REITs. In the near future, we will be doing Hard Money Lending/Discounted Notes and every now and then a BRRRR and Fix-and-Flip.

[Chad: I forgot to ask you about REITS in our interview. We’ll have to do a follow-up conversation on that, because it’s not an asset class I know much about.] 

Target Investing Market

What regional market do you invest in? Why did you choose it?

We invest in the following markets:

  • DFW and Austin, TX MSA
  • Jacksonville, FL MSA
  • Orlando, FL MSA

I always take into consideration the Big and Small Picture. Why did I decide on those markets:

  • Landlord Friendly
  • Business Friendly
  • Historical Data
  • Population Growth
  • Job Growth
  • Economic Growth
  • Affordability
  • Sociability

[Chad: Jay does a great job going more depth into his choice of locations in the podcast interview. I highly recommend listening to it.] 

Do you have a particular sub-market or neighborhood where you like to invest within your market? Why do you like it?

We like to invest in high-quality neighborhoods. A veteran Real Estate mentor, that we both know, taught me that location supersedes instant gratification.

[Chad: I’m guessing that’s John Schaub??] 

Have you chosen a particular real estate investing niche to focus on, like a type of property (ex: single family houses), a certain price range (like A, B, C, or D properties), or a type of end customer (ex: student rentals)? If so, why?

Although we own small multifamily real estate, we have decided to focus our efforts on Class A and B SFR.

[Chad: I like how you’re taking what your particular markets give you. You’ve chosen strong single family residential (SFR) markets, so that’s a good place to focus.] 

Jay’s Jacksonville, Florida property
Kitchen renovation in Jay’s Jacksonville property

[Chad: Can I live in your rental?! These look great!] 

Investment Property Criteria

What formula or numbers do you use to decide if a deal is a good one?

I use a combination of the 1% Rule and IRR.

[Chad: Jay and I discuss both of these analysis tools in more depth in the podcast interview. I also explain IRR and share a spreadsheet for using it to buy rentals in my Rental Property Analysis course.]

Your Team

Do you have any “inner circle” team members like a spouse, business partner, or mentor? If so, how have they helped you to get started.

Along the way, I have met great mentors through books, podcasts, and blogs that have helped me out tremendously. A lot of them don’t know who I am nor I will ever meet in person, but some of them have become great friends.

[Chad: I definitely agree with having virtual mentors in the authors and podcasters you follow. I have books on my shelf from Warren Buffett, John Schaub, Benjamin Graham, and others who I return to over and over.]

Financing & Cash

What type of financing did you use for your first deal (or deals)? And was it difficult to obtain this financing?

On my first deal, I used conventional financing and a line of credit.

No, it was not difficult for me to obtain these loans because I had a W2 job.

Do you plan to continue using this financing in the future? If no, what financing is next? Why?

Right now I’m still using conventional lending since I’m funding all my deals.

I will like to do and explore more the seller financing side.

[Chad: I used seller financing and private financing by necessity because I didn’t have a W-2 job that made bank lending easy. But I still love using both sources of funds now even when I can get bank financing.] 

Where did you get the cash for your first down payment, fix-up money, and reserves? How much did you need to raise?

I saved up all the money from my W2 job.

Deal Finding

How did you find your first deal(s)? What was the owner’s situation that motivated them to sell?

I found my first deal on the MLS. The owner wanted to sell. They wanted to move to another area.

Did you try any deal-finding strategies that didn’t work?


How many potential properties did you look at and/or make offers on before buying your first deal?

Around 10 properties.

Jay’s property in Austin, Texas

Your First Real Estate Deal

What were the basic numbers like purchase price, remodel costs, rent, resale price (if applicable)?

Price: $175k

While I lived in the property I invested around $20k, then I sold it for $244k

At the same time, I had a roommate who paid me rent.

So, I did the Live-In Flip with House Hacking at the same time.

[Chad: I love that combination!] 

What were the biggest struggles and challenges on the way to your first deal?

The biggest struggle was making the decision.

What has been the overall effect of this deal on your life? Lessons learned?

The overall effect on the first deal has been a positive one.

After my first deal, I got cocky and thought that I knew everything. Then I went for my second deal and that deal really made me learn.

Final Tips & Recommendations

What books, blogs, podcasts, and/or YouTube channels have helped you to get started or do you just find extremely valuable? (Can be categories in business, investing, or life/philosophy – other than a sacred book)

Books: John Schaub, Early Retirement Extreme, John Bogle, Ray Dalio, Richard Duncan, Charlie Munger

Blogs: Coach Carson

Podcasts: Coach Carson, We Study Billionaires, The White Coat Investor, Macro Voices.

Any big mistakes you’ve made that others should avoid?

A big mistake that I made was to act on the bias of: Fear of Missing Out (FOMO).

[Chad: Oh, that’s a big one for so many of us. It’s like the curious cat who has to see what’s inside the other room. When others are using a strategy, making money, and posting all over Instagram – we just HAVE to try it out, too. Meanwhile, the boring yet successful strategy you’re currently using is making lots of money! Ha. That’s my version of it. But maybe Jay has had something similar.] 

Anything else you’d like other current or aspiring real estate investors to know?

Get educated on the basics before getting into the Real Estate Investing Business. Every investor needs to learn to take the risk that they can live with. Sometimes we get cocky and confuse luck with skill. It takes time to build experience.

[Chad: Well said, Jay! We wouldn’t become a doctor or an AIR TRAFFIC CONTROLLER without proper training on the fundamentals, would we? Here’s to the never-ending game of learning and improvement as successful investors and people. You’re definitely a great role model in those categories, Jay! Thank you for sharing your wisdom and taking the time to do this interview] 

Do you have questions or comments for Jay? Please leave them in the comments section below.


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    1. Hey Jay. Enjoyed the article. I’m a new real estate investor who lives in Fleming Island. I also invest while having a full time job as a healthcare professional. 2 kids as well, 9 and 3. Could I ask you some questions? I also follow the WCI, as well as Chad Carson (obviously). Keep up the great work, Chad!

  1. Hi Jay. To What type of education are you referring when you say get educated? Books by current investors… courses by investors…??

    1. Hi Vann,
      When I talk about Real Estate Investing education is starting from the basics. Once you start developing the Investing Mental Model, then you need to start learning how the whole economic system and the world works.
      I can tell you that you can start with the Coach Carson courses. He is a great teacher and Real Estate Investor.

  2. There are only few people who shared honest content on this internet & you are one of them & You have done one the fabulous job. This article is filled with a lot of information keep on sharing this kind of information and keep us more educated.

  3. Love the companion article to go along with the podcast. Gets right down to the meat and potatoes of Jay’s journey. Grrat read!

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