Trial, error, and listening to their gut: Stories from a husband-and-wife real estate team

Real estate investor stories
by Brad Cartier, posted in Investor Stories

Real estate investment team Gwynne Wharton and her husband John currently own 5 commercial units, 7 single family homes, and 2 homes used for Airbnb rentals in Charlotte, North Carolina, and Greenville, South Carolina. In addition to their 14 investment properties, stay-at-home mom Gwynne also manages her family and 4 children. She describes herself as the visionary while her husband John is the numbers guy.

Gwynne was kind enough to take time out of her busy schedule to answer a few questions for this month’s investor profile. Here’s what she had to say about why they invest in buy and hold property in the Carolinas.

1. How did you get into real estate – what’s your background, how did you get started, and how does it fit into your life?

Answer: I grew up around real estate. As a kid, I watched my dad build and sell houses and manage his apartment building and other investments while appraising and selling houses. I remember loving the smell of cut wood and sawdust but I didn’t pay much attention until I married my husband. Now though, I owe a lot of what I know to my father and I still pick his brain constantly.

When I got married, my husband John had already purchased a few investment properties and had read Rich Dad, Poor Dad when he was only 15 years old. We decided to grow our real estate portfolio when we were still newlyweds. After making the winning bid online for a really dilapidated foreclosure house, we spent our weeknights and weekends fixing up our first rental. And the rest is history.

Gwynne and John’s first rental property (it cost less than a used car!).

John and I are a team and we learn from each property we invest in. I find and manage our investments and John puts the deals together. He still has a full-time day job but will eventually leave when the time is right. Sometimes it’s crazy trying to raise 4 kids and manage 14 properties, but we’ve figured out a way to make it work. Real estate investing provides us the security in our financial future that we want and lets us teach our kids valuable lessons about life, working hard and delayed gratification.

2. What’s currently in your real estate investment portfolio?

Answer: We own and manage 14 properties: 5 with commercial tenants and 9 single family residential, 2 of which we use for short-term nightly rentals. They’re mostly located near where we live just outside of Charlotte, although we have one in the North Carolina mountains, one at the beach in South Carolina, and a commercial property near Greenville, SC.

Gwynne and John renovated this bungalow and now rent it out on Airbnb.

3. Describe your real estate investment strategy for us – where & what types of property do you invest in, and why you choose the properties you do.

Answer: Buy and hold property has been our bread and butter, going back to when my husband was in active duty in Iraq. During the real estate bust of 2008 – 2011 we scooped up several foreclosures in blue-collar areas. We fixed up the homes to be nice and respectable, but also with a budget-friendly renovation. 

Lately, we’ve been investing in properties that we’re gutting and renovating. It’s more work and more money, but they’re performing well due to the great locations and design. We’ve turned a couple into Airbnb rentals which I have surprisingly really enjoyed. Being a hospitality host on Airbnb requires a different mindset from being a landlord. So far, we’ve been successful at adding them into our property mix and I’ve enjoyed renovating to a different level.

4. Why did you start using Stessa?

Answer: Over the past 10 years I’ve tried several programs, along with using our own self-designed property spreadsheet. Every program seemed difficult to use and the spreadsheet just seemed constraining and slow to enter. If we were to continue to acquire properties, I knew I needed a program that worked for me, not one that slowed me. I strive to find efficient systems to implement so that real estate works for us, not the opposite.

Not too long ago I randomly clicked on a link for Stessa on Facebook and have never looked back. It makes it super easy to organize our property portfolio and analyze key financial metrics like cash flow. Another huge plus is that Stessa is a cloud-based rental property financial management system. I can use it on my cell while I’m waiting for the kids at preschool and then pick up where I left off when I’m back home on my computer.

5. How do you use Stessa to track and manage each property in your portfolio?

Answer: Stessa uses bank-grade security encryption, so I can link to my company credit card and business PayPal account. Then I go through each income and expense transaction online and connect it to the corresponding property. When my handyman sends me an invoice, I take a picture and upload the photo to the right property. Stessa is easy, simple, and extremely user-friendly.

6. Tell us about your – best deal, favorite experience, biggest success – with real estate investing so far.

Answer: I’m proud of the leaps of faith we took. From clicking and winning our first online auction when we were young and naive, to our latest renovation project where I handled every single detail as the “contractor” and crafted it into a nightly rental that guests leave five-star reviews… which happened only after turning one of our long term rentals into an airbnb because my husband trusted my gut and my research.

Investing in real estate doesn’t just happen. You have to set out and work for it. We’ve been blessed with the way real estate blends into our lives and how it’s helped provide for our family but it is not a get rich quick strategy. It takes self-disciple, patience and perseverance. 

Gwynne and John’s latest renovation outside of Asheville, NC, that is now on Airbnb.

7. What’s the biggest mistake you’ve made that you’d like to help other investors avoid?

Answer: We learned the hard way that investing in lower income, Section 8 housing wasn’t for us. Right after I had our first daughter, we purchased a group of six lower income houses. On paper, the deal promised a great ROI, so we decided to go for it. Big mistake. 

I could give you a laundry list of why Section 8 housing didn’t work for us. Let’s just say we sold those houses as quickly as we could. But like President Lyndon Johnson once said, “There is no bad experience unless you gain nothing from it”. We’ve always gleaned something from every property we’ve invested in, both good and bad.

8. What’s the one thing you know now that you wish you knew when you started to invest in real estate?

Answer: Make a lot of offers, because you have nothing to lose. Finding good deals in real estate is a numbers game. If it was easy, everyone would do it. Analyze potential property, because investing in real estate is a business. But don’t become paralyzed by analysis and overthink things.

And keep the naysayers out of your life. There are plenty of people out there that will give you free advice and tell you what not to do: it’s crazy to fix up that house, you don’t qualify, you can’t do this, etc. All those people looking for reasons to not invest though, won’t and just tune them out.

9. What is your favorite book on real estate investing?

Answer: Managing a family of 6 and 14 properties – reading is a luxury I don’t have right now, except for my Stessa emails. I love how they’re educational and the way they keep me current and up to date.

10. What’s your favorite thing about Stessa?

Answer: Would I break the interview rules if I gave you four favorite things about Stessa? It’s easy (and believe me, I need easy in my life!). It works, I can tailor Stessa to our investment portfolio, and it simplifies and streamlines. The CPA who does our taxes is also very impressed with the way Stessa helps us maximize our deductions.

Knocking on doors to make deals happen

Gwynne and her husband John invest in buy and hold rental property in North and South Carolina. They manage and automate their portfolio using the free online property financial management system from Stessa. As Gwynne says, “I hope to encourage others from what we have learned, and if we can do it others can too.” Here are some key takeaways from Gwynne’s experience as a real estate investor:

  • Buy and hold rental property in blue-collar areas can be bread and butter investments
  • Run the numbers and then make offers to purchase based on your investment criteria 
  • Learn what property types work for you and avoid paralysis by over analysis
  • Keep negativity out of your life and go with your experience and your gut – there are always plenty of people around who’ll tell you why something can’t be done!