Winston Deloney Shares Four Reasons Why He Stuck With Real Estate Investing And Didn’t Quit

5 Reasons FSBO is a Bad Idea for Sellers

Making the decision to enter the world of real estate investing is no small undertaking. It can be challenging, and like any investment, there is the potential for loss. But there are plenty of reasons why real estate investing is worth the difficulties, and that’s why many savvy investors choose to diversify their portfolios with real estate investments. 

Winston Deloney, a real estate investor based in Chicago, Illinois, knows the ups and downs of the real estate investing world all too well. We sat down for an exclusive interview with Deloney, to talk about some basics every new investor should know, and why he stuck with real estate investing, and didn’t quit.

Winston, tell us about your experience with real estate investing.

I’ve been investing in the real estate market in the Chicago area for quite a while now, and it’s a very interesting place to learn the ropes of real estate investing. The market has changed a lot over the past few years, and it was a great place for me to learn the essentials and challenges of investing in the market. 

While I was learning, I definitely went through some challenges. Now, as I grow my own portfolio, I like to share advice and tips I’ve learned along the way, to help others learn the things that I learned first-hand. In fact, I recently spoke about the 2020 real estate trends that I think every investor should be aware of.

If you want to stay ahead of the curve and educate yourself, you can check out my most recent interview with TheDailyBlaze:

What are some of your main methods of real estate investing?

There are plenty of ways to invest in real estate, but two of my favorites are wholesaling and fix-and-flips. I invest in real estate using both of these methods regularly, and they can be great for both beginners and seasoned investors alike. 

Why would someone choose to invest in wholesaling or fix-and-flips?

There are plenty of differences and distinctions between wholesaling, and fix-and-flip investments, and it’s important to know those differences before choosing to invest. I just recently launched my website and wrote an article about five things all investors need to know about wholesaling and fix-and-flip investments.

If you are a new investor and would want to try wholesaling and fix-and-flip, I recommend you to give it a read.

You say you went through some challenges, what were they?

Well, when you’re new to real estate investing, you’re learning a lot of things on the fly. With fix-and-flips for example, you have to learn to judge how much work a property is going to need when you start the remodel, and it can be tough to know what you’re going to find under the surface. 

Honing that eye can take some time, and at first, I wasn’t investing in the right fix-and-flip properties, and that definitely presented me with a lot of challenges. And with wholesaling, you have to really have sharp marketing skills, and develop a network. That was also a learning curve for me at first.

But despite those challenges, you still stuck with real estate investing? Why?

Yes, and I’m very glad I did. Firstly, I saw other people around me succeeding, and I knew I couldn’t quit, because I saw that succeeding in real estate was attainable. Real estate investments are also stable, and somewhat independent of the stock market, so in general, I find them to be a wise investment. 

I also feel that things that are difficult can often give you the biggest reward, and that’s definitely my experience with real estate investing. The payouts have been well worth it. And lastly, I was really looking for ways to create new revenue streams, and real estate investing helped me get there.