In Chicago, we tend to be critical of so-called “bandwagon” fans. They’re the ones who only start rooting for the Bears or the Sox when the season’s going good. But I don’t mind them, maybe because of my real estate experience. I know that people jump onto the real estate bandwagon when the market is good. 

The market in Chicago in the last year has been particularly good. There have been more houses on the market and pent-up demand from the beginning of the pandemic has been released. More people have started to invest in real estate during the pandemic. Unfortunately, not everyone knows how to do it right. 

Getting started in real estate investing means doing a lot of research. It also involves following the right people—those who have done this before. 

If you want to get into real estate investing, here are some of the best Chicago real estate investors you should follow this year. 

best Chicago real estate investors

Why You Want to Follow Chicago Real Estate Investors

If you’d asked me what would be the best way to become a real estate investor during a pandemic, I wouldn’t have known what to tell you. Though, I can tell what it’s like to be a house flipper in Chicago in a market high, as a result of a pandemic. And that’s the thing I love about this business: there is a playbook, but each situation in each area for each investor is different. 

That’s why I recommend listening to and following different successful investors in your area. They know the market and they know how to start off on the right foot to maintain during difficult times. There are a lot of people with the experience to be flexible when the market calls for it. Those are the lessons you want to learn. 

The Best Chicago Real Estate Investor Groups to Follow

In a city as big as Chicago, there are many types of real estate investor groups to follow. Here is a couple. 

Real Estate Investor Clubs 

Real estate investor clubs exist for investors and other industry professionals to regularly meet, network, and learn from one another. The Chicago Area Real Estate Investor Association (CAREIA), for example, is a non-profit group of real estate professionals who meet to support each other and advance the industry. Becoming a CAREIA member also means you become a member of the National Real Estate Investors Association (National REIA). Membership also includes access to networking events and support from seasoned investors. 

If you’re just starting out, real estate investor clubs in Chicago can be a great way to network and gain mentorship. 

Real Estate Agents (and Those Who Use Them)

When you’re looking for real estate investors to follow, you’ll likely come across a ton of advice. Some will tell you that the best way to start investing in real estate is by partnering with a real estate agent. In hiring a real estate agent, you’re essentially paying them to give you leads. Here in Chicago, companies like the ProInvest Realty Group offer services to help with ongoing management in addition to leads.   

Of course, these are not exclusive leads. Very few real estate agents have a one-on-one relationship with an investor. More than likely, there will be competition. But that doesn’t mean you shouldn’t work with them. It just means there might be better people to turn to for advice. 

If you’re looking for a more individualized networking relationship, consider following a real estate investor in Chicago who’s had a long, successful career.  

The Best Chicago Real Estate Investor to Follow 

When I think of successful real estate investors in Chicago, one of the first names that comes to mind is Alan Washer. Alan started his career in Dallas in 1999 and moved here to Chicago in 2003. If you remember back in 2003, there was a lot of growth here, especially in the downtown area before the bubble burst in 2008. 

Those were pretty good years for investors, though, if they knew what they were doing. Alan, an independently owned and operated HomeVestors® franchisee, did really well during that time and continues to do so today. 

It was tricky for him to move to a new city to continue his real estate investing career, especially in a new market. He had to learn the market, understand the trends, and figure out which neighborhoods to invest in. He’d told me that being a HomeVestors® franchisee gave him access to training and information that shortened the learning curve, setting him up for success. 

In 2010, Alan became a HomeVestors® Development Agent to help new franchise owners learn the lay of the land and build a foundation so that their businesses can thrive, even when the economy is fluctuating.

There are many more successful real estate investors like Alan who maintain a pulse on the Chicago market but also take the time to mentor up-and-coming investors.  

Join a Network of the Best Real Estate Investors in Chicago

Alan and I have a few things in common; most notably, is the fact that we both invested in independently owned and operated HomeVestors® franchises. It was the best decision I ever made in my real estate investing career. Their program, tools, and technology allowed me to focus on getting quality leads and actually closing deals. 

HomeVestors® has one of the best real estate lead generation method in the business. The We Buy Ugly Houses® campaign is known everywhere in Chicago. When homeowners need to sell fast, they call HomeVestors®. And I can get the quality lead. 

If you’re just starting out, getting quality leads can be hard. And, you don’t want to spend money paying for leads that come without motivated sellers and tons of competition. With HomeVestors®, you’re in contact with motivated sellers and you’re able to learn from experienced real estate investors like Alan and me. 

The real estate investment bandwagon is rolling. It could be time to get on. If you’re considering investing in real estate in Chicago, request information about becoming a franchisee today


Each franchise office is independently owned and operated.


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