Matt and Michele recently moved back to Chicago after having lived in Los Angeles for several years. Tired of working in the corporate realm, they wanted to try their hands at buying, renovating, and selling houses in their old stomping grounds. The only problem was, outside of a few old high school connections and family, they didn’t know a lot of people—especially in the world of real estate investing. When I met Matt and Michele, they were looking at joining one of the many real estate investor clubs in Chicago, hoping to learn more about investing, do a little networking, and maybe find a mentor.

Because I’ve lived and worked in the Windy City my entire life, and have been a real estate investor for much of that time, they looked me up and asked my opinion. Certainly, sifting through the many investor clubs available here to find one that’s worth your time can be a daunting task. Together, we took a look at the most popular local options so that they could choose the best one and get on with their new career in real estate investing.

Real Estate Investor Clubs in Chicago: How to Connect With the Best Mentors

Connecting With Mentors at Chicago’s Real Estate Investor Clubs

Maybe it goes without saying, but a real estate investor club should be a place where investors and other industry professionals regularly meet, network, and learn from one another. Though the experience of the members will naturally run the gamut from novice to expert, the best clubs will also help investors of all levels establish mentor relationships with those who have seen the kind of success they hope to achieve and who are willing to freely share their insights without furthering their own agendas.

Of the Chicago real estate investor clubs that Matt and Michele were considering, there were several that looked promising. Let’s take a closer look at each:

  • Chicago REIA Northshore is a Glenview-based club hosted by the founder of Chicago Cash Flow. There is no cost to join, but donations are encouraged. A glance at the calendar of past and upcoming events shows that the organizers are very active, scheduling meetings at least once a week on topics such as deal structuring and evicting tenants. With over 850 members in the group, ranging from private and hard money lenders to real estate rehabbers, the breadth of experience available appears to be far-reaching and the likelihood of finding a mentor easy. But, for as many members as this group has, less than 1% typically attend meetings–including the hosts. That makes the chances of finding a mentor pretty slim.
  • Chicago Real Estate Investing Group (RING) has an even more impressive number of members: 945. Since 2014, this Chicago-based club offers a place to meet industry professionals, get inspiration, and find or bring “off-market” deals. Donations are accepted, but the club is also sponsored by several other businesses. Of course, therein lies the rub. Two of the sponsors are also the organizers: Diamond Equity Investments, a platform for buying and wholesaling properties, and the REI Diamond Show, a real estate investing podcast. As infrequently as this club meets–only 17 times in the last three years–its purpose may be more focused on promoting their own business interests, rather than educating and inspiring other investors.
  • Chicago Real Estate Investing Success Group was founded in 2016 by a long-time Chicago investor and developer. Their once-per-month meetings center on the specialties of multi-family, residential, condo conversion, and commercial real estate. All investors, agents, and other real estate professionals are invited to take part in the free talks on real estate law, picking contractors, and how to Airbnb your property. Unfortunately, as we’ve seen before, very few of the club’s 500-plus members show up. And though the organizer himself is a mentor, he’s likely the only one you’ll meet if you go.
  • Chicagoland Real Estate Investment Group offers members training on how to be a real estate investor, in addition to the opportunity to network with other pros in the Northbrook area. This free-to-participate club has been meeting since 2015 to learn topics from getting deals funded to acquiring out-of-state properties. But, though the organizer has some very impressive credentials, the group’s expertise and loyalties may lie elsewhere. After all, it’s run by members of Barnett Capital–a company with its own real estate portfolio to manage. This might explain why there hasn’t been a meeting for its 261 members since January 2017. A club that only meets a couple of times a year, and that’s hosted by a lending firm with its own agenda, probably won’t bolster the success of new local real estate investors.
  • North Side Chicago Real Estate Investors – Redevelop U holds free meetings for its 2,000-plus members at rehab and construction sites where, in addition to seeing the various stages of renovation first hand, members can network and bring wholesale deals. Started in 2014, Redevelop University focuses primarily on Chicago’s north side and discusses everything from raising capital to flipping houses and finding deals on the MLS. Attendance is stronger than at other clubs, but not by much. Still, as a real estate broker, builder, coach, and speaker, its founder seems to have the right stuff to lead these meetings. Unfortunately, they don’t happen very often. So any chance of meeting a mentor, or receiving a good education, may have to wait … till next month.

All in all, none of these Chicago real estate investing clubs offer enough in the way of connecting members with a real estate investing mentor who’s legitimately vested in their success. Nor do any of them provide ongoing, relevant, actionable training in any form. At best, these and other real estate investor clubs are vehicles for networking with some of your peers or vendors who want your business. That’s not always bad, but it’s not the best you can do either.

Connecting with the Best: HomeVestors® Development Agents

In light of the options before them, Matt and Michele asked me what I would do if I were in their shoes. I told them what I did long ago: become an independently owned and operated HomeVestors® franchisee.

As a franchisee, I received training in real estate investing and personalized one-on-one mentoring with a HomeVestors® Development Agent, in addition to marketing and lead generation tools that set me apart from most of the new real estate investors who join investor clubs. After my own real estate investing business took off, I decided to share what I’d learned and become a Development Agent too. Now I get to help new franchisees like Matt and Michele see their dreams come true.

If you’re ready to ditch your old career and land a new one in real estate investing, contact HomeVestors® today!


Each franchise office is independently owned and operated.


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