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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
There is still money available. There are still lenders, contractors, property managers, brokers, wholesalers, and resources to help investors execute once they find the right opportunity. But in today’s market, the hardest part is often finding the actual property.
In this Straight Up Tuesday Tip, Mark Ainley and Tom Shallcross talk through three simple ways Chicago real estate investors can create more deal flow without overcomplicating the process.
The message is direct: stop waiting for the perfect deal to appear on the MLS. If you want to buy a property before the end of the year, you need to tell people what you are looking for, build relationships with wholesalers, and work with brokers who actually understand investment property.
For Chicago landlords and investors, this episode is a reminder that deals do not usually come from one magic source. They come from staying active, building relationships, creating more at-bats, and staying consistent long enough for the right opportunity to show up.
Questions We Answer in This Episode
Q: What is the main challenge for investors right now?
A: Mark says the toughest part of being a real estate investor today is finding the actual property. Financing and resources are available, but good deals require more effort to uncover.
Q: Are there still deals in today’s market?
A: Yes. Mark and Tom both say they are still finding deals, but the process is harder. Investors need to be more intentional and consistent instead of only checking the MLS and giving up.
Q: What is the first step to finding more deals?
A: Tell everybody you know that you are looking. That includes family, friends, office contacts, chat groups, real estate groups, and anyone else who might hear about a property before it hits the market.
Q: Why should investors tell non-real-estate people what they are looking for?
A: Deals often come from unexpected sources. Mark shares that his uncle texted him about a neighbor who may sell before going to market because Mark had already told him he was looking to buy.
Q: What does Tom mean by creating more at-bats?
A: Tom says investors need to become process-oriented. The more conversations, leads, and opportunities they create, the better chance they have of finding a deal that works.
Q: How did Mark’s sale-leaseback deal lead to another opportunity?
A: Mark had lunch with a tenant from a prior sale-leaseback deal and mentioned that he wanted to do more deals like it. Later, that tenant connected him with someone else interested in a similar arrangement.
Q: Why should investors build relationships with wholesalers?
A: Mark says many active investors are finding deals off-market. Even if wholesalers keep some deals for themselves, investors should stay connected because overflow opportunities still come up.
Q: How should investors respond when a wholesaler sends the wrong deal?
A: Tom recommends replying instead of ignoring it. Tell the wholesaler what you are actually looking for, ask them to keep your number, and offer to connect them with someone else if the deal fits another investor.
Q: Why do investment-minded brokers matter?
A: Mark says a regular agent may eventually help you buy something, but an investment-minded broker is more likely to hear about opportunities, understand the numbers, know other investors, and help you move faster.
Q: Should investors look at both the MLS and off-market deals?
A: Yes. Mark recommends doing both because it helps investors understand what is happening on and off the market. That perspective makes it easier to recognize a real deal when it shows up.
Show Notes
00:37 Mark and Tom talk about still finding deals in a tougher market
01:08 Why finding the actual property is the hardest part for investors right now
01:57 Step 1: tell everybody you know that you are looking to buy
02:22 How family, friends, chat groups, and real estate groups can create deal flow
02:24 Mark shares how telling his uncle led to a possible off-market opportunity
02:40 Tom explains why investors need to create more at-bats
03:14 How a prior sale-leaseback tenant brought Mark another potential deal
03:56 Step 2: build relationships with wholesalers and stay connected
05:07 Step 3: work with investment-minded brokers, not just any licensed agent
06:21 Why investors should use both wholesalers and the MLS to understand the market
Takeaways for Chicago Property Managers and Landlords
Finding the property is often the hardest part of investing right now.
Investors need to be intentional about telling people what they want to buy.
Deal flow can come from family, friends, tenants, neighbors, brokers, wholesalers, and real estate groups.
The goal is to create more at-bats, not obsess over one perfect opportunity.
Prior sellers and tenants can become future referral sources.
Wholesalers may not always send the right deal, but every conversation is a chance to clarify your buy box.
Replying to the wrong deal can still build a relationship.
Investment-minded brokers can create better opportunities than general agents who do not understand investor numbers.
MLS and off-market deals should both be part of the process.
Consistency over six months can separate serious investors from the people who only talk about buying.
Guest Name: Mark Ainley, Founder and Partner, GC Realty and Co Host, Straight Up Chicago Investor Podcast
Guest Company Website: www.gcrealtyinc.com
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
