Investor-Friendly Realtor in Chicago: Matthew McMahon, Net Gain Realty

The Seven Bars

1. Deal math, natively. ARV from comparable sales, demand by price band, the 70% rule and what it has to cover, rehab scope, holding costs on real local speed. Not a feeling. Every number I quote comes from MLS comps or public record, and everything that is an estimate gets called an estimate.

2. Lowballs without flinching. A data-backed offer 25% under list is arithmetic, not an insult. An agent who is embarrassed by the number presents it badly, and the presentation costs you the deal or the discount.

3. Deal flow, not alerts. The difference between “I set you up on a search” and “here are the listings in your buy box that aged past their band’s days-to-contract and just cut price, with the seller’s motivation story on each.” I run that screen weekly across 26 Chicago-area suburbs. It’s called the Investor Target Screen, and the aggregate numbers are public.

4. Deal speed. Showings, offers, and attorney-review turnarounds that move at investor pace. Illinois closings run through attorneys; an agent who treats attorney review as leverage instead of friction is saving you money with it.

5. Repeat economics. Investors transact several times a year. The traditional model, where the agent needs a maximum commission on each transaction, was built for tradition, not for you. My model is built the other way around, and the next section shows the math.

6. Chicago-specific competence. Cook County transfer stamps both directions, tax prorations, suburb-by-suburb market speed that varies more than most agents realize, 2-4 flat and garden-unit quirks, and knowing which suburbs flippers actually work.

7. The bench. Contractors I know from working flip crews alongside them, not from collecting business cards. Investor-savvy attorneys and inspectors. If you need a name, you get one I can vouch for.

The One-Conversation Test

Ask any agent, including me, one question about a specific listing: “What’s the most I should offer on this, and show me why.”

An investor-friendly agent answers from comparable sales, the band’s days-to-contract, and the listing’s own history: cuts, relists, time sitting. The answer arrives with numbers attached, on the spot or shortly after with real comps.

A retail agent answers with a feeling, a delay, or a question about how much you love the property.

That’s the whole test. It costs nothing to run.

The Fee Model: Where Flips Stop Leaking Money

Here is the part that makes the rest of this page more than positioning. Most of a flip’s brokerage cost sits on the exit, because the traditional listing fee is a percentage of your resale price, the highest number in the whole deal.

The flat fee is not a lighter service tier. It’s the same full listing job I do on every sale: pricing from MLS comps, professional listing, showings, negotiation, contract to close. The fee is flat because the work of selling a house doesn’t scale with its price, and on a flip exit that tradition-sized percentage comes straight out of your margin.

Run the round trip: $7,500 on the buy plus $1,995 on the exit is $9,495 total brokerage per flip cycle, and $6,905 of the buy side is requested from the seller in the offer. Against a traditional 2.5% listing fee on a $400,000 exit, the exit side alone saves roughly $8,000, and the acquisition side never touches a percentage. There’s a second edge on the buy: your offers request a flat balance from the seller instead of a percentage, so at the same price your offer nets the seller more, which is exactly the help a lowball needs. Round trip, both numbers are fixed before you write the offer, and they repeat on every flip. Two exits a year at a 2.5% listing fee versus flat is roughly $16,000 staying in your deals, using the $400K example. All figures are estimates; run your own numbers in the cost-to-flip calculator.

How the Flat Fee Changes Your Net Gain on a Flip

The listing fee is quoted on the sale price. Adjust it against your actual margin, because that is where it gets paid from.

Example, labeled as an example: you buy at $250,000, put $70,000 into the rehab, carry $20,000 of holding and closing costs, and exit at $400,000. Your gross margin is $60,000. A traditional 2.5% listing fee on that exit is $10,000, which is 17% of your margin. Net Gain Realty’s flat $1,995 is 3% of the same margin. The percentage is charged on money you borrowed and money you paid contractors; the flat fee is charged for the listing job.

Call that the fee-to-margin ratio. It is the number a percentage agent never puts in front of you, because it gets worse as you get better: push the same $60,000 margin through a $500,000 exit and 2.5% becomes $12,500, 21% of a margin that did not grow.

Two things follow for an investor.

The fee stops scaling with your exit. On the example above the exit-side difference would be about $8,000 per flip. Four flips a year at that example would keep about $32,000 of net gain in the business instead of paying it out as a percentage. That is arithmetic on the example, not a promise about your deals.

The exit fee becomes a pricing tool. Roughly $8,000 of fee you are not paying is roughly $8,000 of room. In a price band where demand, supply, and days-to-contract all say the house will move, I believe an investor can list a few thousand under the comparable set, draw more showings and a faster contract, and still net more than the same house priced at the comps with a percentage fee on top. Where the band is slow, that room is margin you keep. Either way the decision is yours to make with the numbers in front of you.

Net Gain Realty’s flat fee has kept $56,645 with sellers across its four closed listings (August 2025 through August 2026), measured against an example 2.5% listing fee. On a flip that repeats every cycle.

How I Measure Against the Seven Bars

• Deal math: every offer range I produce comes from comparable sales and the suburb’s real market speed, and I will show you the comps. What I will never hand you is a resale projection. Resale underwriting is yours; the Target Screen gives you condition-verified targets, motivation stories, and market speed to run it on.
• Lowballs: the Target Screen exists to find houses where a low offer is defensible, and the motivation ledger on each target (relist trails, failed listings, estate sales, long aging) is what makes it defensible in the presentation, not just the spreadsheet.
• Deal flow: weekly screen, 26 suburbs, addresses to clients.
• Speed: all four of Net Gain Realty’s closed listings (August 2025 through August 2026) sold over list price, and each went under contract within five days. Observed results on those sales as of September 2026, not a promise about yours; they tell you how a listing gets run.
• Repeat economics: the table above.
• Chicago competence: I work the southwest Cook suburbs where Chicago-area flipping concentrates: Oak Lawn, Burbank, Country Club Hills, Alsip, Midlothian, Oak Forest, Orland Park, Tinley Park, Worth. Nobody claims this territory as an investor specialty. I do, because the county’s own parcel records show it’s where the flips actually happen.
• The bench: contractor referrals come from crews I’ve worked alongside. Ask for names when you need them.

Who This Is For, and Who It Isn’t

This works if you already think like an underwriter: you want verified inputs, defensible offers, and a fee structure that respects volume. It is not for you if you want an agent to tell you what a flip will make, carry your conviction for you, or find you a deal nobody has to negotiate for.

Start With the Screen

The fastest way to evaluate all of this is to see the product. I run the Investor Target Screen weekly across 26 Chicago-area suburbs: qualified lowball targets with offer ranges and motivation stories, the watch list, and each area’s exit windows. Aggregate numbers are public. Addresses go to clients.

Apply for this week’s screen →

Run your deal math first →

Deciding whether to use an agent at all? Start here →

Net Gain Realty is a licensed Illinois brokerage (#481.014232). Commission rates are negotiable and not set by law. All figures are estimates. Traditional fee comparisons use example rates of 2-3% on the listing side only.