In this episode of Bow Tied in Real Estate, Mahmoud “The Bow Tie Attorney” Elkhatib talks with Chicago broker Jamie McDaniel about what it really takes to build an investor-focused business in off-market real estate: losing early wholesale deals, spotting scams in joint ventures, trusting your gut, and using CHA mobility areas and opportunity zones to build stronger rental portfolios.
Jamie McDaniel lives in the messy middle of Chicago’s investor world: wholesalers, off-market deals, Section 8 tenants, CHA mobility areas, and all the things that can go wrong between contract and closing. She is not a guru with a highlight reel. She is a licensed broker who actually walks buildings, talks to tenants, and helps investors make decisions based on what is real, not just what is on paper.
In this episode, Mahmoud “The Bow Tie Attorney” Elkhatib brings the legal counterweight from EV Häs, LLC. Jamie shares the war stories from the field; Mahmoud explains how those same issues show up in courtrooms, title reports, and lawsuits when people try to skip steps.
There is no shortcut in real estate that does not come back later. Process is the only thing that consistently survives the market.
Jamie’s path back into real estate wasn’t glamorous. After years as a stay-at-home mom inside a family structure, she re-entered the market and had to build an investor-focused business where she is marketing, operations, accounting, and sales all at once. The pressure of keeping a business alive while still showing up for her family is exactly why she is so blunt about boundaries, process, and saying no when something feels off.
If you are under contract on a “special” zone property, our team can quickly flag zoning, program, and contract issues before you pour rehab dollars into the deal.
This scan is a fast, business-focused review—not full legal advice—but it will help you ask sharper questions and know when you need a deeper attorney consult.
This episode is for investors, wholesalers, and small business owners who are tired of highlight reels and want to understand how deals really work in Chicago. Mahmoud and Jamie break down the emotional and practical side of building an investor-focused business: the early losses, the sleepless nights, and the systems you have to build if you want to survive more than one cycle.
You will hear how missed water bills, zoning surprises, and pulled funding can kill a deal at the closing table; how scams and power plays show up around “joint venture” offers; and why tools like CHA mobility areas, opportunity zones, and enterprise zones are still wildly underused by most investors.
Jamie has been a broker for years, but the story that matters starts when she went all in with investors and off-market work. After time at home raising kids, she came back into a completely different world—one where she was hunting deals, managing risk, and trying to keep a business alive while still carrying family responsibilities.
“There’s no substitute for the process.” You do not walk into the gym and deadlift 150 pounds on day one, and you do not walk into off-market investing and immediately pocket easy five-figure spreads.
Her point is simple: your brain, your emotions, and your systems can only handle so much at a time. You take hits, you learn, and you build capacity one rep at a time. That mindset is what keeps her grounded when a deal blows up or a month does not look like the spreadsheet—and it is what she wants investors to absorb before they chase the next “easy” win.
Jamie’s first year in the wholesale world was brutal. She jokes that she paid tuition directly to the school of hard knocks: every single wholesale deal she locked up in that first year fell apart before the finish line. The reasons were not exotic. They were exactly the issues rookie investors and wholesalers tend to ignore until it is too late.
If you do not have a checklist, you will pay for your education in cash, time, or both.
Water bills that were large enough to blow the numbers. Zoning changes right before closing that suddenly turned a four-unit into “three plus one.” Funding pulled at the last minute because the paper did not match reality on the ground. From the EV Häs side, Mahmoud has seen the same thing: full table, funds wired, everyone suited up—and the deal dies because no one read the zoning certificate or confirmed the legal unit count with the city.
Those are the moments when a competent real estate attorney is not a luxury; they are the difference between closing and starting over.
EV Häs, LLC reviews JV agreements, assignments, and side letters for Chicago investors so you understand exactly what you are signing—and can walk away from structures that quietly strip you of control.
One of the most important themes in this episode is learning to sniff out scams and power plays in Chicago’s investor space. Jamie shares a recent story: she had a contract on a property, agreed verbally to joint venture with another investor, sent a proper JV agreement—and got back a document labeled “joint venture agreement” that was actually a fully filled-out assignment of contract trying to grab control of the entire deal.
When she confronted him, the responses were classic scammer moves: “That’s how we do business,” and “Why does this throw you off?” The goal is to make you feel ashamed or overly emotional so you override your intuition and sign something that only benefits them. Jamie did not bite. She paused, called trusted colleagues, and confirmed that this person had a reputation.
If it feels off, slow down. Say out loud, “This doesn’t feel right. I need time,” and route it to your attorney before you sign anything.
Jamie is very clear about how she positions herself. She is a licensed real estate broker who works almost exclusively with investors, understands wholesale and off-market dynamics, and actually goes to the properties instead of winging it from a spreadsheet. She sits between two extremes: traditional agents who live only in MLS world, and unlicensed wholesalers who stack fees and never put boots on the ground.
On the front end, she helps investors find and evaluate deals, walks interiors and blocks in person, and connects clients with contractors, architects, board-up crews, dumpster companies, and other local vendors. On the back end, if someone buys through her, renovates, and wants to sell, she can list the property for a flat fee instead of a traditional six-percent commission—protecting investor margins when it makes sense to exit, and advising them to hold when it does not.
One of the most practical parts of the conversation is Jamie’s breakdown of CHA “mobility areas.” Most investors hear “Section 8” and picture only one type of neighborhood. In reality, mobility areas are higher-opportunity parts of the city and suburbs—often with better schools and lower crime—where voucher holders can qualify for higher rent ceilings.
Jamie gives the example of a two-bedroom condo in Beverly, where market rent might be in the $1,400–$1,600 range, but the right mobility voucher can support around $2,600 per month if the owner and unit qualify. For investors who combine quality rehab, careful screening, and good management, that mix can create resilient, cash-flowing assets.
Local programs like mobility areas and opportunity zones are not “secret hacks”—they are public tools that can quietly turn a marginal deal into a great one, if you slow down long enough to use them correctly.
Jamie and Mahmoud also talk about opportunity zones, enterprise zones, and local grant programs that can help pay for façade work, roofs, windows, and other structural items. In the right project, investors may even qualify for sales-tax exemptions on rehab materials—saving thousands of dollars on a single job—if someone on the team actually checks the rules and files the paperwork.
Underneath all of this is a simple recipe they both stand by: integrity over flash, intuition over pressure, process over shortcuts, and strong legal and professional support instead of winging it. For Chicago investors who want to work in mobility areas, opportunity zones, or off-market deals without feeling like an outcast or a mark, having the right circle around you is non-negotiable.
With partners like Jamie McDaniel in the field and The Bow Tie Attorney on the legal side, you can evaluate Chicago-area deals with local eyes and a clear plan instead of guessing from a spreadsheet.
These answers are general education, not legal advice. Contracts, programs, and zoning rules vary by property and by county. Talk with a licensed Illinois attorney and qualified tax professional about your specific situation before you invest.
An investor-focused broker helps you buy and manage properties as investments, not just “homes.” Jamie finds and evaluates both on-market and off-market deals, walks properties in person, coordinates with contractors and vendors, and structures transactions so investors understand the real condition, risk, and upside before they commit.
Traditional agents usually focus on owner-occupants, MLS listings, and emotional priorities like “dream homes.” An investor-focused broker speaks the language of rent ranges, rehab budgets, ARV, cash flow, and exit strategy. The goal is not just to close a sale but to help you build a profitable, sustainable portfolio that still makes sense after the dust settles.
Mobility areas are neighborhoods identified by housing authorities like the Chicago Housing Authority (CHA) as higher-opportunity areas—typically with better schools, lower crime, and more stability. In those zones, tenants with vouchers can often qualify for higher rent ceilings than in standard areas, as long as the owner and unit meet program requirements.
If you buy in the right mobility area and work with qualified voucher tenants, you may be able to earn stronger, more stable rents than you would with a typical market-rate tenant in the same building. You also anchor your portfolio in neighborhoods with better long-term fundamentals.
The tradeoff is that you must follow CHA rules, pass inspections, and structure leases properly. That is where having both a knowledgeable broker and a real estate attorney matters.
Opportunity zones and enterprise zones are areas where government policy encourages investment through tax incentives, fee reductions, or grants. For investors, that can mean access to funds or tax relief for certain improvements, or long-term tax advantages when projects are structured correctly.
You still need solid legal and tax advice to qualify for these benefits and avoid missteps, but when used well they can drastically change your project’s numbers.
Red flags include being pressured to sign documents you have not fully read, “joint venture” agreements that are really assignment contracts in disguise, partners who resist written agreements, and people who make you feel ashamed or “too emotional” for asking questions.
Slow down, keep control of your contract, insist on clear written terms, and have your own attorney review JVs, assignments, and side letters before you sign. A small legal fee up front is cheaper than fighting over who controls the deal later.
Tell us what notice you received or your next court date. We’ll confirm where you are in the process and recommend your strongest next move—without panic or guesswork.
We typically respond the same business day or the next business day.
