Thinking about wholesaling or buying? Talk to The Bow Tie Attorney first.
Whether you’re assigning contracts, taking properties down, or buying from wholesalers, Mahmoud “The Bow Tie Attorney” Elkhatib helps Chicago investors structure cleaner deals, avoid legal landmines, and protect their long-term reputation.
Wholesale real estate in Chicago looks glamorous on social media: quick checks, fast flips, endless “just assigned” posts. The reality is messier—dead leads, confused sellers, title nightmares, and brutal months where nothing closes and the bills keep coming.
In this episode of Two Bald Brokers and a Bow Tie, Mahmoud Faisal Elkhatib, also known as The Bow Tie Attorney, sits down with Dane from Property Pals USA, a Chicago-based wholesale company doing dozens of deals a year in Cook County and the surrounding suburbs. Together they strip the hype away and talk about what it actually takes to build a real business around distressed property in Illinois.
They cover work ethic, marketing, KPIs, AI, bilingual outreach, mental health, marriage, and why the difference between “busy” and “effective” can be the line between scaling and burning out.
Who Is The Bow Tie Attorney?
- Represents investors, wholesalers, and end-buyers in residential and small commercial real estate across the Chicago area.
- Cleans up title issues, foreclosure risk, code problems, and inherited-property chaos that usually come with distressed real estate.
- Acts as what he calls an “after-the-fact” attorney—often brought in once a deal is already tangled, a seller is scared, or a buyer has signed something they don’t fully understand.
Meet Dane and Property Pals USA
Dane is part of Property Pals USA, a wholesale real estate operation focused on distressed single-family homes and small multifamily properties throughout Chicago and its suburbs. The company does 80–100 deals a year in a good season, and everything is built around one mission:
That means stepping into situations with:
- Behind-on-taxes properties
- Foreclosure timelines
- Inherited homes with multiple heirs
- Properties tied up in old divorces
- Code violations and city headaches
- Houses that are just too rough for the open market
For most owners in these situations, calling a wholesaler or investor is not about chasing top dollar; it’s about finally getting out from under years of stress.
From Military Bases to Backpacking to the Wholesale Grind
Dane’s work ethic wasn’t born in a real estate office. It came from growing up as a military brat, moving from base to base—including a long stretch in Italy—where he learned early that if you want spending money, you work for it.
He mowed lawns on base, picked up odd jobs, and later:
- Bartended his way through late nights and long weekends
- Backpacked through Australia and Southeast Asia, meeting people, improvising, and figuring out how to create opportunities on the fly
- Worked in tech sales, learning how to handle rejection, follow up, and close deals over the phone
That mix—small-business hustle, travel, sales, and constant change—became the perfect training ground for distressed real estate.
From “Hustle Mode” to Building a Real Business
One of the rawest parts of the episode is Dane describing a year where, on paper, his company did a ton of deals—and still ended up negative six figures.
They were working constantly:
- Chasing every possible lead
- Answering every call personally
- Patching together systems as they went
But they didn’t have clear KPIs, clean books, or a reliable way to separate what was urgent from what was important. The result? High volume, low profit, and stress levels through the roof.
That pain forced a shift:
- Building SOPs (standard operating procedures) for acquisitions, dispositions, and transaction coordination
- Getting serious about accounting and knowing, in real time, whether a marketing channel was actually profitable
- Learning to say no to distractions—even if they “felt” like work
This is a recurring theme throughout the conversation: activity is not the same as progress. In the wholesale world, “looking busy” can hide a business that’s silently bleeding out.
Understanding the Distressed Seller in Chicago
Mahmoud and Dane spend a lot of time on the human side of wholesale.
Distressed sellers in Chicago and Cook County aren’t just numbers on a spreadsheet. They’re:
- Adults dealing with a parent’s estate while grieving
- Former couples whose divorce never truly ended on the paperwork
- Landlords burned out by bad tenants and city inspections
- Families behind on taxes, facing sheriff’s sale dates they barely understand
Dane emphasizes leading with empathy:
- Taking time to listen before pitching
- Walking sellers through timelines, even when they’re choosing not to sell
- Being transparent about how wholesaling works, so they don’t feel tricked
Mahmoud underscores why that matters legally and ethically. When wholesaling is done sloppily or deceptively, it can invite lawsuits, attorney-general scrutiny, and regulatory crackdowns that hurt the entire investor community.
See yourself in that distressed seller? Talk to The Bow Tie Attorney.
If you’re behind on payments, facing a sheriff’s sale, or stuck in a messy inheritance or divorce, Mahmoud “The Bow Tie Attorney” Elkhatib can walk you through your real options under Illinois law—before you sign anything or give up your home.
The Role of The Bow Tie Attorney in Wholesale Deals
In a market like Chicago, wholesaling sits at the intersection of contracts, licensing rules, disclosure, and consumer protection laws. Mahmoud explains how his office supports investors and wholesalers who want to operate cleanly:
- Reviewing assignment contracts, purchase agreements, and addenda
- Making sure marketing and scripts don’t over-promise or misrepresent what’s happening
- Helping investors understand what they can and can’t do under Illinois law when they’re not licensed brokers
- Stepping in on foreclosure defense, tax-sale issues, and code violations that might block a closing
The message is clear: in distressed real estate, a good attorney isn’t just damage control. Used early, counsel can become part of the business model, reducing risk and keeping deals from collapsing at the eleventh hour.
Data, AI, and Smarter Lead Lists
The conversation also touches on technology.
Instead of hitting every absentee owner in Cook County with the same postcard, Dane’s company now leans heavily into:
- Layered data – combining multiple distress signals (taxes, equity, time owned, code activity, etc.).
- AI-assisted prioritization – using tools to rank which homeowners are most likely to need help soon.
- Better call structure – giving callers frameworks that sound natural, not robotic, while still gathering key information.
This doesn’t replace human connection—if anything, it makes space for more of it. By cutting down on complete dead-end leads, the team can spend more time genuinely talking with the sellers who actually need them.
Serving Chicago’s Hispanic Communities with Bilingual Outreach
Chicago’s real estate world doesn’t look like a generic CRM avatar. A huge number of distressed properties sit in predominantly Hispanic neighborhoods, where language barriers and fear of legal systems keep people stuck in bad situations longer than they need to be.
Dane talks about:
- Hiring bilingual callers
- Learning Spanish himself (his wife is Puerto Rican, which helps with practice and motivation)
- Understanding cultural nuance—why some families resist “bothering a lawyer” or are nervous about signing anything
Mahmoud, who works daily with immigrant and mixed-status families, reinforces the point: the combination of bilingual outreach plus ethical, clear legal guidance is one of the biggest value adds a wholesaler can bring to these communities.
Stress, Panic, Health, and Marriage in the Wholesale Trenches
It’s easy to pretend that grind culture has no cost. This episode refuses to.
Dane opens up about:
- Experiencing panic attacks and health scares during some of his most stressful years
- The way financial pressure can bleed into marriage and family life
- How easy it is to justify every late night and weekend as “for the business” while slowly burning out
Mahmoud challenges listeners—especially hard-charging investors—to build habits that keep them in the game long-term:
- Clear time boundaries
- Actual days off
- Systems that allow the business to run without one person carrying everything
Long-term success in Chicago real estate is not just about who hustles hardest; it’s about who can still show up healthy, sane, and ethical five years from now.
Sharp in law. Grounded in your next deal.
Whether you’re assigning a contract, buying from a wholesaler, or trying to clean up a messy title, The Bow Tie Attorney helps investors structure deals that close—and protect their long-term reputation in Illinois.
FAQ — Illinois/Cook County Foreclosure
What is wholesale real estate, and how does it work in Chicago?
Wholesale real estate typically involves putting a distressed property under contract at a discount and then assigning that contract to an end buyer—often another investor—for a fee. In Chicago and across Illinois, this has to be done carefully to comply with state law, local regulations, and licensing rules. The paperwork and disclosures matter just as much as the marketing.
Do I need an attorney if I’m just wholesaling and not actually buying the property?
Yes, at least if you want to operate long-term. A good attorney can help you structure your contracts, protect you from claims of misrepresentation, and keep your assignments compliant with Illinois law. It’s much cheaper to have counsel help set up your templates than to fight a lawsuit or regulatory complaint later.
How does The Bow Tie Attorney help wholesalers and investors in Illinois?
Mahmoud “The Bow Tie Attorney” Elkhatib reviews and drafts contracts, addenda, and assignment agreements; advises on marketing and disclosures; handles closings for both assignments and double closes; and steps in when deals are tangled with foreclosure timelines, tax sales, or code issues. His goal is to keep investors doing deals without stepping on legal landmines.
I’m a homeowner in distress. Should I work with a wholesaler or go straight to an attorney?
If you’re facing foreclosure, tax issues, or serious code problems, it’s wise to speak with an attorney first. A wholesaler may be able to buy or assign your property, but a lawyer can explain all your options—including solutions that don’t require selling at a discount. Many of Mahmoud’s clients discover they have more leverage than they were told.
Can investors outside Chicago still work with The Bow Tie Attorney?
Yes. Mahmoud represents investors and homeowners throughout Illinois, including the Chicago suburbs and other counties beyond Cook. If your deal is in Illinois and you’re worried about risk, paperwork, or foreclosure exposure, his office can review the situation and help you map out next steps.
What’s one change wholesalers in Chicago can make right now to run a more sustainable business?
Track real numbers—every marketing dollar, every lead source, every closed deal and assignment fee. When you actually know what’s working, you can cut the noise, protect your time, and build a machine instead of riding an emotional rollercoaster from deal to deal.
