Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
A lot of people look at wholesalers and assume they started by blasting out marketing, locking up deals, and flipping contracts right away. That is not how Brendan Mlaney’s story started. His path began with house hacking, learning construction the hard way, screening tenants himself, and slowly building enough confidence to move from owning a couple of properties into creating off market opportunities for other investors across Chicago.
What makes this episode good is that it does not pretend the path was clean. Brendan talks openly about doing bad rehab work on his first house hack, spending money on marketing without getting quick results, using 0% credit cards to keep things moving, joining a mentorship when the business was struggling, and learning some expensive lessons from deals that fell apart. That honesty matters because a lot of people want to get into off market real estate, but not enough people talk about what the early mess really looks like.
For Chicago investors, there is also a bigger lesson here. House hacking was not just Brendan’s first deal strategy. It was what gave him enough financial breathing room to survive the slow months, keep marketing when results were delayed, and stay in the game long enough to get traction. That is a big theme throughout the episode. The first move does not need to be flashy. It just needs to put you in a stronger position for the next one.
Housing Provider Tip of the Week
The housing provider tip of the week focused on suburban Cook County security deposit limits under the RTLO. Mark pointed out that a lot of landlords still do not realize they cannot just collect two or three months of security deposit anymore in suburban Cook County.
The rule he discussed was that landlords can collect no more than one and a half times the monthly rent as a security deposit. He also noted that the tenant has the option to pay that extra half month over the first six months in installments. This does not apply to Chicago in the way he framed it here. He was specifically talking about suburban Cook County municipalities like Schaumburg, Berkeley, Hillside, and other suburban areas covered by the ordinance.
Questions We Answer in This Episode
Q: How did Brendan first get interested in real estate?
A: He said it started pretty young, back in his teenage and high school years, when he began thinking about what kind of life he wanted. At that stage, he viewed real estate as a path to passive income and freedom, even if he now laughs at how simple that seemed when he was younger. Still, that early curiosity was real, and it pushed him to start learning, networking, and eventually taking action.
Q: What got him from interest to actually buying his first property?
A: After college, Brendan worked a W2 job as an actuarial recruiter. Because the job was mostly commission-based and he had some success in it, he was able to save for a down payment. From there, he started focusing on house hacking as his way in, and that eventually led to his first purchase in 2018.
Q: Who helped Brendan get started the right way?
A: He gives a lot of credit to Brie Schmidt. He explains that she took him under her wing, showed him how to evaluate properties, walked a lot of deals with him, and helped him understand what to look for in a house hack. She also helped him get his first and second deals, and he is clear that her guidance played a major role in where he is today.
Q: What was Brendan’s first deal?
A: His first house hack was in Kilbourn Park, and he still owns it today. That first purchase gave him a place to live, rental income, and a hands-on education in rehab, leasing, and ownership. It also turned into a huge financial advantage later because it created monthly cash flow that helped support him when he transitioned into wholesaling.
Q: What did he get wrong on the rehab side early on?
A: A lot. He openly says he had zero experience and was learning everything through what he called YouTube University. He painted the wrong way, struggled through flooring installation, and made mistakes with uneven floors and cement board that later caused cracking. He also leaned on his dad to help, which turned simple favors into much bigger projects. The work was not perfect, but it taught him a lot about construction, labor, and what not to do next time.
Q: Was doing the rehab work himself actually worth it?
A: In some ways yes, and in some ways no. He gained firsthand knowledge, learned how the work gets done, and now has a better eye when contractors price jobs or when repairs are discussed. But looking back, he also believes he probably lost money by taking too long. Since he was working a full-time job and only rehabbing nights and weekends, he delayed getting the unit rented and carried more stress than he probably needed to.
Q: How did Brendan handle leasing and tenant screening on his own rentals?
A: He built a simple but smart process. He used Zillow and Facebook for marketing, created templated responses, shared video walkthroughs and pictures before people ever came out, and required prospects to fill out a Google questionnaire before he would show the unit. That let him screen for basics like income, reason for moving, timing, and whether someone could follow directions. It helped cut down on wasted showings and tire kickers.
Q: How did Brendan get into wholesaling?
A: His first wholesale opportunity came through a personal connection. His mom had a friend who wanted to sell a three-flat in Portage Park. Brendan talked to the seller, got a sense of the price, and then called Mike Baker, who he had met at a real estate event hosted by Brie Schmidt. Mike walked the deal with him, confirmed it was worth locking up, and helped guide him through the process. That first wholesale deal ended up coming full circle because Tom actually bought it.
Q: Did that first wholesale deal immediately make Brendan want to become a wholesaler full-time?
A: Not exactly. He still saw real estate more broadly at that stage. He knew he wanted to do more than just house hack, and he liked the idea of either flipping or wholesaling as a side business while he still had his W2. What pulled him toward wholesaling was that it was more of an in and out model. He did not have to take on the contractor headaches and renovation risk the same way he would with flips.
Q: What did starting a real wholesaling business look like for him?
A: At first, it was pretty modest. He was spending about $2,000 a month on marketing while still working full-time, and it took four to five months before he got the first real result from that effort. That first deal made around $35,000, which was a big moment, but he is honest that the early stretch was not easy and definitely tested his confidence.
Q: What would Brendan do differently if he were starting wholesaling over today?
A: He says he would do the cheapest thing possible in the beginning and spend more time learning sales before throwing more money into marketing. His point is that new wholesalers often assume a channel is broken when really they are the weak point in the process. He believes many beginners would be better off focusing on something like cold calling and getting more real conversations with sellers instead of burning cash on more expensive channels too early.
Q: When did wholesaling become full-time for Brendan?
A: He got laid off from his W2 job during a restructuring, but by then he had already started building the wholesaling business on the side. He also received three months of severance, which gave him some breathing room. Rather than go back into corporate work, he used that moment to go all in on wholesaling.
Q: How important was house hacking to that transition?
A: It was massive. Brendan explains that the first house hack was already producing more income than the mortgage even while he lived there, and once he moved out and rented the final unit, the cash flow improved even more. Then he repeated the process with another house hack. Together, those properties gave him enough monthly support that he could survive stretches where wholesaling income was inconsistent.
Q: What were some of the hardest parts of building the wholesaling business?
A: Inconsistent results, bad sales conversion, and the temptation to constantly switch marketing channels. Brendan says one of the dumbest mistakes they made was stopping and starting different marketing strategies before really mastering any of them. They would try one thing, get frustrated, stop, and then jump to another. He now believes the marketing source matters less than the ability to handle leads, understand KPIs, and convert at the sales level.
Q: What is one deal that taught Brendan a painful lesson?
A: He shared a deal in Calumet City where they had a tenant-occupied property under contract and could have sold it with the tenant in place for a decent profit. Instead, they tried to squeeze more money out of it by waiting for the tenant to move out so they could sell it for more. The tenant had trouble finding a new place, the seller stopped paying the mortgage and started using the rental income himself, and by the time the property was vacant the payoff had climbed so much that the deal was dead. They made nothing. His takeaway was clear. On messy deals, take the money and move on.
Q: What changed in Brendan’s business after those early struggles?
A: He got more focused on the right areas, cleaner deal profiles, and better process. One big shift was realizing they were spending too much time in areas where title problems, tax issues, water bills, and other complications made deals far more likely to fall apart. That pushed them toward stronger zip codes and better neighborhoods where the success rate could improve.
Q: What kind of deals excite Brendan the most now?
A: North side Chicago deals, especially B+ type neighborhoods like Albany Park, Mayfair, and Portage Park. He explains that distressed opportunities in those kinds of areas do not come up nearly as often, so when they do, buyers move quickly. That is very different from lower-demand pockets where deals may be everywhere but much harder to exit cleanly.
Q: Where does Brendan want to go over the next five years?
A: He wants to build a rental portfolio, but not one made up of single-family homes. His focus is more on six to twenty unit buildings. He likes that size range because it lets him scale faster, concentrate units, and work more in the commercial valuation world where value is tied to NOI and income rather than just what sold nearby.
Top 15 Timestamps
03:18 Housing Provider Tip of the Week on suburban Cook County security deposit limits
04:24 Brendan gets introduced and the conversation starts with his real estate journey
04:55 Why real estate interested him from a young age
05:55 Saving commission income and preparing to buy the first house hack
06:19 How Brie Schmidt helped him learn to evaluate deals
07:23 First rehab mistakes, YouTube University, and learning construction the hard way
09:57 Brendan explains his leasing process and Google prescreen form
12:47 How his mom’s connection led to his first wholesale opportunity
13:53 Meeting Mike Baker and getting help on the first wholesale deal
17:17 Starting paid marketing while still working a W2
19:44 Getting laid off and using severance to go full-time into wholesaling
22:17 Why beginners should focus on cheaper marketing and better sales skills first
25:23 A painful tenant-occupied deal that fell apart after trying to push for more profit
35:46 Why Brendan narrowed the business toward better zip codes and cleaner deals
47:36 Brendan shares his longer-term plan to build a six to twenty unit rental portfolio
Takeaways for Chicago Landlords and Investors
House hacking can do more than get you into your first property. It can give you the financial cushion to take bigger swings later.
Doing your own rehab work teaches a lot, but it can also slow you down if time is your bigger cost.
A simple prescreen system can save a lot of wasted time when leasing units.
Your first wholesale deal does not need to come from some big marketing system. Sometimes it starts with one relationship.
Marketing alone does not fix a weak sales process.
If you keep changing channels every few months, you may never get enough reps to know what actually works.
On messy deals, trying to squeeze out every last dollar can cost you the whole assignment.
Better neighborhoods usually mean cleaner exits, fewer surprises, and stronger buyer demand.
Credibility matters more as you grow, but a lot of trust still gets built through how you communicate.
If your long-term goal is multifamily, flipping and wholesaling can be a tool to build the capital that gets you there.
Guest Info
Guest Name: Brendan McElhaney
Guest Company: Cash for Chicago Houses
Guest Link: https://www.cashforchicagohouses.com/
Guest info
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
 (3)_14.png)
