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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Wholesaling looks simple from the outside.
Find a motivated seller, put the property under contract, assign the deal, make a fee, and move on.
But as Eric Field explains in this episode, the real business is much more complicated. There are marketing costs, seller conversations, attorney issues, licensing rules, investor relationships, construction estimates, dispositions, distressed property problems, and the need to build a real company instead of chasing one-off deals.
Eric entered real estate after building and selling an auto shipping company. That background gave him experience with operations, customer service, Google Ads, lead generation, and building teams. He then brought that same operator mindset into wholesaling and quickly learned that the Instagram version of wholesaling is not reality.
In this episode, Eric breaks down how he got started, how his first deal almost fell apart, why Google Ads became his strongest marketing channel, why he started taking down more properties himself, and what it takes to build a serious wholesale and flipping operation in Chicagoland.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Always do your final walkthrough the day of closing. Even if the property is vacant and being sold as is, something can change before closing. You could find storm damage, a fallen tree, water damage, missing utilities, or even someone occupying the property.
Q: Who is Eric Field?
A: Eric is an entrepreneur who started in logistics, built an auto shipping company, sold it, and then moved into real estate wholesaling and flipping in Chicagoland.
Q: How did Eric get into real estate wholesaling?
A: Eric had experience generating leads with Google Ads from his logistics business. He realized that if he could generate motivated seller leads, he could connect those sellers with investors and build a real estate business.
Q: What happened on Eric’s first wholesale deal?
A: His first deal was a two-bedroom, one-bath ranch in Joliet. He got it under contract, found a buyer, and expected to make around $20K, but the deal almost died because he was not licensed and did not fully understand the assignment rules.
Q: How did Frank Montro become part of Eric’s story?
A: After the first deal ran into attorney and licensing issues, Eric was introduced to Frank Montro. Frank helped him find a path forward, and Eric later hung his real estate license with Frank.
Q: Which marketing channel worked best for Eric?
A: Eric tested text blasting and Google Ads. Texting produced early deals, but it created too many low-quality leads and too much follow-up. Google Ads cost more per lead but produced higher-intent sellers.
Q: Why did Eric start flipping more properties instead of only wholesaling?
A: In a competitive PPC market, bigger buyers can close faster and buy tighter. Eric realized that to scale, he needed to take down more properties himself, renovate them, and control more of the upside.
Q: What does Eric say people misunderstand about wholesaling?
A: The online version makes it look like an easy laptop business. Eric says the real version is a full-time company with marketing spend, staff, office space, vehicles, construction resources, systems, and customer service.
Q: What kind of markets is Eric targeting?
A: Eric says the suburbs have been strong, especially DuPage County, Lake County, and Northwest Cook County. His team has pulled back from many South Side, West Side, and South Suburban deals unless the numbers are strong.
Q: What is Eric’s biggest advice for estimating construction costs?
A: Build relationships with experienced flippers and contractors who understand both construction and the deal. Eventually, you start recognizing patterns, like what a typical ranch rehab should cost and what level of work is needed to reach the right exit.
Show Notes
01:51 Housing provider tip: always complete your final walkthrough on the day of closing
02:31 Eric Field joins the podcast and explains how he connected with Frank Montro
03:45 Eric’s background, military school, U of I, and moving into entrepreneurship
06:00 Building and selling an auto shipping company before entering real estate
07:49 Why Eric chose wholesaling after learning Google Ads and lead generation
12:31 Eric’s first wholesale deal in Joliet and the licensing issue that almost killed it
23:03 Text blasting versus Google Ads and why Eric chose higher-intent leads
28:43 Why PPC forced Eric to start taking down and flipping more properties himself
32:52 The real overhead behind a serious wholesale and flipping business
57:03 Eric’s three-year vision for Big Door Home Buyers and moving toward new construction
Takeaways for Chicago Property Managers and Landlords
Final walkthroughs matter, even on as-is purchases.
Wholesaling is not as simple as assigning contracts from a laptop.
Licensing rules matter, especially when assigning contracts in Illinois.
High-intent leads can be more valuable than a large pile of low-quality leads.
Google Ads can work, but competition from larger buyers makes follow-up, speed, and certainty critical.
In-person seller meetings can build trust that virtual wholesalers may not be able to match.
A real wholesale business has overhead: marketing, people, software, office space, vehicles, construction help, and systems.
A and B areas can create stronger exits because buyers have more ways to add value.
Construction costs are hard to estimate until you build relationships with people who know the work.
The best investors and operators move forward even when they feel out of their depth.
Guest Name: Eric Field
Guest Company: Big Door Home Buyers
Guest Link: https://bigdoorhomebuyers.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
