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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Finding great real estate deals in Chicago has never been more competitive. MLS listings are crowded, buyers are aggressive, and off-market deals are often locked down before they’re even public. In this episode, Tom Shallcross and Mark Ainley sit down with Eli Goodman, founder of Illinois Real Estate Buyers and host of one of Chicago’s largest real estate meetups, to unpack exactly how he built a thriving wholesaling business from the ground up.
Eli started with nothing but a few thousand dollars, grit, and a borrowed Google Ads campaign, and now manages 100+ leads a month while closing consistent off-market deals. From personal stories of risk and failure to the automation systems that run his business today, Eli shares what it really takes to build a successful direct-to-seller model in Chicago’s tough market.
Tom and Mark dive into the real-life grind behind successful wholesaling, no hype, no shortcuts. Eli opens up about how he left personal training to pursue real estate, how his first contract took eight months, and how one bounced check nearly ended his business.
They discuss what separates top wholesalers from those who burn out, including how to manage marketing budgets, follow up for years on cold leads, and automate systems to handle hundreds of sellers without losing track. Eli breaks down his approach to Google Ads, seller psychology, and why understanding emotions matters more than numbers when closing deals.
Whether you’re an investor, landlord, or aspiring wholesaler, this episode is packed with actionable advice on generating your own deal flow in Chicago’s fast-moving market.
Questions We Answer in This Episode
Q: How did Eli get started in real estate?
A: At 20 years old, Eli was juggling party promoting and personal training before realizing he was trading hours for dollars. A friend introduced him to wholesaling, and after several failed attempts, he finally closed his first deal through Google Ads. That one success led him to go all-in and build his own business in 2020.
Q: What was the biggest challenge early on?
A: The wait. It took Eli eight months to close his first deal and another six for his second. He learned quickly that wholesaling is less about luck and more about perseverance, follow-up, and learning from each failed lead.
Q: How did he fund his first marketing campaign?
A: With just $5,000 in savings and a $5,000 zero-percent credit card, Eli committed everything to Google Pay-Per-Click ads. He knew that consistency, not luck, would make or break his business.
Q: What did he learn about dealing with sellers?
A: Empathy matters. Many sellers are in distress, so understanding their emotional needs is key. For some, selling quickly matters most. For others, privacy or time to move is the real motivation. Tailoring the pitch to what they want is the difference between getting a deal and losing one.
Q: What’s the craziest seller situation he’s dealt with?
A: A lead that took over three years to close. After hundreds of calls, the seller finally sold only after burst pipes caused massive flooding. Persistence paid off, literally.
Q: What systems keep his business organized?
A: Eli runs everything through REI BlackBook, where every call, text, and email is logged, recorded, and transcribed by AI. Automated workflows follow up with sellers for months or even years, saving time and ensuring no opportunity slips through the cracks.
Q: What’s the average deal flow?
A: About 100 leads per month, which translate into one to two closed deals every few weeks. The conversion rate is typically one contract per 20–30 leads.
Q: What’s his marketing strategy today?
A: Google Ads remain his #1 source, with campaigns targeting top Chicagoland counties and neighborhoods. He also runs Facebook groups with over 40,000 combined members, where he builds relationships with buyers and other wholesalers.
Q: How does Eli handle multiple offers on a deal?
A: He used to run “highest and best” bids, but now prioritizes first come, first serve at asking price with no contingencies to maintain relationships and keep transactions smooth.
Q: What’s his advice for investors trying to find off-market deals?
A: Commit long-term. Marketing is a six-month to one-year game. You might spend $50,000 with no return, but the next $1,000 could bring a six-figure deal. Consistency beats luck every time.
Show Notes
00:00 Intro – Why this episode matters for cash buyers and investors
01:53 Housing Provider Tip – Why you should have a HELOC ready
03:00 Eli Goodman joins the show
03:16 From personal training to real estate investing
04:19 Partnering with a friend and learning the hard way
06:14 Going all-in with $10,000 and a credit card
08:00 First deal through Google Ads and early mistakes
09:40 How COVID affected his new business
10:15 Lessons learned about marketing consistency
11:05 Learning to connect emotionally with sellers
12:38 Why empathy wins deals
14:08 The three-year follow-up story that finally paid off
16:15 Breaking down CRM systems and automation
17:44 Using AI for lead summaries and follow-ups
19:32 What messages actually get sellers to respond
20:58 Google Ads targeting and keyword strategy
22:00 Monthly call volume and conversion rate
24:15 Building a massive buyer network and Facebook groups
26:16 How to safely market deals and avoid competition stealing them
27:16 “First come, first serve” vs. “Highest and Best”
30:12 Red flags that show a buyer is inexperienced
32:26 What’s next for Eli’s business – scaling, flipping, and new markets
34:11 Illinois-specific challenges for wholesalers
36:08 Attorney delays, title issues, and city-by-city quirks
37:40 Comping properties across Chicago and suburbs
38:39 Why buyer feedback is critical for wholesalers
39:22 Partnering with investors for joint marketing campaigns
41:12 Understanding the risk and reward of co-marketing
42:03 Eli’s biggest competitive advantage: follow-up persistence
42:24 Advice for new investors entering Chicago’s market
42:35 Personal interests: travel, tennis, biking
42:49 Favorite book – Never Split the Difference by Chris Voss
43:08 Shoutout to Dan Clarton with Investor Title Services
43:46 How to connect with Eli
44:29 Chicago Fact Trivia Challenge
Takeaways for Chicago Property Managers and Landlords
Direct-to-seller marketing works, but only if you commit long-term.
Google Ads remain powerful, especially when managed consistently.
CRM systems are non-negotiable. Without automation, you’ll lose track of leads.
Empathy closes deals. Understand the seller’s motivation, not just the numbers.
Follow-up forever. Some of Eli’s deals took over three years to close.
Protect your relationships. Off-market deals depend on trust between buyers and wholesalers.
Illinois is unique. Expect longer timelines, heavier attorney involvement, and tougher sellers, but bigger payoffs if you persist.
Guest Information
Guest Name: Eli Goodman
Guest Company: Illinois Real Estate Buyers
Guest Link: LinkedIn
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
