The DealMachine Real Estate Investing Podcast
The DealMachine Real Estate Investing Podcast · Sep 11, 2026 · 38:07
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Wholesaling real estate in Chicago takes more moving pieces than most markets, and AJ Fattori and Charlie Pyles have built a business on it in their early 20s. They break down the escrow holdback that keeps a deal alive when a seller can't move out, and why they keep three to five buyers on speed dial instead of a list of a thousand. They also get honest about blowing through the money early on and worrying about rent while deals were closing.
KEY TALKING POINTS:
0:00 - Intro
1:30 - How AJ & Charlie Started
4:53 - Their First Flip
5:56 - Funding the Deal
8:52 - Escrow Holdback Explained
14:11 - Finding the Deal & Motivation
18:21 - Building Trust With Sellers
21:24 - Building a Buyers List
25:07 - Speed & Title Work
27:16 - Scariest Moments & Money Lessons
32:42 - Advice for New Wholesalers
37:13 - Wrap-Up & Where to Find Them
37:55 - Outro
LINKS:
Instagram: AJ Fattori
https://www.instagram.com/ajfattori/
Instagram: Charlie Pyles
https://www.instagram.com/charliee.pyles/
Instagram: David Lecko
https://www.instagram.com/dlecko
Website: DealMachine
https://www.dealmachine.com/pod
Instagram: Ryan Haywood
https://www.instagram.com/heritage_home_investments
Website: Heritage Home Investments
https://www.heritagehomeinvestments.com/
Episodes: The DealMachine Real Estate Investing Podcast