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587: Wholesaling Houses In Their Early 20s (Here's What's Working) episode artwork

EPISODE · Sep 11, 2026 · 38 MIN

587: Wholesaling Houses In Their Early 20s (Here's What's Working)

from The DealMachine Real Estate Investing Podcast · host AJ Fattori, Charlie Pyles, David Lecko, Ryan Haywood

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/

Episode metadata supplied by the publisher feed · Published Sep 11, 2026

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Two wholesalers in their early 20s break down how they keep Chicago deals alive and closing.

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587: Wholesaling Houses In Their Early 20s (Here's What's Working)

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