Podcast Episode

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

The DealMachine Real Estate Investing Podcast·David Lecko, Ryan Haywood·13 September 2026·38 min

About this episode

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 - Intro1:30 - How AJ & Charlie Started4:53 - Their First Flip5:56 - Funding the Deal8:52 - Escrow Holdback Explained14:11 - Finding the Deal & Motivation18:21 - Building Trust With Sellers21:24 - Building a Buyers List25:07 - Speed & Title Work27:16 - Scariest Moments & Money Lessons32:42 - Advice for New Wholesalers37:13 - Wrap-Up & Where to Find Them37:55 - Outro LINKS:Instagram: AJ Fattorihttps://www.instagram.com/ajfattori/ Instagram: Charlie Pyleshttps://www.instagram.com/charliee.pyles/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/