Real Estate Underground
Real Estate Underground
Ed Mathews
3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale
34 minutes Posted Jun 30, 2026 at 4:00 pm.
The leap of faith: no money, bad credit, no clue
Welcome to Real Estate Underground
28 years, thousands of houses, and Puerto Rico zombie homes
You don't have to stay in a broken system
Quitting at 25 and the Carlton Sheets first deal
Scaling to a couple of houses a week for 20 years
Using AI every day in a lean flipping business
The markets: Florida, the online shift, and Puerto Rico
The three-question filter for entering a new market
Investing with impact and the Ukraine orphanage house
Working with his son McKenna in the business
The deal you don't do: the joy of missing out
Purpose, legacy, and what gets him out of bed
The free FlipFlop Flipper community
The biggest mistake: flipping everything, keeping nothing
Lightning round: books, success, and travel
Where to find Robbie
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Show notes
Robbie Crager bought his first house at 25 with no money, bad credit, and no idea what he was doing. He had just lost a corporate job and had watched Carlton Sheets on late-night television promise he could buy a house with no money down. So he found a wholesaler in the newspaper, contracted the house, and jumped in with both feet while everyone around him begged him not to. Twenty-eight years and thousands of flips later, he calls it one of the best deals he ever did.
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