He Made $60,000 in 2 Months with This “Failed” Real Estate Deal

Every rookie thinks their first deal will go according to plan (it almost never does). Today, we’re bringing on a guest who had a long list of all the worst-case scenarios that happened to him, and still walked away winning (to the tune of $60,000!). He’s walking us through it all, so you can master your first deal, too! 

Welcome back to another episode of the Real Estate Rookie Podcast! This week, we’re sitting down with Caleb Smith, a real estate agent who bought his first rental at 21 with next to nothing in the bank, and then watched two very different deals go sideways in two very different ways! One taught him an expensive lesson about lenders. The other got hit by a zoning surprise nobody could have predicted, and forced him to pivot on the spot.

Getting your numbers right isn't always enough. Sometimes the thing that changes everything isn't the market, the property, or the strategy—it's something buried in a permit office you never saw coming! 

If you're trying to figure out how to get your first deal done with limited capital, wondering what can quietly derail your plan, or just want to hear how a rookie handles it when things don't go the way he expected—today’s episode has real numbers, real setbacks, and a few hard-won lessons worth taking with you into your next deal!

In This Episode We Cover

How Caleb bought his first rental at 21 with only $2,000 to his name

Pivoting to a live-in flip strategy (and the huge benefits of doing so!)

How to knock on doors to find off-market investment properties 

Turning a seller credit into an interest rate buydown 

The $10,000 origination fee mistake that taught him to shop lenders

Surviving a falling chimney, botched kitchen, and a zoning reversal mid-deal!

And So Much More!