Skip to main content

The Landlording Show Episode 10: Investing / $100 Challenge

Everyone, welcome to the Landlording Show. There are plenty of podcasts that show you how to get into real estate investing, how to find, finance, and buy property. But we are your source for what to do once you have it. We aim to make your investments as profitable and as stress-free as possible so that your investments can lead to your life goals. I’m your host, Tim Harstead, a property manager on the South Side of Chicago. I’ve seen it all and lived to tell about it.

Today's Topic: The $100 Challenge

Today’s episode is a bit different from our usual content. I wanted to talk about my $100 challenge. This is about preparing real estate and getting into the game. I notice many people at events want to start real estate investing but haven’t yet jumped off the ship. The number one reason we see is that they don’t have the money for the down payment. So, I wanted to show everyone that, given enough time and energy, you can actually do it.

How to Follow Along

You’re going to be able to follow this project on our YouTube channel, and you should subscribe anyway because we're putting a lot of good content there, including these podcasts in video form. Search for Chicago Style Management on YouTube.

Addressing New Investors

Another issue we see is with new investors—not by age but in terms of experience. Many get into property investing without the proper training. They are so inundated with YouTube videos and TikToks about how if you just get this property, it doesn’t matter the loan type, and you could find a way to put 2% down and all these things that just put them way behind the eight ball.

The Long Haul

Again, this is the long haul. I’m not putting a whole lot of effort into it in the sense of my amount of time; maybe an hour or two a week, every two weeks. I want to prove that no matter what your schedule is, no matter what your excuses are, you can get this done.

The Strategy Explained

Here’s the outline of the project: I’m starting with $100 and going to estate sales, thrift stores, garage sales, things like that. Find items that I can take and put on eBay or Facebook Marketplace and just build up until I have enough money for a down payment. My goal for the down payment is to be 20% down, find a property under $100,000, buy it, get it rented, and take everyone through the process.

Not a Quick Scheme

But again, this is not a quick process. This is not a scheme to work the system. This is just to show you that if you put a little extra work in and allow enough time, you’re going to be able to make this money.

Empowering through Side Hustles

If you can't find a $100 to pull from your budget somewhere, then you really, honestly, shouldn't be investing in real estate yet. You need to work on your 9 to 5, work on getting your income up to a level where investing actually makes sense. That might mean finding a completely new job, figuring out side hustles, doing Uber, Lyft, Uber Eats, all that kind of stuff.

Engaging Activities and Findings

This is something that for me is fun. Me and my wife actually enjoy going to garage sales and estate sales, and we got a couple of cool ones that I’ll touch on in a minute. We started this a few weeks ago, and we got some items that we have listed, and I have more items that I need to list.


Thanks, guys. One more note, if you guys have any questions that you want us to answer on the show, send us an email to I'll see you guys around, and I’m sure I'll see a lot of you listeners at different real estate conferences. We'll talk soon.