Real Estate

Real estate side hustles comes in many different flavors, including:

wholesaling (often no money down)
traditional buy-and-hold rental properties
fix-and-flips
vacation rentals
raw land investing
rental arbitrage

Which one is best depends on your goals, available time and money to invest, and risk tolerance.

For example, while I LOVE the idea of building a mini real estate empire and having tenants pay off my mortgages, the direct cash returns and the risks involved don’t get me that excited. At least for the moment, I’ve steered toward some more passive real estate investing options.

Check out these real estate-themed posts and podcast episodes and choose which strategy makes the most sense for you.

169: The Best Passive Income Model: Raw Land Investing Update (Part 2)

October 14, 2024April 15, 2016

This is the second in what will (at least) be a 2-part series on side hustlers earning income from their land investment endeavors.

In this special Friday edition of the show, I’m joined by Chris Pritchard. Chris is a software developer by day, but has built his land investing business up to $1500/mo in recurring revenue.

In addition, Chris does the occasional cash flip and also has more than $70,000 worth of land payments under contract. Not bad for a year of dedicated focus and effort!

168: The Best Passive Income Model: Raw Land Investing Update (Part 1)

October 14, 2024April 14, 2016

In episode 108 of The Side Hustle Show last year, we met Mark Podolsky, a real estate investor specializing in raw land. He called it “The Best Passive Income Model,” because there are no products to build, no tenants or toilets, and you can start without a huge upfront investment.

This year, I wanted to feature a couple listeners who took action based on that episode. The first is my friend Josh Brooks, an Army Battalion Commander and founder of The Enduring Charity Foundation.

148: 7 Houses at 27: Building a Real Estate Empire on the Side

November 6, 2021December 10, 2015

Elizabeth Colegrove and her husband are budding real estate moguls. So far they’ve acquired 7 houses, and neither of them are 30 years old yet.

Between their 7 properties, they’re earning around $1800 in cash flow every month, and their tenants are paying off $1650 in loan principal.

But real estate investment is not without risks and Elizabeth joked that I just have easily could have called the episode 27 and $1.1 million in debt.

108: The Best Passive Income Model?

July 3, 2025April 30, 2015

I was very excited to sit down with Mark Podolsky, The Land Geek, to talk about his side-hustle-turned-full-time-biz of investing in raw land.

In fact, he was able to replace his day job income and quit his job only 18 months after starting.

Mark calls it the best passive income model because you don’t have to worry about building a website, building a product, dealing with tenants, dealing with repairs, or selling a service.

79: Getting Started in Real Estate Investing for Less Than $100

April 26, 2024November 6, 2014

J. Massey discovered real estate as a business out of necessity. He and his wife were both in poor health, and as he explains, had a 398 credit score and $75 to their name.

Then, introduced to real estate wholesaling, the picture began to turn around. This strategy allowed J. to develop some cash flow without risking his own limited assets, and he says he got started by dedicating just 2 hours a day, or 10 hours a week to this new side hustle.

30: How to Build a $10,000+ Per Deal Flipping Factory, with Nick Ruiz

October 16, 2018December 5, 2013

In Episode 30 of The Side Hustle Show, we learn how to build a real estate wholesaling side hustle, without any experience and without risking your own money or credit score. Veteran investor Nick Ruiz shares how he earns $10,000+ per deal with his “Flipping Factory” system. This is definitely an interesting one! Subscribe to … Read more

Usually Hustling, Occasionally Social