Real Estate


Real estate investing comes in many different flavors, including:

I’m even experimenting with Fundrise (affiliate link), a crowdsourced commercial real estate investing platform.

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.

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)

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)

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

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?

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.

80: How a Single Apartment Turned Into a $60,000 a Year Hands-Off Business

Jasper Ribbers is one of the leading experts on building an Airbnb side hustle, having done it himself with his Amsterdam apartment and having co-authored the bestselling book on the topic, Get Paid for Your Pad.

(He also runs a blog and podcast by the same name.)

I was introduced to Jasper by Jesse Krieger (Episode 62, Generating Lifestyle Business Ideas That Work), and grew fascinated by his story. He gets to travel the world while his asset back at home earns roughly $60,000 a year from short-term Airbnb rentals.

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

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.

How Much Is That Spare Bedroom Worth? More Than You Think!

Traditionally, real estate investors don’t live under the same roof as their tenants. However, most don’t consider the income potential that stems from renting out excess space in primary residences.

Whether you’re after short-term or extended-stay renters, this post is intended to get your brain thinking about the pros and cons of becoming a micro-landlord or hosting out-of-town guests.

Aspiring spare bedroom real estate moguls can implement the following tips to best prepare, price, and market their homes and rooms.

28: How to Live Rent Free

In Episode 28 of The Side Hustle Show I sit down with Scott Bold to discuss how Airbnb bookings pay the majority of his rent. Just imagine, if a side hustle could cover your living expenses, would that give you a sense of freedom from your job? Airbnb.com is the peer-to-peer accommodations site where you […]

How I Became a Deadbeat

HOW I BECAME A DEADBEAT: The true story of how this Eagle Scout Valedictorian turned into a high stakes mortgage delinquent. Like pretty much everyone, I’ve made some poor decisions along the way. But none worse than this. Nothing else comes even close. In 2007, I decided to buy a townhouse. (Bryn was a willing […]