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.

117: The Fastest Path to Side Hustle Cash Flow?

One podcast I’ve been following for a really long time is the Empire Flippers show with Justin Cooke and Joe Magnotti. It’s been fun to watch their evolution from building tiny Adsense sites, running an outsourcing company in the Philippines, selling WordPress themes, and now really focusing in on their website brokerage business.

Consider this: it’s MUCH easier to buy an existing cash flow than to create one entirely from scratch.

In this episode we get into the business model of investing in sites, where to look for these “digital real estate” opportunities, some pitfalls to avoid, and even some creative financing options.

12 Ways to Save Money on Conferences

Last month I attended two industry conferences, ICON15 in Phoenix and New Media Expo in Las Vegas. My total travel and registration expenses were just $249.98 for both shows combined.

(Not including food and drinks.)

No matter what industry you’re in, I believe conferences are a great way to make lasting connections and friendships, and to learn from leaders in your space.

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.

105: How to Retire in Your 30s

I’ve been medium-obsessed with the idea of early retirement ever since I discovered this little blog called Mr. Money Mustache a couple years ago.

The basic formula goes like this: once you have 25x your annual spending in invested net worth, you can theoretically live off growth/interest/dividends in perpetuity.

On today’s episode you’ll meet Jeremy Jacobson, who retired at 37 and now spends his days traveling with his wife and soaking up new cultures and experiences — and blogging about financial independence.

94: Tax Saving Tips for Side Hustlers

It’s tax season, and I think it would be foolish to give Uncle Sam more than you’re legally required to.

This week I’m joined by Joshua Sheats from RadicalPersonalFinance.com and the host of the Radical Personal Finance podcast.

He explains there are 2 tax codes: the personal tax code and the business tax code. As a business owner, even as a side hustler, there are a number of distinct tax advantages available to you. Listen in and keep your hard-earned dollars!

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.

Usually Hustling, Occasionally Social

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