Investing


Investing might sound scary or intimidating, but really it’s about one simple idea:

How to make your money work for you.

You earned it once, now how can you multiply it in a way that aligns with your risk tolerance?

It’s weird, but I sit on both ends of the spectrum on this, at once having made big bets on my own business and experimenting with “alternative” investment platforms, and on the other hand being paralyzed into sitting on the sidelines by fear the market might go down.

In this section of the site, you’ll find information on real estate investing, peer-to-peer lending, and even buying businesses.

Before You Get Started

Know your net worth. Your net worth is the sum of all your assets (cash, savings, mutual funds, equity in your home, etc.) minus your liabilities (student loans, credit card debt, mortgages, etc.).

One tool I like to help calculate your net worth is Personal Capital. It’s free!

Know your objective. What’s the goal of your investment? A goal of accumulating wealth to retire in 30 years is very different than a goal of earning $1000 a month in positive cash flow.


182: Digital Real Estate Investing for Cash Flow

As you know, I’m excited about alternative investments like peer-to-peer lending. And if your aim is to replace your income, I think it makes sense to invest for cash flow.

This week’s Side Hustle Show guest argues when you want something in other areas of your life, you go out and buy it: a pair of shoes, a computer, a new car. You don’t make it from scratch!

So why are we so insistent on building income from scratch? He says there’s a faster way, and that’s to “buy” assets that are already generating positive cash flow.

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.

Peer-to-Peer Lending 5-Year Performance Update

My experiment with peer-to-peer lending at Prosper.com continues, and it’s been another busy year.

The platform has seen some impressive growth, both in terms of the number and volume of “originations,” and the number of lenders competing for the most attractive loans to lend on.

I used Lending Robot to automatically deploy idle cash for all of 2015, which has worked out pretty well so far.

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.

How a $200 a Month Side Hustle Can Change Your Life

If you’ve got a business that generates even $200 (or less), it can change your life.

I know this first-hand because that’s what happened to me.

(And if you don’t have such a business now, you are in the right place to find one. Nick’s site is a goldmine full of business ideas and he tells you exactly how to implement them.)

I’m a successful money manager, but back in 2008 I was in a world of pain.

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.