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.


225: High-Yield Investments in a Low-Yield World

Dr. Kenyon Meadows MD is a practicing Radiation Oncologist by day, but by nights and weekends he’s a self-proclaimed alternative investment enthusiast.

Tune into this edition of The Side Hustle Show to hear how Dr. Meadows is earning double digit returns in Turnkey Rental Properties, Real Estate Private Lending, and Business Lending.

He also shares you can get started yourself for as little as $10.

222: 5 Real Estate Side Hustles You Can Start on the Cheap

Chad Carson is a 30-something semi-retired real estate mogul, who together with his business partner, oversees a portfolio of 90+ rental units.

In fact, he and his wife are in the middle of an exciting adventure — a year abroad in Ecuador with their two daughters.

But of course he didn’t start there. Fresh off the football field at Clemson, Chad’s real estate career started more modestly by “bird dogging” and house hacking — two of the tactics he shares in this week’s show.

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.