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, trading stocks, 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 passive cash flow.

Get tailored recommendations.

If you’re evaluating all your different investment options, it can be a little overwhelming. This cool quiz from my friends at Money Made can help narrow down your choices and point you in the right* direction.

Discover investing opportunities on MoneyMade.io

*Nothing on this site should be considered financial advice.

Options Trading 101: 8 Rules for Success for Total Newbies

April 30, 2020July 4, 2019

In this episode, we’re tackling a topic that’s been frequently requested by listeners, but is somewhat foreign to me, and that is options trading.

To help school me on this, I’m excited to welcome my friend Kirk DuPlessis to the show. Kirk runs the super popular site OptionAlpha.com, where you can get all sorts of free options trading training. He’s been at this for over 10 years and the site has over 150,000 members.

Options trading is a high probability form of investing, but as with all investments it’s based on risk. Risk, that Kirk is able to leverage with his in-depth understanding of the market — and by following a few key rules he’s sharing with us today.

303: The 15 Income Streams I’m Working on Right Now

May 31, 2024October 4, 2018

Could you live for free?

That’s what The Side Hustle Snowball framework proposes: to erase your expenses with new income streams.

Here are 15 things you can start this year to begin living for free. These are my primary income streams today.

Dividend Investing: How to Get Paid Over and Over Again — From Work You Do Once

July 10, 2024May 16, 2018

Regular Side Hustle Nation readers and listeners have a whole brain full of strategies on how to get paid.

The question is:

What do you do with the extra income?

What if your savings could pay you growing passive income every year? This article covers how to make your side hustle earnings continue to hustle for you – without doing anything.

280: How to Start a Bounce House Rental Business (Investing in “Inflatable” Real Estate)

August 28, 2023April 26, 2018

Corey Jeffreys turned an $800 investment into $3k in the first year and has been growing his business and adding more automated processes each year.

His entrepreneurial adventure began by exploring the world of real estate investing, when he happened upon a slightly different rental business model: inflatable bounce houses.

272: How the New Tax Law Impacts Entrepreneurs and Side Hustlers

October 31, 2021March 1, 2018

Want to know how the new tax laws that came into effect at the beginning of 2018 impact the amount of tax you pay as a side hustler or business owner?

I invited Mr. CPA on fire Josh Bauerle back onto the show again to talk through the most important tax changes and what they mean for you and your business.

258: 20% Cash on Cash in Mobile Home Park Investing? The Real Estate Side Hustle You Probably Hadn’t Considered

October 9, 2022November 23, 2017

It’s like owning a parking lot, Jefferson Lilly explained. And you can earn 20% cash on cash returns too.

That got my attention, though those returns are coming from a surprising real estate niche: mobile home parks.

247: How To Shortcut Your Financial Freedom with Short-Term Rentals ($15k a Month, Part-Time)

October 31, 2021September 14, 2017

Zeona McIntyre is earning $12-18k a month through her portfolio of vacation rental properties and her “co-hosting” service for other property owners.

All this has afforded Zeona financial independence at a very young age, as she built her operation largely by piggybacking on the growing popularity of Airbnb.

208: Pay Less Taxes: Your Side Hustle Tax Questions Answered

November 5, 2021December 23, 2016

Just 30 minutes with Josh saved me thousands of dollars, so you owe it to yourself to listen to this episode and see if you can put some money back in your pocket too.

Josh Bauerle is the CPA on fire at cpaonfire.com. Josh specializes in tax preparation, tax planning, bookkeeping, and general consulting services for online entrepreneurs.

182: Digital Real Estate Investing for Cash Flow

August 28, 2023July 7, 2016

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.

The Most Important Number You Won’t Find on Your Tax Return

November 9, 2020April 18, 2016

Your tax return will show you your total income, your adjusted gross income, and your taxable income, but those numbers don’t show the most important figure of all.

Your “taxable income” is meaningless.

So what’s the most important number the IRS doesn’t care about but you should?

Your net profit.

Usually Hustling, Occasionally Social