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.

Co-Living: $1k a Month with Your First Co-Living Rental Property

February 5, 2026

What if you could create $1,000 to $2,000 per month in cash flow from a single property and need just three homes to replace your W-2 income?

Sam Wegert discovered this path 14 years ago when he started house hacking a single property.

Today, he owns over 200 rooms across his co-living portfolio, all passively managed while he lives overseas.

Co-living is when you buy a larger house and rent out individual rooms instead of the entire property.

It’s the difference between earning $250 a month from a traditional single-family rental and $1,000 to $2,000 from the same-sized property set up for co-living.

From the Scale Your Co-Living Real Estate podcast and ScaleYourRealEstate.com, Sam Wegert shares how he turned a simple house hack into a six-figure business addressing affordable housing from the ground up.

(Join his Free 5-Day Co-Living Challenge to learn how to develop the mindset that will take you to success as a CoLiving investor!)

From $50k in Debt to Mortgage-Free Millionaire: How Coast FIRE Led to a 3-Day Workweek

January 26, 2026

Owning your time is a goal we all share, and today’s conversation is about giving you concrete steps you can take to reclaim some of that time.

Andy Hill went from $50,000 in debt to mortgage-free multi-millionaire and now works a three-day work week. His new book is Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind.

From MarriageKidsandMoney.com, Andy Hill shares how he built financial independence through Coast FIRE, side hustle income, and intentional life design.

65 Alternative Investment Platforms to Earn Stronger Returns, Build Cash Flow, and Diversify Your Portfolio

January 16, 2026January 10, 2026

I’ve been excited about alternative investments since my early days as an aspiring real estate investor and peer-to-peer loan shark.

If you’re bored/scared/disillusioned with the “traditional” stock market and mutual fund asset classes, or if you just are curious what else is out there, this post is for you.

The cool thing is we’re living in a golden age of alternative investment opportunities, and it was quite an undertaking to compile these options.

Passive Real Estate Investing: Build Cash Flow and Equity—without the Sweat!

January 17, 2026January 7, 2026

Real estate investing is perhaps one of the oldest side hustles in existence.

Buy a house, rent it out, and build wealth. It’s a tried and true formula, and certainly a way to stop trading time for money.

This idea was popularized by books like Rich Dad Poor Dad, explaining (often with real estate as an example) how you can “escape the rat race” when income from assets you control exceeds your monthly expenses.

But real estate investing comes in many different “flavors” — and some take more time and money than others to get started with.

Fundrise Review: My $100,000 Commercial Real Estate Side Hustle

January 16, 2026January 5, 2026

In 2015, I started building what I call “my cash flow portfolio.” This is a specific set of investments designed first and foremost to generate interest and dividends.

My thinking was: how can I get paid over and over again from work I do once?

And by investing for cash flow, I could turn every “extra” $1,000 I earned into $20-80 a year in truly passive income … forever.

23 Best Real Estate Side Hustles to Build Wealth and Cash Flow

January 23, 2026January 5, 2026

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.

Neighbor.com Review: Can You Really Make Extra Money Renting Out Your Space?

January 16, 2026November 18, 2025

Neighbor.com Review: Make Extra Money Renting Out Your Space

According to Neighbor.com, you can make money turning your extra space into into storage.

But is it a legit side hustle? How does Neighbor work — and how much work does it take?

In this review, we’ll explore the pros and cons of Neighbor.com, so you can decide if it makes sense to monetize your unused space.

From Zero to $50k in Monthly Vending Revenue in 16 Months

October 20, 2025October 20, 2025

Vending machines are a classic passive income source that continues to be profitable today.

We had Mr. Passive himself, Mike Hoffman, in the show before to talk about how to scale up his vending machine business.

And one of his mentees is here today.

Anthony Kolodziej from H&H Vending scaled his vending operation from zero to over $50k per month in just 16 months.

That’s 30+ locations, thousands of transactions, and a strategy that turns vending into something way beyond the old-school snack machine in the corner of a breakroom.

House Hacking 101: Live Free and Turn Your Biggest Expense into a Profit Center

January 16, 2026October 5, 2025

What if you could make your rent or mortgage payment go away?

Or, what if instead of paying that expense every month, your living situation actually paid you?

It’s not as far-fetched as it may sound.

In fact, that’s exactly what today’s guest, Craig Curelop, has done by intentionally “house hacking” over the past few years.

One House a Year: Your Simple 10-Year Path to Financial Flexibility

January 17, 2026August 14, 2025

Dustin Heiner from Mister Passive Income

Want a roadmap to build time-leveraged cash flow and long-term wealth without the complexity of traditional business ventures?

Dustin Heiner is back on the show to share his proven strategy: buy one profitable investment property per year for 10 years.

It might sound easier said than done, but Dustin has retired early from the cash flow of his 30+ rental properties and now helps others replicate his success at MasterPassiveIncome.com.

Dustin treats real estate as an “income building” business, not speculation. He’s built systems that generate consistent monthly cash flow while building equity — and his 16-year-old daughter just bought her first property using these same strategies.

(Check out Dustin’s free real estate investing starter course and learn more about his proven systems.)

Usually Hustling, Occasionally Social