Side Hustle 101: Proven Ideas to Make Extra Money

99: Ideas are Worthless? Nate Earned $300,000 in Passive Income From His (An Intro to Product Licensing)

May 8, 2023March 19, 2015

Nate and his brother earned $300,000 in passive income by licensing one of their ideas to Mattel. They didn’t have to design it, produce it, or sell it. But they found someone who could, and they cashed the checks.

And to be fair, Nate will be the first to tell you these kind of results aren’t typical — but he’s proof they ARE possible.

Nate’s actually a dentist by day, but a pretty serious side hustler by night, and on this call we take a deep dive into the world of product licensing.

96: Essentialism and Finding Your ONE Thing

October 15, 2018February 27, 2015

In Hawaii and on the plane home I read two books with very similar themes:

The ONE Thing by Gary Keller
Essentialism by Greg McKeown
Both titles share the common message of FOCUS — de-cluttering your day, your work, your mind, and your life.

They came at a good time because I was starting to feel overwhelmed with projects and wanting to pursue new ideas and opportunities as they came up.

Not Loving Your Day Job? The 3 Keys to Side Hustle Satisfaction

September 9, 2019February 16, 2015

Even though they say money can’t buy happiness, we all want to earn more — and employers use raises and bonuses as a tool for motivating their workers.

However, according to author and speaker Dan Pink in his bestselling book Drive, compensation isn’t the only — or even the main — key to worker happiness.

16 Timeless Business Lessons from The Simpsons

March 29, 2025January 20, 2015

The Simpsons is one of the most entrepreneurial shows on television. Throughout its more than 500 episodes, the characters engage in, and interact with, dozens of small business ventures.

(I was going to call this “Evergreen Business Lessons from Evergreen Terrace” — but I figured not everyone would recognize Evergreen Terrace …

The Complete Guide to Pricing Your Side Hustle Service

March 31, 2025January 19, 2015

So there I was in my entry-level job earning barely enough to cover car, gas, home, and all the necessary stuff, yet my friends were out 3 nights a week without me.

Frustrating.

My income just wasn’t good enough for my lifestyle.

I started coaching youth soccer, pulling from my playing experience (not coaching) from college, and I was getting a side-stream of income.

Behind the Scenes of My TEDx Presentation on The Entrepreneurial Generation

September 11, 2024January 12, 2015

In September I had the opportunity to speak at our local TEDx event, making the case that millennials are the most entrepreneurial generation in history.

And it’s true; 1 in 3 of us has already started one or more businesses.

Over the weekend I got word that the “official” video from the event was live and ready to share. (It’s about 13 minutes — embedded below.)

This was my first public speaking gig since high school graduation.

87: The 5 Step System to Quit Your Job In the Next 12 Months

January 5, 2023January 1, 2015

If you’re not already following Bryan Harris, I recommend you do. The guy is super smart and has a unique way of breaking things down so that they’re easy to understand and implement.

He doesn’t mess around, and gives super-detailed actionable advice with some awesome examples, but gives the caveat that it takes real work. This is not a 4-hour workweek passive income system — at least not at first.

But that’s OK, because we’re hustlers and ready to make something happen in 2015, right?

8 Side Hustle Lessons From Spain and Portugal (The Obligatory What I Learned On My Vacation Post)

October 15, 2018December 1, 2014

Bryn and I just got back from a couple weeks in Spain and Portugal. We had a great time exploring the sites, trying the food (and wine!), and playing digital nomad a bit.

Exposure to different cultures always triggers some new creative thoughts or ideas, and so here are a few of my notes from the trip.

(And if interested, you can check out my notes from last year’s 5-week journey to Japan and SE Asia.)

82: The OMG and 5 Other Habits That Will Make You a More Effective Entrepreneur

April 26, 2024November 26, 2014

Happy Thanksgiving!

I hope you’re having an amazing holiday with friends and family, and taking a moment to reflect and recharge. Even though it’s an American holiday, the idea behind giving thanks for what we have is universal.

What’s your Turkey Day tradition?

I’m behind the mic solo this week, talking about 6 habits I believe have made me a better entrepreneur, and how you can implement them in your own life.

Killing My Baby: Why I Shut Down My Longest-Running Business

March 17, 2023November 24, 2014

This is a tough post to write.

This summer I pulled the plug on ShoeSniper, my original side hustle and my longest running and most successful business.

A moment of silence.

It wasn’t an easy decision, but I was confident it was time to move on. I think this is an important story to share because most of what you read in the entrepreneurship world is about perseverance and “never giving up.”

Usually Hustling, Occasionally Social