Service Businesses

Many freelancers in Side Hustle Nation eventually grow their business into an agency that no longer ties their time to their income. What that looks like in practice is often bringing in other team members to deliver the work.

The business ideas and case studies featured in these archives are generally a little “bigger” than a traditional freelance business, even if the actual work offered is the same.

What separates a service business from a freelance business is a matter of scale. No longer are your hours directly tied to your income, and you may not even be directly responsible for doing the work; that’s what your team is for.

67: The Hustler’s Path: From Freelance to Agency to Product

January 10, 2023August 21, 2014

It’s been quite a while since our last discussion of a software business here on the show. Even though we touched briefly on Long Tail Pro with Spencer Haws, I really have to go all the way back to Josh Isaak in episode 12 to find an in-depth breakdown of a Software as a service business.
So that means today’s conversation with Garrett Moon from CoSchedule is long overdue! After all, the low incremental cost and recurring revenue potential of the SaaS model is such a trendy holy grail of business right now.

39: Hacking Your Side Hustle for Growth and Passive Income

March 31, 2025February 20, 2014

In Episode 39 of The Side Hustle Show, I’m joined by Mike Newton from HackingPhotography.com.

We discuss how to make a name for yourself in any business, how to score corporate clients (and why you’d want to), and how to generate passive income streams from a service business.

34: How to Build a 5-Figure Subscription-Based Service Business in Your Spare Time

April 29, 2024January 16, 2014

In episode 34 of The Side Hustle Show, fellow side hustler Ryan Cote from WPAmplify.com discusses how he’s built his part-time service business into a high-value recurring-revenue machine.

We talk scoring customers, pricing, delivering the goods, retention, and much more.

19: How to Start a Part-Time Virtual Assistant Business, with Lee Drozak

June 9, 2025September 12, 2013

In Episode 19 of The Side Hustle Show, Lee Drozak from shares how she got started as a virtual assistant and how you can do the same. We talk setting up shop, getting your first clients, setting your prices, establishing a niche, and more. Quick background on this side hustle if you’re not familiar — … Read more

The “Accidental” Side Hustle that Earned Me $1185 in 6 Weeks

June 9, 2023July 29, 2013

Some side hustles you relentlessly pursue, trying day after day to make something happen. Others sometimes just find you. This was a case of being in the right place at the right time, and the opportunity finding me. I won’t chalk it up entirely to luck though, because this side hustle was actually the result … Read more

6: How to Build an Offline Side Hustle Around Your Passion, with Emma Perez

May 23, 2022June 13, 2013

In Episode 6 of The Side Hustle Show, I have a chance to sit down with Emma Perez of OrlandoWeddingDances.com to discuss how she’s built her side hustle business by leveraging her passion for dance along with some savvy marketing moves. This show has some great tips on how to crack the multi-billion dollar wedding … Read more

4: How to Quit Your Job and Move to Hawaii, with Kai Davis

August 23, 2023May 30, 2013

In Episode 4 of The Side Hustle Show I’m joined by fellow entrepreneur Kai Davis, who built an impressive freelance business in his spare time that allowed him to move from Oregon to Hawaii. Kai’s a real hustler and drops a ton of great value in this interview. Subscribe to The Side Hustle Show via … Read more

1: From Heavy Metal Band to International Marketing CEO, with Chris Kilbourn

July 2, 2025May 16, 2013

In the inaugural episode of The Side Hustle Show podcast, I have Chris Kilbourn as my guest. Chris is one of those guys who started more companies by the time he graduated college than most people will start in their lifetime. He’s a tremendous entrepreneur, full of hustle, and a perfect guest to kick off … Read more

Usually Hustling, Occasionally Social