"Changing the world with chess" and making $100,000 per year on the side.

That’s the story of today’s guest, Jeff DiOrio from EliteChess.net.

Jeff went from earning $17/hr working in summer camp chess programs teaching kids how to play chess, to running his own camps and earning five times as much.

He then transitioned to an online recurring membership model, in part due to the pandemic, while also keeping the in-person coaching side of his business alive.

Jeff’s approach to growing his student numbers so rapidly?

Organic growth through giving to charities and delivering a value-driven service, all while doing something he loves—teaching chess.

Tune in to The Side Hustle Show interview to hear:

Full Show Notes: From $17/hr to 6-Figure Side Hustle

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OpenPhone — Streamline and scale your customer communications with Open Phone. Get 20% off your first 6 months at www.openphone.com/sidehustle.

Back in the day, you needed someone technical (or paid someone technical) if you wanted to build any kind of software.

Today, with the popularity of AI tools, not so much.

Pete McPherson from doyouevenblog.com is earning $100k by using AI tools to help build a series of small-ish web apps, usually built to solve a very specific problem for a very specific customer.

And he's here to share with you how he built all of this... without being a developer himself.

Tune in to Episode 659 of the Side Hustle Show to learn:

Full Show Notes: $100k with AI-Coded Apps

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Streamline and scale your customer communications with Open Phone. Get 20% off your first 6 months at www.openphone.com/sidehustle.

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

Heff Gerlach started The Keeper League Podcast on the side from his teaching job.

It's not about football, not just about fantasy football, but about a very specific flavor of fantasy football for Australian Rules Football.

That’s a niche within a niche within a niche — where fans don’t just draft players, they build teams that last for years.

And now it serves as the hub for player data, draft tools, and expert analysis for football keeper leagues.

Tune in to Episode 658 of The Side Hustle Show to learn:

Full Show Notes: 160k Talking About Australian Fantasy Football

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

It’s time for another round of business idea giveaways, and to help me out is a long-time friend and friend of the show, Steve Chou, a serial entrepreneur who built not one but two 7-figure businesses starting both as side hustles — MyWifeQuitHerJob.com and BumbleBeeLinens.com.

It’s becoming a tradition; this is our 3rd round of business idea giveaways. If you find you like this format, make sure to go check out the other two.

Full Show Notes: 19 Business Ideas Free for the Taking

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

I called the Amazon Influencer Program the easiest money I'd ever made online.

I made $100 in my first month, over $1200 in my first year, and last year, still made over $700 doing almost nothing. Set it and forget it.

The basic premise with this branch of Amazon Associates is to create short product review videos, and earn a small commission when your review convinces someone to buy.

You do need some level of social following and engagement to get accepted, but after that, you really don't need to drive your own traffic. Amazon posts your review videos on the relevant product pages.

In this episode, we check in with Tyler Christensen from TylerChristensen.com — a serial side hustler, teacher, and dad of four who's lately been earning around $5k a month on the side from his product reviews.

Tune in to Episode 656 the Side Hustle Show interview to hear:

Full Show Notes: $5k/mo Reviewing Products Part-Time: An Amazon Influencer Update

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

Why go through the trouble of building your own cash flow when, with a little determination and a little hustle, you can insert yourself into some income streams that are already happening?

That’s what Link Moser from linkmoser.com and his web design agency windhill.com have done, not once, not twice, but 5 different times, generating $200k a year in semi-passive income.

He was on the show in 2022, where he explained how he makes money with a real estate lead generation site, NHFineHomes.com, where a single referral can be worth tens of thousands of dollars.

But today, we’re diving into a different strategy: business acquisitions.

Tune in to Episode 655 of the Side Hustle Show:

Full Show Notes: How to Earn $200k/Year in Semi-Passive Income Through Small Business Acquisitions

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

Service businesses can get a bad rap.

After all, there are clients to deal with, and actual labor involved in fulfillment. They’re just not as glamorous as other more “passive” income models.

But you should know that more Side Hustle Show guests started with a service-based business model than any other.

This week’s guest has a unique approach to service businesses -- one that doesn't rely on your skills as the expert.

Tyler Gillespie has built two successful service businesses and had a clean exit from both -- the last being just 13 months from startup to sale.

Tune in to hear:

Full Show Notes: Built to Sell: Design a Business to Run Without You

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It’s 2025, and the line between reality and science fiction is getting more and more blurry every day.

In this episode, I sit down with someone I’ve never met, but they know me pretty well. He even kind of sounds like me in an eerie sort of way.

I was curious how well today’s AI models could pretend to be someone else, given a few simple prompts. The result is this chat with Robo-Nick, my AI alter ego.

Let’s see how well Robo-Nick answers these questions, plus my real thoughts about them.

(This episode relied heavily on ElevenLabs to generate the voice for Robo-Nick.)

Tune in to episode 654 of The Side Hustle Show to learn:

Full Show Notes: I Interviewed My AI Self … What it Got Right, Wrong, and a Little Weird

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

Getting out of the rat race is simple, but not necessarily easy.

To escape, all you need is monthly income -- from non-job sources -- that exceeds your monthly expenses.

For example, if you spend $3000 a month, you'll need to bring in at least $3000 (after taxes) outside of your day job.

Simple, but not always easy.

In this episode, I'll break down:

Ready? Let's do it!

Full Show Notes: 3 Ways to Get Out of the Rat Race

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!

In 2022, Summer Fisher discovered the world of renting out dresses.

"Oh, well, I have all these dresses. Let me just put one up," she told Yahoo Finance.

Now with a streamlined inventory of around 200 pieces, she made $150,000 last year using what she calls a "double-dip profit strategy" — renting dresses multiple times before selling them for more than she paid.

(Check out her free masterclass at theprofitcollective.co/RookieResellerMistakes.)

Tune in to episode 652 of The Side Hustle Show to learn:

Full Show Notes: $150k Renting Out Dresses as a Side Hustle

New to the Show? Get your personalized money-making playlist here!

Sponsors:

Airbnb — Discover how much your home could be worth and find a professional co-host today!

Mint Mobile — Cut your wireless bill to $15 a month!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

OpenPhone — Get 20% off of your first 6 months!

Gusto — Get 3 months free of the leading payroll, benefits, and HR provider for modern small businesses!