The Side Hustle Show “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 … Read more
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 … Read more
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 … Read more
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. … Read more
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 … Read more
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 … Read more
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 … Read more
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 … Read more
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 … Read more
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 … Read more