The Side Hustle Show

  • From $17/hr to 6-Figure Side Hustle (Greatest Hits)

    “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…


  • 659: $100k with AI-Coded Apps

    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…


  • 658: 160k Talking About Australian Fantasy Football

    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…


  • 657: 19 Business Ideas Free for the Taking

    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…


  • 656: $5k/mo Reviewing Products Part-Time: An Amazon Influencer Update

    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…


  • 655: How to Earn $200k/Year in Semi-Passive Income Through Small Business Acquisitions

    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…


  • Built to Sell: Design a Business to Run Without You (Greatest Hits)

    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…


  • 654: I Interviewed My AI Self … What it Got Right, Wrong, and a Little Weird

    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.…


  • 653: 3 Ways to Escape of the Rat Race

    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…


  • 652: $150k Renting Out Dresses as a Side Hustle

    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…