81: The Path to $5k a Month Passive Income Sharing What You Already Know

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When I asked listeners last month who they’d like to hear on the show, Rob Cubbon is a name that came up from a couple different people.

It was actually a little weird, because it made me realize that even though I considered Rob a good “online friend,” we’d never actually spoken!

Rob’s been crushing it lately between is online teaching efforts and his Kindle publishing business, and as luck would have it, is a Side Hustle Show listener himself.

I’ve been following Rob’s blog for some time myself, and have been really impressed with his journey. In fact, it’s pretty inspiring and eye-opening to see some his quarterly income reports, with much of the money coming from Udemy. (His latest was over $5k!)

And a fun fact is that all of this stuff, all the digital product sales, is essentially a side hustle from his main gig as a freelance graphic designer.

In this episode, he joins me live from Chaing Mai, Thailand, where he’s living the digital nomad dream this fall.

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  • Get $25 off your first Airbnb stay through this link.


  • How Rob got started blogging, and how his blog generated freelance design clients.
  • How to write blog posts that target “buying keywords” to attract qualified traffic.
  • How Rob re-purposed his YouTube videos into a free course on Udemy. (Packaging and organizing creates higher perceived value.)
  • How you can gently expose your free students to your website, your brand, and your email list.
  • How he’s creating the courses, primarily with screencapture software. (I use Screencast-o-matic.com)
  • How he prices his courses, and how he releases them.
  • Why Rob has chosen to focus on Udemy rather than his own platform (and why that is changing).
  • The other places you can syndicate your digital education products.
  • How re-purposed content from your courses can fuel Kindle books, blog posts, Slideshare presentations, and more.
  • Rob’s #1 tip for Side Hustle Nation.


Your Turn

What do you think? Could you teach some in demand skill on Udemy? The results are pretty attractive!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, The Penny Hoarder, GoBankingRates, and more.

18 thoughts on “81: The Path to $5k a Month Passive Income Sharing What You Already Know”

    • Passive in that the income is not directly tied to hours of input — there’s leverage in creating products once and selling them many many times. But yes, definitely takes a time investment to build those products.

    • I agree with Nick, Patrick. Yes, there is a time investment in setting up a video course and writing a book but the income you receive from these products eventually exceeds how much you would have earned if you swapped those hours for dollars AND they build your brand and add authority so that you can earn more passive income from other products in the future.

    • I do use a guy I know really well from oDesk to help me on the video editing, Andy. I wouldn’t use Fiverr. When I started out I did all the video editing and everything myself but I started outsourcing some of the product creation tasks as soon as I started making some regular cash from the video courses.

  1. Hi Nick, thanks for having Rob on the podcast. I’m a huge fan (and friend) and I’m following Rob’s strategies for creating online courses. I put up 3 of my YouTube videos on Skillfeed and I’m already generating more income than I do from AdSense on my YouTube Channel. My first Udemy course is a free one and I’m heading over to Skillshare now….

    • Hey Ileane, glad to hear you’re doing well on Skillfeed. You can put as many of your YouTube videos on there as you want as “Skillsnacks” – and why not, you may as well get paid for your awesome content, what do you think? I know Skillshare will make us money but I’m not sure how much as I’m still waiting for my first check!

      However, Udemy is the biggie. i would concentrate on that. You already have 1000+ students on your free course. This is huge! Later on (when you have nearer 10,000 students) you can add a few videos to that course, take some of the YT videos on that course off YT and make it a premium course. Then you will start making money from it and, more importantly, you will be able to promote to those 10,000 students a newer, premium course – this is when things start getting serious on udemy! :)

  2. I love the idea of having Skillsnacks but I didn’t realize those could be paid classes. There is so much to learn about the Udemy platform – and I’m so glad I have you to teach me the ropes! I agree that I need to focus on Udemy. Thanks so much for the advice.

    • Sorry to confuse everyone, Ileane, Skillsnacks are only on Skillfeed where you can be paid for 5 minute long videos (or videos of any length at all) that are already on YouTube. As long as these videos are of sufficient quality and are helpful tutorials – as most of yours are.

      Skillfeed will bring in a bit of passive revenue but, yes, Udemy has the potential to bring in more :)


  3. Hi Nick and Rob, Another great show! some great tips!
    Please could you explain more about how Udemy is limiting links back to your own site? Is it still permitted to promote your brand outside udemy. For example if you had resources relevant to your course on your own website can you share the link with students?

    • Hello Mr Explainer. You can promote your brand inside (and of course) outside Udemy. I have calls to action to my squeeze page and site throughout my Udemy courses and my videos are branded with my logo and site name. You can add links to video descriptions and PDF downloads. You just shouldn’t make it too obvious.


  4. Awesome tips! I learn something new every time I read new post about passive income! so I keep looking for them. Way to teach by example!

  5. Just finished listening to this podcast as I spent a good portion of my morning putting together my 1st Udemy course. I had no idea about Skillshare or skillfeed. I took a quick look & it seems a lot of it is technical. Even the “beauty” section is basically photoshop videos. I teach women how to DIY their own airbrush makeup, do you all think skillshare & skillfeed are worthwhile platforms for me?

    • Hey Kellie, Udemy is the big boy at the moment and I would definitely concentrate on that. Technical career and entrepreneurial skills definitely do better there but that’s not to say that a makeup course won’t do well. Skillfeed is produced by Shutterstock and definitely favors graphic and web design courses. Skillshare is maybe more general.


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