Jenna Rainey


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hey friend!

I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

(with me)


It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

Wanna Learn Watercolor?

i wrote some books



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Secrets to Recurring Revenue as an Artist

Business Resources


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DISCLAIMER: This article contains affiliate links, which means that if you click on one of the links for select products or services (that I've vetted and love, btw), I may receive a small commission at no extra cost to you. This helps support the podcast so that I can create more free, valuable content for you. Thank you for the support!


Having consistent income would be nice, right?

So many creatives struggle with the dips and valleys in income with their freelance work. Feeling stretched thin and wondering when the next paycheck is coming are all too common. And the key to beating the constant hustle?? Recurring revenue. This is the KEY to scaling your creative business and generating income that allows you to rest!

In order to grow and scale a creative business you’ve got to unlock consistent and recurring revenue streams. Recurring revenue is the FASTEST way to scale and reach revenue goals. This is the bread and butter of making consistent income as a creative entrepreneur. Whether you're an artist, a photographer, illustrator, designer, whatever you are, hairstylist, etc. recurring revenue is the secret to growth. So, if you're feeling stretched thin, I have a few tips for you!

When I was a custom wedding stationery designer, about three years in, I was generating six figures a year. In the early days I was barely making a profit and then I eventually hit that six-figure-a-year income goal or marker. But even with making those numbers, I still felt behind and like there were big gaps in income! There would be seasons of hustle and feeling overwhelmed where the money was good, but then seasons of famine were right around the corner.

I know this isn't just the case for, artists, stationers and calligraphers in the wedding industry. This is the same for photographers, for designers who are working with clients, etc. So, how do we tap into recurring revenue as a creative, so we can scale and grow our business?

I've mentioned this before in previous posts, but 2015, I got desperate for recurring revenue. At that time, I decided to design and release do a semi-custom invitation line. This ended up being a huge fail. Nobody bought a single collection! This ended up flopping mainly because I wasn't listening to my audience and what my audience needed from me.

This was a huge mistake on my part. I was seeing other calligraphers other wedding invitation designers having success with their semi-custom lines and thinking, well this is just what we do. This is the next step. And so I did it for my audience as well! But this was the time in my career when started posting more tutorials and watercolor work on social media.

Because of this, my audience was eager for more education from me…not semi-custom invitations! If semi-custom invitations work well for your audience, it's a great way to generate recurring revenue! But the most important step here before spending time developing anything is to LISTEN TO YOUR AUDIENCE.

Below are my secrets to recurring revenue. Maybe they all don't fit within your business or goals, so think about what works for you!


Write a book

Like I said, my audience was eager for more tutorials and education.

This was when I was approached by a literary agent.

In 2015 I put together a pitch deck and proof of concept for 30+ different book ideas to send to publishing houses. In 2016 I signed my first book deal with Ten Speed Press. Over the last three years, I get a check every quarter from book sales. I barely promote it, but because it's on Amazon, it's discoverable! It's also in retail stores like Target, Barnes & Noble, etc. and customers share their progress through the book on social media, which helps promote the book for me! So, just gradually over time it has become more and more popular.

But it's not just about writing a book if you're an educator. You have to continue to serve your audience with FREE tutorials and material. This will make them eager to learn more from you! So, I'm constantly posting new watercolor tutorials on my YouTube channel and Instagram!


License your work

Around 2017 I started getting into licensing. My very first licensing project was with a yoga towel company, Nomadix. At the time, all I had experience in was wedding stationery and writing how-to books. I had no idea how to structure pricing for licensing, if I should request a flat fee, a flat fee plus royalty rate, just royalties, etc., but I went for it and hired an agent!

Licensing is a huge way for artists and creatives to make recurring revenue each quarter from different products, collections and collaborations over the years. If you want to get into licensing and learn all the ins and outs, check out the course I did with my agent Julie: Brand Plus Brand!


Teaching online classes

I absolutely love teaching. I come alive when I'm teaching workshops, tutorials on YouTube, etc.. I've had online classes since 2015. I've done courses through other hosts like Brit + Co, but in 2018 I launched my very first, in-depth stationery course for wedding stationers. I teach everything from the artwork, scanning, designing, putting together mock ups and proofs and prepping their files for print properly for letterpress, foil and digital.

I launched Pen to Press in December, 2018. I was eight months pregnant and I had bronchitis. It was a crazy time, but that is when I really felt like I had found my true passion and purpose—helping creatives scale their business and build thriving creative businesses. Since then I've launched more creative courses and I absolutely love getting down and dirty with creatives and helping them grow and build thriving businesses!

But the trick here, like any recurring revenue stream, isn't to just list it and think you'll make all this money!

“If I build it, they will come” does not work in this scenario. If you don't have an audience, you can list a class on Skillshare where there are MILLIONS of users on the platform. The opportunity to have tons of people seeing and watching your course is much greater than listing it on your own site.

Or if you want to get into licensing but don't know where to start, get your feet wet with something like Creative Market or Society6. Similar to Skillshare, these marketplaces have millions of users, so if you're utilizing keywords properly, you can make great recurring revenue!

The first year I launched one of my courses on my own,  I made over $150,000 in one week. That was the first time I ever launched on my own. The reason why this did so well is because I knew the problems my audience was having. They had no idea how to set up their files for print. They were making constant mistakes with their clients and they didn't know how to take their clients to the next level. Because of this, I put together Pen to Press.


You HAVE to listen to your audience and create your offers around the conversations they're already having, or the questions they're asking! If I would have thrown in the towel after I listed that semi-custom stationery line that failed, we wouldn't have these online courses today. I would've never put together Pen to Press. But I kept digging deep and trying to find out what my audience truly needed from me.

I got my feet wet in licensing before I hired an agent. I listed a few things on Creative Market and I had a calligraphy font. This helped me learn about keywords and discoverability…if you don't have a large audience but you're on one of these marketplaces, people can find you! If you know how to craft discoverable product descriptions, your products, classes, etc. can generate good money!

So because I'm all about helping you out and I want you to know how to do keyword research for your own business, I've got an entire keyword research guide for you to help you generate more recurring revenue. This can apply to any search engine—Skillshare and Creative Market, to Google and Pinterest! Download the FREE Pinterest Research Guide HERE!

by Jenna Rainey 

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  1. Girl you are amazing! I loved this episode! Thank you for sharing your secrets!

  2. Jacqueline says:

    So great Jenna! Thank you for sharing so much helpful information!

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