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. 

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2021: A Year in Review



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How in the Lord’s name is it already time for another year in review?

Last year I did this 2020 recap and it’s always fun for me to look back at the year and see what goals we hit or missed, systems we changed up and how the business grew in 12 months. If you’re a creative business owner like me, these posts are like peeling back the curtain and looking at some of our biggest milestones. You ready?


YouTube Growth

Since starting my YouTube Channel in 2019, we’ve been able to grow the channel to over 148K subscribers. John (camera guy and husband) and I now have a system for posting two videos a week on our channel. And we finally crossed over the 1 million views threshold. Let’s breakdown those stats:

Channel Analytics 2020:

Views: 1.8M

Watch time (hours): 272.0K

Subscribers: +58.6K (how much we increased from the previous year)

Channel Analytics 2021:

Views: 3.2M

Watch time (hours): 606.2K

Subscribers: +77.4K (how much we increased from the previous year)

Now. Let’s get real here. I had this moment the other day when I was looking at our revenue from the YouTube channel and I realized something. I make more than what I made at my old desk job from my YouTube channel. While it’s a barely liveable wage for southern California, it still amazes me that I can do what I love, share it with a community of amazing artists and earn money doing it!


Launched a Patreon

Because the YouTube Channel has been doing so well, we decided to launch a Patreon! This is where I share exclusive monthly tutorials and hold live art classes every month that I don’t share anywhere else. Since launching the Patreon in April of 2021, we’ve grown to having about 347 patrons per month!


Growing My Team


While YouTube has been a big driver of organic traffic to my website, I wanted to hone in on making my Pinterest account more efficient in boosting traffic. So we started working with Byte Bodega to help with posting regular content, SEO strategies and more! Since working with them, I now average over 1M views per month on Pinterest and this helps to drive more traffic to our lead magnets, website and my YouTube Channel!


I’ve mentioned my Operations Manager Kelly on here before and she’s been working with me since 2019. One thing that’s new this year is she’s helped me with automations and blocking my calendar in Asana for more efficient work weeks. Since having my son Myles, I’ve never really found a regular system or schedule with consistent work hours. But, the system we now use is the closest to it we can get without having a nanny or help during the day. If you want to see what this looks like, I have a highlight on my Instagram called “Asana” where I show you what I’m talking about!


And speaking of Kelly, her husband does number-crunching by day for a large US corporation and stepped in to help us here at Jenna Rainey LLC with some of our reports and analyses, numbers breakdowns and more! This has been a real game changer for me.

As a creative business owner, I am NOT a fan of the financial department, but working with Andres has helped simplify this side of being a business owner and I’ve learned a ton. We’ve also been able to analyze the performance of each product and offering we have with really clear data to see if something should be revised or even eliminated. We decided to shelf one course after realizing it performing just okay and instead decided to double down on courses like “Brand Plus Brand” and spending more money there because we can afford to!


Another big move we made this year was bringing on Jos Sipowicz to help me build out my print and pattern library for licensing collabs. While I know how to create repeat patterns, there’s a whole world to it that I don’t understand. And I’m definitely not quick at it.

So, I decided to bring on Jos who is now a guest instructor in Brand Plus Brand and an in-house print designer for large companies, to help create prints for my collections. This way I get to focus on the painting and development of the elements and story. Then she bangs out the prints! We make quite the team!


New Collabs

The licensing category of my business has grown a lot this year. I started licensing my work in 2018. Because I’ve been heavily focused on teaching and launching online courses, it’s been a slow trickle over the last few years. But this year, I put a lot more focus into building out my library of work. Kelly and I (mostly Kelly) spent a lot of time organizing our backend library and I added a TON of new collections and work this year. I spent a good three months earlier in the year focusing on alignment and shifting to what I really want to create and it’s proven beneficial.

I picked up a collab with Crate & Kids, CASETiFY, Blue Sky Planners, Society6 x Pixar and more this year and have a whole lot more in the works for next year!


Financial Goals Reached

Work harder, not smarter. This year was alllll about alignment for me and becoming a better delegator. I don’t know if you ever feel this way, but I didn’t quit my 9-5 job to work 24/7, you feel me? Owning a business is hard work, it’s chaotic and you’re thrown into jobs that you have no training in (ahem, bookkeeper, financial department, etc.) overnight! So, this year, we made sure to shift focus on some things so we could work more strategically and efficiently instead of just straight up frazzled.

What do I mean? Well, we have REGULAR meetings and check-ins. Whether you have team members or not, having regular (weekly or monthly) check-ins on what’s up and coming, urgent tasks that need to be addressed, and what the numbers are looking like, etc. has allowed me to address what’s truly working and what’s not. These meetings allowed me to slow down and realize that one of our courses wasn’t selling as well as we hoped. We can rework it, take it off the shelves or focus energy and funds on creating something new! Without these regular check ins though, I probably never would have realized that something needed to be changed!

We also started using a break-even calculator to assess what new products or offerings to launch and at what price! If you don’t know, a break-even calculator allows you to see how many units of a product you need to sell to cover all the costs involved in producing and selling the product. In other words, it tells you when you break even and start making a profit. For example, in the beginning of the year I was certain I was going to launch a specific program this year. It sounded exciting and it also seemed like it would make good money as well. Before creating the program however, we decided to pass it through the Break-Even calculator and realized that if I charged X amount of money for the program, I’d have to sell a ridiculous amount of seats, where I’d be hustling and only focusing on this one thing, OR I’d have to charge a higher price that I didn’t feel comfortable with charging right now after what we’ve all been through over the last 20 months. So, I didn’t launch this program. I’d probably be working longer hours right now!

Owning a small business is challenging, it keeps you on your toes, but it’s something that I am so grateful for! Every year is so fun to look back on and see what we were able to accomplish, the hiccups, the exciting projects and more!

by Jenna Rainey 

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