Jenna Rainey


Course Login ➞

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.



                                              Take the quiz to get your flow back! 
Feeling creatively stuck?  
Let's be friends!

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



Getting Started With Email Marketing

Business Resources


written by




Having an email list and focusing on email marketing is non-negotiable in my opinion.

If you are a business owner and don’t prioritize email marketing, the time is NOW. Nearly ten years into being a full-time entrepreneur, I’ve seen the growth of my revenue and reputation as an educator, artist and leader directly tied to the consistency and growth of my email list. Now, maybe you have a list and it’s just collecting cobwebs or you don’t have one and have just been focusing on social media growth first, I know you’ve heard it all…

>> There’s no algorithm with email!

>> With over 4.3 billion email accounts 90% of emails sent to subscriber’s inboxes are seen vs. the 2% of your posts that are seen on Facebook and Instagram!

…And DMA did a study looking at investment data and found that “Email marketing has an ROI of 3800%.”

I could go on and on, but I won’t bore you with more data and statistics. Email is more relevant and reliable than ever, can we all agree? And it’s not going anywhere anytime soon.

How often do you get frustrated with a post you put tons of effort into for IG annnnd *crickets*??

Or thinking about how much money you’d have to spend in FB ads, IG ads, etc. to sell a product or book a new client?

With the right email strategy… Email marketing can increase your revenue by over 5x when it’s done right according to McKinsey Consulting Group.

Related: An Overview of Email Marketing


Getting Started With Email Marketing

So, what is an email list?

So that we’re on the same page, let’s talk briefly about some main points or factors that make up an email list:

According to Campaign Monitor, Email list building is the act of getting more people to subscribe to your emails. If you have a CTA on your homepage, that would act as a source to build up your email list. The more ways you can encourage visitors to subscribe to your email, the stronger your email list will be.

But, it’s not just about creating some sign up forms and sending an email or two here and there. In fact, emailing your list sporadically will just lead to more unsubscribes! 

Think about your own activity as a subscriber to someone’s email list. If someone is sending you valuable information at the right time, you’re more likely to stay engaged. But how often do you receive a newsletter from a brand out of the blue and go “wait, when did I sign up for this?? UNSUBSCRIBE!”

So, there’s a balance of finding the right content to write about, not always selling to your list and committing to a regular, expected amount of frequency to end up in people’s inboxes.

Let’s talk about how to get started with email marketing then, shall we?


1. Define Your Purpose to Define Your Strategy

Before you sign up for that email service provider your favorite podcaster is promoting, let’s first discuss your purpose for growing an email list and sending them regular emails. Just because so-n-so with a lotta followers promotes this or that platform (ahem, they’re probably getting some kickbacks. Hey, I love a good affiliate strategy, no hate, just something to be aware of), doesn’t mean that same platform will be the right fit for you, your business and revenue goals. Let’s let’s start with this formula first:

>> What am I passionate about?

Example 1: Maybe you’re a lactation consultant and you’re reeeally passionate about helping new moms figure out the hurdles that come with breastfeeding. 

Example 2: You’re an artist who loves painting landscapes and feels the peace and serenity of what you create and you’re passionate about providing people with unique wave/water paintings that provide peace and awe in the home.

Every business should start from this place of passion. If you begin with the sole purpose of profits, you’re going to come across as just another sleazy marketing person. So with that, your passion should come across in all of your messaging from your website, social media posts and you guessed it, emails!

>> What am I providing?

There are two main structures of business: products-based and serviced-based business. Are you providing a virtual or physical product to customers (ie. art prints/commissions, online courses, gluten free cookie mixes)? Or do you meet with clients one-on-one or in group settings to provide them with a service (ie. business coaching, lactation consulting, wedding stationery design)?

The type of offerings your business is formed around is incredibly informative to your email marketing strategy. Firstly, both of these structures will be totally missing the mark if you’re only emailing your list when you’re selling something, discounting something, or in a launch. That’s rule #1. So now that you know what not to do and how to define your purpose, let’s start talking about some strategy first before you choose your email service provider and start emailing your list!

A) Importance of consistency and knowing what you’re able to commit (weekly, bimonthly?)

Let’s talk about email frequency. I’m not talking about how often you should email your people when you’re in the middle of a launch or promotion, I’m talking about nurturing your people. We first need to talk about how often, each month you will be emailing your people just to stay in touch.

This would be considered a “Broadcast,” or weekly newsletter. For the last 4ish years, I’ve been writing and sending weekly emails. Every Monday morning I send a useful tip, or a story about something I’ve learned that I know my audience would like to hear from me. This is a way for me to stay front of mind for my subscribers, it builds my reputation and relationship with them as an expert in my industry, and leads to more customer retention and revenue, because most people want to buy things from people they trust! 

These stories or tips I’m sharing are relevant information to that particular audience, and usually have to do with art or business owner things. For example, about a week ago, I sent out an email that talked about how I received a rude message from somebody. I wasn’t selling anything, just connecting with my readers and sharing something vulnerable. This email received an overwhelming response with hundreds of replies and because I am consistently emailing my subscribers with value focused messages that either provided them with connection or answers to their questions, I have consistently opened emails. 

It’s that simple.

If your email frequency isn’t optimized, you might be missing opportunities to convert more leads (or stop chasing away those currently in your funnel/list). The #1 reason people unsubscribe is because they receive too many sales heavy emails from the same person. That’s frustrating and annoying! Unsubscribes are unfortunately inevitable, but finding the right frequency is a huge step in minimizing the amount of people who say bye bye.

So, how frequently should YOU email your list?

My Tips:

  • Start with sending 2 emails a month
  • After a few months, split test it!
  • Segment half of your list to be the group that continues to receive 2 emails a month, while the other half starts to receive weekly emails. 
  • Track open rates, click through rates and unsubscribe rates for a few months!

B) Don’t write boring subject lines.

Writing compelling subject lines is about half the battle of email marketing in my opinion. You could put together a stunning email with all the beautiful, compelling story archs and wit, but without an openable subject line…it won’t get read.

Sometimes it doesn’t matter if I know I’m getting sold to, I’m just so impressed with the subject line and the hook, that I open the email to read the rest. Writing subject lines like “You won’t believe what I just saw” or “I’m embarrassed.” are compelling, create this feeling of hot gossip and definitely hook the subscriber scrolling through their inbox.

C) Welcome your subscribers FIRST before selling to them!

This is probably THE most important step in successful email marketing. Whether someone “opts in” to your list through a general subscribe button or to receive something in exchange for (ie. lead magnet/freebie such as a discount code, a free guide/workshop/etc.), you MUST then send them through a welcome sequence (series of automated emails) that help to warm up that new lead. Picture this:

You invite someone over to your house for the first time. Maybe you just met them or a friend invited them and you don’t know them at all. Wouldn’t it be rude to invite them over for dinner and never open the door? Never welcome them into your home, give them a tour and make them comfortable in your house? Yes! A good host opens the door, shows them around the house and offers them at least water to drink right? This is the exact same with email marketing. So many business owners just provide the handshake and never send them another email until it’s time to sell them something…that is sooo off-putting and will definitely increase your likelihood of unsubscribes!

Our welcome sequence currently is a series of 5 automated emails that tells my story, hits on my biggest pieces of advice and value and helps to boost brand awareness, reputation and relatability. We’re soon going to be testing out a 30 (yes 30!!) day welcome series, so I’ll make sure to write a blog with updates on that soon!


2. Choose Your Email Service Provider

OK, now that we’ve talked about defining your purpose and strategy, let’s get into some of the nitty gritty tech stuff with email marketing. First up, choosing your email service provider.

ActiveCampaign: I decided on this service provider because it can handle the complexity of our campaigns, automations and triggers, while keeping things well organized and visual. I switched from MailChimp to Drip then to AC a few years ago, and love the capabilities I have access to (though it is quite a bit more expensive than MailChimp or FloDesk)!

ActiveCampaign plans start with Lite at $29/month but this plan won’t offer the robustness of running split automations and such, so if you plan on getting reeeally dialed with your email marketing strategy eventually, you could always start here and then move up to the Professional plan ($129/month), which is what we use.

Convertkit: is an excellent choice if you are just starting out but you want to leave room for growth and advanced tagging and segmenting features in the future. It’s kind of like a CRM tool, without the big price tag.

Pricing starts at $29/month for up to 1,000 subscribers and goes up gradually from there.

Mailchimp: is a really popular service provider, especially for those just starting out. Because it’s more user friendly on the tech end, however, the more complex functions like segmenting, triggers, etc. are a bit more limiting than others. This is the main reason why I left Mailchimp. Side note: Migrating service providers is NOT fun!

Mailchimp has a free plan for up to 2,000 subscribers. Paid plans start as low as $10/month and can go up to $30 for 2,500 subscribers. The bigger your list size, the more you’re going to pay.

MailerLite: Similar to Convertkit capabilities!

You can get started for free for a list size of up to 1,000 subscribers.

Besides the providers listed already, you can also look into HubSpot, which is a more complex CRM/marketing tool or FloDesk, which is newer on the scene but seems very user friendly, design focused and cute, but not as robust as a CRM like ActiveCampaign or even Convertkit. 

The main thing you want to keep in mind is: Growth. Just because Mailchimp is the cheapest now, doesn’t mean it will be down the road, and it isn’t my top recommendation for brands who want to use tagging and segmentation to minimize unsubscribes. My recommendation if you’re just starting would be to gravitate towards ConvertKit or check out FloDesk if you’re not the tech-savvy person and don’t want to ever learn to become one (tee hee)! I personally use ActiveCampaign because both my Operations Manager Kelly and I are nerds and love all of the tech and we need a very robust system that can carry all of the content we produce each month.


3. Build That List

There are TWO ways to grow your email list:

>> Content Marketing 

>> Social Media Marketing

The first, content marketing, is the most effective from my own personal experience and research, so let’s get into that one first.

What do I mean by content marketing?

According to Wikipedia: Content marketing is a form of marketing focused on creating, publishing, and distributing content for a targeted audience online.

Content marketing could be everything from writing and publishing blog posts, to podcast episodes and YouTube videos. Next we’ll be talking about social media marketing which is great (especially Pinterest), but what MOST business owners leave out and what I believe to be the most important and effective is a solid content marketing strategy.

Most entrepreneurs focus on Instagram or “Oh shoot, I should post about that thing I made,” but when you’re creating regular, valuable content on a searchable platform, that’s where the real growth starts to happen! A searchable platform (ie. search engine) is how you drive consistent, organic traffic to your website, online shop, etc. and is the best way to find new leads for your email list.

For example, if I write a blog post on “The Ten Best Ways to Increase Your Website Traffic,” optimizing that post with keywords and search terms that my ideal reader is typing into Google and have a CTA (call to action) that leads them to a free guide on “The Ultimate Guide to Search Engine Optimization,” then that free guide is automatically and daily, generating traffic from the search engine Google without me having to actively promote it each day. The keywords do the work for you!

But content marketing doesn’t just start and end with writing blogs. Content marketing is anything with a search bar: YouTube and Podcast being some of the biggest ones.

Now let’s talk about my favorite social media platform for email grown…Pinterest:

Your pins have the potential to reach hundreds, even thousands of people and all you need is an hour or less each week to create content for this platform. Why is Pinterest my favorite? Well, it’s a blend between a search engine and social media. People hop on this platform looking for tips and inspiration and use the search bar to discover posts that reflect their exact needs, hopes and desires.

If your pins, profile and boards are optimized for what your ideal audience is searching for, then guess what?! You’ll have people hopping over to your free guides, your checklists or your website to learn more! We generate 2 Million monthly views on Pinterest with very minimal effort (in comparison to the games you need to play on IG) and it generates loads of traffic to my YouTube channel, my website, my courses and more!

But the goal with any platform, just like email marketing is consistency. Whether you’re posting to Pinterest or Instagram, Twitter or a blog, consistency is literally king. If you’re overwhelmed with all of the content you need to create, just choose one platform and start there. Then guess what? In 3 months, six months, etc. you’ll have a large library of content that you can reuse on another platform! Take your pins on Pinterest from six months ago and expand them into Instagram posts and captions or vice versa!

>> And to tie it all up and show you what content marketing and list growth is all about, don’t forget to sign up for my email list if you haven’t already. I share loads of tips in there about starting and growing an online business!

by Jenna Rainey 

add a comment

  1. Thank you Jenna. Very helpful and concise. I will have to get back into posting to Pinterest. I tend to forget about it when I think social media.

Leave a Reply

Your email address will not be published. Required fields are marked *

The Complete Beginner's Guide to Watercolor

Get a rundown of all my recommended supplies, learn fundamental techniques and tips including color theory and composition, and walk away feeling super confident with your new love of watercolor!

Free e-book

The Complete Beginner's Guide to Watercolor

Freebie Alert!

*Signing up will subscribe you to our email list, You may unsubscribe at any time, though doing so means we cannot contact you with more free, valuable education and tips on this topic. You also agree to our Terms and Conditions and Privacy Policy.