Jenna Rainey


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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!

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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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3 Simple Techniques for Selling Without Feeling Sleazy

Business Resources


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John and I were in New York City for the first time together for my watercolor and calligraphy workshops back in 2015. We had a free day in the city to stroll and shop around. I remember being in a record store (John’s a big record collector), and thinking to myself “I should probably check how much money we have in our account.”

*Cue heart throbbing sounds in the ear drums*

All I remember was my vision getting narrower, all of the chatter going on around me became completely silent, my skin feeling hot and sweaty and my heart pounding.\

We have less than $1,000 to our name, rent is going to be taken out soon and I still owe my printer for that client job from last week.”

John could see the panic on my face in the middle of hipster haven (aka a record store) and came over to see the reason why.

This is when I knew things had to change. I could no longer feel the immense stress and pressure of feeling constantly behind financially.

And I couldn’t understand why this was still such a struggle for me. I felt SO GOOD at business. My Instagram was crushing it, I started booking celebrity stationery jobs and I was travelling the freaking world and selling out my workshops…WTF is going on?!

Obviously I was a bit naive about business and THIS was the moment of transformation for me. When we got back from this trip, I set out on an intense journey of learning and figuring out everything I possibly could for creating and selling online courses.

I knew I was good at teaching and I knew with the power of the internet I could reach thousands of people with my ideas and teaching. Fast Forward another 8 years and I now run a 7-figure digital course business.

Do you see what I did there?

I just sold you on my expertise as an online course creator and coach without being pushy, salesy or sleazy. Let me show you how to do it with 3 simple techniques for selling.

Related: How to Sell Your Work and Not Feel Sleazy


3 Simple Techniques for Selling Without Feeling Sleazy 

#1: Tell your pivotal moment story

That story above is my pivotal moment story. The “what changed everything for me” story. This is the key element to selling without sleaze because the selling element is infused with your story! You're not blabbing on about the features of your product, what it costs, why it’s better than the competition, like every other used car salesman and pushy marketing bro out there.

You’re connecting emotion to your product or offering. It humanizes what you are offering and builds that relatability and desire within your audience.


#2: Your story is actually their story

What’s also happening when you’re telling your pivotal moment story is the person listening isn’t hearing your story. They’re hearing their story. This is huuuuge because it then helps activate the visualization part of their brain and shows them that “Hey! This is possible for me too?!” and on top of that, when emotions come into the decision-making part of the process, the person is more likely to trust and buy because it moves them out of their conscious and critical mind and into the subconscious mind.


#3: Use NLP to your advantage

NLP stands for Neuro Linguistic Programming and is what allll the storytelling gurus and experts use when they’re at public speaking events, teaching a webinar, etc. This technique is THE gamechanger for any story that is impactful, meaningful and memorable. To distill this down a bit, I want you to remember these three “p’s”: picture, press in and hear, pause to feel.

This is how the brain subconsciously processes any bit of language, conversation, problem, etc.! It first pictures what it’s processing and goes through a visualization period. Then it hears the sounds and thoughts associated with it and once it’s done that, your brain feels the emotions and sensations behind the information being received.

Go back to the story above to see how I demonstrate this in my pivotal moment story! I’m sharing visual elements from the story by describing where John and I are, then I pull out auditory elements like my thoughts and the chatter in the room going away, and then I moved into the feeling part of it. Feeling stuck, frustrated, lost…these are all extremely relatable emotions and feelings and with those three “p’s,” I’ve created a very memorable story of transformation that allows me to sell my coaching services or online courses for business owners without being sleazy!


There you have it! Techniques for selling that aren't sleazy! You don’t have to feel like a salesperson, but rather a real, authentic, vulnerable, skilled storyteller. You’ve got this.

by Jenna Rainey 

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