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From Unemployed Writer to Head of Marketing: Lessons From Aaron Orendorff

From Unemployed Writer to Head of Marketing: Lessons From Aaron Orendorff

Last Updated:  
March 18, 2024

Over a decade ago, Aaron’s life was on a downward trajectory, and he was out of a job. But, he knew he could write. So he threw up a website and made a bet on himself. Ten sober years later, he’s currently the Head of Marketing at Recart and founder at iconiContent, having previously worked as Editor in Chief at Shopify Plus. The lessons he learned along the way are valuable for anyone in entrepreneurship, and he sat down with Rabah on our podcast You’re Not Your ROAS to deliver some life lesson nuggets of wisdom. 

The Hero’s Journey

Aaron’s journey is inspiring not only because it has so many twists and turns, but because it’s got the kind of character development arc you’d find in a blockbuster film. From joining the military, to joining a seminary and obtaining a Master’s in Divinity, Aaron is no stranger to the unique path. We’re sure he’d say that everything he’s done prior has prepared him for what’s coming next. 

When his life imploded, he was unemployed and unemployable (his words). He could have easily just laid down and let life come at him, but instead he created a website to feature his writing. He knew he could write, and he knew a little bit about how to effect change, which is what marketing is all about.

A Master’s in Divinity: A Secret Marketing Tool?

We’re not telling you to go to divinity school, but in his discussion with Rabah, Aaron was able to point out a few interesting ways marketing and religion can go hand-in-hand. 

As Aaron spent time in religious circles, he connected with people whose sole purpose was to communicate in a way to effect change. When someone promotes the church, they’re working their way into the mind of their audience and connecting to the thing they already want. If you’re listening to an evangelist, you’re hoping to hear something you’ve already decided deep down. A marketer’s job is to articulate their position better than they can. You’re not creating desire for an item or a religious experience, you’re simply channeling it (we don’t just call Rabah our Brand Evangelist because it sounds cute!). 

Aaron discovered that one of his skills was articulating that very quickly, whether it was about religion or the next trend everyone was writing about. So he got right down to sharpening the sword on that particular skill, and it paid dividends.

Any time he writes something, he wants to get “the nod”. Essentially, you’re getting the audience to agree with you. For example, the copy on Recart’s front page states: “Overpaying for your Shopify SMS platform and don’t trust “the results”? You’re not alone”. A customer that visits the site who feels this way will think, why yes I do feel like I’m overpaying for SMS and don’t trust the results! This opens the door for them to listen to the sales pitch and how Recart can better serve them. 

The other tactic he likes to employ is the hard stop - saying something so provocative the person either wants to punch you or hug you. You’ve seen it employed on social media: just make people so mad they come at you in the comments. It works. As the Founder of iconiContent, Aaron’s mission is to save the world from bad content by providing B2B content strategy that’s “built for humans, generates qualified leads, and scales over time.”

But, let’s start at the beginning. Taking what he knew about channeling a desire, Aaron got to work crafting the life he wanted with desperation pushing him, ignorance motivating him, and consistency at the wheel of the whole operation.

Lesson #1: Ignorance and Desperation are the Key to Success

When Aaron started on this path, he had no idea how hard it was going to be. All he knew was that he had to do it (he was desperate). He made it a goal to get a ‘no’, basically saying “let’s be rejected.” He had his bar set super, super low, so he didn’t get disappointed by rejection - he was emboldened by it. He believes that this is one of the characteristics that all entrepreneurs have, to be just a tiny bit out-of-touch with reality. Because to have dreams come true, you have to reach outside the box reality has created.  

So he wrote, prolifically. He wrote articles for Forbes and sent them over, and if they didn’t want them, he sent them on to the next publication. He reverse-engineered what was popular at the time and handed over article after article. He faked his way into getting people to give him money to write for them. And it worked. 

During the first couple of years, his marketing work amped up and he also started teaching at a community college. Eventually, he established himself as a writer that publications began to seek out. He created that opportunity by putting in the work, over and over again until it became second nature.

Lesson #2: Consistency is a Superpower

Putting one foot in front of the next, over and over, is the key to success. Aaron says a lot of people focus on the big things, when in reality doing the next smallest thing you can do towards your goal is what really can make an impact. 

When Aaron first started on his path towards marketing mastermind, he was renting a room from a guy on Craigslist. He was writing tons of articles, and applying for many positions. He applied to work at Buffer four or five times and was rejected each time, but he notes that without that rejection he never would have worked at Shopify Plus. 

One of the consistent things he did when writing articles was send a message to the subject of his piece through a SaaS-based tweet. While writing for Conversion XL, he sent a message to Tommy Walker at Shopify Plus. Tommy didn’t know Aaron, but he liked what he saw and brought Aaron on as a freelancer, and Aaron became the third hire in Shopify Plus. All because of a little, consistent practice he had of messaging the subjects of his articles. He got on the Shopify Plus rocketship, and soon became Editor in Chief. In his words, he “got a front row seat to large, growing businesses and was responsible for a lot of things he had no business managing”. If he’d taken a job at Buffer, he never would have been Editor in Chief at Shopify Plus, later working with Common Thread Collective, and now at Recart. But Aaron knows opportunity was born from consistency and trusting his gut. 

Aaron’s advice nugget: “if all you do is show up having done the thing you said you were going to do, when you said you were going to do it, you beat out 95% of the people who are competing with you out there.” 

It’s a bit counterintuitive to focus on the small things, but focus and consistency will expedite anything you’re trying to do. 

Dabbling in Darkness

In Paulo Coehlo’s The Alchemist, there’s a quote that states: “the darkest hour of the night comes just before the dawn.” In many ways, dealing with darkness can really show you who you are. Aaron’s pursuit of excellence started with a decision - while in the dark - to pull himself out. Aaron said he finds solace in Nihilism: “this universe came from nothing, I’m going to nothing.” If we’re so small and insignificant, we simply don’t need to take things that seriously. Whether it’s religion or some kind of cosmic faith that connects you to something bigger than yourself, the main realization is: you’re not the center of the universe (sorry to break it to you). We’re all just riding around on this pale blue dot. If we take the hits and the lows a little less seriously, we can celebrate the wins while also knowing we’re not the world’s most important person.

One thing that both Rabah and Aaron believe, though, is that once you actually go for something and commit wholeheartedly - the universe starts to conspire with you. And eventually, you get to a spot in your life where you look back and trace the invisible strings that connected you to where you are now. 

Maybe you believe in messages from the universe, and this one found you at just the right time. Don’t give up - suspend your reality just a little bit. Give the world something it doesn’t know it needs just yet! Take these lessons from a formerly unemployed guy who found a way.  

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