When Simon approached me a couple of weeks ago, we quickly realized that we shared a lot of the same values. His podcast, Music On Your Own Terms, is all about promoting the entrepreneurial mindset to musicians and having open discussions about mental health.

In his day job, Simon is a graphic designer working for a merch company. He’s got lots of tips and tricks that a lot of bands don’t even think of when they’re ordering merch.The first half of this episode we discuss merch strategy and what you should do if you’re looking to get new merch items in your band, while the second half of the episode dives more into personal development journey, and mental health – which is a very huge passion of mine. Simon answers all my questions about whether creatives are particularly susceptible to mental health issues compared to non-creatives (the answer will surprise you!)

What’s his story? How it all started

If there’s a goal – whether it be selling out a stadium, releasing an album, or just be picking up a guitar – what are the very small steps you do from A-to-B?

Originally from “Merry Old England,” Simon moved to New England (USA) during his 20s where he achieved moderate success as a guitarist. He opened up for the likes of Tantrik, won a Battle of the Bands, and got some radio time. 

Shortly before opening for Lynch Mob, the band dissolved but Simon had already met so many people within that local scene. Making many friends and valuable contacts. 

The Music On Your Own Terms podcast spawned from this experience of playing in a band and hearing a lot of people saying “you can’t make money from streaming.” 

Simon knew that kind of thinking becomes a self-fulfilling prophecy. He wanted to flip the script on that shit.

Inspired by other podcasts and literature on self-improvement and business concepts, Simon thought about how to shift that mindset of “you can’t” to “how can I?”

Many of the contacts he’d made in the scene were more than willing to be interviewed when he launched his podcast. So started his journey down the path of helping fellow bands and musicians.

Life threw a serendipitous curveball a short while later when his family had to move to Texas. Ditching a corporate job as an engineer, he used his graphic design chops to land a job at a t-shirt printing company – The Skinny Armadillo

It all fell into place from there. 

Now for his podcast and in his day job he helps bands and businesses make money from their merch. The Skinny Armadillo knows what’s selling, and what people are receptive to. 

So pay attention and listen up, legends!

Trending Tendencies & What Merch Works Where

Pro tip: don’t buy the same number of every size!

In the USA sizes Medium and Large usually account for 50% of sales.


So stock up on your M and L sizes because that’s going to be your big seller. Then sizes like Small or XL and above will tend to wane off. Like a bell curve. 

Lastly, think about where you are and the styles your audience is into!

If you’re an American band, don’t take baseball hats to Europe. People don’t wear them. It’ll be a waste of money you don’t have and space you can’t spare. 

If you’re in a European band coming to America, bring on the baseball caps! That style is very big over there. 

In Canada, hockey jerseys are super popular. Plenty of bands do that whole hockey thing when they go to an arena, buy a hockey jersey from that store that houses that hockey team, and they’ll wear it on stage. 

Double down on your beanies when you go play a winter festival.

Things like that.

Do your research. Find out what styles work in the region you’re targeting.

Thou Shalt Have Kickass Artwork!

Believe it or not: you can get people to buy your shit. 

Whether they like you or not. Whether they have heard your band or not.


With an eye-catching design!

As a general rule, the main thing that you want to worry about with merch is that your art looks really good.

No-one really wants a shirt with just a band name on there, it’s not going to win any prizes for design. This is one of the core areas that a lot of bands go wrong: they just get their logo on the shirt. 

Guys, I get it, you need the merch but don’t have the budget or aren’t willing to spend extra money on design. The logo has already been paid for. It’s so much easier to just put your logo on a shirt, but it ends up biting you in the ass when you can’t really sell them because when you aren’t a big band or your band isn’t at the point where people are buying the merchandise for the sake of having something that your band produced.

A lot of bands are also getting creative with print-on-demand merch, or releasing collections seasonally – like a normal clothing brand would. In fact, there are correlations in the music industry starting to go in more of that direction (considering streaming royalties are lower than physicals and whatnot). 

If they love your band from the get-go they’ll support you. But if they don’t have that connection, you’ve got to do something else to push them towards a sale.

Why wouldn’t you want someone to buy your shirt just because they think it looks cool?

PLUS it’s a walking advertisement! 

Don’t just think about the sale, think about how having more people wearing your shirt will help market your band.

Thou Shalt NOT Use Crappy Shirts

If they’re not wearing it, they’re not advertising your band.

Don’t buy the cheap, crappy shirts. Just. Don’t.

It doesn’t cost that much more for the better fitting, more comfortable shirts.  What adds to the cost is actually the number of colors in your design and the printing process itself. The T-shirt itself really doesn’t make a huge difference in the price. 

Why not buy a good quality t-shirt and have people wear it because they want to wear it, because it’s comfortable, rather than some cheap shirt they’re not going to put on because it doesn’t feel good to them?

Don’t just think about that initial purchase supporting your band, think about the long-term goal of what the shirt actually means.

You Gotta Connect to Convert

The first 15 minutes after you get off stage is the most important, for not only selling merch, but also converting fans. 

Now, a lot of people get it on their high-horse and rag on vocalists because they’re not helping pack down the stage, they’re off talking to people and whatnot. But that is when you are going to start making money and start actually converting people into fans

Make sure you’re mentioning who you are throughout your songs, engage with the audience. Put in the slight effort to say, “Hey, we’re such-and-such band.”

The most important job that you can have (aside from the actual playing of the night) is in that gap between when your band finishes and the next band starts. The room is quieter. People are jazzed from your music. They’re over at the merch stands. You have the opportunity to talk to them! It’s super important for you to be engaging with people. It’s not just that money converting. You’re converting people from viewers to actual fans.

Being A Creative Holistically

Musicians often have a mindset “I should be paid for my music,” and that’s it. 

But the reality is the music itself is the experience that we’re giving the fan. Everything else surrounds that is the tangible stuff that we actually want to get paid for. 

Instead of thinking of yourself as an “artist” try thinking of yourself as a   “craftsman.” A craftsman doesn’t go into the workplace and instantly become a success. They go into an apprenticeship because they’re not only learning the craft, but they’re learning how to run their business. 

The truth is, you have to be a business person.

So many people still are under the impression that they can release something on Facebook and hope for the best and people will come to them. It’s so much more work than that. You lay out all the ways that you’re going to get exposure, connect with your fans, build relationships, social media, come up with your release strategy…

People are successful because of the work they put in, not because of how good they are at their instrument.

Overnight success takes 10 years. It just doesn’t happen overnight.

Mental Health – A Creative’s Curse

Simon tells all about how he struggled with his own mental health for years. In his home of England he battled the “stiff upper lip” mentality, then when they immigrated to the US there remained a stigma around seeking therapy.

Music was a direct, relatable, thing that kind of saved me, it kept me sane, as sane as I could be.

So, the big question was, are creatives more susceptible to mental health issues?

Simon’s thoughts on that was that it’s less a matter of susceptibility and more a matter of being “open to it” because they’re more connected with their creative side. As creatives we tend to get into our zone. Our free flow. Our stream of consciousness. And that opens up that kind of that part of your mind. 

Whereas somebody who’s logical and mathematically based, and their mind is skewed to one side, which means that the other side is closed. 

Having a balanced, left and right brain is absolutely crucial in Simon’s view, because you have to think creatively about logical problems at times. Just doing it by the numbers doesn’t always work.

Simon’s own experiences around mental health, and those around him, are part of why he is so driven to have the stigma of mental health removed. By normalizing it, it eliminates those people that bottle it up and feel trapped.

It’s never gonna be where I don’t have to work on something. But, you know, I’m in the best mental state where I am today. 

So it’s just trying to get better each day.

Developing Your Single Most Important Asset – YOU

Through Simon’s mental health journey, he sought out self-improvement and personal development from a friend who was a serial entrepreneur.

As he consumed all these books and podcasts, it started him on the journey. Simon firmly views progress as a path of tiny steps leading to your ultimate goal. When you focus on your goal, sometimes it can feel so far away. But if you just focus on each step to get there, the journey feels less daunting.

Every day is a new opportunity to start again.

Here’s a curated list of Simon’s personal picks for personal development, self-awareness, and music business:

This content was originally published here.

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