I recently had the pleasure of speaking with Jeremy Vessey, an established type designer based in Charlottetown, Prince Edward Island.  He’s carved out a name for himself in the font industry with his brand Hustle Supply Co. by perfecting the art of the authentic vintage style script font, as well as a variety of beautiful slab and brush fonts.  While perusing his portfolio site, one also comes across some gorgeous outdoor photography that stands on its own while still tying in with his overall rustic aesthetic.  He reflects on how he gained traction in the marketplace early on, what inspires him to create and the struggles he experiences along the way.  It was an enlightening conversation and want to thank Jeremy for taking the time to speak with me and for sharing his insights.

Did you always want to be a designer? How to did you find your way to selling through online marketplaces?

When I was in college, I had a strong interest in logo design, lettering and building custom type.  After graduating, I knew I wanted to be a Logo Designer so I focused most of my energy on trying to build personal projects around that niche, specifically with a vintage aesthetic. I loved looking at old packaging and liquor bottle labels and trying to come up with my own.  

After a year of working as an in-house Graphic Designer, I had built up enough clients on the side to quit my job and become a full-time Logo Designer. Not long after becoming a freelance Graphic Designer, I found Creative Market. Building design products was a way of being in complete control of what I made from start to finish with no revisions or input from outside sources.  I started creating logo templates in the beginning. I had already made a bunch of “practice logos and labels” for sites like Dribbble. So it was a natural first step into creating products.

After a while, I wanted to create products for Logo Designers.  Since it was my main interest, specifically logos of a more handmade or vintage aesthetic, I could identify the typefaces I wanted to own and use myself.  So I started creating products that I myself would want or need for a given project.

Your speciality seems to be creating extensive, high end font families with a distinctly vintage feel.  What do you think draws you to this aesthetic?

Earlier on in my career, as a freelance Logo Designer, I was immediately drawn to that aesthetic.  I enjoyed playing with and pairing various typefaces to create an elaborate composition of type.  So when I started creating typefaces, I ended up trying to create typefaces that I would want or need.  

My most successful typefaces were created to fulfill a certain need. I would imagine a fictional client and create a typeface or multiple typefaces that would pair nicely with each other – the end goal being a type family or type collection that could be used to achieve a desired aesthetic for this fictional client.  

So, if we take the example of a coffee shop, I would imagine one or multiple brands that need a logo, label, etc. made for their company. Then I would create typefaces that could be used and paired together for that imaginary company. Anytime I tried to create products just to fit a certain trend, they always do sub-par at best.  Yet, when I create products with intent, a product that has a purpose, it does much better. It helps to focus the project / product and make it cohesive.

Are you someone who needs to continually out-do yourself or are you content with much of your work?

Yes and no.  I am always trying to create products that are better than before,  but I understand that each project or product is a stepping stone towards improving.  I try not to overthink my Typefaces or products too much. I’ve found perfectionism to be paralyzing and it usually results in a great magnitude of unfinished work collecting dust on a hard drive.  I think everybody who is growing as a creator looks back at their work and thinks “it could have been better”. 

But I also recognize that each product represents a unique point in my career.  It’s almost like getting mad at a 2 year old Oak tree for not being as large as a 100 year old Oak tree.  I was putting out products that were at the edge of my capabilities at that moment in time. It would be easy to fixate on how I could go back and improve all of my older products, but I think that paralyzes you and gives you an excuse to not create. I’ve found the best way to learn is to create, release, repeat.  This helps you to find your niche, then get data or feedback on what works and what doesn’t as you grow. If you’re in a constant state of planning, nothing gets released.

There is an unmistakable authenticity to your fonts and logos that separates them from others I’ve seen.  Are there specific sources you find yourself consistently drawing inspiration from (i.e. books, old type foundries, websites, etc.)?

Usually I’ll get ideas from a lot of random sources that I see throughout the day –  maybe I’ll notice a certain “G” on some packaging, or I’ll see something on TV that sparks some new ideas.  But a lot of it comes from trying to create something for myself.  I try to fill the void in my own font library and create something that I don’t currently have available to me.  

But yes, I find myself looking at a variety of different sources from magazines, old labels, patches, etc. that I come across on a daily basis. I also try to figure out what fonts Designers might need or like. Sometimes a Logo Designer’s work will inspire me to create a font that they themselves would use.  I’ve had various Logo Designers who I follow use my fonts. It’s a great feeling to know that I’m creating something that’s useful to some of my favorite Designers.

About how long would you say a typical Hustle Supply Co. set (including preview images) takes to complete?

I’m a fast worker, so it really depends on how complex the typeface is.  Some fonts take much longer than others.  I spend a lot of time thinking prior to sitting down and working.  I usually have a typeface made in my head before it ever gets created.  Whenever I have an idea fully fleshed out, creating the typeface might only take me 1-2 days, but usually projects will linger for a while. I typically have 2-3 different font ideas going at once, so it might take 1 month before it’s fully completed and released.  I’ve created fonts & display images that have taken me 2 days and I’ve created fonts that lingered on for months. Display images usually take me a 3-4 hours if I’m in a decent state of mind.

An interesting point is that the amount of time I spend on a product has no impact on how well it sells.  One of my top selling products took me 2 days to make. Some of my worst selling products have taken months to make.  Sometimes a simple typeface or product just clicks with people.

What do you find to be the greatest struggle(s) for designers selling online?

I would say the greatest struggles are persistence and patience.  Many people feel defeated after doing a bunch of work and not seeing any reward for their efforts.  I can understand this – I think it’s a natural feeling.  I think the differentiating factor that I had when I started out was that I considered Creative Market more of a personal project.  I was creating all of these personal projects on Dribbble to get my work out there in the beginning and I thought to myself: “why not create products instead of personal projects?” 

I went into it with low expectations.  My goal was to eventually earn an extra $250-$500 a month.  Now, it’s been a full-time gig for 5 years – I stopped taking on clients 4 years ago.  I think the key to persistence is creating a business, shop, or product that comes naturally to you.  Doing something because it’s on trend, or because others have made money, isn’t a good reason to start it.  You’re competing with people who love what they do.  So if you’re doing it for the wrong reasons, you’ll give up much faster.  People who love what they do naturally continue on in the face of adversity. 

As another example – I love photography.  It’s not work for me to go for 2-3 hour drives searching for landscapes and wildlife.  I plan trips around travel photography – not because it’s something I ‘have’ to do, but because it’s what I naturally want to do. I don’t make a penny from photography, but I put the work in as if I do.

So I guess my point is: find something that aligns with you.  It’s much easier to do something for 5 years if it’s an exciting, fulfilling business and not a burden or an annoyance.

You’ve amassed an admirable following for your work.  Do you love, hate or feel indifferent toward promoting your own designs?  How do you reach your audience?

I’m a big fan of marketing.  Over the years I’ve learned bits and pieces about how to best market your work.  I’m no expert by any means, but marketing and strategy have become interests of mine over the years.  I would love to get better at communicating.  One day I’d like to have more of a community driven audience that I interact with regularly, but for now I’m still learning and trying to figure out how to implement something like a blog, AMA, podcast, etc.  I like answering questions, so someday I might try to create a more active, involved community.

As far as sharing and promoting my work, I try to give every product a chance.  I will typically send out an email and post something on Dribbble notifying people that I’ve made something new, but I’m not constantly sending out promo posts on a weekly basis.  I have no problem sharing on social media or design sites, however.  I’m a big believer in not being afraid to post your work, so I try not to overthink anything.

Is “Hustle Supply Co.” your full-time job or a side project?  If side project, what’s your day-time gig?

Hustle Supply Co. has been a full-time gig since January 2014 and has consistently grown over the last 4-5 years.

Do you listen to music when you work and if so, what are you listening to?

I honestly like to listen to music without vocals as it can just live in the background while I think.  For work music, I want it to be more ambient.  Some of my favorites on Soundcloud are Tony Anderson, Chris Coleman, and Lowercase Noises.  Sometimes I’ll just throw on film scores or soundtracks like “Lord of The Rings”, “Game Of Thrones”, “Westworld”, etc.

Half of the time I’ll just have a podcast on in the background if I’m doing more repetitive tasks.