Skateboarding Trading Cards

‘I have to say just the fact that I’ve been able to design for Stereo is a dream.’

Derek Michael Brennan

February 2023

Tell us something about yourself?
I would be leaving out a major part of who I am if I didn’t say that first and foremost, beyond skateboarding and art, I am a follower of Jesus. A real season of depression, emptiness, and searching for meaning brought me to Him (in 2014), and my life has been restored through Him. Secondly, I am a husband of a wonderful woman, and father to two beautiful daughters. Those are the most important aspects of me and my life.

You started skating by end of the 90ies. Which was your first pro board?
Skateboarding was something I knew bits and pieces of through friends of mine in the 90s for sure! I always thought it had an appeal to it…and I rolled around on my neighbor’s boards sometimes. But around 2004 is when I really started to pick it up. Age 16/17. So, later than most, especially these days. My first board was a Status, if you remember that brand. I think I bought it used from a friend. Then I had an Element team board next, and my first real pro model board , I believe, was the Bam Margera plunger board from Element, haha. Watching CKY videos was part of my introduction to skating.

You have an impressive portfolio of work on your website. What do you like to do most?
Thank you! I really appreciate that. More than any one piece, I have to say just the fact that I’ve been able to design for Stereo is a dream. I can honestly say Stereo has been one of my favorite brands since I got into skateboarding – you know, had their photos and ads hanging on my wall, watched their videos (especially Way Out East) on repeat…got introduced to records, jazz, Super 8, and vintage design through them! So, now knowing I have the privilege of contributing to a brand that I’ve loved for so long is pretty unreal. I imagine going back to 2005 and telling my younger self that I’m doing that and not believing it.

What type of design work do you do for Stereo?
I’ve been designing for Stereo since May 2021, alongside Ron Rauto who has been with them since 2011. In addition to re-creating some classic graphics, I’ve also done some original designs for boards, stickers, tees, the web, and social! Like I said, Stereo has always been one of my favorites and a major influence on me! I met Chris Pastras at the Phx Am contest in Arizona (where I live) in 2018, and then again in 2019, and we’ve stayed in touch after that. I have previously sent Chris ideas for the brand, and in 2021 he gave me a shot to do some stuff for the website and social. That grew into being able to do the other work that I mentioned! Stereo is such an amazing company, I just try to stay true to what they’ve represented over the years.

Stereo Skateboards - 90s Reissues - 30th Anniversary

On your website it says ‘…he found himself particularly attracted to the individuality of how each skateboarder uniquely interacts with their environment.’ Can you give me an example?
Yeah, I mean, first of all we know from experience that once you become a skateboarder you look at the world differently, especially in regards to urban landscapes, and you see possibilities in things that most people wouldn’t even notice. But then among fellow skateboarders, the obstacles that you choose to skate, the tricks that you do on them, and the style of how you do those tricks, is also unique…there is such variety and individuality. And that was and is really attractive to me. A specific example: Heath Kirchart and Gou Miyagi. Two of my favorite skateboarders, but their style and approach is very different. And for myself – I can go on skate trips with friends, and we’re all gonna skate different things and film different tricks, and our unique personalities are going to show.

Here you are creating skateboarder trading cards. When you look back when you first started, are you happy how it evolved over time?
I am! Absolutely! I just started making them because it was fun… as I’ve said before, it is a blend of several interests of mine, and trading cards in general are nostalgic for me. I’ve gotten a lot of really positive feedback and connected with a lot of people through them. Something I’ve been wanting to do since the beginning was to get some of the skaters to autograph some cards so that I could randomly insert them into the packs. Thanks to Chris Pastras and Jason Lee, I was just recently able to do that in the second edition of Series One that came out recently!

Do you draw them by hand?
All of the cards up as of now have been my illustrations. The process is actually a combination of handmade and digital. I draw all of the elements and paint all of the different colors and textures, but then I compose them digitally. That is a process that I’ve developed over time, given my fine art background and the digital design that I currently do as a profession. So again, it’s a blend of two aspects of my world, and I think it creates a really unique aesthetic that would be harder to create with just one of those methods.

‘So out of respect for her, I never released that one.’

Chad Muska Trading Card - Series 5

Do you have to obtain permission from the individuals and their board companies you are creating trading cards for?
It depends. I have always at the very least tried to make sure that each skater has seen the card before it comes out. And they’ve always been supportive. Gonz is one I could never get ahold of, but Krooked did share them on Instagram at one point, and I know he has since signed one of them for a friend (Patrick Faalafua, Skate Punk Skateboard Co). The ones I have specifically gotten approval for are the three from Series 5 that were based on specific photographs – each photographer agreed to let me use their photo as a reference. And the two for DeckAid have been approved beforehand. I also created a card of Dylan Rieder and reached out to his mother about it. I was hoping to ask her to write something for the back of it. But she said it’s been hard to manage his image since he passed, and felt the safest way to do that was to try to mostly stick to releasing products from his most recent sponsors. So out of respect for her, I never released that one.

Your online shop is all sold out. Marketing strategy or supply chain issues?
Thankfully I haven’t had any supply chain issues, other than the cost of production going up slightly since I started this project in Fall 2017. I just like the idea of limited editions. Kind of like art prints. And when they are gone, they’re gone. In a way that is also a bit of a marketing strategy: it creates a sense of urgency and scarcity when they do go up for sale.

Why are trading cards so popular in the US you think? People go absolutely nuts over baseball and basketball cards or has this changed now?
Yeah from what I’ve seen over the past few years there has been a resurgence for sure! I don’t know what all the factors are, but it does seem like it was accelerated a bit by the pandemic. Maybe with people staying home more they started looking to collect things for their homes/home offices, or found themselves digging back into old collections that they had.

‘Stereo is such an amazing company, I just try to stay true to what they’ve represented over the years.’

Stereo website - team album covers 2021

What else are you working on? I noticed you also have your own board company.
Yes, it’s called The SunnySide Company. It’s a little brand that I started with some friends in 2006. It was something I always wanted to do. I’ve always been interested in everything that goes into creating the look and feel of a brand, and it was my main creative outlet for a while. Lately it’s sort of on- again off-again as other things have taken priority, but it’s had a special place in my heart for a long time so I like to keep it around. I feel like the early years of doing that brand really shaped me as an artist and designer. I do have some new things in the works for it that I’d like to release soon (I’m actually wearing a sample of a new SunnySide tee right now).

Last question: If you could interview a person, who would it be and why?
If we’re talking one person in all of history, I’d of course say Jesus. I believe Jesus is who he says he was: one with God, God in the flesh. So no one can have greater knowledge and wisdom to share than one who’s outside of our time, has witnessed all of our history, and knows where we’re headed. But then to bring it back to the topic of skateboarding – I consider myself a bit of a skate nerd, and I’ve read and watched a lot of interviews. But I realized recently that earlier than maybe the mid-80s of skateboarding, there’s a lot I don’t know. So I think I would interview somebody like Tony Alva, to go in- depth on the 70s/early 80s era… Thank you again for the opportunity to express myself, Michele!

‘I would be leaving out a major part of who I am if I didn’t say that first and foremost, beyond skateboarding and art, I am a follower of Jesus.’

Kareem Campbell Trading Card - Series 5