We’re excited to introduce you to the always interesting and insightful Chester/Chess Plum. We hope you’ll enjoy our conversation with Chester/Chess below.

Chester/Chess, appreciate you joining us today. So, one thing many business owners consider is donating a percentage of sales or profits to an organization or cause. We’d love to hear your thoughts and the story behind how and why you chose the cause or organization you donate to.

Seeing this reminded me about how CML got started! I had the interest in leatherwork, but was unsure how to get to the part where I was making things for people. It was smack in the middle of 2020, when all those protests were happening, I really wanted to participate but due to my health and old job (I was a teacher at a Montessori school and the only one bringing in income for my household, so I was worried about being arrested) I couldn’t make it out to many of the protests. So instead, my first 10 commissions I donated all profit to Freedom Inc. And only kept what covered the cost of supplies. I wanted to do this to help and also because I did not feel my work was good enough yet for me to feel comfortable making profit while I learned.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’ve wanted to be a fashion designer since I was 7 years old and saw Jay McCaroll show at New York Fashion week. I watched every season since and it wild for me to believe this is the origin of it all, but looking back at Jay McCaroll’s final collection as an adult I was mind blown; I recognized my own personal style in him and his work SO MUCH, it made my partner say “Oh wow” when I showed her.

I have always known I was going to show at New York Fashion week, I just wasn’t sure how. I emailed Parsons The New School for Desing when I was in 7th grade, and was crushed to be informed it was $20,000 for a single semester. I gave up my dreams of being a Fashion Designer then. I didn’t even have a sewing machine.

I briefly considered being a makeup artist (maybe that’s how I could get to NY Fashion Week) and went to Aveda for 2 months before quickly realizing it was not the industry for me and yes, became a beauty school drop out.

I wanted to be an artist so bad, but nothing stuck. I never had inspiration, I never knew what to create. Someone once told me “Maybe the job you’re going to be doing some day hasn’t even been invented yet.” So I hung on to that.

Years went by, years I somehow survived to make it to the year we all remember most: 2020. Stuck at home alone sent me back to being a child and the need to create took over. I started small, I mended all the holes in all my socks and underwear. Then I painted a large -very percise- back patch of my favorite band “The Dresden Dolls”. But I was running out out ideas. Then I saw the handmade leather carebare patch I won from a bingo game at Twin City Leatherweekend in Minnesota a few months prior (it had a butt plug on the stomach) and started thinking about how it was made, deconstructing it in my mind and the thought popped up “I could make that” so the next day, I spent all morning watching cowboys on YouTube explain the craft and the tools. I decided I was going to spend my stimulus check on a new hobby. I took a week to make a list of tools and materials, then pulled the trigger on the online purchase. It took about a week for all my supplies to come, and I let them pile up on my new desk till they were all there. I opened a bottle of wine, and in one sitting made my first collar, a “Bolo Tie Collar” (which I should REALLY revisit)

So yeah, Checkmate Leather started because I won a bingo game, and if I didn’t create something; I was going to die.

Can you talk to us about how your side-hustle turned into something more.

My “side hustle” became a career completely by accident and survival. I had a lot of different jobs until in 2018, I saw a job posting to be an Assistant Teacher at a Montessori school no experience needed. I’d never been around a child for an extended period of time in my life, but I applied and got the job. I ended up falling in love with teaching, at one point during the pandemic I ended up with a class of 7 elementary aged students where I was essentially their main teacher for 6 months. I was teaching children how to read. I loved it, I stayed there for 3 years and had intended on staying longer; unfortunately the head of the school for some unknown reason decided not to offer me a contract for the 2020-2021 school year; all they said was “it was decided back in January”, the month I came back from top surgery. I can’t help but feel it had something to do with me coming out as trans that year.

So I lost my health insurance, a job I loved that paid me better than any job had before, I had experienced a relationship ending in a traumatic way. So I tried to work at Sally’s: that didn’t go well. I tried to go back to teaching, even landed a job as a LEAD Preschool Teacher with my own classroom and all. But I struggle from a lesser known Eating Disorder (ARFID) which had taken a toll on my health, and physically I could not preform the tasks needed to be a teacher.

I made the gut wrenching choice to leave, where I made a post in a Facebook group asking about a part time job somewhere safe and not soul-draining so I could recover and focus a little more on leatherwork (That was the other thing, working at Sally’s was killing me because all I wanted to do was leather.) I met Julia McConahay who owns Chrysalis Hair and Body, a half salon/half vintage shop.

Julia has played a major part in me moving into leatherwork FULL-TIME. She encouraged me to, by sending a text one night saying she believes I could do it fulltime. I thought I wasn’t ready, but one month I realized I only worked 6 shifts the entire month at Chrysalis; Leatherwork was paying my bills and I didn’t even relaize.

So really, it’s that if I don’t create and share my art with the world, I will die. I know it’s dramatic, and I’m not saying I would harm myself. I’m saying my brain and soul won’t let me do anything else at this point.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

have gotten so much feedback that it’s rare Makers offer custom sizing! My slogan is “Your body, your budget” because I want my art to be accessible. I’m scrappy, if someone says they want something custom and only can spend $100, I can make something that showcases their personality/concept through my eyes AND it fits them because I ask for all my clients to send me their exact measurements. I didn’t relaize this wasn’t the standard, that makers just make things within a certain range. It seems more beneficial for both the client and the maker to use exact measurements because there’s also no risk of using unnecessary materials. Leatherwork is expensive, there’s no way around that, but people are allowed to buy themselves nice things and I want to make that as easy as I can for them. I would really love if more Makers would “go through the trouble” of offering custom sizing.

I also have a trick for if people aren’t comfortable measuring themselves where you can use a ribbon and mark it, then mail it to me. A follower once mentioned it’s great I offer custom sizing but they couldn’t handle knowing their size. I related to that strongly and came up with a solution, which I’ve implemented several times already in my work.

Contact Info:

• Website: https://checkmateleather.com/
• Instagram: https://www.instagram.com/checkmateleather/?hl=en
• Facebook: https://www.facebook.com/profile.php?id=100069667308948&mibextid=ZbWKwL
• Other: https://www.tiktok.com/@checkmateleather?_t=8XqnTHx2t8Y&_r=1

Image Credits
Katy Bats Additional- Chester Plum