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An Interview with Winona Kicks: Content, Community, and Turning Passion into a Platform

What began as a hustle often becomes a calling, and for Charley Sneakers, that journey started with flipping PlayStations and Apple Watches just to afford his first few pairs. From the snowy streets of Minnesota to cinematic sneaker reviews and a podcast that dives deeper than hype, Charley has built a loyal following by staying honest, evolving his craft, and showing up with intention. In this exclusive conversation, he reflects on the early days, the lessons learned, and why storytelling, not just sneakers, is at the heart of everything he does.

Let’s start at the beginning. What sparked your love for sneakers, and when did you realise it could be more than just a hobby?


I’ve always been into sneakers but never had the money to buy them. I was broke all through college. I actually started out reselling, not shoes at first, but golf clubs, PlayStations, Apple Watches. Then I stumbled into sneakers around 2018 or 2019. It started as a way to fund my own collection. I’d buy and sell a few pairs, then keep one for myself. Within eight months, I was flipping around 100 pairs a month, learning everything from the ground up. At the same time, I made an Instagram page, Charley Sneakers. My now-wife actually suggested I post the shoes to sell them to friends and family. One day, someone commented asking how to ship a pair of shoes. I’d already figured it out down to a science, four pounds, 14x10x6 box, so I made a video explaining it.

From there, it just took off. I started replying to comments with videos, things like “Should you hold or sell this release?” Back then, you could actually invest in sneakers. Buy a pair and the price would rise over a year. Eventually, I made a TikTok. I was a year and a half late to it, but in hindsight, it was still early. I kept diving into content, and pretty soon, I quit reselling altogether. I just wanted to collect and share my thoughts on sneakers. That was four or five years ago. And here we are.

You’ve become known for a cinematic aesthetic, the way you cut your shots, the way each piece of content has a beginning, middle, and end. Was that always the goal? Or did that style evolve over time?


I’ve been trying to do content my whole life. I had a Madden YouTube channel back in 2010 called CheezyChuck. Posted Madden Mobile videos. Then I made a golf page. I’ve always just loved the internet. In college, I studied creative digital media and digital marketing. At first, I was filming three videos a day on my iPhone and just pumping them out. Then I realised, no one’s posting short-form content using actual cameras. So I bought a Sony A7C and started learning how to use it.

I was one of the first in the sneaker space posting short-form, high-quality videos. That’s what helped me stand out. Now a lot of people do it, but I always wanted my content to look professional, like the long-form YouTube stuff I enjoy. A good friend of mine, Elliot Page, had super high-quality early sneaker reviews, and I think that really helped him. I was trying to bring that same quality to short-form content. So I started upgrading, new cameras, better lighting, and kept building my style from there.

I love the way you incorporate your surroundings, it feels natural and real. Has your Minnesota location influenced your content?

Definitely. We’re in the Midwest, very blue-collar. It’s not like LA, New York, Chicago, or Atlanta where there’s a fashion scene. And for seven or eight months a year, it’s snowing. I can’t wear Jordan 4s without them getting destroyed. So yeah, the location affects things. But there is a community here, and it’s growing. I’ve got good friends at shops like Piff Minneapolis, now called Cache Minneapolis, who are going for that high-end aesthetic.

One of my early series was called Wear Tests. I’d wear a single pair of shoes for 30 days straight, through rain, snow, heat, whatever. I realised I had a unique opportunity to really put sneakers to the test in all conditions. So I leaned into that. Yeah, I really enjoy it. It feels super authentic. Especially since so many content creators live right next to each other, it’s refreshing to see something completely different.

You recently covered the Jordan 3 Pure Money, that video really stood out to me. What’s your honest take on the release? And how do you even get your hands on early pairs like that?

Yeah, so when it comes to getting early shoes, there are really two ways to go about it, and I’ll get into my thoughts. When you’re just starting out, you can buy early pairs, paying above market to get them in hand before release. But that gets expensive fast. I’ve been burned before, I bought the new Union Jordan 1s for $700 thinking, “There’s no way this goes under $600, it’s a Union Jordan 1.” Sure enough, they dropped to $300. So that can backfire.

Thankfully, because of the professional aesthetic I’ve developed, I’ve been able to attract partnerships with bigger brands. One of those is Champs Sports, who I think were recently acquired by Dick’s Sporting Goods. I’ve built a close relationship with their team. Any releases they get, I usually get sent pairs. I create content for them, and I get to keep a personal pair. So major props to the Champs Sports team.

As for the Pure Jordan 3s, they’re much nicer than I expected. I’ve never been a huge fan of that color scheme, but the quality is there. They’re super clean. Jordan Brand really didn’t do anything wrong with them. It’s a pair I never got the first time around, so I’ve got to grab them now. That’s just the world we live in.

From visuals to voiceovers, your content quality is next level. What’s your process when putting together a short-form video?


I approach short-form content like it’s long-form. I think that’s what sets me apart. Every video starts with a script. Then I shoot 30 to 45 minutes, sometimes even an hour, of B-roll using different lenses: macro, wide-angle, the works. I use a high-end camera setup because I’m not just chasing viral moments, I’m building a community. That’s always been the goal, making videos that people actually enjoy and want to come back to. Right now, I’m editing a Crocs video that’ll go live today. Even a short video like that takes two to three hours to edit. I’m always learning new styles and looking for ways to improve. Constant evolution, that’s the goal.


James : I appreciate you even sharing some of the behind-the-scenes stuff, I know it’s the “secret sauce” for a lot of creators.


I’ve never been a fan of gatekeeping. Apart from what I learned in college, everything was self-taught. You could put all your creative secrets online, but people still need to put them into action. That’s what separates creatives. You can bookmark tutorials, watch them, take notes… but unless you do something with it, it’s just information. So yeah, I’m always happy to share, but it’s the action that matters.


You’ve worked with a lot of brands. You’ve helped launch, leak and release product. What makes a partnership feel right for you? And do you ever turn collaborations down?

Yeah, I say no to a lot. I’ve been in this community for five years now, and I’ve worked with a bunch of brands. At the end of the day, it really comes down to gut feeling. There are brands that have had shady practices, lawsuits, going out of business, or just moving funny, and I avoid that completely. It’s usually obvious when something doesn’t feel right.

For me, I only review things I genuinely like. And I make that clear to the brands: I’m going to be 100% honest in my videos. If I don’t like something, I’ll say it. If it’s amazing, I’ll say that too. I’ve never been paid to say anything — only to do something, like review a shoe. But the opinions are always mine. I think integrity matters, especially in this space.

You also run a podcast “BeyondKicksPod” with SameOldSeth. How did that come about? How did the friendship start, and what’s it been like switching from solo content to podcast conversations

Yeah, I think we’ve been doing it for over two years now. I was just at his wedding two weekends ago, actually, down in Atlanta. We first met at Sneaker Con Atlanta, maybe in 2020 or 2021. Just two content creators linking up. We hit it off instantly. At the time, there weren’t many sneaker podcasts outside of the big ones, like Complex, or the ones overseas. And I thought, I want to do this. But I didn’t want to do it solo so thats how BeyondKicksPod started.

I needed someone who genuinely cared about the community, someone I could talk sneakers with every week, for years, not just months. Because with podcasts, you can’t do it for three months and expect it to blow up. It’s a long game. It never works if you’re not consistent. So when I thought about starting a podcast, Seth was the first person who came to mind. I think he had around 4,000 followers at the time, but I loved his content, we hit it off, and now we’re good buddies.

I said, “Let’s start a podcast,” and he was down. Now we’re over 100 episodes deep, and even a couple of years in, it still feels like we’re just finding our footing, in a good way. Short-form content limits you, you only get a minute or so to share your thoughts. We started Beyond the Kicks to have a platform where we could just talk. Once a week, no filters, just our unfiltered thoughts. And it’s fun.

With so much hype-driven content out there, how do you stay grounded? You’re not just posting hyped collaborative releases. How do you keep your content varied?

It’s really just about what I like. My taste is pretty broad, I love the hype stuff when it makes sense, but I’m also into trainers, New Balance, Asics, and those Jordan 3 Lucky Shorts that I’ve been wearing into the ground lately. If the colourway and materials are good, I’m into it. Sometimes it’s something completely different, like the Harry Potter x Puma collab. I thought that concept was fun, so I reviewed it. Same with 3D-printed sneakers, anything I find interesting.

There’s a part of me that thinks about the audience too. There are so many creators out there making the same video on the same pair of shoes. After a while, people don’t need to see yet another review on the same release. So I try to bring something new, whether it’s a story or tapping into a different audience. That Harry Potter Puma review I mentioned? It hit 12 million views across TikTok and Instagram. That wasn’t sneakerheads, that was Harry Potter fans. That’s the kind of stuff I think about: what’s interesting to me, and what might reach outside the sneaker bubble. If it’s a basic pair that’s wearable, high quality, and I like it, I’ll make a video on it.

For fun let’s say you get handed a sneaker collab tomorrow, any brand, any silhouette. What brand are you picking, and what story do you want to tell?

I think it’d be something Minnesota-based, maybe something outdoorsy, with a nature vibe. I’d love to say New Balance or Asics, but if I’m being honest, Jordan Brand is the S-tier for me. A Minnesota-themed Jordan 3 inspired by the lakes and landscapes out here? That would be incredible. So yeah, Jordan Brand would probably be my top pick.

Finally, what’s next for you? Anything coming up you’re excited about?

So I’m still going strong with shoe reviews. I’ve got a huge stack of pairs I need to work through. But something new I’ve been introducing into my content is my other passion: golf. I’ve been golfing my whole life, middle school, high school, over 100 tournaments. Before sneakers, that’s what I was fully into. Things got busy with content and the business, but now that life’s slowed down a little, I’ve had time to start golfing again, and I’m posting about it too.

Golf is in this interesting phase right now where streetwear and style are bleeding into the culture. And golf shoes are such a crucial part of that experience. So golf shoe reviews felt like a natural extension. I’ve already connected with a few companies, and I’m really excited to explore that world creatively.

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