A Conversation with Mike Sykes, Creator of “Kicks You Wear”

Dennis Huang
Fourth Realm
Published in
14 min readJan 5, 2021


The Kicks You Wear’s Sneaker of the Year Winner: Nike x Ben & Jerry’s “Chunky Dunky”

Fourth Realm is a venture capital firm that invests in companies tackling problems at the intersection of productivity, content, commerce and community. Recently, we spoke with Michael Sykes, who is the founder of “The Kicks You Wear” (KYW), a publication dedicated to the culture, business and community around sneakers.

As the media industry becomes increasingly fragmented, consumers have more choice than ever before in what they consume. I mean, it really does feel like everyone has an email newsletter these days, doesn’t it? We’ve watched the unbundling of content creators from larger publications and seen them spawn communities across all shapes and sizes and find creative ways to monetize online. We wanted to speak with creators who are on the front lines of this digital change, and get a better understanding of how they view their work, the audiences they’re cultivating, and what it all means going forward.

I’m incredibly thankful to have sat down with Mike Sykes of “The Kicks You Wear”. Mike works in a traditional media newsroom (currently at USA Today, previously at Axios and SBNation) and runs KYW full-time, so he has a foot in each world and a unique perspective on both.

And while I’ve always considered myself a bit of a sneakerhead (I love my Parra Blazers), Mike is a true master. He delivers sharp, critical commentary on the industry, is a trusted source for many, and has cultivated a passionate following. We cover a lot of ground, including: how he originally started KYW, his thoughts on monetization and growing an audience, where media goes from here, and his most hated shoe(s) from 2020.

If you’re at all curious about sneakers, or the culture and business around the sneaker industry, “The Kicks You Wear” and Mike’s Twitter are must follows!

If you’re a founder, operator or just someone who’s interested in creating something in the media world, I’d love to meet with you! Please reach out to me at dennis.huang@fourthrealm.vc or partners@fourthrealm.vc.

My questions are in bold; this transcript has been lightly edited for clarity. Some explicit language below.

How did KYW start?

Mike Sykes (MS): KYW started out as a pet project of mine, and it had been something that I’d been thinking about for a while. I’ve always wanted to write about sneakers in some capacity. I’ve covered the NBA, the sneaker business, retail and the sports world in general, and I wanted some way to combine those loves.

I actually started another newsletter back in 2017, but that one didn’t work out too great. Until I started working at Axios, I actually didn’t think too highly of email newsletters because of that experience. [Axios is a media publishing company who primarily delivers news via email newsletters]

At the end of the day, it’s a passion, so I just went for it. I thought it was a fun idea, and honestly didn’t think more than like 30 people would read it.

Wait, so what was the 2017 newsletter? And what did you learn at Axios that made you like newsletters again?

MS: To be honest I don’t remember the name, but it was sneaker related. I had a Soundcloud podcast to go along with it as well. I just kept running into the problem of not having enough things to write about or people to talk to for the podcast. I was at SBNation at the time, and was spending a lot of time trying to move to a full-time position, so I couldn’t dedicate enough time to the project either.

At Axios, they’re all about newsletters! I originally started at the newsdesk but I moved to covering sports with Kendall Baker. I picked a lot of bits and pieces from my time there around how best to run and manage a newsletter, and I actually wanted to have a vertical of my own around fashion or something but I wasn’t sure how to pitch it.

After I moved to USA Today, I decided to take my learnings from Axios and just go for it.

So why Substack? Did you consider any other options?

MS: I had a few friends using Substack at the time, and also knew of a few other people covering really niche communities on Substack as well. I’d seen the platform before and was curious about it.

It was between Substack and Patreon. Both seemed to have their own pros and cons. Substack at the time didn’t have its own podcasting/audio products and Patreon did, but I felt like my strengths were primarily around writing, not audio content. Substack also has a really clean CMS (content management system), and has since added podcast hosting as well.

So how’s the experience been like on Substack? What do you like/dislike about it?

MS: Honestly, there’s not much I dislike about Substack. Their analytics offerings are very thorough, and I can pull any number I want. Basic analytics, who’s opening what, who individual subscribers are, clickthrough rates (CTR) on different links, raw page numbers etc. Rarely run into any issues around sending, and the CMS is nice and clean.

I do wish that there was more I could do from a website/landing page standpoint though. I wanna be able to tinker with what people see when they navigate to my page, have it be a bit more like what you can do with Squarespace or Wix. For example, we just launched some merch, and I wish I could include a link to that on the landing page.

What’s the most important metric(s) for you?

MS: Open rates are the most important. I want to be able to see what people are interested in. CTR is the next big one, I want to know what people are clicking on, and where my readers are going when I send them away from the newsletter.

I’m constantly doing informal A/B tests on the content. I change up how I’m writing, what I’m writing about, how it’s displayed, etc. I’ve sent a lot of drafts to myself just to make sure I know what the end result looks like and how the email system(s) respond. At some point you build up a mental model of what gets you a higher open rate or CTR, and you can start working off of that.

You’re not monetizing your newsletter today. Can you explain the rationale behind that, and if that’ll change in the future?

MS: It’s definitely something I’ve thought about quite a bit, especially over the past 6 months. It’s work at the end of the day, and I’d like to get paid for my work.

However, my biggest thing is prioritizing and taking care of my audience. This is as much their thing as much as it is my thing, and I don’t want to alienate them in that respect. In the middle of a global pandemic, it feels kinda shitty to ask people for money to read about sneakers!

The sneaker industry today is all about access. You can’t get the latest and greatest shoe unless you have bots running sequences, or if you have a plug, or whatever. I make it a point to rail against this in the newsletter. Sneakers should be egalitarian. For me to cut out different aspects of the newsletter out, especially during these times, didn’t feel like a move that would be right to make.

It might be different if I didn’t have a day job and needed to make ends meet, but I’m fine. I’ll focus more on monetization in the future, for sure, but my main focus right now is building and nurturing the community.

If you don’t mind me asking, are you making any money at all off of KYW today? You mentioned some merch, is there anything else?

MS: Yeah, we just launched the merch arm. It’s very early, and we’re setting up some more concepts. I really hope this can turn into its own thing eventually.

Other than that, I’ve been thinking about other types of “sponcon” (sponsored content). If there are brands that run adjacent to the ethos of KYW, it’d be interesting to run an ad with them. For example, I live out of the DC area, and I’ve reached out to some local shops to do affiliate links, give them ad placement, and drive traffic to their store. If my readers want to buy some of their stuff, great! I’ll get a percentage from sending people to their site.

Most importantly, it’s keeping the user experience authentic and coming up with creative ideas to do that.

What have you noticed from your audience base with regards to monetization? Are people more open to the idea of paying for content now?

MS: [Laugh] People have definitely hit me up asking if they can give me money. I don’t want people DM’ing me to shoot money to my Cash app! I guess it’d be nice to eventually give people the option to give money, but that’s just not what KYW is about right now. It’s not bad per se to ask for like, $70 a year, to read the newsletter, but a lot of people just don’t have that kind of money right now. When people hit me up I usually say “Yo that’s dope, but I’d appreciate it if you used that money to buy something for your kids or something”, and people appreciate that.

And it’s that 1:1 relationship with fans that’s really special. This is as much of my audience’s newsletter as it is mine. We’re all just fans of sneakers. I want to eventually end up in a place where if you want to pay, that’s great! But it doesn’t get in the way of accessing the content.

I value access way more, especially given where I’m at. I’m not struggling to eat or to put a roof over my head. I’ve been incredibly fortunate throughout the pandemic. Yo if I can bring someone some joy from this thing, that’s way more valuable than any dollar that they can give me, because I know they’ll keep coming back. This is something that they’re going to read every Monday and Friday. And as KYW continues to grow, there’ll be other ways to raise and generate money. The most important thing is to grow this audience, and we can go somewhere great together. Growing and maintaining my audience is more valuable than any money today.

Speaking of that audience, how did you start building your subscriber base? And what are you doing to encourage a stronger sense of community today?

MS: [laugh] I think it was just a tweet. I’ve always been vocal about my love and passion for sneakers. People would DM me and reach out to me about sneakers, I was their go-to person.

I tweeted “I’m thinking of starting a newsletter on sneakers” and people were like “Do that shit!” and said “Ok, I’m doing it” [laugh]

In the beginning, I just wrote down some initial ideas and topics that I thought would click with people. I didn’t have a single subscriber when I hit publish on my first post, but by the end of the week I had 300 followers and I said “Oh shit, this is really something”. So I just continued to tweet and post on IG about it.

It’s been mostly the same since, but I’ve started doing some things like taking out Instagram ads. IG ads suck, honestly, I hate using it, but that’s where a lot of my subscribers come from. Sneaker culture lives on IG. I’ve done a few “promo for promo” things as well, where I do some collaborations with other writers who have audiences of their own and we plug each other.

A lot of the initial community came from word of mouth, which was very cool. I really didn’t think this would be something that people would give a fuck about! It’s really niche, and can get really nerdy. But at the end of the day, the internet is a big wide place, and there are a lot of people who are interested in a lot of things. There’s an audience for everything, and you just have to find your audience.

That brings me to a broader point: is this the future of media creation and consumption? Just following hyper-focused creators on niches you care about? I’d be curious to get your thoughts as someone who is working in legacy media but is also running a niche media publication.

MS: It’s really hard to predict, especially with this year. You look around and you see major players cutting staff left and right. But I mean, at the end of the day content creation isn’t going anywhere. You see people moving from legacy companies to more individualized projects either on the side or full time. There’s just not enough money going around to rank and file employees in media, and that’s definitely driving this trend.

On the one hand, I think it’s a good thing because it enables people to tap into a well of creativity that they normally wouldn’t have, or be able to. If I pitched this to Axios, I dunno how interested they’d be in this because it’s so niche. As someone who’s a writer and content creator, I think that freedom is a great thing.

On the other hand however, in the long term, you can’t really sustain yourself doing this, unless you build an audience and are able to monetize it. And not everybody is comfortable doing that or even can do it. There’s a lot that comes with it. I mean sure, you can build an audience of 10,000, but if you only have a 15% open rate, then what good is that? Collecting email addresses and getting subscribers is easy, but you also need to be able to tap into that audience. You need to put in the work. This isn’t an indictment on anyone or anything like that, but it is work, and you need to do it.

There’s probably a happy medium somewhere, between people working for legacy media companies and creating their own brands. But I honestly have no idea how this is going to end, and I don’t want to be a media forecaster [laughs]

I mean, USA Today and FTW have been really, really great. They let me be creative, and let me cover everything from sports to like… fucking murder hornets. And then I can shift to KYW and chop it up with my sneaker community. I cannot state how fortunate I have been in this situation.

Anything else to add on what the future of KYW entails?

MS: I’m figuring a lot of it out as I go. To be honest, the initial goal was just to see where this could go!

I’ve got a great group of advisors and mentors, and I’ve actually met some of them through the newsletter, which is crazy. The people who read and support you, there’s no better feeling, and it’s been awesome to see just how supportive people can be.

So I couldn’t let you go without us talking about sneakers for a bit! Give me your diagnosis of the industry today. Are you feeling bullish or bearish?

MS: Damn… that’s tough. I wanna say I’m bullish, but it’s a nuanced take.

The sneaker industry has lost a lot of what made it what it is today. The spirit of the thing isn’t there anymore. A lot of it feels so transactional, trying to get something for resale. It used to be about finding something you loved, that aesthetically spoke to you, and then wearing it and growing with it. Today, you wake up on a Saturday, click a couple of buttons to try to cop something on an online drop, and you get it or you don’t. And the people who are fighting over these shoes are despondent because of the bots and shit. And it’s like… it’s hard for people to fall in love with this the way it used to be.

But through the newsletter, I’ve found people who are just as passionate about this as I am. Let’s be honest, there’s no putting the toothpaste back in the tube, but there are people who’re working on bringing back the spirit and passion that the sneaker world used to have. I think we’ll have a golden age when we get there.

Tell me about some of these new projects you’ve come across? What makes them special to you?

MS: There are other people who’re writing content on fucked up all this shit is, people who are shining a light on bad practices and share the same egalitarian ideals I do about sneakers and want to favor access above profit.

There are other people who’ve developed communities that allow people to buy shoes at retail, where that’s the norm, as opposed to resale today where shoes go for 3–4x retail. SoleSavy is a good example of this. On the surface it’s a group where people share links to try and buy shoes manually at retail. But they’ve done a great job of creating a community of people who really love sneakers and share the wisdom they have around getting kicks at retail prices. Another Lane is another community of buyers and sellers, and they have no seller fees and it doesn’t encourage you to sell for crazy resale prices. Stuff like that is really dope, and it’s made by people who came from the culture and want to support it.

Not to say the people who made StockX and other similar products don’t have passion, but it’s an avenue of abuse. There are people on their platforms that really take advantage of others who really are passionate about these products.

The PS5 comes to mind. You don’t even have to be a gamer trying to buy this thing, you could just be a parent trying to get this for your kid. You have people buying 30 PS5s to resale, and if you do the math you’re not even making that much of a profit off of it! So why do it or enable this in the first place? There should be incentives for people to not be able to do this. There are people who have been saving up for the whole year with the expectation of buying this for a loved one, and now they can’t. In the middle of the pandemic, it’s hard as hell for people to save already. The PS5 is ~$500 retail, and now it’s close to $900 on StockX. And if you’re one of those people who’ve been saving, it’s like well fuck. This was supposed to be the highlight of my shitty year, so now what am I supposed to do?

I suppose it’s a bit idealistic that we’ll get to a place that’s more equitable than what we have today, but man, at some point this all gets ridiculous. I have in faith in people that we can do better.

I appreciate your thoughts around resale, and I admit it’s refreshing to hear about people who are trying to create better structures around access. And I want to be mindful of our time here, but before we go, I have to ask. What’s your favorite sneaker of all time, and what’s your favorite sneaker of 2020?

MS: Favorite sneaker of all time… the Raygun Dunk. I love that shoe man. That shoe got me into this whole thing. I was in middle school at the time and I heard about it in a rap lyric. And I was like “Holy shit, this is awesome”. I would say my favorite sneaker silhouette of all time is the Dunk. It’s just iconic.

Favorite drop of 2020… man there’ve been some really good ones this year. I would probably say the Strangelove Dunk. Although I’ve been running a March Madness style tournament on KYW to see who the community thinks is the best sneaker of 2020 and I think it’s down in the tournament right now.

What drop did you hate the most in 2020?

MS: Of 2020, whatever Balenciaga dropped. It had candle wax or something on it. It was the dumbest thing I’ve ever seen. I don’t know why anyone would wear that.

Actually, I’m trying to debate if it’s the Dior 1 or this candle one.

The Dior 1 isn’t a bad shoe, but for two grand I’m expecting a Jordan 1 that’s SO much better than anything that’s ever existed. And it’s not, I’m sorry. I’ve never held it in my hand, so I’m sure the materials are great, and I’ve heard the swoosh is made out of their premium Dior fabrics or whatever the fuck… but I don’t even think it was better than the Chicago 1 that Off-White dropped.

The Dior 1, available at StockX for only ~$8.5K 🙃

Haha I have to agree with you that the Dior 1 was definitely one of the more annoying/disappointing releases of 2020. Hey, this was fun man. It was a pleasure talking to you and getting your thoughts on shoes and media! I appreciate you taking the time.

MS: Of course, thanks for having me!