Do What You Want! Interview with Content Creator and Sprezza Founder, Clayton Chambers

This week’s interview is with Clayton Chambers, a content creator and the founder of Sprezza, a newsletter that explores men’s style through a mix of education, curation, and discovery focused content.

Clayton grew up in a small town in Florida where his father was a Southern Baptist preacher. His earliest memories of fashion and style were influenced by the blazers, oxford shirts, khakis, and penny loafers his mother would dress him in for Sunday church. Ultimately, his college years in New York transformed and expanded that early love of style. During that time he started a creative lifestyle brand called Brothers & Craft with his brothers; a platform that took off as Instagram began to transform the media landscape.

Eventually, Clayton found himself burned out by the growing influencer movement and the fashion world. He made the decision to step away and spent the next several years working for technology and e-commerce startups; it was a break that slowly but surely helped him rediscover his love of fashion and style. Sprezza was born out of a desire to find a creative outlet once again. What started as a side project on Twitter quickly took on a life of its own, growing into a community, newsletter, and media company.

Sprezza is derived from the Italian word “sprezzatura” which means “studied carelessness” or “doing things with a sense of ease.” It’s an approach that influences how Clayton operates as an entrepreneur and lives his life. He grounds himself by listening closely to his intuition, being open to experimentation, and taking care to hone in on his own voice and the unique way he’s meant to operate in the world. As he told me, “There’s a powerful lesson in thinking things and wanting things for yourself, putting them out into the universe, and then seeing those things happening. It’s about you taking active steps to get what you want from it, and then that thing unraveling or unfolding for you.”

Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.

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How would you describe what you do for work?

I’m a content creator, and I work in the media world. When I say media, I think a lot of people have this image of this old guard. At the same time, there’s this new wave of content creation merged with media, where you can have a newsletter, make a video, run your own YouTube channel, have podcasts, and really do anything you want as an individual operator. That’s the world that I operate in, and it’s something that I’ve been pushing towards for the last few years. I have audiences and people who follow what I write and say and talk about. I spend most of my time trying to find the most interesting and authentic ways to share things that I think are interesting.

I want to talk more about how you got here. I think a lot of people in their twenties and thirties in particular can relate to the idea of feeling burnt out but unsure of how to find their way to a career that intersects with their interests and makes them feel creatively inspired. Based on your experience, what advice would you give them?

I think it all depends on what stage of life you’re in, but if you don’t have kids, and if you have the freedom to kind of move about and try stuff, I highly recommend it. For me, movement is one of the most important things that you can do for yourself. Whether that’s physical movement, like being active and keeping yourself and your mind physically fit, or just having movement in terms of trying new things and having experimentation as a core part of your life. That’s the stuff, when I look back at a lot of the inflection points or changes that I’ve experienced in my own life, that’s helped me the most. When I’ve been operating from a place of movement, trying things, taking conversations, putting shitty stuff out in the universe and seeing if it’s gonna stick, I’ve learned about what I want out of those things and what I don’t want.

I think it’s easy to get complacent, or feel defeated or discouraged about your own life trajectory or what you think you’re supposed to be doing. During those times, I think it’s easy to want some magic bullet that’s gonna appear or some special word that’s going to come through and tell you what you’re supposed to be doing with your life. I haven’t found that to be the case. Often that path and direction emerge from just doing and trying stuff.

I call that “the myth of the grand plan.” The idea that you’ll have this magical epiphany where the path is laid out for you and then you get started doing things.

I’ve found for myself and a lot of people that that kind of idea is just a recipe for never getting what you want. Getting what you want is a complicated thing, right? I don’t think that really any of us know what we want. I think part of the knowing what you want comes from living and trying stuff, meeting people, having experiences, and going through successes and failures in life. It’s through those things that you start to discover, here’s what I really want to focus on, or here’s where I want to put my energy towards, and these are the people that I want to surround myself with. I don’t think you can shortchange that experience by any other way than just trial and error. I’m a big proponent of fucking around and finding out.

Movement and experimentation definitely require a degree of comfortability with the unknown and uncertainty. How have you noticed your own relationship with the unknown has shifted the longer that you’ve been pursuing entrepreneurial endeavors and this unconventional path?

The image I have in my head is just this idea of loosening your grip on something that you feel really attached to. I think early in my career, I felt a lot more attached to and obsessive about the creative projects I would start. I felt that I needed to control the outcomes of them, and that I shouldn’t let anyone else into my circle because I didn’t trust that they were going to take care of the thing that I wanted to grow and evolve. I think there was a little bit of grand plan syndrome locked in to that mindset, too, where I was afraid to let other people into this thing that I had, because they might mess up this grand plan I thought I was supposed to have for myself.

I’ve found that life is so much more forgiving with those experiences. I’ve also learned with creative projects, ideas, and businesses, that they can just be about something you need to learn. They’re not all necessarily meant to be something you see all the way through to the end. To be clear, I think that’s different from starting something and then just quitting. But I think part of the lessons you can learn in life come from starting something and taking it as far as you can intuitively feel like it’s supposed to go. Then you can say, “Cool, maybe now I’ve learned my lesson and it’s time to graduate to the next thing.” I’ve learned to be a lot more receptive to those types of experiences, to be a lot more open-ended, and not feel like everything is that serious, because it’s not that serious.

The only way I’ve been able to learn those things is by having enough of those creative repetitions, pushing myself in a certain direction, and then realizing what happened when I shared something with someone, or invested my time and energy into a certain project, and how those things turned out. You go through enough of those motions, and then eventually you start to find what works for you.

I have a feeling this is related, but I was curious about the meaning behind Sprezza. You named Sprezza after the Italian word “sprezzatura” which means studied carelessness, or the idea of moving through life with a sense of ease. I’m getting the sense that moving with ease wasn’t always an easy thing for you. What do you think were the realizations or mental shifts you’ve made that have allowed you to bring more of that ease into your life and work?

I’ve always loved clothing and style and personal taste, and developing my own personal taste, and I loved the concept of sprezzatura as an approach to personal style. It’s something that I’ve always tried to emulate in other areas of my life to make things feel easier, to have this kind of rhythm or flow about your life and life decisions, such that you don’t feel like you’re forcing it. That’s important to me because I operate a lot out of intuition. When it comes to business stuff, and life, and relationships, I’m constantly trying to gut check: Is this for me? Is this something I should put more energy and time into? I want it to feel easy.

What helps you tap into that sense of intuition?

Shutting my phone off. Not comparing myself to other people and what they’re doing. I think a lot about dating and that early stage of having a crush on someone. Often a crush can be about a lack of information. I think that applies in so many other areas of life, right? We all seem jealous of other people’s lives, and what they have, but the reality is no one knows what’s going on behind the scenes with someone else’s life. You can never fully know, but the more information you get, you often realize it’s never as pretty as it looks on the outside. I think the sooner that you realize that you need to tune out what other people are projecting onto you, it’s probably for the better.

I did want to ask you about learning to let go of what other people think. You recently tweeted on X saying, “I’m living the life my younger self dreamed of having. Living in Europe. Running my own business. Playing the long game. Funny how life changes when you stop listening to what other people think. Go and get what you want.” What was the shift that you made in getting to that point where you were able to turn down the volume of those outside voices?

I spent most of my 20s working for other people. I’ve been on the founder side, I’ve worked at 400-person companies, I’ve been very low on the totem pole, I’ve been super high up, I’ve hired people, I’ve fired people, I’ve been fired myself. Through all of that, I think what I realized is that you’re the only person who’s accountable for your own life, and you’re the only person who’s in charge of making decisions for yourself and making yourself happy. No one else cares and no one else is gonna do that for you. The moment you realize that you get to be in the driver’s seat and make decisions for yourself is the moment when you can just start having fun, and that’s when you get to start playing or treating life as if it’s something that feels playful, and less of this big thing that you need to conquer. I’ve tried to apply that in every area of my life, where I remind myself: this is not that serious, take a step back, and just see life for what it is. There’s a lot of fun shit to do in life. There are a lot of cool people to meet and fun projects to take on. You have the ability to act on impulse and to try things that you always wanted to try. The only thing that’s holding you back is your internal monologues and what you believe are other people’s expectations of you. There’s a power in realizing that no one really cares so go do what you want.

I don’t think you get to a point that you’re at now without some intentionality. What do you think were some of the choices that ended up making the biggest difference in getting to this chapter of your life where you feel like you are letting intuition and what you want lead?

I think that one of the biggest things that happened to me was having kids. Having kids has given me this level of expansion in my life that I wouldn’t have had if I didn’t have kids. I remember the version of the person that I was pre-kids, and I would never want to go back to that version of myself. I’m so much happier on this side of it. There’s obviously trade-offs, and there’s exhaustion, and there’s different things that come with raising humans. Having kids helped me level up and understand where to trim the fat in my life. You realize you can’t keep operating under the same kind of pretense in these areas of your life. Something’s gotta give, and you have to make some changes, or you’re not gonna get where you want to go.

Therapy is another thing that really helped, just stuff related to childhood and growing up. The people that you were raised by (shocker!) have a huge influence on the way that you make decisions, the way that you feel about yourself, and how you view yourself. So many people leave that part of their life unchecked, and don’t ever get the help they need, and I think that that’s a huge missed opportunity for growth and development. Those are the kind of things that have changed me and given me a different view of myself and the confidence to get what I want out of life. I don’t think that I would be able to be where I am if I hadn’t gone through those experiences and made some of those changes.

What are some of the biggest things that stand out in how you’ve changed as an entrepreneur as a result of having kids?

I’m still in the thick of that learning. I have a 3-year-old and an almost 2 year old now. Time management is the biggest thing – choosing who to give your time and energy to. For me, I’m huge on relationship building and connection, and one of the hardest parts for me about having kids is that when you actually have work stuff to do, and you’re juggling childcare, you can’t go get 4 coffees with people during the week, even though it’d be cool. I want to keep my mind open to serendipity, making space for meeting cool people, and seeing what happens, but I simply do not have the time. That’s hard, and I’m still trying to figure out what the balance between making space for that is and scripting videos, writing articles, doing admin stuff, and doing things like filing my taxes. Time management really is the biggest hurdle.

The other thing that’s been important as an entrepreneur with young kids is finding people in your corner who are at a similar stage of life on the entrepreneurial side. You start to gravitate towards people, not out of a sense of superiority or anything like that, but more from a desire to find people who can empathize with where you’re at and offer some insight or advice. I’m always looking for people like that.

You’re also at a stage where Sprezza is evolving in new directions. You’ve directly invested in other companies, begun doing in person brand activations, and continued to grow your community. Speaking of the idea of intuition, what helps you know when it’s time to push and evolve in a new direction? Are there any signals or things that generally let you know, “Hey, I think something new is trying to emerge?”

My intuition is always changing. I have a pretty mutable energy so I can make changes and adjust and tweak whenever I feel it’s time to move on. I think one of my gifts in life is to be able to know and spot those changes. I’ve always operated from a place of independence and had a pretty good feel for when I want to make a change or try something new. I just kind of barrel into it.

There were definitely times when I had to get over the fear of taking a risk, but for me, the most important thing is that if you have a general idea of where you want to go, the small little steps and the small little details in between aren’t that big of a deal, as long as you feel like you’re still trending in the right direction.

Are there any lessons you’ve learned looking back where you’ve realized, “Oof, when I was in that mindset or had that motivation, it generally led to a decision that was wrong, or ended up feeling very unaligned?”

I still struggle with that in particular because I’m in a world of a lot of self-starting entrepreneurial people. I think when you look at other people’s paths, you often very easily get sidetracked by what someone else is doing and thinking. You start thinking, “I need to be doing that, too.” One of my business partners, Oren, is an incredibly talented, multi-hyphenate, focused creative who has been around the block many times. He’s building this media empire for himself, and there’s even times where I look at him and we have brainstorming conversations, and I find my brain asking, “Do I need to do more of this?” I’m having to learn to steer myself back and be like, “No, you need to take your own approach. What do you want to talk about? What do you want to say? What do you want to work on? What do you want to do?” It’s not about trying to match the energy of other people’s paths, because that’s for them. What’s for you is the stuff that you need to work on, and the mystery is figuring out what those things are.

That aligns nicely with the theme of the blog – the idea that there are no directions for the life that is unique to you, and what you’re meant to do. What are some of the puzzle pieces that you’re putting together right now regarding what the life that is uniquely yours looks like?

When I first started Sprezza, it really was just a creative side hustle while I had a day job. Once it started to grow and create a sense of community, I realized that it could be bigger than just me. Part of what I’ve been trying to figure out with Sprezza is where it fits into the bigger universe of my goals. Where I’ve landed with Sprezza is that the biggest value it can provide is the community. That’s number one. Number two is about being a style publication for men and helping them develop personal taste and feel more confident by providing education, shopping guides, events and activations, and programming.

Then there are other businesses that I want to eventually launch that are adjacent to Sprezza. Hyper is a business I started with my partner Oren as a creative resource and marketing strategy newsletter for brand builders, art directors, creative people, and agencies. If you work in any part of the marketing sphere, this is for you. There’s some connection to fashion and style, but it’s more about general marketing focused on the consumer side.

As for my personal content, I think part of my calling is to help inspire and lead people into realizing the creative limitations they’ve set for themselves. I’m trying to do that by showing what I’m working on and helping inspire them to step into whatever creative thing they’re thinking about. I think that’s the future brand building and the work that I really want to be known for.

I’ll just finish up with one more. If you had to put a title on this chapter of your life, what would you call it?

Going back to my initial point, I would just say the title would be: Fucking around and finding out. There’s a powerful lesson in thinking things and wanting things for yourself, putting them out into the universe, and then seeing those things happening. It’s about you taking active steps to get what you want from it, and then that thing unraveling or unfolding for you. I think a lot of times people just don’t ever let themselves dream enough. It’s always been really important for me to try stuff and find out. That’s what I’m experiencing and feeling right now.