Get ready to delve into the captivating world of tattoo artistry with the eminent PennyBoy. In this exclusive interview, we embark on a journey through his remarkable career, exploring the profound impact of his travels and the boundless sources of inspiration that have shaped his art. PennyBoy offers a unique perspective on the tattooing craft and shares his invaluable insights into what drives his passion.

Let's start with our traditional questions: tell us a bit about yourself. Where are you from, what were you doing before tattooing, and how did your career actually begin? Who was your mentor? Were there any difficulties in the beginning?

- I'm PennyBoy. I'm 34 years old, and I'm an Italian traveler tattoo artist from Milan. I've been tattooing since I was 18, but I've been drawing and hanging out in a tattoo shop since I was a kid, around 14 years old. Next to my parents' house, there was a tattoo shop that I've always been fascinated with. Day by day, I became the little "mascot" of the shop, and as soon as they realized that I was indeed a good drawer, they let me stay at the shop, and I started to learn from them.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

It's been a long journey, but I did arrive where I always wanted to be: an international traveler tattoo artist able to share art and emotions, and connect with more people through my art than I could have ever possibly imagined in this life... all while doing it around the world! I had the pleasure of working with some of the biggest names in this industry (I won't disclose names for privacy), feeling the duty to humbly learn, share, and improve myself as a person and as an artist from them. I also gave my best to each and every client who believed in me and offered me parts of their body to create something magical.

It wasn't hard for me to get into a shop as an apprentice, but it was definitely challenging to accept the way they were treating me. At the very beginning of my apprenticeship, they treated me poorly! But you know, that's sort of how it should be... Otherwise, you can never understand if you would sacrifice all you have to become a tattoo artist. I think that today, it's too easy to become a tattoo artist! When I started, I had to clean tubes all day, build needles, draw, paint, and listen to all the stories they had to teach me about tattooing. To be honest, I didn't really learn much about tattooing techniques from them, but I did learn a lot about how to build my own machine and tattoo cultures in general. I understood how a coil machine works, learned how to draw, and how to manage a tattoo shop.

After I left that shop, I went to Rome where I studied medicine, infectology, and dermatology because I wanted to know more about how the skin works and reacts to ink. Thanks to this acquired knowledge, I felt ready to approach real skin with tattoo machines.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

For you, is tattooing an art, a job, or something else?

- For me, tattooing is not simply a job; it's more of a lifestyle. It's a form of art for which you have to sacrifice a lot of nights staying up late to draw and many mornings waking up early to change your drawings completely because you're not happy with how they turned out. It's definitely something you choose for life. As a traveling tattoo artist, I've sacrificed a lot of my personal life back home in Italy.

What drew you to traditional tattooing?

- The thing that has always attracted me the most is the fact that, even in its simplicity (which is the key to traditional tattoos), to create tattoos that may seem super simple, there's actually a whole world behind it. Its difficulty lies, for example, in drawing a face with just a few lines, giving it an expression and emotion while keeping it simple. This has been one of the things that has fascinated me more and more from the beginning. Also, the way I've always drawn aligned spontaneously with the traditional style, and as a result, it became natural for me. Following my own artistic path, I managed to develop my own unique style and images to differentiate myself from others.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

What designs are your favorites?

- I love animals in general, and I think that women are the embodiment of perfection. So I like to create these nice, weird lady heads mixed with animal details. It just comes from my heart and my soul, and I feel it's completely mine. But, in general, I love to look around me and draw inspiration from everything that surrounds me.

What is the most important aspect of tattooing for you?

- To be honest, I enjoy the whole process and all its little aspects. But if I really have to pick one, I love the connection I create with my clients. I often become close friends with most of them, and it enriches me and warms my heart when I see their smiles and reactions to the final result of their new tattoo.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

Do you have favorite tattoos, clients, projects, or perhaps some unusual stories in your career?

- I have recently designed this Mother Nature lady head that I fell in love with, and I couldn't wait to tattoo it. Sometimes it can also get very emotional. For instance, there's this touching story about a lovely lady for whom I tattooed a simple little symbol, which held incredible meaning for her, representing her victory over fighting cancer. She started to cry when she saw it (happy tears, I swear!), but it touched me so much that I couldn't accept her money for the tattoo.

Do you travel a lot? Where have you been already, and where do you feel most comfortable?

- Yes, I travel a lot! I've been traveling since 2012 when I spent nearly two years in England. From there, I started traveling all over the world. For example, in Europe, I've been to almost every place, city, and convention they've ever organized. I've also visited Australia (Melbourne and Sydney) and New Zealand (Auckland, New Plymouth, and Queenstown). As for the US, I've covered almost every place, with just a few exceptions. Personally, I feel most comfortable in Hawaii, Orange County, Vermont, and the entire New England region up north. It doesn't necessarily align directly with my job, but these are the places where I feel at home.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

You're not just a regular attendee at tattoo conventions but also a recipient of numerous awards. How many awards do you have in total? Tell us about your experience. Which past event was the most significant for you? And where do you aspire to go in the future?

- Thank you for your recognition! Well, initially, I used to participate in conventions to gain experience and make a name for myself around the world. Then, of course, it helped solidify my image as an artist, my persona, and my actual work and client requests. By taking part in contests, I began winning a lot. In the last few years, from 2017-2018 to today (excluding the two COVID-affected years), I've won more than 70 awards in various categories, such as Best of Day, Best of Color, and Best of Traditional, among others. These are certainly very gratifying achievements that hold significant personal value. Additionally, the prestige can vary depending on the convention and the artists in attendance.

Looking back, the most significant event was undoubtedly participating in the Hawaiian convention. I placed first in the Best of Traditional category the second year I attended. Winning this award was a pivotal moment in my career, confirming all the hard work and sacrifices I had made. It's worth noting that winning the Best of Traditional in Hawaii is one of the highest aspirations in tattoo contests, given that traditional tattooing originated in Hawaii. Being the only Italian to ever attend the Hawaii convention and win the award was a significant achievement. It opened many doors for me, including an invitation to the Montreal convention and other major events.

As for the future, I have many projects in various fields. Concerning tattoos, I plan to open several tattoo shops around the world, with one soon to open in Europe (I won't specify the location yet, but it's a little spoiler: it will be in Switzerland). I aspire to further establish myself in the tattoo world and possibly participate in TV programs like Ink Master. I also have a project to help a specific category of people through tattooing in a unique way, but I can't reveal more details at this time. Hopefully, this project will lead to something on TV or within a niche of people who appreciate that I want to help them without seeking financial gain.

Among other things, you have an impressive list of sponsors from renowned tattoo brands. Tell us how you managed to achieve this and what it means to you as an artist.

- The list of all my sponsors has been the result of many factors, including my personal effort, entrepreneurial spirit, consistently meeting new people and making myself known, and always aspiring for something greater. Let's say that ambition has always been a crucial key for me - and still is - in achieving my goals. Every time, it's as if my ambition keeps surpassing my previous achievements, and I find it extremely gratifying. When I reach a goal, five minutes later, after the initial excitement, I'm already thinking about the next one. This trait has always characterized me and been essential for my growth.

Currently, I am sponsored by some significant names in the tattoo industry, such as Hustle Butter, Radiant Ink, Jconly, Sullen Art, Inked Magazine, and many others. I'm very proud and honored because these sponsorships happened quite naturally. As a young tattoo artist, I was somewhat obsessed and wanted to pursue as many sponsors as I could, but in the end, they actually came over time as I immersed myself in certain environments and became known in the tattoo scene. The company representatives got to know me in person, and they all said the same thing: "Your work is spectacular in terms of quality, and your Instagram is top-notch. But we want to sponsor you because you set yourself apart from many other tattoo artists with your personality and how you interact with people."

Tattoo artist PennyBoy (@pennyboy_tattooartist)

I’m a genuine person, and I love to truly support my sponsors and care about their brands. It's not just about getting exposure on Instagram or receiving free stuff. They saw it and appreciated it. You know, free items are nice, but what truly makes me feel good is having that support from a brand when I'm traveling on my own around the world, which isn't always easy. And knowing that there's a family that supports me with products and care, always there for anything I need, is absolutely gratifying.

How do you assess your popularity? And in your opinion, how can it be measured?

- If I can be honest, I don’t really care about being popular just for the sake of it. What truly matters to me is being a globally recognized artist, earning respect from fellow tattoo artists, and, of course, having popularity among clients. I do appreciate the recognition because the more I have of it, the more I feel appreciated, and it directly translates into work and income.

I'm not the type to seek popularity just to show off, you know? Popularity among tattoo artists means a lot to me because, for example, in the US, many appreciate, follow, and respect me. When I meet them at conventions, it's as if they already know me, which I'm thrilled about because I'm a very humble person. So, I really like this aspect because it means that my work and my concept of it reach people both technically and in terms of the finished product.

As for clients, I'm very happy because I have received strong and positive feedback, and they continue to grow. This results in more work for me.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

Many successful tattoo artists strive to share their acquired experience. Tell us if you have any such activities in your life and for whom they are.

- I considered holding seminars, and I was supposed to conduct one in Peru with Stefano Alcantara, but it didn't happen due to the COVID-19 outbreak. Since then, I've primarily focused on my work, serving my clients, and all the traveling I do. So, I haven't conducted any seminars for the time being, but I have received several requests to do them, and I will consider whether to organize them in the near future or not.

Let's say that I'm quite fascinated by the idea of seminars and teaching in general. I have various ideas about it, and I believe I can offer a lot, perhaps even in the form of mentorship. I'm interested in discussing topics like the life of an artist while traveling, or delving deeper into tattooing. Not just the technique, but also aspects like color selection, the why and how, the machines... In other words, more specific themes.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

What is the most important thing in your career as a tattoo artist? What goals do you set for yourself? Share your creative plans for the near future.

- I would say the most important aspect of my career has always been the ability to express myself, my vision of tattooing, and my idea of "drawing on people." This leads to seeking the freedom to do that on people's skin and make them happy. My ultimate goal, indeed, has always been this: to gratify myself through art, the designs, and the tattoos I enjoy creating, while making my clients happy and giving them something that will stay on their skin for a lifetime.

Well, of course, the aspect of traveling is highly important too, as it has helped me grow as a person and as an artist, allowing me to see many places around the world, make numerous friends, and meet so many people who have become like family over time. This is certainly a significant and beautiful part of my life.

Tattoo artist PennyBoy (@pennyboy_tattooartist)

Regarding future projects and plans, as I mentioned before, I don't want to give away too much, but there's definitely a lot in the works. Many things will be realized in the next 3-4 years. There will be numerous projects that will come to fruition, so only time will tell. Stay tuned!