Jayen Villarosa | Barber | Artist | Entrepreneur
We weren’t in a studio. No backdrop, no soundproof walls, no polished set. We were in a meeting room at a café. Chairs and a giant table separate us, some background noise, and an interview turned into a conversation.
It felt too quick, too real.
Across from me sat Jayen Villarosa, barber, artist, and the mind behind Pretty Boy Lounge and now FLORY. At 25, he’s already spent years cutting hair, building a clientele, and quietly shaping a movement out of a garage that feels more like a creative space than a barbershop.
He didn’t grow up dreaming of being a barber. Like many of us, he stumbled into his calling by following what felt good, what felt real, and what felt like his.
This isn’t just a story about haircuts. It’s about trust, mistakes, family, and the reps no one sees. Jayen doesn’t just cut hair; he cuts through the noise, the ego, the expectations. And in doing so, he reminds us that mastery isn’t loud. It’s consistent. It’s intimate. It’s earned.
In this conversation, me and Jayen walked through his journey, from being the kid in the chair to the one holding the clippers. Slowly, he opened up and gave us a story that goes beyond fades and tapers.
Let’s begin.
His energy was already through the roof. I told him to clip the lapel mic onto his shirt, but he had other plans.
He snatched it up and started talking into it like it was a handheld equipment, completely unfazed.
I didn’t mind; it fit him.
We traded a few quick pleasantries before he leaned in, grinning.
“Mic check, mic check, are we live?”
“Yes, we are.”
I glanced at my notes, took a breath, and fired off the first question.
What first drew you into barbering?
“In Grade 12, I wasn’t really doing well in school. I skipped class a lot. I didn’t like homework. So, I thought, if I can’t do well in school, I might as well start a skill, be good at it and make some money. Something where I can be my own boss.”
“My brother was a barber. He used to cut my hair. And before that, I’d go to this Asian couple across from City Hall on Number Three Road. I’ve been getting haircuts in Richmond my whole life and It’s crazy to think about how it all lined up.”
And those few lines became the foundation of everything that followed…
How did you go from cutting for fun to taking it seriously?
“It started with friends and family, people who trusted me.”
Cutting his friends in rotation, one by one, provided him with confidence and purpose.
“We had this school event; we called it black and white dance. I told everyone, ‘Come through the shop, I’ll cut you for free.’, I skipped school and did like 10 to 12 cuts that day which was the same day as the event we were all attending to.”
That day wasn’t just about the free cuts. It was about proving to himself that he could do it, that there was something here worth building.
From there, he started charging. Slowly, the hobby became a hustle. The hustle became his craft.
Clients often only see the finished cut. What part of your journey do clients usually not see?
“Definitely the reps that I put in”
He explained it simply, as he adjusted his chair to face me…
“You might come to me once every two months. But I’m cutting every day, constantly practicing and trying to improve. Every single cut I’ve provided matters, because that’s what got me here.”
The hours of practice, the small adjustments, the way each client adds to his experience even if they don’t see it, has been instrumental in his progression both as a person and a barber.
He also added…
“When I raise my prices, it’s not random. It’s like me saying, ‘Hey, this is how much work I’ve put into this. Sure, I consider inflation and adjust accordingly, but I also consider how much time and effort I put into this craft, because I care about the product and the service I provide.’”
Do you ever doubt yourself?
“I definitely doubt myself,”
He admitted.
“It’s a balance.”
He shared that he has mentors, friends, and loved ones who give him advice and constructive criticisms, which sometimes challenges his direction, and that makes him doubt.
But all of it, he said, “comes from a place of love.”
“they’ll say something I didn’t think of, and it makes me doubt my path. But I know it’s coming from a place of love. I’ve learned to not to take it too personally.”
And he admits he’s still working on that.
“Yes, I take things personally sometimes. But I’m trying to change my mindset. To see it as love, not criticism.”
How do you balance technical skills with creativity when it comes to cutting hair?
“Cutting hair is definitely technical, but there’s also an element where you can be creative.”
Jayen sees haircutting as both technical and visual, comparable to painting.
He began to put his arms up, one still holding the mic, the other, palms facing me, he created circular motions, as if shaping an invisible head, he explained:
“Technically, the hair might not be cut into perfect, identical centimeters but visually it works. That’s the point. It makes the style look more natural and more alive. It’s like painting, the beauty comes from the way everything works together, but obviously, I still do what the client wants too.”
“Some clients come in with a specific cut in mind. And some say, “Do whatever you want. I’d say it’s fifty-fifty. Some follow trends. Some don’t really know what they want and just trust me.”
What’s your philosophy as a barber and as a person?
As a barber, he kept it simple:
“Trust the process. Cut as much as you can. Put in the reps. Be friends with a lot of people.”
As a human being, his philosophy shifts.
“Don’t take life too seriously. Have fun and find balance in everything.”
What’s a mistake that taught you something important?
It took him a while to give me this answer, his shifted his gaze on the table in front of us, looking down he was hard at thought…
Giggling, Jayen gives me this…
“I remember one of the first times I cut hair, I put a bald spot in my friend’s head,”
Laughing…
“He kept telling me, ‘Just fix it, man.’ And I was like, ‘Bro, what are you talking about?’”
His friend went to class the next day with a bald spot on the side of his head.
Feeling the guilt and incompetence, he confessed;
“I actually stopped cutting after that for a couple months. I was in Grade 11. I thought I wasn’t good enough. I thought, ‘I’ll just work retail or something, because the drive or motivation to become a barber was not really there at that moment.”
But when his older brother decided to stop barbering and told him to take over the shop, everything within him came back.
“That taught me I shouldn’t run from mistakes. I should stick through them. Not be ashamed.”
And even now after 7 years, he admits that he still makes mistakes here and there, but that doesn’t stop him from getting better. If anything, it taught him how to be more patient with himself.
“Sometimes it just doesn’t come out how you imagined it. And that’s okay. Learn from them instead.”
The Shop as a Creative and Human Space
Tell me about your shop. What do you want people to feel when they sit in your chair?
“I want it to feel grungy and punk,”
He further described it…
“It’s not a clean-cut, polished barbershop vibe. You sit down, music’s bumping, there’s art around you. You’re in and out, but you’re getting a quality cut.”
He keeps his tools and station clean, but the environment has this edge.
“I’m cutting out of my own little garage. It’s like a speakeasy. If you know, you know.”
There’s an intimacy to it. A sense of exclusivity without pretension. A place where you can sit down, breathe, and be yourself. It’s not polished. It’s not corporate. It’s not trying to impress you.
You don’t just stumble into Pretty boy Lounge. You’re invited in.
If you’ve ever gotten your haircut from Jayen, you’ll know exactly what this means.
What have your clients taught you about people and about yourself?
Barbers and bartenders share a strange, sacred role: People tell them things they don’t usually tell anyone else.
“You take a deep dive into people’s lives,”
Jayen says.
“It made me more sympathetic. But it also taught me boundaries.”
He continues…
“I care how they feel. But I’ve learned there’s a line. We’re two individuals. We might disagree on things, views, opinions, but I still have to hold space and handle that respectfully.”
Not every client becomes a friend. Not every conversation is easy. But everyone teaches him something for sure.
Was there a conversation in the chair that changed how you see your work?
“Cutting my dad,” he says quietly
At this point in our conversation, I noticed that he was slowly opening up to me, his answers have become less guarded and now tapping into something deeper…
So, he takes his answer back and gave me a better one,
“Cutting my family actually, all of them, sometimes even my sister and mom. Every conversation with them changes my perspective”
Jayen looks away for a moment, scanned the cafe and the people outside of the room we were sitting in,
He continues…
“It reminds me barbering isn’t just about money. It’s about showing up for the people who matter, and who needs my help.”
After that he brings back his attention towards me…
“I can make myself available for anyone; for my clients and customers, but if I can’t make time for my dad or my family? That’s not right.”
For Jayen, barbering isn’t just a craft. It’s a way of showing up. For his friends. For his clients. For his family and for himself.
When did you start thinking like a business owner, not just a barber?
He traces everything back to 2018.
“My first official cut was October 2018. I was 17. I started with my friends. Then that school dance. After that, I started charging.”
What began as a casual favor quickly turned into a small operation that ran entirely through a private Snapchat story.
“I added all the Grade 12 guys. I’d post my schedule. At first, it was called ‘JVillz Cuts.’ Then ‘Headquarters.’ Then ‘Pretty Boy Headquarters.’”
Even the name carries a lineage. A tribute.
“My brother’s shop before I took over was called 1z Lounge. Eventually it became Pretty Boy Lounge to pay homage.”
As he got more consistent, the money followed.
“That’s when you start thinking differently. Not just about cutting, but about handling money. Investing. Thinking long-term.”
What’s the hardest part of running a service-based business like yours?
“Definitely the personalities.” He said…
“You never know who’s going to sit in your chair. Some people vibe with you. Some don’t. And that’s okay.”
He’s learned to read energy quickly. To adjust. To stay grounded even when the vibe is off.
“As long as you don’t treat me as a slave or a robot, I’m ok, at the end of the day, I am a barber and have a responsibility to my customers.”
What about marketing, how do you approach that?
“That’s the fun part,”
He said, smiling.
He later explained that he goes through phases, sometimes shooting a lot of videos, sometimes less, but he’s always creating, and that’s probably the secret here. To work consistently regardless of the mood or phases.
“I love making stuff. Content, visuals, whatever. It’s fun.”
Where do you see hair trends going?
We talked about fades, undercuts, wolf cuts, and the phases we’ve all seen.
He sees the future leaning toward more natural looks.
“Scissor cuts for sure. Longer hair. More natural, lived-in haircuts. Less flashy. More casual.”
He thinks traditional barbering will always have a place, tapers, clean sides, and simple twos on the side with a natural finish.
“But overall, I think people are going more natural. Especially our generation and younger millennials. Gen Alpha though? They’re flashier.”
Vision, Ambition, and the Future
When you think about mastery or success in life, what does it mean to you?
“Mastery for me is the result of multiple reps and intense effort when honing a craft.”
Jayen has been cutting hair for more than seven years. Beyond the experience, what really drives him is his passion to get better and creating art. He might not consider himself a master just yet, but he admits that many of the things he does now feel second nature. That’s what time and repetition quietly do.
Only time will tell how much any of us can improve. When we put our mind, heart, and soul into our work, what else is there except to keep going and see how far we can really grow.
“Success on the other hand, is all about my family, health, community and just being able to be alive. I am grateful that I am working for myself and maintaining great relationships. Money may be a factor for success, but it doesn’t define it for me.”
What’s the next evolution of your career?
This question seemed like an exciting invitation for him to spill out his plans for his future endeavors. Something he was brewing up lately.
“Pretty Boy Lounge was the beginning; it was the come up so to speak.”
“I’m planning to do a revamp for the studio and rename it FLORY after my grandfather. This is my next chapter.”
His face lit, up, adjusted his seat again as he leaned forward.
“If PBL was the come up, FLORY’s ethos is Timeless,”
He says…
“It’s my evolution, and I’m really excited.”
As far as I can see it, It’s a shift from youthful and playful hustle to mature intention.
How exciting indeed.
AS AN ARTIST
How would you describe your art to someone who has never seen it?
“Playful, witty, and a brain dump.”
Enough said. As a multidisciplinary artist, he dabbles into painting, drawing, and writing.
If you’re ever curious, visit Jayen’s studio FLORY, get a haircut, and ask for his artwork.
Do you have a favorite artist?
“I would say these are my favorite artists, because they inspired me and continue to motivate me.”
He lifts his index finger as he starts counting.
Number one…
“My sister Janae. I consider her an artist, and she’s also an entrepreneur.”
Number two…
“My older brother Soliven, a multidisciplinary artist.”
And number three…
“My big brother Joshua, a huge bookworm who paints Warhammer figurines incredibly well.”
“I can’t say anyone else but them. They’re my favorites, and they truly make me better.”
Of course, he also has artists he admires beyond his family. He mentions Jean‑Michel Basquiat, Jimi Hendrix, Juan Luna, and José Rizal.
I’d like to believe it wouldn’t hurt to slip the writer named Xergius into that list, but clearly, I still have some work to do before I can impress Jayen.
What’s your process when you start a new piece of art?
“I start with instinct, then it fleshes out… painting for me is letting go. Whatever comes out, comes out, I don’t even think, I go by how I feel, because that’s what my emotions is telling me to do.”
“However, with writing, I usually have a thought already, it’s just a matter of me putting it on paper.”
Moving on to one of the most overused questions, that the likes of Tyler the creator completely despised, I asked Jayen and even gave him a trigger warning beforehand…
What inspires you as an artist?
He laughs and says that it’s not as upsetting for him, even more so, he was prepared to answer it.
It was actually one of the questions he most certainly answered quickly and confidently…
He looked down at the paperwork I had been reading, with his head slightly tilted with curiosity.
He says…
“That’s easy, my family, I don’t understand why some artists hate this question. I think it’s a pretty simple question.”
He paused a bit, then continued…
“Everything I do wouldn’t exist if it wasn’t for them. It’s the ultimate inspiration for me.”
“It’s easy to answer because it comes from a real place.” I commented.
He gives me a look, his eyes smiling as he nods about three or four times,
I think he agrees…
Do you have a favorite piece of artwork that you’ve created?
“I do, and this is actually so cool because, I don’t even own it myself.”
I was excited to learn more about it. Is it a painting, a sculpture maybe? With great anticipation I waited, maybe he’ll show it to me, I was raring to see what it was, but what he shared with me was even better than what I anticipated…
He goes…
“I visited the Vatican and stopped by the museum gift shop. I bought four journals, one for each of my brothers, one for my girlfriend, and one for my friend Sean. On the first few pages of each journal, I drew the Basilica.”
He recalls vividly as if he was still there…
“I was sitting there with a clear view of the Basilica, my family beside me, just sketching what I’m seeing. Along with my drawing, I also wrote each of them a heartfelt message, and when I came home, I gave each of them their journal. That’s my favorite art piece, brother. It’s memorable and priceless.”
What are you still learning about yourself?
“That I’m getting older every day for sure, and that I’m becoming more mature, I think differently now and I’m more sympathetic.”
He further adds…
“Back then I felt that I was rebellious, I was a legit punk, but now I transfer that energy into something more positive. My art is punk and rebellious, but I am not rebellious or a punk kid anymore.”
What’s the best advice you’ve ever heard?
He thinks for a long moment before answering, eyes drifting upward, searching for something…
“Trust the process,” he said, laughing.
I laughed as well, because I knew exactly who and what he was thinking about.
It’s from Joel ” The Process” Embiid, the basketball player, a great and wacky choice. But at face value, it’s hard to argue with.
What else can any of us do but trust the process?
If we work hard and pour real intensity into our passions, what comes out on the other side is something authentic. Something that’s ours. And how do we become masters of that? By showing up every day with intention. By doing the reps, letting consistency shape us.
Soon enough, we end up where we’re meant to be. And the only way to get there is by trusting our effort, our hard work, and the process itself.
What’s the worst advice you’ve ever heard?
With disgust on his face,
“Probably something from the manosphere, it breathes toxic masculinity.”
Nothing further…
Do you have a favorite quote?
It was escaping him, so he reached for his phone to get it right.
A line from 50 cent’s song; God gave me style.
“Sometimes I feel like I’m the one, but that ain’t my fault.”
He reflects on this line and explains it this way:
That a person should not feel bad for his life; he is blessed regardless of his circumstances.
He even goes further and says,
“it’s not your fault for being blessed with a good life.”
All the questions before this, the craft, the career, the creativity, the discipline, were really just preparation for the one that mattered most. I ask it in every interview, not because it’s clever, but because none of the other answers mean anything if we’re not honest with ourselves first.
“Jayen”, I called his attention and set my questionnaire down…
He looked directly at me, as he nodded with his forehead.
“Our last question…”
“Yessir” he says…
Are You Happy?
“Am I happy?”
He repeated it softly, almost to himself.
“Am I happy?” Louder this time…
Then he nodded, once, with certainty.
“Yes, yes, I’m happy of course, I’m super happy.”
“Because I get to do what I love.”
Arms wide open as if he was trying to envelope the space in front of him,
“I’m alive and get to do amazing things”
“Just like this Interview!”
He jests…and we laughed a bit more.
“It was fun bro” I quickly said.
“It sure is brother, it felt like a podcast” he joked…
We talked a bit more, as we stepped out of the meeting room where this whole thing began. This time with people around us, no chairs and a giant table separating us, the air is cooler and the smell of brewing coffee surrounds me and Jayen again.
The background noise was still there, but it no longer felt like a distraction. This time we chatted not as an Interviewer and Interviewee, no longer separated by roles or questions. Not the same two people who walked in but two individuals who now share a story, a real one.
If you strip away the fades, the trends, and the branding, what remains is simple. Every cut is a chance to help someone feel like themselves again, maybe even a little better than before.
Jayen is not just cutting hair in a garage. He’s building something real. An energy. A space. A community. He started as the kid in the chair. Now he’s the one people wait weeks to see.
And through it all, he’s still trusting the process. Still putting in the reps. Still learning as he goes, shaping his craft one cut at a time as he evolves towards the path he chose to pursue.
Connect and Book a Haircut with Jayen : FLORY
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