Meet Josh Velazquez

We’re excited to introduce you to the always interesting and insightful Josh Velazquez. We hope you’ll enjoy our conversation with Josh below.

Josh, appreciate you joining us today. How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? The world needs to hear more realistic, actionable stories about this critical part of the business building journey. Tell us your scaling up story – bring us along so we can understand what it was like making the decisions you had, implementing the strategies/tactics etc.

I’ve always said that when starting a business, I would begin small and learn the ropes from the ground up. In February 2019, I embarked on this journey with a two chair barbershop (475 square feet) space. It was an ideal setting for me to gain hands on experience and focus on providing exceptional client experiences on a one on one basis, with minimal overhead costs. I embraced the concept of taking baby steps and prioritizing my craft and the details of my clients’ experiences.

However, Here comes COVID-19 and lockdowns presented an unexpected opportunity for growth and resetting. While confined and feeling uncertain, I seized this time to strategize and scale my business. The rent in prime locations like the West Loop of Chicago became significantly more affordable, making it an ideal time to expand. This was a dream come true for me, as I had always aspired to own a business on Randolph Street in the West Loop/Fulton Market District. With a year and a half of experience under my belt, I felt confident in my ability to scale and grow, taking advantage of the affordable rent in this area. I took a leap of faith and secured a lease at my dream location, transforming the 475 square feet space that housed two barber chairs into a 1275 square feet space that accommodated six barber chairs. While my bills increased, the experience of managing Stewart’s business on a micro scale proved invaluable during this challenging period.

My focus shifted to building my brand and expanding its reach. I created cool merchandise that showcased my brand name in limited edition runs, posted my journey on social media, and generated buzz around the brand. All the while, I remained committed to the core values of my business exceptional client experiences, great hospitality, exceptional haircuts, and prioritizing profitability over rushing to make a profit. Within six years of operating my business, we were able to scale again.

Fast forward to May 2025, when I opened my second location in River North with five chairs. This milestone was a testament to my determination and perseverance. It all started with waking up each day, leading my team with honor and love, and fostering open communication. The positive impact of my journey in six years is remarkable, and I can only imagine what I can achieve with another six years of hard work and dedication.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

My name is Josh Velazquez, and I’m a proud Chicago Native (Puerto Rican). I’m a husband and a dad to three amazing kids.

I got into barbering back in high school in 1998. It all started when I saw my best friend, Eric Aponte, cutting hair. A lot of our friends would come to his house after school on Thursdays, Fridays, and get haircuts. We’d just hang out in his basement, talk about girls, cars, and sports. It was such a great way to end our long week of school and get ready for the weekend. It was like a secret club where we could come to relax and get pampered. It was a brotherhood!

I thought that was such a cool feeling, so I decided to learn from Eric. I bought my first pair of clippers and started cutting hair myself. Believe it or not, my first haircut was actually really good! It made a buzz in school that my friends were asking me for haircuts. That feeling that I had at Eric’s house was now mine. I was the one cutting hair and boosting my friends’ confidence with my gift of barbering.

After a few free chaircuts, I started charging $5 for haircuts and $8 for graphic designs. For my senior year, my homecoming and prom were a huge hit. Guys were getting haircuts left and right. It was awesome!

So, after high school, I had this dream of becoming a professional barber. But life had other plans. I became a dad at a young age and had to put my passion for barbering on hold. Instead, I joined corporate America to provide for my family and make sure they had a steady income and health insurance. I worked in corporate America for 13 years, but deep down, I knew it was time to step out of my comfort zone and follow my heart. I had this gut feeling that it was my time to start barber school and get my barber license. I wanted to pursue my new career in the hair industry. It was scary, but I believed in myself and had the unwavering support of my wife. I enrolled in barber school in my early 30s, and that’s when things started to change. Taking that leap of faith and making a bold move towards something I truly wanted was a turning point. I told my wife I had to go after what was mine, even though it would be filled with ups and downs. But I was determined.

After completing barber school, I was honored to work at Solo Salon in Chicago, a place that holds a special place in my heart. It was there that I truly learned how to become a professional barber, how to treat clients, style and cut hair, and pay attention to the little details that make a big difference. I’m forever grateful for that incredible opportunity. I spent over five years at Solo Salon, where I also worked as an educator for a product company called Baxter of California. I became their lead educator and traveled across the US for five years and taught hair dressers in our industry how to groom men (hair, beards, and shaving, as well as how to talk about hair products). That was an amazing experience because it gave me a glimpse into the areas where our industry is lacking. I heard my peers complaining about the owners’ lack of leadership, and I made a promise to myself that I would never lead in such a way. Instead, I would prioritize listening and supporting my team first. My team is the heart and soul of PBCO and they make everything possible.

After all these experiences, I’ve become a student of my craft, staying present and growing into a professional barber who’s trusted and respected. But I’m not just about the barbering; I’m also a leader who can guide my team to success and give them the chance to learn a great living. I have a vision of creating and designing my own barbershops, and I’m excited to bring my own unique style to each one. I love shopping for antiques and furniture, and it’s another way for me to be creative and have fun building my businesses. It means the world to me that I do everything – barber, leader, designer, social media content creator, and educator.

I feel so proud that all of this was earned and not given. A lot of hard work and discipline.

About my businesses, I’ve created a space where I create experiences for others. We welcome every visitor with a warm greeting and offer them a refreshing drink, like whiskey or a great cup of coffee from a local Chicago coffee company. Unlike other businesses, we don’t rush our clients. Instead, we take the time to conduct a consultation and understand their needs. We shampoo our clients’ hair with quality products to remove any products they may have brought in, such as bedhead, hat hair, or gym hair. We want to cut with clean hair, which makes our job easier and helps us understand their hair at its natural state to give a well groomed haircut. Additionally, it keeps our tools clean.

Our services range from 45 minutes to an hour. We’re always present with our clients behind the chair. It’s crucial that we provide our guests with a break from the outside world and build their confidence through hospitality and a haircut or a relaxing hot towel shave. Some of the services we offer include shear haircuts, fades, beard details, and hot towel shaves. We take great pride in our attention to detail and the clean, speak-easy feel of our barbershops.

Seeing our guests leave the shop with a boost of confidence and their new look is simply the best we can give back to humanity with love and respect.

The shop is inspired by the early 1920s with custom-made, one of a kind stations, vintage style barber chairs, antique furniture, and natural hardwood floors. Chicago brick adds to the ambiance. Great music and is not to loud and annoying. Every time you visit, there’s something new to discover. Instagram worthy at every corner! Designed by myself, these vintage barbering goodies are sourced throughout the barbershop. It’s like stepping back in time! Both locations are on the second floor, intentionally hidden from broad daylight to create a sense of privacy. This also prevents unwanted street guests from causing trouble. If you know what I mean! It aligns perfectly with the brand’s Chicago Speak-easy vibe.

How do you keep your team’s morale high?

As an educator at Baxter of Ca, I had the chance to travel across the US and visit various salons and barbershops. During my time there, I gathered valuable feedback on the industry’s shortcomings, particularly in leadership. Artists often felt unheard and undervalued for their hard work. Additionally, shops lacked proper updates and maintenance, and the primary incentive for employees seemed to be a paycheck. It was heartbreaking to hear such negative feedback.

My goal was to turn this around and create a positive and supportive work environment in a clean and creative space. I believe that effective leadership involves highlighting communication skills, both during good times and challenging ones. I make sure to have dedicated time to listen to my team members, not just as a group but also individually. This fosters a sense of respect and commitment to the brand.

I tell my team that they are my top priority. By providing them with the support and resources they need to succeed, I create a positive and productive work environment. I actively engage with my team members, celebrating their achievements and acknowledging their contributions. I also organize team outings and social events to strengthen our bond and create a sense of camaraderie. We also ensure that the shops are kept up to date and well maintained, so that the employees can take pride in their workplace.

Furthermore, I take the time to recognize and appreciate my team members’ efforts. I send them thoughtful messages, celebrate their successes, and show them that I value their contributions. By doing so, I create a positive and supportive work environment that encourages creativity and innovation.

Can you tell us about a time you’ve had to pivot?

During the pandemic, in August 2020, I had to make a quick change of plans. But I chose to take advantage of the situation when I had the chance. With businesses closing, I decided to grow and expand into a new location. I had faith that this was the right move. I know I can handle changes if I stay focused and hungry for success. This opportunity was scary, but I knew I couldn’t miss it. I believe we only live once, so let’s make the most of it, even though it comes with its challenges. I was ready for the challenge again and wasn’t going to look back. If I’m willing to take risks for others, why not for myself? I have to be all in for myself. Let’s just say this leap of faith has paid off big time and has given me even more motivation as a business owner and entrepreneur.

Canvas Rebel. Published October 2025

Original article can be found by clicking this link.