Barbers, Barbershops, Career Advice, Features

Brand Masters: Willis the Barber embodies Hustler Mentality

Episode 2: Well Connected.

words by: Matt Peng
Jul 14, 2021

Brand Masters is a new series that explores what it takes to become a successful entrepreneur in the contemporary landscape of culture. Whether you’re building a name for yourself or your label/store, these individuals have gone through the process and drop dimes.


We kicked off our Brand Masters series last week with Justin Carr from That Feeling and this week, we’re following up with a big local NYC name, Willis the Barber. The owner of Well Connected in the Lower East Side embodies the spirit of New York. A bonified hustler, Willis Orengo never takes a day off. Combining his passion and work ethic has led to him being able to build up a rolodex of clients few can touch. It’s also allowed him to collaborate with brands like Martel, D’USSÉ, Gillette, Jameson, FILA and more. He takes the time to break down how a hustler mentality can turn you into a world class professional in any industry.



The journey

Often times people see the success without realizing the struggles and difficult journey it took to reach the top. Like many others, Willis is a product of his environment. When we asked him how he got into barbering, he talked about how his dad was always fresh – but he was only allowed to get a haircut every season. “My dad was probably one of the freshest guys on the block back in the days, and he always had a haircut. But, with me and my brother, we only got like 4 haircuts a year: Winter, Spring, Summer, Fall.”


Because Willis’ birthday was in May and fell in between seasons, he said he always looked wild during the celebration and wanted to change that as he got older. So he started to experiment and learn the craft.


“When I started getting haircuts, like, myself, going to the barbershop, I was about the age of like 13, maybe 14, and I was getting out of junior high. I was like you know what, I’m gonna grow out my hair – my dad always made me get certain haircuts. I started growing my hair – I had my hair for like 6, 7 years in braids, so, I always wanted to have, like, a nice shape up, so I would always have a razor on my shit, cutting myself open, but, like, you know, with practice you’ll master your craft. So practice made perfect, and I got nice, with just passing the blade, not saying with haircuts, but passing the blade I got nice with.”


Passion leads to practice which leads to professionalism. Willis took all his passion and combined it with his New York hustle and he started cutting hair at uncles’ shops in East New York before moving to Manhattan.


“I started ruining everybody else’s hairlines and all of their shape-ups, aha – Like, you know, my cousins would let me practice on them, and a couple of my friends, and then, little by little, you know, I had the confidence, eventually, to, like, work in a shop, and I worked for my uncle’s, or my cousin’s uncle’s, shop, it was called Next Door Barbershop, in East New York, on Fulton and Essex, which is no longer there.”


After a few months, he took a huge risk and decided he needed to open up his own barbershop.



Well Connected

With advice from Rich the Barber of Filthy Rich Barber Shop, and friends like 10 Deep’s Josh Fishel complaining about long waits at the time, Willis was motivated to open his own spot. And the name of the shop says it all. Since he knew so many people in all sorts of industries and trades, and since NYC is the melting pot of the world, the name fit perfectly.



Adding onto that train of, Willis explains why New York barbershops and barbers that have cut in NYC hit differently and why New Yorkers are different from people across the country and globe.



It has to be the water or something because New Yorkers just want it more and are willing to work hard as f*ck to get it.


How to define success

So with that hustler mentality in place, you can reach successful heights in the barbering industry and also apply it to the profession of your choosing. For Willis, his definition of success keeps him on the grind and working harder than anyone else. He’s one of the few that still opens and closes his shop each day even with his high-end clientele.



Seeing the people around you flourish is often times lost on those who reach boss status but Willis doesn’t let a title shift his attitude. “But just to see, like, the guys in my shop, you know, make money, that’s what really does it for me, because, at the end of the day, like I’ll, like – I’m a boss, and I guarantee you’re gonna eat, like, what Rick Ross says ‘ A boss gonna guarantee we gonna eat’, and that’s what I like.. That’s what I thrive off of! Like, seeing other people be successful and, like, you know, seeing other people happy, because, at the end of the day, you know, making money in a barbershop makes people happy!”


“Never feel like you made it.”


So we had to ask him how the pandemic has not only affected him, but his shop, and community. The whole experience enforced the notion of being connected and making sure that you are constantly nurturing connections and relationships and checking in on people just on a human level. You have to actually care about people and the community.




Meaningful relationships are built over time and through multiple interactions. Willis gave primo advice on how to navigate tradeshows and why he only attends them to seek out help in specific areas of interest and to also send clients to others in the industry too. You really reap what you sow and a hustler has to know that.



Tradeshows are give and take, a two-way street like everything else in life. “I’d say the best thing about, like, going to these events, like, if you see a barber, he’ll get tagged on, like, barbershop pages, and if you follow him you’ll see that he does amazing work, always, you know, throw some fire emojis, and send a DM like, ‘yo, amazing work, would love to chop it up one day, hopefully one day we’re in the same area, we can link.”


“That’s the reason why I go to those events now, it’s to meet guys like that, because, you know what’s gonna happen? If people come to New York, which… New York is a place that people travel to thinking about, ‘ yo, I gotta get cleaned up,’ where is everybody going to send him to? Me.”


Advice for new barbers

So how do you put yourself in a position to succeed the way Willis has after you’ve set yourself up with a hustler’s mentality? Consistency, perseverance, determination, confidence and a whole list of other adjectives. But the most important trait is to stay humble and never think you’ve made it.



To keep up with Willis the Barber and Well Connected, check out the social media accounts below. He’s always cooking up something new.

Willis the Barber Instagram
Well Connected Instagram


This series was made possible by Squire, the premier barbershop POS software. To learn more, hit up


If you’re a first time barber or even someone established, look out for more episodes of Brand Masters each week.


Written by Matt Peng
Interview conducted by Curvel Baptiste
Transcription by Olivia Hawkins
Produced by Madeline Carpentiere
Photos via Willis the Barber/Well Connected