Raf Simpson: 5 Things I Wish Someone Told Me When I First Became An Artist

Yitzi Weiner
Authority Magazine
Published in
10 min readJul 30, 2023


It is weird to show people your work when you first start painting, especially later in life. But you just have to do it, get it over with. You’ll be surprised how supportive people can be.

As a part of our series about “5 Things I Wish Someone Told Me When I First Became An Artist” I had the pleasure of interviewing Raf Simpson.

Raf Simpson is an abstract painter based in New York City. Raf’s signature format can be characterized by grand, minimalist, large-scale works of art. These paintings come to life through the layering of acrylics, delicate touches of oil, charcoal, pencil, and the incorporation of wax. Simpson’s creative process is derived from putting everything on the canvas which often starts with either a singular sharp shape, or a thin black line. His method allows for the gradual emergence of sections, formation of a color pallet, and the convergence of all design elements. To Raf’s art, imperfection is key. The imperfect colors, shapes, and corners allow for everything to then form organically.

Raf Simpson’s overall style and influence is derived from his love of the creative process. This process includes telling stories, and finding ways to convey an idea so that it can be understood in the most simplistic manner. Raf’s work showcases an impressive scale that captivates many viewers. The sheer magnitude of his abstract work leaves a lasting impression, immersing observers in the meaning of life. His vision goes beyond the surface, delving into the depths of existence itself. Simpson’s paintings explore the fundamental question of “why are we here” and the vast mysteries of the universe.

Thank you so much for doing this with us! Can you tell us the story of how you grew up?

I grew up in Barbados at the Crane House. It is a beautiful estate right down the beach from the Crane Hotel that my Great Grandfather built. Growing up in the 90’s in Barbados, I had the privilege of living like how I imagine Americans grew up in the 70’s. We surfed, rode dirt bikes, kayaked, and spent most of our days outside. I’m the oldest of 15 grandkids and our family was very close. We all lived in and around the same property, around a lot of people who cared about me.

It was such an amazing time. I grew up with just the right amount of technology to where being outside was more interesting than waiting for a dial up internet signal to work but I still got to have a Game Boy and a Sega genesis. I think it was the perfect balance. My childhood was epic and I’m grateful for being able to grow up in Barbados.

My grandfather is an amazing entrepreneur and he inspired me to find something that I was passionate about and to live a “nontraditional” work life. I always preferred risking it and finding a way to make it on my own. I feel claustrophobic in a way with my time being controlled by outside forces. The most important thing to me in life is time. Time with people you love doing things you enjoy.

I moved to Florida when I was 11 to be in the US school system. Our family had always spent time in West Palm Beach where we had a home that we would visit so it wasn’t too unfamiliar to me, but it was crazy to be outside of Barbados for school. Everything was so different. It took time to adjust but I made amazing friends, kept up surfing and enjoyed my time in Florida as a teenager.

My first time being exposed to art was through surfing and skateboarding — those things went hand in hand. My best friend growing up is an artist and we had a surf/skate brand together as teenagers called Madison Apparel. I often look back and think that we should have kept it going because it developed a great following. He did the art and I built the story / brand. Being friends with Matt opened my eyes to a cooler world than what I was used to. I am grateful that we are still friends to this day. Our weekends were surfing, skating and music. We were all into pretty indie stuff. The Postal Service, AFI, Coheed and Cambria, Norma Jean, and Cursive to name a few. That was a big part of growing up just being around music every chance we got. My dream was to be in a band but I just wasn’t good enough to really make it. I pursued other passions. We went to the Surf Expo every year and I decided that I wanted to own a brand, that was my dream. We had given it a good run but that one day I would be in control of the brands that all of my friends would want to wear. I felt like there was no limit to potential.

I reluctantly went to college in Florida and then moved to New York City the first chance that I had. I was 22 when I moved and that’s where I really felt like I was where I was supposed to be. Everyone was doing something and the whole experience of spending time in the city was energizing and inspiring. I had a great set of friends who had moved to New York around the same time that I did. We would spend our free time there just walking around the city and finding inspiration everywhere. The restaurants / stores / music venues. First time watching a Knicks game as MSG, first club, first “real” business. The 2010’s were a cool time to be in NYC. I lived in Midtown but right on the F train and would jump down to Union Square or the East Village every day and that’s where I really enjoyed spending time. Our friends would always go to Pianos which I’m pretty sure is still around. Always something fun happening there — music / people. We would always go to Saturdays Surf and have coffee. It was the first time that I saw an elevated surf brand that resonated more with my personal style. Again, it was something about New York that was different for me.

My first art show that I ever attended was in Soho. I couldn’t believe that world really existed in a sense. Artists and buyers and the whole ecosystem.

Moving to Miami has been incredible. People love to hate on Miami but it’s my favorite city now. The art scene is wonderful and I think Art Basel and the whole art culture in Miami really cemented my desire to be an artist.

Can you share a story with us about what brought you to this specific career path?

My wife Lauren Bakarian of Bakarian Studio is an amazing interior and furniture designer and she encouraged me to start painting. She could tell I wanted to be expressive that way but needed some encouragement. I began painting at the beginning of 2020 as a way to have something new to enjoy. In 2019, I went to Santa Fe to see where my wife grew up. The art community there is really strong, and I felt something inside of me light up when I was there. There I also discovered my great aunt Dorothy Brett had become a renowned artist. She had sort of disappeared from her life of privilege in the UK and joined an artist colony in Taos. The whole story of her life inspired me.

Lauren’s love for architecture, especially mid-century modern architecture and design began to open that world up to me. My art is heavily influenced by that time period.

Can you tell us the most interesting story that happened to you since you began your career?

The most interesting thing that has happened to me is that my friends were all very supportive right off the bat. My friend Stephen Olesky who is a designer that currently works for Ralph Lauren really complimented the work’s compilation. I think that gave me the confidence to share it with other people. I never thought I could create something that would be appreciated by people with a sophisticated design background / experience.

What are some of the most interesting or exciting projects you are working on now?

I’m working on a collection of paintings in a series, ART IS HARD. Every day I’m excited to paint. It is not work for me; it is pleasure.

I’m also working on a restaurant called Harry Roy and we’ve named it after my great grandfather. The restaurant is an upscale European / wood fire focused spot. Going through the design process, menu, branding, and working on touches like the uniforms has been an amazing process to go through. Harry Roy was an inspirational figure who married a princess and spent his years playing music in all the best places around Europe. We are opening sometime in August of this year.

Our furniture brand is taking off and our online store opens in August called Haus of Hue. My wife started the brand and we hired a full time CEO who has experience in the furniture retail space. Every month we continue to see major growth and we are finally launching our online presence with our own collection of furniture under the Label www.HausofHue.com

Who are some of the most interesting people you have interacted with? What was that like? Do you have any stories?

Louis Upkins:

I went to Greenwood Tulsa with Louis Upkins who I count as a dear friend. Louis and I worked on acquiring a major US media company together. He helped me see things from a new perspective and his ability to always bring amazing people around projects is unparalleled. Louis is a role model with a beautiful family. He is an inspiration, and he always brings amazing people around.

For context, if we had been successful in acquiring the media company, we were planning to put a center for entrepreneurship in Greenwood that would focus on the African American community there and contribute to the revitalization of Greenwood. There are many good things happening there and people who really want to see Greenwood flourish again.

In one of our trips, he organized Demario Davis and Josh Norman to go with us to Greenwood, Tulsa. There I saw Black Wall Street and learned the history of Tulsa. Again, one of those life changing experiences that I’m forever grateful for. You need to be woken up and reminded of what people go through in life and that trip was that for me.

The injustice that happened there was insane and being there with those three guys was special. On top of that Josh and Demario are two of the nicest, most genuine people I’ve ever met. Josh especially is one of my favorite people. He invites me to go run with the bulls in Spain every year and I politely decline. Watch the video of him jumping over the bull in the arena and you’ll see why; no way I could keep up. Louis is my guy.

Where do you draw inspiration from? Can you share a story about that?

I draw inspiration from my wife Lauren Bakarian of Bakarian Studio. She is the one who keeps amazing design in and around our entire family. My daughter is just like her — she’s only four but she has an eye for design. She also loves to paint, and they both are my biggest inspiration. My wife Lauren knows all the best designers, brands, restaurants because she has impeccable taste. It is like having your entire life curated and I have the privilege to be her husband and get to enjoy all of those things. It is a life filled with amazing design and beautiful things.

Interior design and architecture specifically are where I draw art inspiration. Great design and architecture are where I like to start. I paint things that I believe fit into spaces and try to complement the space and not overwhelm it. I usually start with a room from a house that inspires me and then paint something that I feel compelled to fit in the space. Even if the painting never makes it to that space, it inspired the art.

How have you used your success to bring goodness to the world?

Every day we have a chance to inspire people. I try to always encourage people to pursue their dreams and goals. In some circumstances I’ve been fortunate enough to invest alongside people and see their goals come to life. My favorite part of being successful is putting other people in a position to have success as well.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

1 . It’s expensive.

2 . Finding space to paint in New York City is insane, I got lucky with my loft in Soho.

3 . It is weird to show people your work when you first start painting, especially later in life. But you just have to do it, get it over with. You’ll be surprised how supportive people can be.

4 . Someone told me to just paint, that’s what I hope every aspiring artist hears from someone. That’s the most important thing even though I was lucky enough to actually be told. I know I’m breaking the rules with this answer.

5 . Get your work professionally shot and in the right context as early as possible.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Treat others how you want to be treated. We can all be so self-serving. If everyone treated people how they wish they were treated, we would solve the world’s problems.

We have been blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she just might see this.

Adrian Zecha. My dream is to own hotels and create spaces that are in themselves art. He achieved that with Aman.

What is the best way our readers can follow you on social media?


This was very inspiring. Thank you so much for joining us!



Yitzi Weiner
Authority Magazine

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator