Selling Graffiti-Inspired Paintings at Bars to Pay Rent in a Recession — Reflections of a 20-Year-Old Artist

If I could give advice to my younger 20-year-old self… the list would be long. Albeit I would cover with certainty, practical advice for business.

In this story, I’ll show you the magic that happens when you say “Yes” to a dream, even if it’s in the middle of a recession, including concrete business lessons.

When I began my first business, I decided to create and sell pop art paintings that I made in my shared-apartment. It was 2008 in Burlington, Vermont. With the recession, jobs were seldom secured and I knew I had to find a way to live.

As a newly college graduate, I had a fervor and passion for art and creative endeavors. Drive and ambition were my two best friends and I relied on them frequently so starting a business sounded like a good idea. I graduated from college in with a 4-year degree in 3 years, and with honors. Needless to say I had some experience with hustle.

I didn’t have a job (although I was definitely on the hunt), so I ventured to create my own job doing something I loved. Paining was a new passion of mine. I had just wrapped up an independent study on graffiti and hip-hop’s influence on street art culture. I thought to myself “why not sell my paintings? I’ve already created so many of them, there must be a market for this.”

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Without a job, and just a vision of a crazy idea I got to work.

Upon further reflection, this is often what it takes to start something new.

I bought the most economical supplies I could find (mainly plywood) and .10 cent recycled vinyl records to make my creations. I also leveraged funding from friends to pay for the supplies. A few friends accompanied me to the hardware stores while I gathered everything I needed to paint, and in exchange for buying the supplies, I promised them a piece of artwork from the collection. They were elated to help, and felt like it was a total deal on which they didn’t want to miss out.

I remember laying the plywood pieces out on the grass outside my new apartment paining outside because I didn’t want to damage the house now that I was on the lease for the first time.

Somehow, this business kind of worked. I didn’t become rich overnight (who knew!? HA). Ultimately, I didn’t get the business to a really profitable level because this was really my first real business as a 19/20-year-old and I had next-to-no-experience.

However, the journey itself is a magical one.

Business and marketing strategy decisions lined up for me naturally, without me having the past experience.

I had the gift of not knowing what could and couldn’t work, so I tried it all. I didn’t have limiting beliefs around selling art because I didn’t know that it wasn’t “a thing”. I was told by my art professors that getting famous making art was far-fetched, but otherwise was oblivious.

When you don’t know what will work and what doesn’t, this is a gift. It’s the gift of the young and the lucky. It’s what sets the stage for “beginner’s luck”.

Receive the idea, allow yourself to be curious, and take inspired action.

I remember walking into a coffee shop in Burlington, and seeing art on the walls. I looked closer, and noticed that they were all from the same artist, and they were also for sale. In that moment without hesitation, I walked up to the counter. I asked for the manager and spoke to him how I could also show my artwork on the walls including hanging little business cards with pricing to purchase the pieces.

They told me I would need 20–30 paintings or pieces to book a show, and that I would need to show them my work in advance to be accepted. They asked me if I had this quantity of pieces, and I immediately said “Yes, of course! That’s not a problem, I paint fast.” I had maybe 3–6 paintings that I felt suitable I could display. Honestly I had no idea how I would create 20–30 pieces but I knew I could find a way.

Within just a few days, I walked back to the cafe with photos of my graffiti-inspired bright paintings.

The coffee-shop manager loved my work and booked my art show on the spot. They planned my showing for 2 months in advance. I went to work. I created dozens of paintings in just a few weeks, and designed many pop-art inspired graphic prints on my computer to sell.

Before the official art show, I had diligently created over 40 pieces of artwork.

Don’t think, just go for it.

I had no idea what failure looked like, or any limiting beliefs around this career. The result? When the opportunities came up, I pounced on them. I just made it happen.

My first show sold well. Again, I didn’t become famous or rich. However I did make probably around $300-$400 without having to cover my supplies, so this was pure profit. It was almost enough to cover my shared rent, and I had only worked part-time to achieve it.

I was hooked.

Once I understood this was a way for me to create a job and income for myself, I found my recipe and kept booking art shows. I found there was less competition to book shows in cafes, restaurants, and bars, so this is where I focused my energy.

Once you know what works, apply massive action to see reliable results.

I booked 20 art shows in 24 months. Some of the shows I booked 2 or 3 in the same month in different locations all over the east coast. At one point I was showing my work in Boston, Manhattan, and Vermont simultaneously.

I remember my thinking and mentality behind the shows as well.

One particular moment stands out in my mind…

Decide your ideal outcome.

The time was ticking. I had one month before I had to pay the next month’s rent. I knew it was crazy, but I made the bold decision: I would pay for rent with the sale of my artwork.

I had decided that my artwork would pay for my living, and that was it. I wasn’t available to entertain any other idea. In my mind, it was done.

As fate would have it, I had a show coming up in a trendy upscale bar in Burlington, Vermont. I wanted to create new work that would be stunning, trendy and get attention. I wanted to show off my value as a creator.

Channel focused energy into new work.

I created custom stencils of iconic celebrities like Marilyn Monroe, and iconic imagery that I felt reflected the nostalgic trendy 80s-90s hip-hop culture. I envisioned stencils with Africa Bambaataa, cassette tapes, and Koss headphones lining the brick walls of the cocktail bar.

I used metallic gold paint with my hand-crafted stencils to paint on 24 inch square 100-year old glass vintage window panes. I painted the frames a gloss black, and attached a mat black board-stock to the back. The paintings had dimension. I loved how they pieces cast shadows onto the black board at different angles throughout the day in the shapes I had painted on the glass.

I was really proud of my new work. It had an energy to it.

I was ready to show.

Assume the best & allow the Universe to exceed your expectations.

I remember a night about a week after this particular show launched. At 12:30 in the morning, I get a text to my phone that startled me awake. Someone had asked me if I could meet him at the bar, and that he’d like to discuss purchasing one of my paintings.

I rushed around my small room to get dressed. I threw my sneakers on and one of my *only* button down shirts to “look professional”. Then I jumped on my bicycle, and rode the 1.8 miles to get to the bar. I locked up my bike, took a deep breathe and centered myself. “He’s going to buy one of my paintings” I thought to myself. I believed it, and walked into the bar with confidence.

I approached the man gazing at my work on the white brick walls. He said simply, “These are beautiful, I’d like to buy two of them. Would you take a deposit?”

My mind was ready to explode— he had just offered to buy not one, but two of the largest paintings in the show!

He told me that he was in Burlington on business, explaining that he lives in Chicago and this artwork would look amazing above his couch in his condo. After confirming that I could indeed ship the artwork to Chicago, he said “Consider them sold. Please mark them, I want to make sure everyone know’s I bought them and they’re no longer available.”

He walked to the ATM around the block, and came back with $250 cash in hand. I took it as a deposit, and wrote “SOLD” on the little business cards pricing my work.

Trust your instincts.

Before this particular art show— I had no idea how I was going to exactly pay rent and that everything would work out better than I could have imagined.

I just decided that it could happen, and I assumed the best.

I assumed the work would sell, because it was my best work at the time.

When you know your outcome clearly, the right actions tend to just fall into place, providing the well-lit path to your metaphorical castle of gold.

I knew what I wanted, and all the right things fell into place:

  • I showed trendy work at an upscale cocktail bar, with expensive drinks. The bar was known to be a place where affluent 30–40 somethings would hang out and discuss business after hours.
  • I created the art to meet the clientele of the bar. The artwork was monochromatic and would fit most interior-designed homes. I thought it to be trendy enough that young professionals would want to buy it and show it off to their friends.
  • The artwork I created added to the environment of the bar— it felt like I designed the work to live there.
  • I priced this work a little higher than I normally had in the past.
  • I created more “show pieces” than I typically did to allow for a greater chance of increased income.
  • The artwork and the establishment gained earned media and press for the level of the creative work.

In hindsight, the strategy I employed to sell the work was a good one! If I had considered the marketing strategy ahead of time I would have known it to be a successful one.

However, I was an ammeter at the time, and didn’t have an idea how to officially market my artwork. This was even before social media existed as a marketing platform.

Have a burning desire to succeed.

All the success came from a burning desire to be a successful artist.

To sell my artwork to people who would love it, and pay for my lifestyle simultaneously. I was dedicated, and of course I took massive action along the way. I was completely unavailable to entertain any idea that it wouldn’t work. I knew it would, I just didn’t know how.

Most importantly, I believe I could… so I did.

I’d love to hear what you think about this story. What’s a dream you could take ahold of now, even though we’re entering a recession?

Drop a comment below 🙂

Main photo by Hermes Rivera