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Rising Stars: Meet Matt Chessco

Today we’d like to introduce you to Matt Chessco

Hi Matt, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’m known for my entertaining painting videos. There are thousands of artists who post their stuff online, but no one does it like me. In my videos, I wave my paintbrush over the canvas to the beat of sounds and paint magically appears on the canvas.

In November 2019, I made a painting I was proud of for the first time. I was looking for an innovative way to promote it online. I wanted to do something different that would set me apart. One day, I woke up and got this idea of hitting the canvas to the beat of sounds while the painting comes to life. In the 2 weeks that followed, I worked on the logistics of my idea, I created my first video ever and I decided to post it online. At the time, I only had about 200 followers on Instagram. They were mainly my friends and family. I posted the video on my page and the reaction was crazy. Dozens of people I knew reached out to me saying they absolutely loved my video. One girl I didn’t know reposted my video in her Instagram story and wrote something along the lines of “Wow this is so good and original! I watched this video 20 times”. At this very moment, I knew I had a good concept and I had to go all in with it. In the months that followed, I started posting 1 or 2 videos per week. Within 6 months, I went from zero to over 500,000 followers across all platforms.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
The biggest challenge I ever faces was quitting my engineering career 4 days after getting my first job.

In the summer of 2018, I finished my Mechanical Engineering degree. I got my last exam on a Saturday and I started working the next Monday.

I had a really interesting job. I was working for a company that was making over a million dollars in revenues per year with just 4 employees. I was the right arm of the CEO on day one. All my friends were a little jealous of my position.

Every hour I was working there, I would stop myself and wonder “What am I doing here?”. After 4 days, I came back to my place and I listed the pros and cons of keeping my job. In the pros section, the only thing that I wrote was that I was making money. It was pretty clear for me that I had to quit.

The next day, I went to the office, I learned how to use the printer and I printed my resignation letter. My boss came in at around 10 am and I told him I was quitting engineering for good. He probably thought I was crazy because I had just studied for 5 years to become an engineer. He asked me what I was going to do next week. I had no idea, but I wanted to give him an answer, so I told him the first thing that came to my mind. I said: “You know what, I’m gonna become an artist”. At this moment, he probably thought I was even crazier. A few minutes later, I was gone.

At the time, I was doing abstract paintings in my free time for fun, but my paintings were ugly and nobody around me knew I was painting. In the weeks and months that followed, I started painting whenever I could while I was building websites and creating logos to make an income.

A year and a half later, I became a full-time artist.

Quitting my engineering job after four days was the riskiest and boldest thing I ever did in my life. But it turned out to also be the best decision I ever took and it forged my ability to take risks. It made me realize that taking risks is totally worth it, can make my life better and help me achieve my goals.

Can you tell our readers more about what you do and what you think sets you apart from others?
If you’re early in your journey, I would recommend reading a lot, finding ways to have several revenue streams, and staying on top of new technologies and trends.

I believe a big part of my success comes from reading lots of books about business. Being an artist is like managing a business. You have to do your own marketing, maintain relationships with partners, deal with deadlines, do your own accounting, manage sales, and so on. I believe the most successful artists are not the most talented ones, but the ones who understand business the best. And you can learn a lot about business by reading books! If I had to recommend only one book, it would be “Good To Great” by Jim Collins. This book will teach you how to understand your art passion, identify your artistic strengths, and find ways to monetize your work.

If you’re an artist, selling paintings should be one of your several revenue streams. I personally have countless revenue streams. I make money from brand deals, selling the rights of my videos, ad revenues on YouTube, selling NFTs, NFT royalties, promoting products in my Instagram stories, selling prints/t-shirts/hoodies, and the list goes on! This way, if one of my revenue streams stops working, at least I got other ones to keep my business going. If you want to live from your art, or anything you do, find several ways to make an income. Money is everywhere. Be creative!

My last advice is staying on top of new technologies and trends. I’ve been a full-time artist for 4 years and a half. During that period, I took advantage of the rise of TikTok, I took part in the NFT boom and I also was the first mainstream artist to create a painting in collaboration with a robot. All of these didn’t happen by chance. I spend a lot of time every day reading the news, scrolling through social media apps and trying new things like getting involved in the Montreal startup ecosystem. In November 2019, I heard about TikTok by reading the news. I downloaded it right away and became one of the first artists to post on it. Back then, everyone was saying TikTok is just an app for kids and it will get banned in the US within a few weeks. Turns out everyone was wrong. And because I was one of the first artists using the app, I was receiving all the attention and I rapidly gained millions of followers. In the summer of 2021, I heard about NFTs by scrolling through Twitter. Within a few months, I created my first NFT collection called “Pop Art Cats” and released it to the public. It sold out in 2 minutes. Back then, people were saying NFTs were ponzi schemes and they wouldn’t be around in a couple of months. Turns out everyone was wrong again. And because I was one of the first artists to create NFTs, I became a major player in the space and it strengthened my reputation in the art world. In 2023, I became involved with the Montreal startup ecosystem. For this reason, I was invited as a guest on a podcast about startups. The CEO of a company called Acrylic Robotics listened to the podcast and got in touch with me. We started talking and she explained to me that her company uses a robot to create replicas of paintings. We started working on a replica of my Lion painting. In July 2023, I posted a video about it on my social media pages. The initial reaction was not good. It was the first time a mainstream artist was collaborating with a robot. People in the comments were mad because they were scared robots would replace artists. Turns out, two years later, lots of well-known artists like Sabet and ZHC now use robots to create paintings for them.

I got the opportunity to be one of the first artists to use TikTok by reading the news. I got the opportunity to create a successful NFT collection by scrolling through Twitter. I got the opportunity to be the first artist to collaborate with a robot by getting involved with the Montreal startup ecosystem.

What were you like growing up?
Growing up, I was always drawing. As soon as I entered my house, I would run to grab paper and crayons, and immediately start drawing. I filled walls with drawings. I was obsessed.

I was a quiet kid who did everything possible to avoid attention. I spent a lot of time in my own head, imagining, thinking, and dreaming. People called me a lunatic. The truth is, my thoughts were more entertaining than the real world. This hasn’t changed.

I have one twin brother and a younger brother who’s almost the same age as me. Growing up, everything we did together turned into a competition. We tried to see who was the best at this or that. I think I’m still very competitive today because of this. Every time I do something, I want to become the best at it, number one. Art is no exception.

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