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Ep. 141 – Blake Jamieson studied economics and today is a Portrait Artist for Professional Athletes

Blake Jamieson Headshot

Blake Jamieson is a pop portrait artist in Manhattan, NY. He paints pop art portraits for professional athletes and celebrities, including Howie Mandel, Drew Brees, Joe Montana, Gary Vaynerchuk, and over 250 other professional athletes in the NFL, NBA, NHL, MLS, and PLL. 

Blake’s path to becoming a full-time artist was far from traditional. Despite his passion for art at a young age, Blake decided to forgo art school for a more “practical” degree, studying Economics at UC Davis. After graduating, Blake began his career in digital marketing at Zynga. He worked in digital marketing for nearly a decade, working for small tech startups to publicly traded companies.

On his 30th birthday, Blake decided it was time to stop building someone else’s dream, and start to following his own passions. He began painting full-time nearly five years ago, and has carved out a niche that allows him to paint every day.

Most passionate about

  • I’m a portrait artist located in NYC. I’ve had an interesting rollercoaster of a journey up until this point, but what I do now is paint portraits of professional athletes.
  • Primarily, I have worked in the NFL, although I do work with other athletes who play soccer, lacrosse, hockey, and more.
  • I created this niche for myself where an athlete, or the spouse or girlfriend of an athlete, is looking for a painting that will capture special sports moments for them. I’m often the person they turn to and I’m very fortunate to work with awesome people and get to paint every single day.

Blake Jamieson - Athletes paintings


Blake’s story

  • I grew up in a very creative household. I was always encouraged to paint, or draw, or do photography – all the things I do today. However, I convinced myself, from a young age, that art was about being a starving artist and that it was not a career path.
  • Instead of doing what my parents encouraged me to do, which was to study art in college, I decided to study economics and tech. I thought this was the safe path at the time, and I aimed to have a career in marketing.
  • When I graduated from college, social marketing was just starting to become an actual, respected career. I was able to get into very grounded levels for some reputable companies and work my way through several different companies. Then I spun off and started working for myself as a freelancer.
  • Ultimately, on my 30th birthday, I decided that I was tired of working for someone else’s dream. I wanted to follow my own dreams and I realized that maybe my parents had been right all along…
  • I’m very grateful. Due to my background in marketing – especially digital marketing – and my experience in marketing a wide range of products, I understand how social selling works and how it is really a relationship-building business. I built up a moderate following of friends, family, colleagues, and people I met along the way.
  • When I first decided to start painting, I knew that I had to specialize and come out with a specific niche. I decided that I would paint a specific painting for a specific subset of people.
  • Because of my networking at the time, I decided to paint for offices, especially for tech companies. I met with the people on my contact list and told them that I was an artist and that I painted office art for tech companies.
  • At first, I painted many paintings of Steve Jobs, Gary Vaynerchuk, and different iconic tech founders. Those tech companies aspired to be like them and wanted to put a picture of Steve Jobs, or motivational quotes, in their offices.
  • I did that for two years and it was going well. I had my niece called out and I was gaining a reputation as one of the leaders in the space of Portrait Painting for Professional Athletes.
  • There was a really lucky coincidence that when I delivered art in Las Vegas, I met a guy who played in the NFL and who was now a manager of existing players. He really loved my art and asked me to paint a few of his clients as a gift that they would post about and promote to their followers. It might create new opportunities.
  • I did some paintings of a few of his NFL players. In the process, I learned that NFL players are very competitive. If one guy has a painting, the other player wants a bigger painting. They also have the income to pay for that, as well as a lot of followers.
  • I pivoted my business three years ago. Today, I paint more professional athletes than any other painter in my space.

Blake’s best advice about approaching customers

  • I’ll go back to the story about when I thought I was taking the safe path by working in marketing instead of doing something I really cared about. I know that it’s kind of cliché to say “follow your passions,” but I will say that if you do something you really enjoy, it doesn’t feel like work.
  • As an entrepreneur trying to solve problems, try to scratch your own itch. Try to solve a problem that was your own problem. Don’t try to solve a problem that someone told you offers a lot of money. It should be something that you want to use and that you want to do every single day.
  • Another piece of advice: I worked for free so many times because I wanted the exposure and I wanted to do what I love to do. So, don’t be afraid to work for free. To this day, I do a third of my work for free as a way to promote myself and my paintings.

Blake Jamieson - Youtube Cover


Biggest failure with a customer

  • I’ve had a lot of failures, to be honest, but there was something especially important that I learned years into my journey toward becoming a full-time artist. Some years ago, I was doing an art project that was on a big scale. It involved a lot of money and it was very important to me. Certain expectations were set up with the client at the beginning. It was a big project that cost a lot of money but still, I was giving a massive discount because I had other expectations, like promoting it on social media, offering links to my website, and so on.
  • There were things that I thought were very clear. At the time, the client said, “Yes, we will do that and more than that.” Yet at the end of the day, when the product was done and delivered, the client said, “I paid you for that and I don’t owe you anything else.” And to me, as I’m trying to grow my art business, sometimes a shout on social media or a link or a video is worth much more than the paycheck itself.
  • That was the turning point for me: realizing that this is a business, that I need contracts, that I need things in writing. That was when I hired my current lawyer, who has been my lawyer ever since and who has helped me put things in writing for the business side of my art, especially for big projects for large entities and organizations.

Biggest success due to the right customer approach

  • I’ll share two. They’re both very meaningful turning points in my career. I told you about how supportive and amazing my parents were throughout my journey and my art career. When I started with art as my career, my first studio was in their house (today I have my own studio in NYC) and they were really happy for me. I was painting icons they didn’t recognize for tech companies they had never heard of.
  • I was painting a comedian named Howie Mandel from “America’s Got Talent,” who has a pretty deep resume. A lot of people know who Harry Mandel is, including my parents. When I told my parents that I was going to paint him, they were excited and texted all their friends: “You know, Blake is going to paint Harry Mandel…” I painted him at his studio in LA and I shared this story about how excited my parents were when they heard I was going to paint him. He recorded a video especially for them, with me, saying how proud he was of me for following my passions and my heart. Being able to send it to my parents was so meaningful for me!
  • The second one was: I left the studio in California, which was in their house, and moved to a studio in NYC. I was so afraid that I wouldn’t be able to afford it and that I would become the starving artist I was so afraid of. But it worked and I felt that I was no longer the guy who worked from his parents’ house. I actually live in one of the most expensive cities in the country and have not only an apartment but also my own studio. That was huge!

Recommendation of a tool for customer focus, marketing, or sales:

  • I have two. Number one is LinkedIn because LinkedIn is geared toward professionals. As a visual artist, I don’t have competition there. Tons of people are on LinkedIn and they expect that I’ll talk as a finance person or a developer or a tech person. So, when I can share my paintings, everyone says, “Wow, that’s different” … and, actually, that’s how we connect.
  • For me, LinkedIn is so fantastic because the competition isn’t there. Artists don’t go to LinkedIn but most of my clients do. For any other entrepreneur, the answer is not necessarily LinkedIn, but any network where your competition isn’t active but your clients are.
  • The second one that is often overlooked is Twitter. It’s the only place where you can find real-world conversations in the public space and it still feels organic. You can become part of the conversation without feeling like spam.

Blake’s key success factor

  • I think that I have to credit my years in marketing and sales, when I really learned how to look at customers. Because it’s not about the product. It’s not even about problem-solving. At the end of the day, humans want human connections. And I have the ability to connect with people and make them care.

Blake’s mountain

Because we believe that the best way for entrepreneurs to get fast, big, and sustainable success is by leading your (new) market category, and the entire entrepreneurial journey reminds me of mountaineering, or conquering a mountain, I want to ask you: Is there a mountain you dream of climbing or a mountain you have already climbed?

  • I’ll go for the metaphorical mountain because, for me, my highest mountain is: How do I make myself feel? To me, doing things that I enjoy doing, feeling in control of my life at the end of the day, no matter when it comes … I should able to look back and say that it was worth it.
  • I need to feel comfortable in my own skin and be happy with whatever thing I’m doing. So, this is my never-ending mountain and I hope there is never a top.
Metaphorical Mountain

Metaphorical Mountain


Best ways to connect with Blake

More resources for Entrepreneurs

  1. Don’t Miss – Customer Focus Strategy & Execution: Market Analysis for Fundraising
  2. Hayut Yogev’s Latest postOne Move Or Did you download the 100 tips for entrepreneurs (to master Twitter)?
  3. Former interview: Nick Loper, host of the Side Hustle podcast, helps thousands of people earn extra money outside of their day job

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