Meet Keegan Hall — once a startup operator, now an artist for athletes, Grammy winners, and President Obama

The viral artist tells us how his previous business experience influences his work and how to succeed as an artist-entrepreneur.


April 1, 2021

***

Keegan Hall’s painstakingly detailed pencil drawings can take hundreds of hours to create. Through his work, he has raised over $550k for communities in need and topped the Reddit charts.

But while Hall’s pieces have gone viral overnight, he’ll be the first to admit his success didn’t happen that way — that it’s the result of a lifetime of experiences and challenges, few of which had anything to do with art.

In fact, Hall spent much of his life pursuing nearly everything but art — getting an MBA, leading sales for the Seattle SuperSonics, and operating startups — long before he ever sold a print.

The Hustle recently sat down with Hall to learn:

  • How his humble beginnings and business background influence him today
  • How his time with startups enables him to be a great artist
  • What it takes to succeed as an artist-entrepreneur

***

So, Keegan, where does your story start?

The fun part about my story is that we can just go so deep down any element, but I’ll start from the beginning.

So, I grew up in Sumner, Washington. We were pretty poor — I lived in a trailer park for much of my life. 

I was always interested in sports and art, and the bridge between those was business. I used to collect sports cards and comics, then would go to our mall to trade them.


Young Hall with his mom and sister (Source: Keegan Hall)

Fast forward to college… I went to pursue a degree in studio art at the University of Washington. Actually, one time in an intro to drawing class, a teacher humiliated me during critiques. They roasted my art. That was a big, devastating punch in the gut because I was always a shy kid.

Then coming out of college, other people in my corner told me, “The arts — that’s not a career, you can’t make any money there.” Being relatively quiet and without a lot of confidence in myself, I kind of just believed them.

So the art plan didn’t work out as hoped. What’d you do next?

Having no plans of ever going into art again, I shifted back to that love for sports and went to work sales for the Seattle SuperSonics. I spent 5 years with the team until they moved away.

Around then, I also went to get my MBA from the University of Washington. That’s how I got deep into startups.

So you were an entrepreneur long before you were an artist?

Definitely. In grad school, we started one company as a class project that we took through the University of Washington’s business plan competition.

We ended up placing in the top 3 of 100 teams, and we exited with a return high enough that everyone got their money back — nothing crazy.

Immediately after that, I joined another startup as employee No. 1 — and this was the kind you hear about. It went on to raise $4m and get acquired by one of the biggest payment processors in the country.

At this point, you’re well past grad school and just helped sell a 2nd company. How does art come back into play?

So my mom had battled cancer and was cancer-free for a while. But one Friday we got news that it came back, and on that Sunday she passed away. It happened so fast where it was just devastating. The abruptness of it was probably the hardest part. 

A few months later, I was driving my car thinking about her and my childhood. I realized that a lot of the good times centered around my art, since she was always so supportive of it.

At that moment, I just wanted to sit down and draw. It was such a weird feeling because I hadn’t drawn in almost 10 years.

And did you draw something?

Yup, I sat down, drew a picture of Michael Jordan, posted it on social media, and a bunch of people actually reached out saying things like, “That’s incredible, I didn’t even know you could draw.” 

Following the death of his mom, Hall drew this Michael Jordan piece (Source: Keegan Hall)

Then one person asked me to do a piece of Kam Chancellor — of the [Seattle] Seahawks at the time — so I did. Somehow, Kam saw it and reached out asking me to do another piece for him personally.

And that’s kind of where the story gets big.

But you were still working full time at this point?

Yes. At this point I was just wondering if I could use my artwork to raise money for charity — that’d be so cool.

I saw that Richard Sherman of the Seahawks had put out a tweet for his foundation event coming up, and it got my wheels turning. I had this idea of doing a drawing, then selling 200 prints for $200 each.

I tweeted back to Richard, and right away he was like, “Let’s do it.”

Hall drawing “The Huddle” for his campaign with Richard Sherman (Source: Keegan Hall)

So in a very short time, you went from not drawing in 10 years to working with top-tier NFL players.

Haha, yup. I remember watching the project with Richard make its way into an official press conference for the Seahawks. They were asking about me — and I was just some dude.

Seahawks legend Richard Sherman discussing Hall’s work during a press conference

But we sold out on the first day, raised $40k, and donated 100% of the money to charity.

All the money went to kids like me — underprivileged kids that didn’t have a lot growing up. It was just awesome seeing it come together so fast.

At that point, did you think, “Hey, maybe I can do this full time?”

I thought about whether I could turn it into a career of drawing and selling art, while simultaneously doing campaigns for charity.

Then other opportunities continued presenting themselves — like campaigns with Macklemore & Ryan Lewis and Russell Wilson — and I got approached to do an original drawing for President Obama, who actually flew out to Seattle and got the piece.

Washington governor Jay Inslee presenting Hall’s portrait to Obama (Source: Keegan Hall)

And it’s just kept on growing. Even the Eddie Vedder project I did recently raised over $100k. Having grown up in Seattle during the grunge era, that was just bonkers. 

Now we’re up to over $550k raised, which is just a mind-blowing number from where I come from.

At the beginning, you were still working full time. That must’ve been a grind.

It was, but I wanted to see if I could figure it out. The first couple years I would do my day job, come home, eat dinner with the family, and draw until 2 o’clock in the morning. 

It’s those big questions for entrepreneurs: how do you get started and when do you take the leap.

I was lucky — that opening was almost made for me. During an acquisition at my company, a bunch of employees were let go and I was like, “Well, I guess now’s a good time to do this.”

After that, there was absolutely a time of panic. There was no more safety net to lean back on. But — it’s something like, “I don’t need more time, I just need a deadline.” In other words, when your back’s against the wall, you get things done.

Would you describe yourself as an entrepreneur today?

Absolutely, that’s one of the most important parts of art — the business side. My business background has helped me so much. 

For years, I spent my career figuring out how to build businesses, market products, tell a story, and get adoption from customers. One of the reasons I’ve been able to work with all these big names is because I created a process that’s so easy for them.

Hall with Seattle Seahawks quarterback Russell Wilson (Source: Keegan Hall)

I think that’s what a lot of the best businesses do. You don’t know how it works, it just works, and that’s the kind of customer experience that I want everyone to have.

How did you realize your talent?

I see it as 3 phases. First, ask a kid, I just drew a lot. I once won the contest to draw my school’s yearbook cover of our mascot, a husky. Still, they told me it was too aggressive, and asked me to redo it. So I did and — though I hated the new drawing — that’s the one they used.

Next, in college, I was one of the youngest students invited to a studio art program in Rome. I guess that’s phase 2 — where I was a good artist. 

And now I’d say I’m in phase 3, where I am constantly working on refining my craft. That first Kam Chancellor drawing was the best that I could do at the time, but I look back at it now and think it’s just terrible.

Hall with an early drawing of Kam Chancellor (left) next to a recent drawing of baseball Hall of Famer Roberto Clemente (Source: Keegan Hall)

Has your experience with startups helped artistically?

It’s definitely helped me refine my art. I try to fail fast in the sense that I test a lot of different things and see what works.

In art, just as in business, when you think that you’re successful and you take a breather, that’s when you start going backward in terms of progress. So for every drawing I’ve done, I’ve taken that focused approach to refining myself and trying to take it up another level.

Your Jordan drawing absolutely exploded on Reddit — what was that like?

With that drawing, I originally hedged my bets and said I would blur out the background. But once I saw how much time it was taking, I thought, “If i’m going to do this, I’ve got to go all in with the details.” And you can see the change in the time-lapse video.

Hall adding details to his “Taking Flight” piece, which took over 250 hours to create  (Source: Keegan Hall)

I did that drawing for literally 5 or 6 months. I would work on it for an entire day and maybe make 1 inch of progress.

When I finished, I posted it on Reddit, went to bed at night, and the next day it was on the front page. My website crashed.

Hall’s viral Reddit post of his Michael Jordan “Taking Flight” piece (Source: Reddit)

Did you learn anything from that Reddit experience?

If you put in the extra work and take the time to go that extra mile, you’ll see things explode on a whole other level. People notice.

Everybody in the NBA is amazing, but that’s just the price of entry. What makes the best players the best? How do you get to that next next level? 

Do you have advice for other artist-entrepreneurs?

I want to see so many more artists succeed. What’s funny is that it seems so obvious: create good content. But on the flip side, a lot of people just don’t do it.

As an artist, you have to remember to tell your story. That’s always been the foundation for me, for my business, and for many businesses in general.

Lots of people are better drawers than me, but being an artist today isn’t just about art. That’s why I’ve been so fortunate to learn about selling and brand building.

You’ve said your mom played a major influence on your success — how so?

One year my baseball league had a shortage of coaches, and my mom was just like, “I’ll do it.” Back then, women didn’t have those types of positions — head coaches of boys teams.

Hall’s mom stepped up to coach his Little League baseball team (Source: Keegan Hall)

My mom instilled in me this idea of, “Why not you.” One time as a kid, when I was doing a class project on Nike, my mom told me, “You know, you might be Nike’s CEO one day.”

I said, “That’s so ridiculous. Me? Nike’s CEO?” And my mom was just like, “Yeah, why not you?”

So that seed was planted then. And as I’ve gotten into startups and art, I’ve learned to have this balance of naive optimism in challenging environments, along with putting in the work, that helps me achieve awesome things.

Any thoughts on NFTs?

I think NFTs are the future of collectibles. Though, like any collectible, once they hit mainstream, when things become overly saturated many will be essentially worthless.

My daughter is 13, and she loves Roblox. As part of Roblox, there’s a digital marketplace where you can get limited-edition accessories for your avatar. Because they’re limited, they’re extremely valuable and it’s a huge deal if you get one.

I see firsthand how she’s able to enjoy these digital items without any physical component. I really believe that, moving forward, people will happily enjoy digital assets that maintain a sense of scarcity and ownership but that also can’t get lost or damaged.

One final question. How expensive is your pencil?

Haha, it’s like $10 on Amazon. It’s a good message — look at all you can do with just paper and a pencil.

Hall’s piece “Taking Flight” (Source: Keegan Hall)

***

Want to learn more? Hall’s site contains other information about his art, charitable causes, and current projects.

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