Chris Legaspi

How creating automated courses helped this artist kick burnout to the curb

Artist Chris Legaspi lived the hustle lifestyle creating caricatures and video game graphics until burnout made him step back and figure out how to monetize his courses on autopilot.

It’s early in the morning in Florida where I’m calling from, but it’s dark outside for Chris Legaspi; it’s nighttime in Thailand. Chris is from St. Petersburg, Florida, but has lived in Thailand for the last five years. He’s sad it’s too dark to show me the ocean just outside his window, but he points the Zoom camera out there anyway just in case I can glimpse any moving water in the shadows.

I can’t. All I can see is his reflection in the glass. 

So instead he focuses on showing me what I can see, like all of the paintings and drawings scattered around his desk. There are some hand-drawings and some printed works from Photoshop. On his desk are also two computers and the suspended camera and microphone he uses to capture his drawing and painting courses.

Chris makes his living from those courses, in addition to Hollywood movie poster commissions, which he’s done for films like Deadpool 2 and Birds of Prey

But being a professional creator hasn’t always been Hollywood glitz or ocean views. Chris has dealt with burnout, loneliness, and financial struggles. 

And while he’s been drawing ever since he was a kid and dreamed of being a professional artist one day, when he graduated high school, he went to college for nursing. 

“Doctor, lawyer, engineer.”

“I'm Filipino,” he explains, “so you only have three options: doctor, lawyer, engineer.” He went to college to keep his parents happy. But he didn’t really like it. So when his good friend who’d gotten a job right out of high school as a programmer for a video game company told him they were hiring an artist, Chris sent over his portfolio. He got the job and left his college in Florida to move to Chicago. 

It was 1995, and he learned what was then the early stages of 3D modeling and Photoshop. He was getting paid to learn how to create with the newest technologies, and he loved it.

But he didn’t love the Chicago winters. He was deeply lonely and homesick, and after two and a half years, he quit that job and moved back home to Florida where he got a part-time job as a caricature artist at a Florida theme park, and enrolled at a local college’s fine art program.

Maybe college would work if he studied what he really loved?

He learned a lot about fine art, but he found himself anxious once again to jump back into doing art as a job, not just learning about it.

The program wasn’t quite for him and he left after two years, but it did ignite his dreams again…especially the ones about moving to Hollywood to do work for video games and movies.

After five years drawing caricatures in Florida, Chris packed a suitcase and headed to Hollywood with a savings of $2,000. 

That’s the last time I lived in Florida.

“I was a typical Hollywood wannabe.”

But the next few years in California didn’t look much different from the ones in Florida. Once again, he survived by doing caricatures in theme parks.

But he wasn’t giving up hope that his drawing and art skills could help him make a living outside of caricatures; at least this time he was where he wanted to be. At least this time he was also trying other things like sending his portfolio out for freelance comic gigs. He even got hired to draw a few pages of a comic for the Wayans Brothers.

He was moving forward, and this time he saw the caricature job the way an actor sees a barista job. It was his way of making a living while he pursued his real calling, his real art. Though he wasn’t romantic about it: 

I was a typical Hollywood wannabe, trying to make it, just drawing instead of acting. 

It was tough. But he kept going, drawing exaggerated pictures of out-of-towners on vacation swimming or riding roller coasters to pay for his tiny apartment in Orange County, and networking and sending out his portfolio wherever and whenever he could. Showing his portfolio at Comic-Con also helped him get work, something he says was easier then when Comic-Con was just about comics. 

But it was difficult to piece together a living that way, and he spent two years applying to creative jobs.

When he was offered a full-time job as a concept artist with a video game company in San Diego, he jumped at it.

Especially because this one, compared to the one in Chicago which focused on PC games, would give him the opportunity to work on well-known video games.

It was a dream job and a dream location. 

Finally, he was drawing things he really wanted to draw for a living: video game characters and backgrounds for games like Splatterhouse and Star Trek. He also continued to uplevel his 3D skills.

I spent a few years learning 3D on my own through books. It was before YouTube, before Skillshare. 

He worked that job for six years. 

And then one day I quit. 

“And then I ran out of money.”

Sometimes achieving one dream ignites another. Even though Chris had dreamed of drawing for video games as a kid, he’d also always dreamed of being a fine artist. 

After a few years at the video game company, his desire to be a famous fine art oil painter grabbed hold of him, and he longed to spend his days making and selling oil paintings. 

So I quit my cushy video game job and moved back to LA to try to be a painter.

He left the computer work behind and started painting with real paint again, and enrolled in any art classes he could find. 

And then I ran out of money, of course.

That’s when he remembered what a mentor he’d met through his art classes told him once: that he should think about doing movie poster work. 

So Chris created some samples and sent cold emails for two months. 

He emailed about 50 people in the industry. Forty-nine of those cold emails went nowhere. But one landed him his first movie poster, for the Melissa McCarthy movie Life of the Party.  They invited him to the studio to start working on it right away, and he was “fired up.”

And once he had that in his portfolio, it was much easier to get other projects. To supplement that income, he also taught art classes at private schools in Hollywood, Orange County, and Pasadena.

He was making a living, but just barely, especially because of the cost of living in LA.

It was not comfortable. Let's just put it at that.

At that time he was also teaching online through the YouTube channel and blog he’d created back in San Diego, something he’d started for fun and with hopes to inspire other artists.

Both emerging and professional artists loved his content, and many reached out asking for more. So in 2015, he made and sold his first online course which taught shading techniques in Photoshop, and made about $1,500 in the first three weeks. The audience he’d been slowly building for five years with his blog and YouTube channel was ready for something like this. He was blown away.

So he made a second course, this time on color use in Photoshop and digital painting. It made $1,500 in the first week. His third course, a sequel to the popular color course, made $2,500 in the first three days. He was grateful. But he was also severely burnt out

I literally worked 20 hours a day. On editing days I would fall asleep under my chair and wake up in four hours and do it again. 

After six months of that pace, he moved to Thailand and quit his online business.

“Hey, I'm not dead.”

Or, at least, he stopped making any new content for his online business. 

The business still ran without him because of the marketing systems he had in place, like automated emails. For the next two years he made about $2,500 a month from his old courses, and still got the occasional movie poster gig. It was all more than enough to live a comfortable life in Thailand, allowing him to take a break from business thinking and just paint for a while. 

Then, a few years later while visiting the U.S., Chris ran into his friend Mani in San Diego. Mani was a creator too, and, as Chris explains, a long-time ConvertKit customer, who had made a lot of money selling courses.

Mani, remembering Chris’s art-focused blog and YouTube channel asked, “How's your online thing? How's your blog?”

“I haven't worked on it in two years,” Chris replied. “I haven't made a course in two years.”

Mani was shocked because Chris had even more YouTube subscribers and email subscribers than he did at the time, and he knew how much potential was there. At that time Chris had 40,000 YouTube subscribers and 7,000 people on his email list, all due to the marketing he’d done in the early days, like learning SEO and setting up email signup forms. It had all kept growing organically while he was off the internet painting in Thailand. 

Mani encouraged Chris to think about returning to this amazing thing he’d already created. And Chris considered it, especially because his motto has always been: 

If somebody more successful tells me to do something, I do it without question. He was making money with email and I trusted him. 

Chris also shares that his course sales had tapered off by that point, and he really did need to start thinking about how to make money again. Maybe it was time to return? He also missed teaching. And he knew that long term, passive income like this could support his ability to continue to make art for himself. 

Mani helped Chris migrate to ConvertKit and revive his list of 7,000+ subscribers. 

I signed up for ConvertKit that day. He helped me write a sequence of revival emails that basically said, “Hey, I'm not dead.” 

The list had been dead for two years and I was trying to sell products that had been dead for two years.

But I made $5,000 in four days using ConvertKit. It was unbelievable. 

“Those two things together is a magic formula.”

But it wasn’t just those four days. It was those four days plus seven years blogging and building an audience and 17 years working on his craft.

What also makes me different is I embraced email marketing a long time ago.

He credits his marketing skills to the early online marketing experts he found and watched through YouTube, like the one who said: “Forget what you're doing and build an email list.” Chris, inspired by their passion, decided he had nothing to lose to find out if what they were saying worked.

He admits some of those first online marketing experts could be a bit cheesy, and they certainly weren’t artists. But he took the best of what they knew about sales and applied it to art…and it worked. 

Many of his subscribers come from one opt-in and one YouTube video “How to Start a Digital Portrait Painting in Color.” The video to date has 161,472 views and 126 comments. And the video description below is short and to the point and links directly to his ConvertKit email opt-in form.

That form has gotten him 2,425 email subscribers to date.

But as Chris shares, when it comes to making a living as an artist and a course creator, it’s not just about growing an audience, it’s also about selling. 

Chris learned how to use email to sell by reading emails from people who were really good at selling (i.e. some of those same early internet marketers). He didn’t plagiarize their emails of course, but he studied them, especially the ones that kept him scrolling to read to the end, and he applied those concepts to his own course, all the while making them his own and focusing on writing to help his audience— other artists. 

I do a sequence of emails where I give free content. You give and then you sell: give, give, give, give, sell, give, give, give.

His emails aren’t long either. They’re simple, genuine, and they work. (You can sign up for his email list to read for yourself.)

He also says segmenting his list has had a big impact, sending out surveys and allowing people to group themselves based on interests like drawing faces or color, and then he sends them tailored content and products.

Chris revived his list and came out of his artistic sabbatical in 2017. By 2020, he was making a full-time living from his courses alone.

“At my heart I'm still an artist.”

The movie poster work continued to roll in, and he made time to paint and draw for himself every day. But how did he feel, I ask, running his online business again after burnout and a long sabbatical focused only on art? 

To be honest, it doesn't come naturally. I had to cultivate the business person side of me again. 

For him that involved cultivating an understanding of what money could do for his art, instead of seeing it as something that was taking away.

He saw that the more he invested in learning about sales and marketing and automating his work using a creator marketing platform, the more time he had to create.

And the more money he makes and saves, the sooner he sees himself retiring from “the business side” and going back to only making art, with the courses running on autopilot

I don't want to say it's easy, but I'm making money with a lot less effort now through ConvertKit.

At my heart I'm still an artist. But the teaching is fun too. 

To help with automating and stepping away from some of the things he doesn’t want to do anymore, he’s done some hiring, like hiring a full-time video editor, a VA, and an accounting firm. Next he hopes to hire a social media manager and possibly another editor. 

He’s also learning how to be a manager. 

I used to do the video editing, now I have to manage an editor. That's the thing I'm learning now.

He’s also still learning how to deal with the loneliness that sometimes comes with being a creator. 

A few years ago I got super lonely. I was in a foreign country and didn't speak the language. It was hard for me to make friends.

One of the things that helped me was teaching in person. I taught free art workshops and seminars in Thailand so I could meet and be around people.

It boosted my self-esteem and my morale, and really helped with the loneliness.

And now he has a paid coaching program where he gets to connect with people every week one on one, which also really helps: “Now every week I'm guaranteed to interact with people.”

“I want to build it here.”

Before I go, I ask Chris if he made any changes to his business that kept him from burning out like he did before, when he had to take two years off. 

“Raising my prices,” he answers immediately. In the burnout days his course was $49. Now he doesn’t sell anything under $500. 

Raising my prices and learning the language to sell high-price products was the game changer for me.

He learned how to sell high-ticket items once again by studying emails from other people who sold high-ticket items, in all kinds of industries, and took what he learned and applied it to his art courses. 

You have to change your thinking and your language to sell higher priced items.

You also have to become a person who is willing to spend something similar on a course yourself. Now, because I've spent $5,000 on a course, selling a $5,000 course is easier. 

In addition to creating movie posters for films he loves, he made $10,000 in one month from his courses alone. 

It happened without breaking a sweat. I know that sounds egotistical. But you know what I mean.

And I do. Because we talked about how he “broke a sweat” the 10 years before that 10K month. From the years he spent in the caricature trenches to learning his craft at the video game companies and the nights he slept under his desk (which we don’t recommend). 

He spent 10 full years building his audience through his blog, YouTube channel, and email list before that 10K month. 

But now that his business is stable and he has more money than he needs, he sometimes struggles to feel that fire he felt in the beginning. 

It’s a champagne problem if there ever was one, he says, but still a problem nonetheless, because he knows his business could eventually fizzle if his fire does. 

So how does he keep going when he feels that loss of drive? 

I take breaks from the computer, spend time in nature, and think about my long term goals and how I can benefit others and my community. 

For now, that looks like growing his business so he can have the resources to build a homestead and cultural center in Thailand. 

I want to have a place where people can go to study Western classical art and realism in Asia. Where I live that doesn't exist, and I want to build it here.

He also hopes to have his own organic food farm, art studio, and recording studio, all overlooking the ocean. 

I could probably have that kind of property now, but not over the ocean. Because right now I have my heart set on an ocean view. So, I’ve got to keep writing those emails.

You can connect with Chris on Instagram, subscribe to his email list, or learn more at

Note from the writer:

Chris’ story reminded me how important it is to honor the space between “artistic” mode and “business” mode. He switches daily, but also had long phases where he completely immersed himself in one or the other; it’s important for every creator to find that rhythm for themselves, and know that the time needed to switch is time well spent, however long you might need.

What did this story bring up for you? Let us know by screenshotting this page and sharing on your Instagram stories (be sure to tag us @convertkit so we can reshare) or tweet your takeaway here.

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Isa Adney

Isa is an author and writer and has profiled incredible creators and artists, including Oscar, Grammy, Emmy, and Tony winners. When she’s not writing or interviewing creators, she’s probably walking her dog Stanley, working on her next book, or listening to the Hamilton soundtrack for the 300th time.

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