Art Heals and Creates Opportunity

Using art, Danny Gregory turned tragedy into healing, healing into a community, and a community into a thriving creative business. Still, if you told him as a young man that he'd go on to hundreds of thousands of artists, he might have laughed in your face at the thought.

Like most young creatives, he found himself drawing and doodling any chance he could get. After moving through many countries around Asia and Europe and finally landing in the United States, he gave up on his art practice once he hit high school. From both outside influences and internal doubt, he concluded that art was not a legitimate path to success.

Squashing his dreams, he got a job in advertising once he finished college, which was close enough to creativity to keep him satisfied until tragedy struck.

One day, he received a call from the NYPD saying his wife was involved in a subway accident, leaving her partially paralyzed, which turned his entire world upside down.

At some point in his wife's initial recovery, he turned to sketching as a way to take his mind off the tragedy. That practice helped him grow, and he turned it into a daily creative habit, which ultimately became a thriving business teaching countless others the power of drawing.

Today, You'll Learn:

  • Danny's approach to pushing back against doubt and fear to use his creativity to help others
  • Why diversifying into different creative expressions helps us grow
  • All the ways he's earning (and it's a lot).
  • What Danny could be doing differently to grow more
  • How to apply these lessons to your own creative business

Life Brings Tests

Shortly after, he also started writing about his experience on a blog. Through that blog, he gained a loyal following, which he turned into an early community of people using art to move through healing and give people a way to express latent creativity.

And then tragedy struck again.

While watering plants on the balcony of their highrise apartment, Danny's wife slipped and fell eight stories to her death. This not only left a tremendous hole in his life, but he was now the sole parent to their teenage son, consoling him as well as moving through tremendous grief.

This time, though, he had art to help him through the process. After a short time, he returned to his drawing and writing, and over time, his loyal following grew, and they wanted more lessons from Danny.

Jumping quickly ahead, Danny used his creative impulses to write over a dozen books, start a thriving newsletter, grow a sizable YouTube channel, and produce high-quality online courses. Sketchbook Skool has become a near-household name in the art community.


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The Art School Teacher We Need

Danny Gregory's comforting, fatherly tone will entice you into buying everything he makes and shares if you're not careful. He's the Mister Rogers of art and will put you at ease with the first Sketchbook Skool video you watch.

With nearly 240k followers on his YouTube channel, he's doing exceptionally well for someone with many different irons in the creative fire. Most of his videos get modest attention (the video game has gotten very competitive and challenging), but he has several videos with high 6- and 7-figure views.

From experience, those videos are likely bringing in several thousand dollars a month in revenue for him, but not enough to keep him afloat.

Like his peer, ArtWithFlo, he does not sell any of his art (as far as I can tell), and he's solved that problem by offering up multiple ways for his community to support and learn from him.


Danny has self-published several books through Amazon and his ConvertKit commerce shop. These books are not best-sellers in any category but sell consistently (based on Amazon rankings). It's not Bob Ross's income level from these books, but each book likely brings a few hundred dollars every month, and when you add all those books, that's a solid chunk of change.

Publishing multiple high-quality books creates a compounding effect. Some readers will purchase one book to tackle a specific topic and return for others to add to their knowledge base.


Danny's Essays is his newsletter, which now has over 300,000 subscribers, some of whom are paid members. The free portion of the newsletter is mostly his thoughts and personal experiences surrounding art, creativity, mindset, and sometimes relationships.

His paid newsletter is similar, with more details about his process, tools, and other written instructions. These messages are also more in-depth than the free essays and provide more direct access to Danny. At $7 a month and estimating conservatively at .5% enrollment, that's a whopping $10,000 a month, and that balance sheet is starting to look attractive.

Affiliate Marketing

As part of his newsletters and YouTube channel, Danny often makes references to tools and products he's using, each with some affiliate link, whether that's Amazon or Dick Blick.

Every link to his books on Amazon nets him a small percentage return in his pocket for whatever someone puts into their shopping cart. Maybe it's just a book, or perhaps they decided also to buy an 85" high-definition 8k flat screen. You do the math on a 3% affiliate referral.

This revenue is his smallest line item, but it's at least a couple hundred bucks a month in his pocket.

Courses and Live Training

The most significant part of Danny's creative empire is his training; he has many choice people.

First, there are his stand-alone courses, which are specific art subjects like how to use watercolors or colored pencils, lessons on urban sketching, or how to make art with no talent. The pricing on these courses ranges from $49 to $99 and is the low barrier to entry into Danny's system.

Next comes the live training, and Danny has created an interesting scenario, unlike any other online training I've ever seen. He clocks in dozens of hours of live studio instruction each month with him or several other professional artists with different specialties and concentrations. Danny then takes that live instruction and splits it between two programs.

First is Studio Time, which is a membership at $49 per month, giving members over 35 hours per month of live studio interaction with Danny and other professional artists. Imagine a studio lab where everyone comes together to work, talk, and share their projects. It's not instruction as much as it is a way for artists to work together in the same virtual room.

Spark is daily live classes with different teachers. This one includes studio time and access to a private community page and is offered at $149 a month. Not cheap, but with 20+ hours of live instruction from various professionals, you're guaranteed to progress quickly with your art.

I don't know Danny's enrollment numbers, but it doesn't take a math whiz to know that even with as few as 50 dedicated students a month in each program, that's $10,000 a month, and all Danny has to do is hire people to teach.

Also, with over 500,000 subscribers between his newsletter and YouTube combined, I'm sure his enrollment is much higher than 50 people per month.

Things to Consider

Danny is doing all the right things and has a well-oiled machine, but I question some areas and wonder if something could be more efficient to bring in more revenue.


I noticed that Danny's posting schedule for long-form videos isn't as consistent as it once was, which may be why his videos now suffer in views. He's also doing a lot more short-form videos on YouTube, which might bring in additional views, but subscribers from those short-form videos tend to be more fickle and not as willing to watch the long-form videos, where Danny makes more of his ad share revenue.

His long-form content is also falling behind the times. He's spending a lot of time on producing his training courses. He could use more of that energy in making the YouTube videos and get that posting frequency back to a consistent schedule.


Danny's books are not selling nearly as well as they could because of the price point. Compared to other Kindle books, his are pretty expensive, especially for a self-published author.

I know that his books are illustrated, and anytime you put images into an ebook, the production price that Amazon charges him goes up, which he's probably trying to offset with his higher price tag.


One of the odd things about Danny's free newsletter is that it's mostly about him. Many people do this with their newsletters, but I expect them to be more about the reader and what they need to read about.

He has over 300k subscribers, and I've got nothing close to that, so I may be doing it wrong trying to bring value. I could talk about myself more.

Affiliate Marketing

Danny's use of affiliate marketing is similar to most visual artists. They start with Amazon affiliate links and move on to other e-commerce brands because the pervasive thought is that products are the only thing an artist can promote.

However, Danny also operates his business at a high level, using software tools that might benefit others. He uses ConvertKit for his email list, Kajabi for his courses, and other tools that help keep his digital business running.

Each one of those programs has an affiliate program. Because his followers may want to start their newsletters and training, he could easily integrate those links into appropriate conversations, netting him a nice return for recommending the services he already uses.

I haven't been able to peek behind his curtain so he may be using them in a non-public setting, and if so, you can guarantee he's making a healthy income on those referrals.

Courses and Events

Danny is doing great with his courses; I only have one note. He's already sharing live events to learn from notable artists within his Spark sessions, and an excellent way to get people interested in making that investment is to give them a taste.

Once a month or so, he could open up a live event for the general public to attend. They pay a one-time fee, watch that single lesson, and at the end, Danny could deliver a pitch to entice viewers into signing up for Spark after they've witnessed the value firsthand.

It's easy for me to sit on the sidelines and talk about how someone could make a change in their business for the better, but whenever I share these thoughts, it's always from an outsider's perspective.

There is nuance to Danny's operation that I will never understand, and my thoughts could be moot. That said, there are things we can learn from Danny's approach to build something cool for ourselves.

Danny's Lessons

Daily Practice - Danny used daily sketching to keep his mind from going into dark places during his wife's tragedy. That daily practice was the catalyst for him building his empire. There's no guarantee that daily work will do the same for us, but it couldn't hurt.

Use What You Know - Coming from advertising and working on big projects with large companies taught him how to create high-quality content. He also learned how to speak to others in a way that entices them into becoming loyal followers.

Learn From the Marketers - Danny was a marketer, so he had the training, but he learned those lessons from those who came before him. Creative people often feel that marketing is an ugly word and avoid it because it feels like selling out—it's not! If you learn from the marketers, you can find an approach that feels good in your soul and still helps promote your work. Start with David Ogilvy.

One Thing to One Person - Danny started by teaching sketching techniques to people who didn't know how to draw. Once he established a core audience, he expanded but still shows up with that same initial intention.

If you want people to pay attention, share your one thing with one type of person. As you build awareness, then you branch out further.

Diversify - When you decide to branch out, find ways to bring in additional streams of revenue in ways that feel organically connected with your core audience. Danny started with blogging and then went to videos. Blogging became a newsletter, and videos became video training.

Share Often - Danny's newsletter goes out twice weekly (free and paid). He posts videos on YouTube regularly, even if primarily short form now). He's present and visible, and all things lead to his books and training.

Do Not Be Intimidated by Technology - Danny is an older gentleman, but he's always been curious about how to use technology to help him reach new people. He was an early adopter of online communities, blogging, and self-publishing tools.

He uses online software services to share his videos, newsletters, and courses, and though each one comes with a new learning curve, he embraces the opportunity because he knows it allows him to reach more people.

Collaborate With Others - There's no way Danny could have done all of this by himself. When he started his live training, he knew he couldn't deliver on the promise alone, so he collaborated with several artists to help with the workload and make his training more valuable.

Yes, that means a little less money in his pocket as he pays the other artists, but I'm confident that investment helped him grow his business.

Build to Let Go - This one is speculation on my part. Still, Danny has built Sketchbook Skool so that when he retires, he can easily integrate any of the number of art teachers he works with and let them become the face of the organization.

This would allow him to step away and be the silent figurehead or sell it to someone (with seller financing—thanks, Codie) and walk away.

I don't know if that's Danny's goal, but he's certainly set himself up for a big-money exit and a legacy that will live on for a long time.


Last week, I used several illustrated images to break up the story.

This week, I decided to do the opposite.

Which style do you prefer?

More Images | Fewer Images

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