You probably remember him as the guy with an afro painting “happy little trees” on PBS, but for millions of people who grew up watching, and sometimes painting with, Bob Ross, most are unaware of his entrepreneur side. It turns out Bob Ross was an inspiring entrepreneur and badass.

Let’s start with one of the most important issues for an entrepreneur: legacy. Even nearly 20 years after his death from lymphoma in 1995, Bob Ross is a well known figure both in the world of painting and where it really counts: internet memes.

Most of Generation X grew up watching Ross paint on PBS even if they never picked up a brush. There was something soothing about watching him work and, like a visual tranquilizer, hours could pass as happy little clouds and trees formed on the canvas right before our eyes.

It’s what every entrepreneur is really searching for – a way to leave a lasting impression in their field. So how did Ross do it?

Well, let’s address the afro in the room. It was Bob’s signature style and it was reported that he hated the cut but wouldn’t change his hair. Why not? Because it was an essential part of his brand recognition! Ross even went so far as to put that silhouette on his line of paints for consistency. That’s some serious commitment to your brand!

The paints and painting supplies are actually another reason why Ross was a badass business man. He began his work in the 70s, learning under another painter who created the “wet on wet” technique that Ross popularized. But, after a disagreement over royalties, Ross decided to launch his own line of paints.

Not a lot is said about this arrangement or the falling out but could you put yourself in that situation and imagine how hard it must have been to disagree with your mentor? Someone you respected and admired who then cheated you? What a leap of faith to branch out and brand your own supplies, not letting anything stand in the way of your goal to share painting with the public.

I believe one of the reasons children became so enraptured watched Ross on PBS was his calm style. After leaving a career in the Air Force that required him to be, in his own words, “mean” and “tough,” and “the guy who makes you scrub the latrine, the guy who makes you make your bed, the guy who screams at you for being late to work,” Ross decided that if he ever moved on from the military, “it wasn’t going to be that way any more,” vowing “never to scream again.” (from the Wikipedia entry)

It’s a great turn on the earlier lesson on branding – even if you’re known for one thing (tough guy screaming) you can successfully transition to a new you and embody the traits you want in your life.

Did you know that Ross was never paid for his PBS show? It wasn’t a disagreement or oversight, he intentionally made no income from painting for the show. And, he didn’t even sell the paintings he created, giving them to the network for fundraising. So how did he make money?

The majority of Ross’ income came from art supplies and how-to products. To the tune of a $15M business. It’s not something you’d notice because the show wasn’t full of product placement and had possibly the cheapest studio set up in history but it worked. And, because he was such a swift painter, Ross could actually record a 13-episode season in just a few days leaving him the rest of his time for marketing and business development.

Let that be a lesson as well – if you’re looking at a business don’t assume you know where the money is coming from, and if you’re trying to break into a market, don’t blindly do what everyone else does without knowing the back end of how they create income.

Now, the final reason that Bob Ross was an entrepreneurial badass has nothing to do with the money he made or the brand and legacy he created. It’s all about his teaching.

Ross was a mindset coach before the internet caught on to the phenomenon. There wasn’t “The Secret” or manifestations or affirmations but as he taught, Ross was full of that gentle, positive encouragement.

If you can, watch the video below for a PBS remix of Ross on air. If not, just read some of his words they turned into song:

“believe you can do it, because you can do it.”

“there are no limits here, start out by believing here” (points to head)

“this is your world; you’re the creator, find freedom on this canvas”

“relax, let it flow, think like water”

“you can do anything you want to do, total power”

“we don’t make mistakes, we just have happy accidents”

Watch Video

Whether you take one or more lessons from the life and business of Bob Ross, I hope you were inspired. The man who was known for happy little trees was an entrepreneurial badass.

*Image Credit