Bob Ross’ First Creative Dollar

“If you do what you love the money will come. Don't think about money, just do what you like.” - Bob Ross

After retiring from the Air Force as a master sergeant in 1981, Bob Ross left Alaska with $1,000. He was a one-track mind on a mission to spread the joy of painting. He promised his partner if after a year it didn't work, he would settle down with children and pursue domestic goals. 

Obviously, if you’ve seen public television, you are aware of how this one year experiment went for Bob Ross. His wife ended up moving away from Alaska and becoming a central force in the business side of his artistic career as his secretary. 

Bob Ross’s First Creative Dollar

“In the time you spent sitting around worrying about it, you could have completed a painting already.” - Bob Ross 

The Amount: $60 (worth around $189.67 in today’s money)

The Project: A landscape of the northern lights with a rustic cabin and snowy pines. Sold at a fair in Alaska in 1980.

The Backstory

"I'd come home after all day of playing soldier and I'd paint a picture, and I could paint the kind of world that I wanted. It was clean, it was sparkling, shiny, beautiful, no pollution, nobody upset — everybody was happy in this world… I was 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." - Bob Ross

Bust 'em up Bobby is the nickname Bob earned during his time in the Air Force. Luckily, there were other sides to him, like the fact he bartended as a side hustle. More importantly, he happily sold landscape paintings on gold-panning tins to tourists while at the pub. (I couldn’t find the cost of these but I imagine they were his true first creative dollar.)

Early Finances 

Bob Ross was far from wealthy growing up. Rumor has it, he didn’t have many toys to play with. Under the influence of his nature-loving mother, he thought of wild animals as entertainment. Ross’ father was a carpenter (hence, all the sheds). For a time, Ross even worked with his father doing carpentry.

Early On: Turning Down $1 Million

The business of making money off his painting was not easy at first. Ross painted publicly in shopping malls with the hope people would sign up for classes he’d offer three days later. Oftentimes, it didn't work. 

One time, only one man showed up for a painting class. Bob’s colleagues told him not to bother holding the class. However, he devoted his class to the one man. 

The guy casually said he was - wink-wink - a businessman (his euphemism for saying he was loaded). After class, he offered Bob $1,000,000 to have 40% of whatever he made over the rest of his life. Bob and his business partners took this as a compliment but turned down the man in order to do things their own way. Bob continued to teach in stores and shopping malls.

Growing His Business 

Searching for a way to get on TV, Ross and his business partners looked towards the Midwest. In 1981 public television was going broke. Congress allowed 10 stations across the nation to sell commercials (public radio wasn’t supposed to do this). 

Bob? Well, for some reason he went after an appearance on Phil Donahue in Chicago. This advertising paid off big time and his classes were full. (He later stayed in Indiana across from Chicago and produced over 400 episodes of The Joy of Painting there.)

As Bob balanced both a show and teaching around the country, he gained popularity. He encouraged his students to contact their public radio stations if they enjoyed what he was doing. Well before social media, Bob was an original influencer who used TV in a unique and interactive manner.

He asked viewers for their ideas for future paintings. Also, he would share paintings of people who had followed along with previous shows.

Turning Down Oprah

One time Bob was contacted by Oprah’s staff to appear on her show. But he wasn’t allowed to paint. He was supposed to discuss the topic of business partners that were men and women but not living together. “No thanks. Not my thing,” thought the happily married Bob. 

Business Partner Annette Kowalski

Annette Kowalski served many roles for Ross. She was part painter, part business woman, part patron, part psycho-therapist; she helped him in numerous ways because of the way his painting helped her through the loss of her son. (And no - she was not his wife. However, the couples definitely got along, spoke fondly of each other, and maybe it was the story Oprah was looking for.)

Early in his TV career, Bob Ross wanted to create a how-to book to go along with his show. His network at the time didn’t see his vision and didn't want to publish it. It would cost him $30,000 to self publish it. Annette (along with her husband) agreed to mortgage their house and go for it. 

The book was such a hit, it led to publishing one book for every television series Bob did. Annette also helped with the physical creation of the book. The how-to book was created by recreating the painting he had done on set that day as Bob painted at night and Annette took 50 photographs.

Bad Frugal Move

Bob Ross decided he could save money on getting his hair trimmed if he got it permed instead. He later hated his permed hair but didn't change it because it was part of his logo and part of his mystique. He thought it was a wise business move to keep the hair since it was such a trademark. 

Interesting Facts

  • There’s yet to be a complete and well-researched biography of Bob Ross. His story is told via weirdos like me, tribute pages, obituaries, blogs, word of mouth, Wikipedia, and narratives of interviewed acquaintances. Without verified historical information, he belongs to the land of mythos.
  • An authentic Bob Ross painting will sell online today for $8,000 to $10,000. (EBay has even had one listed for $55,000!)
  • Well into adulthood, Bob Ross was inspired to start painting because of a painting show. (William Alexander taught a wet-on-wet oil painting technique on TV long before anyone heard of Bob Ross. Alexander and Bob had a falling out later on, but Bob was always generous in giving credit to him.)
  • Thanks to Bob’s many influences as an alla prima painter (like Monet and Rembrandt) and the Alexander lessons he took, he reached a point where he was able to finish two paintings during a lunch break in the Air Force!
  • Bob Ross painted in 381 of 403 episodes of his show. The other episodes featured a guest.
  • His show is 26 minutes and 46 seconds. The thirteen paintings for each season were usually batched into a 3 day period.
  • Bob wasn’t all magic. Finished versions of paintings were ready to go off set during his shows. He used them as a reference (except season 2 when someone stole the 13 reference paintings he had ready to go)!
  • Early in the 1990s he agreed to perform two promotional slots on MTV.
  • He made a lot of money with his own line of paints designed specifically for the wet-on-wet technique. This line of paints continues to make a lot for Bob Ross, Inc.

Personal Connection

PBS Painter Bob Ross gained a large following using a tactic you probably first heard about in speech class - imagine you are talking to one person. It’s a psychological speech writing trick for true intimacy. 

“We have little power struggles over who’s going to get the walnuts, me or the squirrel. Guess who wins? The squirrel has got a nest full of nuts and I have none.” - Bob Ross


Less than 10% of people painted along with Ross during his popular show. Years later, my family is in the “paint-brush free” majority who simply turn on The Joy of Painting for his insights on life, his calming aura, and his love of squirrels. 

Full of lovely quotes, quirky rescued animals, and a business story worthy of a movie, we love learning about his “happy accident” philosophy - the ability to work with whatever happens.

Joan Kowalski, current president of Bob Ross Inc., says this about the man her parent’s Annette and Walt discovered in FL and encouraged to be on TV:

“Everything you see on TV was really, really him, including his obsession with squirrels… We’d be walking along, and if there was a squirrel nearby, he would just sort of drop to his knees. And he had a way where they wouldn’t scurry off. It was sort of his favorite, favorite thing.”


If you are interested in references for this post, you can look here, here, here, and here.