The Legacy of Bob Ross: Lessons in Succession Planning
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The Legacy of Bob Ross: Lessons in Succession Planning

All About Estates
By Jessica Butler, May 16th, 2025

Would Bob Ross have called this a “happy little accident”? Doubtful…

When you hear the name “Bob Ross”, most of us think of beautiful oil paintings complete with “happy little accidents”, a calm demeanor and, of course, that head of curls (spoiler alert – it was a perm!). After watching this documentary, I now also think of the sad story of Bob’s estate which serves as a real warning: failing to coordinate your business agreements with your estate planning can lead to unintended consequences.

Business agreements and estate plans need to be considered concurrently and the intention of the individual should be carefully ascertained to ensure that all documents operate together as one whole succession plan. The best way to safeguard against the issues experienced by Bob and his family are good lawyers who can help you ensure your business structure and estate plan can function together and protect both the shareholders and beneficiaries.

It seems that Bob, while an amazing artist, may not have been sophisticated from a business perspective…

Last weekend my husband and I settled in for a typical Sunday night at home – cozy on the couch with a good Netflix documentary. We decided to watch “Bob Ross: Happy Accidents, Betrayal and Greed”. What I didn’t expect was that not even 15 minutes into the documentary, I’d find myself running back to my office to grab a notebook and pen to take notes for what would ultimately become this blog.

Jessica Butler, Law Clerk at Fasken LLP