Chip's father, Art Sansom, first created the strip back in 1965 after over a decade on the strip Chris Welkin—Planeteer with writer Russ Winterbotham. He did go to school for an art degree, but spent his early career working as an engineer for GE. In any event, once Brutus Thornapple became the titular character of The Born Loser, Art continued working on that strip until his death in 1991.
As with many legacy strips, Chip started helping his father out in the mid-1980s. (Meaning, I would likely have read at least a few years' worth of strips that he had a hand in. How much was Art and how much was Chip seems impossible to determine, though.) I recall the strip always feeling a bit dated. Not that it was necessarily unfunny, but it frequently came across like watching an episode of Leave It To Beaver for the first time. You get the jokes and smile or chuckle a bit, but so much of it is rooted in the culture of its time that it doesn't speak to you very strongly.
As I said, Chip took over completely when his father passed in 1991. I've seen it only sporadically since around 1989/90, but the ones I have seen suggest that Chip remains very true to what Art began. And it strangely still feels rooted to 1965. It kind of works given that part of the strip's conceit is that Brutus is always somewhat out of touch, although the strips I've seen that take place in his office, which also looks to be rooted in the 1960s. I've rarely seen even GE CEO Jeff Immelt in a suit, much less wear one every day to the office. Keeping Brutus himself out of step with society makes sense, but keeping the environment frozen is probably making the strip seem more dated than it is.
But here's the weird thing that struck me: Art worked on the strip from 1965 until 1991, 26 years. From 1991 until today has been 25 years. If you add in whatever work Chip did before 1991 (I've seen some places note he was actually the only one working on it as early as 1989; others say he was writing the strip in 1987 but didn't take over the art chores until 1991) that means Chip has worked on more of the strips than his father ever did! So while he continues to include Art's name in the credits, the strip is really more his than his dad's at this point. Regardless of what you think of the strip's humor or illustrative style or whatever, that tenure is certainly something worthy of crediting. Congrats, Chip!