Hmm, very interesting. Our team just went through a discussion of both the “skateboard” metaphor as well as your agile bicycle. Since I read both, it was difficult for me to engage seriously with the skateboard article after having read the agile bicycle.
Our designer stated a generalization that “this kind of thinking (iterative?/skateboard?) is not intuitive or natural for us” and the PM and UXR etc all nodded in agreement. I found this bizarre, because in the sciences iteration is often the meta-model: whether you are constructing series approximations for mathematical functions, better higher order approximations to physical values (Feynman diagrams), constructing theoretical models which iteratively improve our understanding of the world (up to a certain point, recall the Ptolemaic universe and epicycles bloody epicycles) or expand the domain of applicability or building better experiments (the first gravitational wave detector was built in the 1960s, and it took until 2016 and ~ 10 science, design and engineering iterations to finally detect one). Of course, there are paradigm changing theories (Heliocentrism, Newtonian mechanics, special relativity, general relativity, quantum mechanics …) and experiments (the quantum hall effect) as well.
But this (the earlier, pre “skateboard” stance) explains why I faced so much resistance to my desire to simplify the product offering we were considering.
Finally, perhaps due to my science background, one deep flaw I see in both the skateboard and the bicycle models is the assumed linearity — it doesn’t account for evolutionary dead-ends and failures and it incorrectly sets us up to expect some kind of linear progress. Because we are all so positive, somebody pointed out that there is no such thing as “failure” — which again, is too broad a generalization: sometimes you don’t learn anything other than “don’t do this specific thing”.