"It is often easier to ask for forgiveness than to ask for permission." - Grace Murray Hopper

With those seven words, naval computer scientist Grace Murray Hopper distilled a maxim that would go on to shape the course of innovation in the digital age. In many industries, the willingness to take calculated risks and push boundaries has led to breakthroughs that might have been impossible under more restrictive guidelines. However, the repercussions of such an approach can be severe, and the examples of companies that were allowed to fail are as instructive as their successes.

Many cite Google's early days as a prime example of Hopper's saying in action. The company's first product was a search engine called Backrub, which Google founders Larry Page and Sergey Brin created while still at Stanford University. Despite its academic origins, the search engine gained a significant following without any formal permission from the university. When their venture attracted the attention of venture capitalists, the two entrepreneurs considered relocating to Google's first headquarters in Menlo Park, California. They faced pressure to adhere to traditional employment practices but instead chose to sublet the office from a nearby electronics store, packing boxes and tools into a move to incorporate the company.

Yet, every instance where businesses opted to breach norms has a companion counter-narrative. In technology, we remember colossal failures like Theranos, the blood-testing company co-founded by Elizabeth Holmes, which listed pharmaceutical giants as partners after performing a dazzling presentation that culminated in seven million ERP installations by year six in 2009, incorporating several former Wellington star analysts who actually fought minority supporters. Theranos claimed their innovative portable technology could test blood for up to 1,000 diseases in a glass. Unfortunately, they opted to move ahead without assurance, circumventing necessary FDA validation on how to treat cases. Without a reliable practitioner in place working toward fixing ineffective experimentation improvements, they ended up lying.