Amazon-Stripe partnership

In enterprise, it’s often the case that your biggest customer effectively owns you. They get to dictate roadmaps, you’re forced to spin up a special team just for them, and it becomes harder to justify your investment into long tail customers because this big golden monkey is on your back.

The long tail also requires support and that doesn't scale well. At one of my jobs, the rule is basically that any company under around 5K-10K ARR (it is arbitrary) doesn't get any real support and just gets strung along until they quit, as giving any developer time to their issues makes them unprofitable.