> But no one likes contracts and I don’t like conflict, so I didn’t ever transition to long term contracts. Again my lower brain (fear and the desire to be liked) took control and I decided to stick with month-to-month contracts. Then my upper brain came up with convincing arguments and justified this decision by saying I had created a “customer-friendly” pricing model.

Your upper brain was right. You did the right thing, and this is an example of where building to flip is at odds with doing the right thing for the customer. I hope we'll see more bootstrapped companies that are profitable enough to be sustainable and offer a good living for their owners and employees, but don't maximize profit or valuation at the expense of doing what's right.