Start with the least price sensitive customers → use them to improve accuracy and lower costs → attract slightly more price sensitive customers → use them to improve accuracy and lower costs → launch new markets with least price sensitive customers → rinse, wash, repeat
“Humans don’t mind hardship, in fact they thrive on it; what they mind is not feeling necessary. Modern society has perfected the art of making people not feel necessary. It's time for that to end.”
In the end, most of these users would likely migrate back to either free ad-supported services or to subscription services that only make you think about payments once in a while.