“For users like that we'll offer steeper and steeper discounts. Okay, you don't want to give us $40 — will you give us $5? And there are some people who won't, but it allows us to take cohorts that otherwise we're just not monetizing and make something.”

Steep discount ladder ($40 → $5) monetizes long-term free users

For free users 30+ days in (whom data shows won't convert at full price), Lose It! cascades discounts down to as low as ~$5 — monetizing cohorts that would otherwise be $0 forever. They frame it as a loyalty reward to keep it philosophically aligned with the mission.