If you have an executive membership they guarantee that you make back your membership dues. If you fall short you can just ask them to give you the difference (and then they will downgrade you to the regular membership).
But also remember regular members don't get cash back. The ratio is about 50/50. So about 40 million people pay for membership and don't get cash back.
> If you have an executive membership they guarantee that you make back your membership dues.
That's not quite their policy - their explicit policy is "The Reward is not guaranteed to be equal to or greater than the Executive upgrade fee paid." - but they will refund you if you ask for it.
Much like the In-N-Out secret menu, while it's not explicitly stated it's basically company policy.