Prediction: Chelsea has made lots of money by herself
Could be wrong, just a hunch... She is obviously not 'from money', but she has (probably fairly recently) made lots of money, perhaps from a yoga business/influencer thing. The show did a bit of playful misdirection of the audience in Ep1 (her modest "I used to be a yoga teacher"; doesn't know the deal with waiters and checking if the wine is corked; etc), letting us assume that Rick is some kind of wealthy but burnt out sugar daddy figure paying her way. But, the truth is that she is all of: independently successful, wealthy, and carefree, and Rick has a chip on his shoulder about all three of those things.
Could be wrong, just a hunch... She is obviously not 'from money', but she has (probably fairly recently) made lots of money, perhaps from a yoga business/influencer thing. The show did a bit of playful misdirection of the audience in Ep1 (her modest "I used to be a yoga teacher"; doesn't know the deal with waiters and checking if the wine is corked; etc), letting us assume that Rick is some kind of wealthy but burnt out sugar daddy figure paying her way. But, the truth is that she is all of: independently successful, wealthy, and carefree, and Rick has a chip on his shoulder about all three of those things.