The second rival, is she purposely meant to be exponentially harder than the first? To the point where you literally don't even show up on the progress bar, despite a good amount of upgrades applied prior to attempting?
Phillipa is a big step up in difficulty - but it sounds like the explanation for how to beat her was not made clear enough from my side.
Each rival has a specific restriction how to beat them and she will only accept if you manually flip coins and win Money through that.
Thanks for playing and I hope you give it another shot to show the rivals who's the gambling-goat