Uber went from a stylized Ü to the Chase Bank logo [0], as part of a grand brand strategy that fractured regular polygons that somehow supposed to make you think that they weren't just cab service. (Seriously, they called their 2016 suite of logos "Bits and Atoms" [1].) People literally lost the app on their phone. If it wasn't a mistake, they wouldn't have changed their logo to simply the word "Uber" in less than 2 years if it wasn't seen as a mistake.
Grandmas use Google, Facebook and Amazon but generally have not adopted Uber or Instagram yet. Winning over those kinds of customers requires a different GTM strategy and different marketing than your first couple million.