Does deal size/prestige matter?

So my goal is to start my own firm but to start off somewhere else and progress fast. Prestige isn't that big of a deal for me, and if rather work up in a boutique fast then take the bb route.
Also do people care about how big deal sizes are that you’ve worked on?
At the end of the day, would I be viewed more "legit" if I worked as a vp level person at a bb or director/MD level at a regional boutique?

 
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