Rachel Bloom, of The Golden Globe-winning series Crazy Ex-Girlfriend, takes on workplace inequality in #Ladyboss, an “ode to the confusing conundrum of being both a leader and a woman at the same time.”

On point, hilarious and all too real, Rachel and her back-up crew ask the tough questions (how much boob is too much boob?) and expose many challenges women face as professionals in the workplace.

I want you to do what I want
But let me say it in a nice way
Oh, right, I shouldn’t care if you think I’m nice!
Do you think I’m a bitch?
Well, I don’t give a shit!
But if I do give a shit, does that make me weak?

The video was created with Vanity Fair for their first annual Founders Fair, a conference celebrating female entrepreneurs.