Valentina, 26, Nashville — The Bachelorette Party Capital Of America Has Made Her Very Wealthy
Nashville is quietly one of the best cities in America to be a cocktail waitress, and Valentina, 26, from East Nashville, figured that out before the rest of the internet did. She works a honky-tonk-adjacent upscale bar on Broadway that catches bachelorette parties like a net catches fish — every single weekend, waves of women who have been pre-approved to spend whatever it takes. Valentina made $98,000 last year, which she’s quick to point out is more than the finance bro from Memphis who tried to explain tipping culture to her in September. (He tipped 12%. She remembers.) She’s already maxing out her Roth IRA and has a financial advisor, which is more than most people with twice her education can say. She’s got a side business too — more on that in a second, because it’s unhinged in the best way.
Anna, 30, Chicago — She Once Got A $3,000 Tip On A Wednesday
Anna, 30, works a private members’ club in River North, Chicago, where the entry membership alone costs more than her first car. She still talks about the Wednesday in November 2023 when a table of four — celebrating something vague and financial — left her a $3,000 tip on a $700 tab. (She stood in the break room for ten minutes staring at the receipt, she’ll tell you, then immediately Venmo-requested her sister who owed her $40.) She makes around $140,000 a year, works four nights a week, and spends her days doing literally whatever she wants — which currently involves a ceramics class and an aggressive skincare routine. Her Instagram is private, her car is paid off, and she has opinions about compound interest that will genuinely embarrass you. And honestly? She nailed it. But wait until you hear how she handles the customers who try to lowball her…
