Keisha, 28, Dallas — She Turned One Loyal Regular Into A $40K-A-Year Relationship
Not a romantic relationship — relax. Keisha, 28, from Oak Cliff, Dallas, cultivated a regular at her upscale steakhouse-bar who tips her $500 every single visit and comes in twice a week. He’s a petroleum executive, recently divorced, who discovered that talking to Keisha for 45 minutes about nothing in particular was the only time his week felt normal. (His therapist should probably know about this, but that’s between him and his insurance.) Keisha does not consider this unusual — she considers it a service. She cleared $115,000 last year, has three other regulars who each account for five figures annually, and recently moved into a two-bedroom condo in Uptown she bought at 27. She was pre-approved by three different lenders, which she says was genuinely the best day of her life. The thing people get wrong about this job is they think it’s luck — but Keisha built this like a business, and the receipts are literal.
Sophie, 25, Scottsdale — Pool Season Lasts Eight Months And So Does The Money
Sophie, 25, works a resort pool bar in Scottsdale where the season technically never really ends, and the crowd in March through October is a steady rotation of bachelor parties, corporate retreats, and wealthy retirees who have absolutely nothing else to do with their afternoon. She made $88,000 in nine months last year — her first year on the job — which is already more than her older brother made at his “real” accounting job, a fact she mentions only when he brings up her career choices at family dinners. (He’s stopped bringing it up.) She has no uniform to speak of — resort casual — and her entire commute is a three-minute drive in a used Jeep she paid off in six months. She’s also already been offered a position at a second location in Sedona for peak fall season, and the math there is… we’ll just say Sophie has stopped complaining about Arizona summers.
Brianna, 34, Atlantic City — She Watched The Casino Industry Collapse And Found A Way To Make It Work Anyway
Atlantic City has shed half its casinos since 2014, and everyone who knows anything will tell you the money dried up — except Brianna, 34, who will respectfully disagree from her fully paid-off home in Ventnor. She works one of the remaining high-roller rooms at a Boardwalk casino, where the clientele is smaller but spends harder than ever because the competition is gone. She made $121,000 last year and has been over six figures for three straight years, working four nights. (Her ex-husband, who left because he thought she was “wasting her potential,” now works in middle management in Philadelphia and makes $68K — she hasn’t said a word, but her silence is doing a lot of work.) Brianna knows every high-limit regular by name, drink preference, and approximate mood from fifty feet away. That’s not a skill they teach in business school, but it absolutely should be. And her secret to keeping regulars loyal? That, she says, she’ll never tell.
