In this episode of Call Sheet Confessions, host Mia LePage sits down with Kailey – Philly-born former stylist turned artist & athlete relations lead at a live streaming production company – for a raw, no-fluff look at what it actually takes to survive and thrive in a male-dominated entertainment world while getting sober, staying grounded, and loving the chaos.
From moving to LA at 19 to get sober, to accidentally talking herself into a promotion, to running 16+ hour production days between Radio City Music Hall and NBA All-Star Weekend, Kailey’s story is a blueprint for young women who refuse to sit at a desk, know they’re “people smart,” and want to turn that into a real career.
Before live streaming tours, award shows, and album release parties, Kailey opens up about growing up in Philly, nannying kids with special needs, trying to study criminology to join the FBI, and realizing her superpower wasn’t textbooks—it was people.
Together, Mia and Kailey dive into:
Philly roots, LA restart – moving cross-country, growing up loud and energetic, and realizing she was never built for a 9–5 behind a desk
From boutiques to celebrity styling – working retail on Abbot Kinney & in Santa Monica, getting randomly DMed into an assistant role, and falling into styling via closet organizing, events, and brand deals
One client that changed everything – how landing a single celebrity client put her name “in the game,” and what it really takes to hold your ground on rates, travel, and boundaries as a 22-year-old woman
Being young, female, and taken seriously – walking into male-dominated rooms as the only woman, owning her direct “Philly” communication style in an LA world that sugarcoats, and why confidence changes the whole conversation
Constructive criticism as a love language – letting mentors and her Head of Production “hold her to it,” studying powerful women COOs in the room, and treating feedback as proof people care about her growth
From assistant to running point – getting hired on the crypto side of a startup, speaking up in the wrong room at the right time, and accidentally pitching herself into a senior role on the social side after a Love Island project
Future of live streaming vs TV – why she thinks Twitch & Kick are on a straight incline, how Amazon’s integration will change how we shop on stream, and why organic product placement beats in-your-face ads
Crafty Corner & set survival kit – cucumbers with salt over snacks, coffee non-negotiables, the “diaper bag” her assistant built (peppermint hand sanitizer, meds, gum, pen, highlighter, face spray, chapstick, hair ties, and more)
Industry icks & betrayal list – begging for contracts to get signed, delays on payments and decisions, cold emails that drain her soul, and the chaos of managing 3,000–4,000 texts plus dozens of calls a day
Getting fired, then leveling up – the Santa Monica swimwear content “scandal,” an unprofessional boss, and how that firing immediately turned into her first real styling assistant setup and work trips to Vegas
Advice for 19-year-old you – don’t rush into living alone, stop lying about who you work with, start small, and choose being driven, honest, and accountable over looking like you “made it” on Instagram
Living your dream (for real) – what long-term success looks like for her now, how sobriety made this life possible, and staying grounded while being fully desensitized to mansions, money, and celebrities
📸 Follow the show & everyone featured on Instagram:
👉 Host: Mia LePage — https://www.instagram.com/mialepage/
👉 Guest: Kailey. - https://www.instagram.com/kaillleyyyy/
👉 Podcast: Call Sheet Confessions — https://www.instagram.com/callsheetconfesspod/
👍 Like, comment, and subscribe