F'ing Up
F’ing Up is a podcast that peels back the highlight reel of success. Hosted by Deanne Rhynard, each episode features accomplished guests who share the messy, real, and often uncomfortable parts of their journeys—the moments that shaped their eventual success.
In a world where social media sells the illusion of overnight success, F’ing Up reminds listeners (especially those early in their careers or considering a major pivot) that growth is never linear. Deanne invites guests to drop the polished narrative, explore their stumbles, and reflect on what those experiences taught them in real time.
Because the truth is: what we often label as failure is usually just part of the climb.
After all, we’re all F’ing Up.
ABOUT THE HOST
Deanne Rhynard is a Success Mentor and the Host of The F’ing Up Podcast, where she translates failure into clarity, confidence, and momentum. Known for her grounded honesty and sharp emotional intelligence, she helps people cut through noise, confront blind spots, and define success on their own terms.
Before launching F’ing Up, Deanne spent nearly two decades as a Chief People Officer and startup advisor, helping companies navigate the messy, high-pressure stages of growth and scale. She shaped culture and leadership at organizations including Performio and Olo—the restaurant-tech pioneer where she scaled the team more than 30x, led the company through an IPO and two acquisitions, and built a remote-first culture well before the rest of the world caught up.
Her background spans people operations, corporate relations, and management roles at the UVA Darden School of Business, KKR, Marriott, and several early-stage startups. This breadth gives her an uncommon ability to read people quickly and understand what unlocks their potential—whether they’re early in their career or leading from the C-suite.
Deanne holds a Bachelor of Arts in Business from Walla Walla University and lives in Washington State with her husband and three sons.
F'ing Up
Charlie Gray on F'ing Up - S3 Ep7
Charlie Gray has held some remarkable titles for some of the most well known tech companies. He’s been doused with great success. However, what you don’t see, by just looking at his LinkedIn or resume, are all the stops and starts. Charlie has many tales of being hired to grow a company only to turn around and shrink it, often forced to RIF himself.
In this episode, Charlie shares vulnerably about those stops and starts, including the story of his own company that was revered in the tech space, only to have to shut it down. It’s a story of immense pride, gratitude, and heartbreak.
ABOUT CHARLIE GRAY
Charlie Gray has led the people operations of technology, media and healthcare companies for over 25 years. He was instrumental in managing the growth of the Google advertising sales team and helped to develop the company’s People Operations framework.
After providing HR and operations leadership at other start-ups, including RecycleBank and Patch, he founded and led Gray Scalable, NYC’s market-leading consultancy for growing tech start-ups, providing embedded recruiting (RPO), executive search, interim HR and compensation consulting to 200+ early- to-mid-stage companies. Although he closed Gray Scalable in 2023, he continues to provide fractional and advisory consulting services to several clients.
He holds two degrees from the State University of New York at Buffalo, in Music Performance and English Literature, and enjoys skiing and tennis, good food, good company, music and travel.
The views, thoughts, and opinions expressed are the speakers’ own and do not represent the
views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.
