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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
F'ing Up with Rebekah Bastian - S2 E7
Rebekah Bastian's resume is impressive. She worked for companies like Microsoft and Zillow and authored a book, Blaze Your Own Trail, which led to her starting her own company, OwnTrail. Despite positive traction with OwnTrail, Rebekah was met with a challenging feat of raising capital in order to continue to grow OwnTrail. Ultimately, the raise was unsuccessful and she turned to finding a company to acquire OwnTrail, which meant Rebekah would no longer serve as CEO. Rebekah shares vulnerability about that experience as well as all the “No’s” she experienced throughout her career.
About Rebekah Bastian
Rebekah Bastian is a product leader, entrepreneur, writer and artist. She is currently SVP of product at Glowforge, helping people make amazing creations with 3D laser printers. Prior to that she founded social timeline platform, OwnTrail, which was acquired by Teal, and spent 15 years at Zillow, with roles including VP of Product and VP of Community & Culture.
Rebekah wrote the award-winning book, Blaze Your Own Trail and is a Forbes contributor. She serves on the board of Bellwether Housing, founded the AuthenTech and The Time is DAO communities, and is an investor and advisor to technology startups. She has been recognized in the Puget Sound Business Journal 40 Under 40, the Inman 33 People Changing the Real Estate Industry and the Female Founders Alliance Champion Awards. Rebekah earned her Masters of Mechanical Engineering from UC Berkeley and Bachelors of Mechanical Engineering from the University of Washington.
You can view Rebekah Bastian’s Own Trail here.
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.
