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 children.
Episodes
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Krista Casey shares what it was like to spend years building an impressive career—only to realize that the very success she had worked so hard to achieve was leading to her burning out.
In this episode of The F’ing Up Podcast, we explore the hidden cost of high achievement, the pressure to constantly prove yourself, and how understanding one simple truth about herself...
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Casey Floyd shares the story behind her career — including the moments she realized that being the hardest worker in the room wasn't always enough.
In this episode of The F’ing Up Podcast, we explore what it feels like to consistently deliver exceptional results while being overlooked, undervalued, and expected to carry more than your share. Casey opens up about learn...
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Tomide Awe shares the story behind her career journey — including graduating from Wharton without a job, spending nine months unemployed and depressed, burning out in Big Tech, and ultimately getting laid off during maternity leave while navigating postpartum depression.
In this episode of The F’ing Up Podcast, we explore what happens when you spend years chasing the ...
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Heather Wallander shares what it feels like to work relentlessly toward a dream career only to realize the system you trusted may never have been designed to protect you.
In this episode of The F’ing Up Podcast, we explore the reality behind building a career through sheer determination, reinvention, and resilience…and what happens when success collides with discrimi...
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Sylvia Kwan shares what it looks like to build a successful career without a clear plan—and the moments along the way that force you to question everything you thought success would be.
In this episode of The F’ing Up Podcast, we explore the reality behind a nonlinear career—from following the rules and staying invisible, to navigating missed opportunities, fear...
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Atul Sood shares what it looks like to build, lose, rebuild—and ultimately redefine success on his own terms.
In this episode of The F’ing Up Podcast, we explore the reality behind entrepreneurial highs and devastating lows—from leading and scaling companies to losing everything in the span of a month, including his career, identity, and mental health.
If...
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Katie Svilich shares the story behind her career — including the self-doubt, setbacks, and internal battles that shaped her path.
In this episode of The F’ing Up Podcast, we explore what it feels like to navigate high-performance environments while questioning your own worth, and how those moments can ultimately redefine your confidence and career trajectory.
I...
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Josh Perry shares the untold story behind his career — including facing a life-threatening brain tumor, walking away from professional BMX, and rebuilding his identity from the ground up.
In this episode of The F’ing Up Podcast, we explore what it means to confront your own mortality, let go of the identity you thought defined you, and find purpose on the other side o...
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Stephanie McCarty shares the story behind her rise to becoming a Fortune 500 CMO — while her personal life was quietly unraveling behind the scenes.
In this episode of The F’ing Up Podcast, we explore what it really looks like to achieve massive career success while navigating personal hardship, and how those parallel realities shape who you become as a leader.
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Episode 1️⃣ of Season 4️⃣ drops on May 2️⃣0️⃣!!
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The F’ing Up Podcast is dedicated to sharing real truths about the career journeys of successful individuals.
Host, Deanne Rhynard, interviews these individuals, points out what they’ve achieved and immediately throws...
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Philip Eil opens up about anxiety, quiet suffering, and the disorientation of feeling unwell during a season that was supposed to feel joyful and successful.
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In this deeply honest and vulnerable episode, we dive into the personal journey of dealing with anxiety, depression, and the profound effects they've had on both personal and professional life. Philip Eil opens up...
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In this raw and heartfelt episode, we dive deep into the chaos of life, career, and self-discovery. From navigating societal pressures to figuring out how to rewrite the rules of success, this episode is a battle cry for anyone who feels like they’re “f’ing it up”.
Mishae Khan shares her journey of the immense pressures placed on immigrant children, the relentless...
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Description:
This episode is a raw and unfiltered look at what happens when careers come to abrupt ends, rejection feels relentless, and self-doubt begins to creep in. From the business of professional sports to the emotional toll of career pivots, Lyle shares that resilience isn't about never falling—it's about getting back up, again and again.
Episode Takeaways:
- Coping with Rej...
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During this episode with Ashley Chang, we dive deep into the reality of work, growth, and the constant pressure to prove yourself. From job searches filled with self-doubt to leadership roles that come with unforeseen challenges, this episode unpacks the highs, lows, and everything in between.
Episode Takeaways:
- The Comparison Trap: How measuring yourself against others&...
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Description:
In this episode, we explore the raw and unfiltered realities of professional and personal setbacks. From struggling with career uncertainty and mental health challenges to the lingering effects of toxic work cultures, we uncover the lessons learned in the face of adversity. This conversation is a reminder that no one’s journey is perfect, and “figuring it out&rdq...
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Description:
In this episode, we unpack the complicated relationship between ambition, identity, and personal fulfillment. From workplace burnout to the challenges of navigating toxic cultures, and from grappling with misaligned goals to the pressures of leadership, this episode dives into the hard truths of career “success” and what it really means to thrive.
...
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Tyler Schmoker brings a wealth of experience in operations management and supply chain strategy, having developed his expertise through a progressive career in the military and paramilitary sectors. In this episode, Tyler candidly shares the challenges he's encountered throughout his journey, including navigating corporate landscapes, accepting that he may not always be the most popular...
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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, Cha...
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In this episode of F'ing Up, Deanne Rhynard speaks with Julia Arpag, co-founder and CEO of Aligned Recruitment. Julia shares her journey from being laid off during maternity leave and navigating challenging work environments, to ultimately founding her own successful tech recruitment firm. She reflects on growing up as the oldest of seven children, her college experiences, and the uncon...
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Natalie Fergusonis a serial entrepreneur, having founded multiple successful companies, enabling her to find “success” quickly. Her journey wasn’t without strife. Early on she navigated an abusive relationship, which started in the workplace. It took a toll on her emotionally, mentally, and financially. It took years for her to get beyond the grips of that hold. Listen...
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