F'ing Up

Deanne Rhynard

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.

  1. -9 ч

    I Got Laid Off During Maternity Leave—and Felt Relieved [4.7 Tomide Awe]

    Send a private message to Host, Deanne Rhynard 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 career you're supposed to want, only to realize success on paper doesn't always create fulfillment in reality. If you've ever felt trapped by expectations, struggled with burnout, questioned your identity after a layoff, or wondered whether the life you've built is actually the life you want, this conversation will resonate deeply. Topics include: - Graduating from a top-tier Business School without a job offer - Nine months of unemployment and depression - Why she realized finance wasn't for her - Burnout, mental health leave, and losing herself in work - Getting laid off during maternity leave and feeling relieved - Rebuilding a career around freedom instead of expectations This is the side of success most people don't talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    I Got Laid Off During Maternity Leave—and Felt Relieved [4.7 Tomide Awe]
  2. 19 авг.

    I Spoke Up About Discrimination — And It Cost Me [4.6 Heather Wallander]

    Send a private message to Host, Deanne Rhynard 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 discrimination, retaliation, and the painful realization that speaking up can put everything at risk. If you’ve ever questioned your worth at work, felt gaslit by leadership, struggled to prove yourself in male-dominated environments, or wrestled with the cost of doing the right thing, this conversation will resonate deeply. Topics include: * Burning out after years of nonstop achievement—and completely losing herself for a period of time * Chasing validation through titles, promotions, and high-performance environments * Learning that getting the title you fought for doesn’t always mean you’ll enjoy the work * Navigating being underpaid, overlooked, and forced to leave jobs in order to earn what she deserved * Experiencing workplace discrimination, retaliation, and exclusion after raising concerns internally * Wrestling with the impossible choice between protecting career and values * Realizing how quickly people can make you feel like the problem when you challenge the system * Choosing to speak up anyway—and the personal and professional cost that followed * Why she is now building a nonprofit to help others navigate discrimination before their lives and careers implode This is the real side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    I Spoke Up About Discrimination — And It Cost Me [4.6 Heather Wallander]
  3. 15 июл.

    I Turned Down a CIO Role Because I Was Afraid [4.5 Sylvia Kwan]

    Send a private message to Host, Deanne Rhynard 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-driven decisions, and roles that didn’t turn out the way she expected. If you’ve ever felt unsure of your path, struggled to advocate for yourself, turned something down out of fear, or realized too late that a role wasn’t right for you, this conversation will resonate deeply. Topics include: - Growing up with the belief that hard work should speak for itself—and realizing it doesn’t - Building a career by following curiosity and optionality, not a defined plan - Walking away from paths that looked “right” but didn’t feel right - The reality of being underpaid and not advocating for yourself - Learning that visibility—not just performance—is required to grow - Turning down a career-defining opportunity out of fear—and the regret that followed  - Finally taking the leap… into a role she knew on day one was wrong  - Navigating a toxic environment and choosing to walk away to protect her mental health  This is the real side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    I Turned Down a CIO Role Because I Was Afraid [4.5 Sylvia Kwan]
  4. 1 июл.

    My Life Looked Fine, It Wasn't, And Then It Completely Fell Apart at 38 [4.4 Atul Sood]

    Send a private message to Host, Deanne Rhynard 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 you’ve ever tied your worth to your work, questioned your path after a major setback, or found yourself starting over when life didn’t go according to plan, this conversation will resonate deeply. Topics include: Building a career through relationships, not traditional paths Why “success on paper” can mask deeper misalignment The pressure and identity trap of startups and high-growth roles Experiencing total life collapse at 38—and what it takes to rebuild Navigating mental health challenges, including a bipolar diagnosis The impact of honesty and vulnerability in pivotal career moments Letting go of identity tied to work and redefining personal success Why external outcomes don’t always reflect effort, talent, or capability Finding peace, autonomy, and fulfillment later in life This is the real side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    My Life Looked Fine, It Wasn't, And Then It Completely Fell Apart at 38 [4.4 Atul Sood]
  5. 17 июн.

    I Created Something Special—Then Had to Walk Away [4.3 Katie Svilich]

    Send a private message to Host, Deanne Rhynard 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. If you’ve ever struggled with imposter syndrome, workplace confidence, or feeling underestimated at work, this conversation will resonate deeply. Topics include: Imposter syndrome in leadership and career growth Building confidence after being told you’re not enough Navigating career setbacks and self-doubt Personal growth through adversity Redefining success and identity at work This is the side of success most people don’t talk about. -- 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    I Created Something Special—Then Had to Walk Away [4.3 Katie Svilich]
  6. 3 июн.

    I Wasn’t Driven by What I Wanted, But By What I Might Lose [4.2 Josh Perry]

    Send a private message to Host, Deanne Rhynard 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 of uncertainty. If you’ve ever experienced a major life disruption, identity shift, or been forced to start over, this conversation will resonate deeply. Topics include: Facing a life-altering diagnosis and uncertainty Letting go of identity and redefining purpose Rebuilding your life after everything changes Mental resilience and perspective through adversity Finding meaning beyond achievement and performance This is the side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    I Wasn’t Driven by What I Wanted, But By What I Might Lose [4.2 Josh Perry]
  7. 20 мая

    I Became a Fortune 500 CMO While My Life Was Falling Apart [4.1 Stephanie McCarty]

    Send a private message to Host, Deanne Rhynard 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. If you’ve ever felt like you’re holding it all together on the outside while struggling internally, or questioned whether success is worth the cost, this conversation will resonate deeply. Topics include: - Building a high-powered career during personal adversity - What success looks like from the inside vs. the outside - Navigating leadership while your life is falling apart - The emotional toll of ambition and achievement - Redefining success beyond titles and external validation This is the side of success most people don’t talk about. 🔔 Subscribe to the F’ing Up YouTube channel for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show 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.

    I Became a Fortune 500 CMO While My Life Was Falling Apart [4.1 Stephanie McCarty]

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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.

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