F'ing Up

Deanne Rhynard
  • 5.0 (18)
  • CAREERS
  • UPDATED BIWEEKLY

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. Philip Eil on F’ing Up - S3 Ep14

    02/19/2025

    Philip Eil on F’ing Up - S3 Ep14

    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 about the challenges of battling mental health, facing rejection, and pushing through discomfort to pursue his passions. This episode explores the messy realities of self-doubt and rejection. Through all the turmoil, this guest has emerged stronger, finding healing through writing, commitment to therapy, and a sense of purpose in sharing their experiences with the world. Key topics in this episode: The raw emotions behind not following the traditional milestones of adulthood (marriage, homeownership, etc.).The discomfort of being in a job that doesn’t align with your talents and the struggle to find what’s next.Overcoming rejection: how 25 publishers passed on the guest’s book, and the emotional rollercoaster of freelance journalism.A candid discussion about the realities of mental health struggles, including the times it’s knocked them completely out of action.The power of vulnerability and why writing about mental health has become a source of healing and purpose.This episode serves as a reminder that mental health is just as important as physical health and that we are all in this together. If you've ever struggled with your own mental health or faced rejection in your journey, this one is for you. ABOUT PHILIP EIL Philip Eil is an award-winning freelance journalist based in his hometown, Providence, Rhode Island. He is the former news editor of the alt-weekly newspaper, The Providence Phoenix. Since the paper’s close in 2014, he has contributed to The Atlantic, Men’s Health, the Boston Globe, Huffington Post, and the Columbia Journalism Review, among other outlets. He has also taught writing and journalism classes at Brown University, Columbia University’s School of the Arts, and the Rhode Island School of Design. He holds an MFA in Nonfiction Writing from the Columbia University School of the Arts. Prescription for Pain is his first book. Send us a text 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.

    53 min
  2. Mishae Khan on F’ing Up - S3 Ep13

    02/05/2025

    Mishae Khan on F’ing Up - S3 Ep13

    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 pursuit of external validation, and the grind of trying to live up to others' expectations—all while discovering the courage to live authentically. This episode highlights the following: The dangers of expecting overnight success and perfection.How societal and family expectations shape our self-worth and career paths.The emotional toll of navigating parental expectations, including stories of retaking the MCAT and finding identity beyond others' approval.The overwhelming pressure of trying to balance humility and confidence in a world obsessed with highlight reels.The toxic cycle of feeling like you’re never doing “enough” and the importance of learning to love and care for yourself. About Mishae Khan Mishae Khan is figuring it out as she goes. She's an investor, soon to be author and founder.  Leaving the world better than she found it is her obsession. Her company Bold&Kind is a jewelry meets affirmations brand focused on changing the self talk of women that are too hard on themselves. She's no stranger to high pressure environments having worked for 10+ years in training and operations at companies like Google and Samsung. Her designs focus on changing women's inner narrative and have been in publications like Vogue, Glamour and Vanity Fair UK. She's most excited about her puppy getting over his teething phase and editing her book.  Send us a text 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.

    55 min
  3. Lyle Adams on F’ing Up - S3 Ep12

    01/22/2025

    Lyle Adams on F’ing Up - S3 Ep12

    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 Rejection: Why hearing “no” is inevitable—and how to move forward when it feels like no one is saying “yes.”Navigating Career Transitions: The emotional challenges of leaving one dream behind and figuring out what’s next.The Struggle of Starting Over: Whether it’s pounding the pavement for a new job or launching a business from scratch, starting over isn’t glamorous.Facing Self-Doubt: How comparison, rejection, and setbacks fuel doubt. About Lyle Adams: Lyle Adams is the CEO of Spry, a software solution designed specifically for athletic organizations. Before founding  Spry, he worked at Uber and LivingSocial. He completed his undergraduate degree from Wake Forest University and his graduate degree from Columbia University. In his spare time, Lyle loves to solve the Rubik's Cube. Send us a text 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.

    30 min
  4. Ashley Chang on F’ing Up - S3 Ep11

    01/08/2025

    Ashley Chang on F’ing Up - S3 Ep11

    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—especially polished success stories—can hold you back.Leadership Challenges: Managing through layoffs and navigating the emotional toll of tough decisions.Starting Over: What it really takes to build something from scratch and why it’s never as simple as it seems.The Weight of Expectations: Why success doesn’t always feel like you thought it would and facing not realizing the feelings of success. About Ashley: Ashley Chang is the co-founder and CEO of Sundays, an executive assistant service for working parents. She’s on a mission to accelerate parents in their careers while creating more quality time for family. Before starting Sundays, she worked in the technology industry across all stages of companies – she was the first employee at developer tool company ReadMe and helped scale Carta’s Venture Capital business from 10 to $100M+. Send us a text 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.

    43 min
  5. Alexandre Seiler on F’ing Up - S3 Ep10

    12/18/2024

    Alexandre Seiler on F’ing Up - S3 Ep10

    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” is often the most powerful step forward. Episode Takeaways: The Weight of Job Insecurity: How the fear of losing your livelihood can shape your mental and emotional state.Breaking Free from Toxic Environments: The emotional toll of staying in harmful workplaces and the liberation that comes with leaving.Overcoming Career Comparisons: Why success is often a matter of perception versus reality and how to focus on your own path.Facing Uncertainty with Grace: How to navigate moments of feeling lost in your career and find clarity without forcing it. ABOUT ALEX Alex Seiler has 15+ years of global experience in the People/HR space. He has spent time working in various industries and for companies such as Citi, NBCUniversal and WeWork.  Alex’s specific expertise has centered on creating, transforming and building out systems that foster an equitable, innovative and inclusive workplace culture.  While Alex has served as a Chief People Officer, he is currently focused on fractional clients. He is also a start-up advisor in the HR tech space, having worked or working with companies such as When Insurance, Kindred Minds and ChangeEngine. Send us a text 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.

    53 min
  6. Aimee Gindin on F’ing Up - S3 Ep9

    12/04/2024

    Aimee Gindin on F’ing Up - S3 Ep9

    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. Episode Takeaways: Burnout and the Cost of Overwork: The early-career grind can feel like a rite of passage, impacting personal life and well-being. Challenges with Acquisitions: The cultural mishaps that can follow after an acquisition.  Advocating for Yourself in the Workplace: The risks of speaking up, the label of being “overeager,” and knowing when it’s time to move on.  The Lonely Reality of Leadership: experiencing isolation in leadership.  About Aimee: Aimee Gindin is a leadership coach, keynote speaker and author of dozens of published business and lifestyle articles. With a background as both a former mental health clinician and a C-Suite executive, she combines her passion for personal growth with her business and leadership experience to create actionable steps for professionals looking to make positive changes in their lives and in their careers. Send us a text 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.

    1h 4m
  7. Tyler Schmoker on F’ing Up - S3 Ep8

    11/13/2024

    Tyler Schmoker on F’ing Up - S3 Ep8

    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 figure, and managing the constant uncertainty of potential deployments looming ahead. ABOUT Tyler Schmoker Tyler Schmoker is a retired Army Combat Arms Senior Noncommissioned Officer, former Paramilitary Advisor, and Strategic Projects Consultant to Fortune 500 companies. Tyler has worked in Corporate Security, Strategy, Project and Program Management, and Tech.  Tyler is an avid Alpine Climber and Endurance Athlete.  Tyler is the Founder & Principal at Winsly LLC, a High-Performance Coaching, Consulting, and Advisory Services Firm. When the going gets tough, the tough choose Winsly.  Send us a text 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.

    1h 2m
  8. Charlie Gray on F'ing Up - S3 Ep7

    10/23/2024

    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.  Send us a text 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.

    55 min
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Trailers

5
out of 5
18 Ratings

About

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.

Information

  • Creator
    Deanne Rhynard
  • Years Active
    2022 - 2025
  • Episodes
    54
  • Rating
    Clean
  • Copyright
    © 2025 F'ing Up
  • Show Website
    F'ing Up