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Description
Society has programmed individuals, largely by way of social media, to think success happens easily and overnight. F'ing Up gives the listener an opportunity to understand the realities. The host, Deanne Rhynard, interviews successful individuals, points out what they’ve achieved and immediately throws that information out the window and focuses on the tripping hazards along the way. Deanne highlights the tough realities and humanizes the experience of the climb to the top. After all, we're all F'ing Up!
About the Host
Deanne Rhynard is a seasoned HR executive and startup advisor. She has a deep appreciation for understanding the human psyche and how that intersects into one’s career journey.Deanne hosts F’ing Up, a podcast which dives into the [perceived] failures of successful individuals.
Deanne is a serial Chief People Officer. Being a culture catalyst for companies like Performio, a sales compensation software platform, and Olo, the pioneer of digital ordering and delivery programs for restaurants.
Under her leadership, Olo grew its employee base by over 30x, executed a successful IPO and two acquisitions. Prior to COVID, Deanne operationalized a workforce that was 65% remote, creating a unique value proposition in the tech market.
Prior to Olo, Deanne worked in various people, corporate relations, and management roles at UVA’s Darden School of Business, KKR, Marriott, and other technology startups. Her wide-ranging experience enables her to understand people needs from many different facets of life, whether a high-powered money manager or an entry level guest services representative.
Deanne holds a Bachelor of Arts in Business from Walla Walla University. She resides in Walla Walla, WA, with her husband and three sons.
54 Episodes
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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 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, ...
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 li...
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.”Navigati...
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...
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 l...
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 lif...
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...
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 tec...
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 unconventional career path that shaped her professional and personal life. Julia's story offers a candid look at ...
Natalie Ferguson is 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 to her share her story during her episode of F’ing Up. About Natalie Ferguson Natalie Ferguson caught the entrepreneurial b...
Dan Griffin spent a year jobless. After a successful tech trajectory, Dan was laid off by Microsoft. He battled a brutal job market and had to reshape life in many ways to ensure care for his family. Shame, lack of income, and terminated health benefits were a few of the effects he had to navigate. Dan shares his unvarnished truth in his episode of F’ing Up. ABOUT DAN GRIFFIN Dan Griffin has over 15+ years in the Talent Acquisition space and has spent more than half of that supporting...
Sara Mauskopf is an intelligent woman, successful especially in the realm of Tech. She’s worked for companies like Google, Twitter and has gone on to found her own company. Though she had a fantastic trajectory, it has come with extreme challenges, particularly in her personal life. She struggled with finding her footing and identity as a mother and shortly after having her first child, her husband was diagnosed with cancer. Sara shares openly about these struggles with Host, Deanne Rhynard. ...
Jane Boulware came from nothing. As one of five children, she was forced to grow up quickly and learn the importance of caring for herself. Not understanding what attending college really meant, she attended, setting the stage for her future. She rose quickly, creating a name for herself as a powerful leader in business. Eventually courted by Microsoft, she joined as one of very few female executives. While she earned her seat, she felt out of place from the start. Jane found herself trying t...
Austin Moore is a sales and recruiting rockstar, having helped countless people find work. He built his own business and witnessed his net worth climb at a rapid rate. Though he experienced highs in the working world, he’s had no absence of struggle - managing through challenges such as getting fired, addiction, conflicts with a co-founder, and choosing to walk away from a wealth building business in order to choose mental health. Austin feels it’s important to share his struggles so others c...
Luke Coan is an accomplished Chef, working for many successful restaurants including a James Beard Award winning restaurant, The Publican. His journey has been one of grit. He struggled to find his way and contimplated suicide on numerous occasions. The kitchen became his saving grace, enabling him to grow both professionally and personally. Trigger Warning This episode discusses suicide and suicidal ideation. If you or someone you know is suicidal, please, contact your physician, go to your...
Laila Ghambari knows success. She worked her way up in the coffee world, from Barista to Executive, all without a college degree. She even competed in the US Barista Championship in 2014 and won. Though she worked her way to the top, her journey did not come without challenges, with experiences such as poor work culture and burnout. About Laila Ghambari Laila Ghambari has nearly 20 years of specialty coffee experience. She won the prestigious title of United States Barista Champion in ...
Hunter Smith has experienced rocket ship success, both in the world of music and craft beer. Most recently, he built a brewing company and hospitality group that soared, until COVID hit. He found himself holding the pieces of a wildly successful venture that suffered the effects of something unexpected. About Hunter Smith Hunter Smith is the founder and former President of Champion Brewing Company and Champion Hospitality Group. Hunter attended Northeastern University for Mus...
Arielle Kilroy is a successful CEO, spending time growing her career at companies like Sierra Club, Mozilla and Small Improvements. Though she has achieved the ultimate title, she didn’t have an easy road getting there. She encountered many bumps which taught her hard lessons, shaking her belief system at times. About Arielle Kilroy Arielle Kilroy is a co-founder and CEO at Dado, an Employee Experience Management startup. Previous to founding Dado, Arielle has been a Webby Honoree Product ...
Scott Landers grew up on a farm in Texas, forced to grow up quickly and tend to the needs of the farm. Some days that meant driving the tractor and some days that meant ditching the broken down tractor to walk 40 acres back home. This early education prepared Scott for hard work with grit and determination, but it didn’t come without its challenges as there was a learning curve when it came to working with others as opposed to always “cowboying it” on his own. About Scott Landers Scott L...
Kit Campoy has a successful career in retail, working for well known brands such as Anthropologie, Lucky Brand Jeans, Old Navy, and Tilly’s. She worked her guts out in each of her roles - dedicated to the core. With that level of dedication came a realization that working hard and long doesn’t always pay off. There were some tough realities she had to face in her journey. About Kit Campoy Kit Campoy spent 24 years leading teams in retail stores. In 2022, she threw her store keys in the s...
Rita Cidre’s resume is impressive, her career trending up and to the right. She steadily worked her way toward the top however, once there, she had an identity crisis. She found it hard to find the joy in herself and her every day work. Everything she wanted was in her lap yet she struggled to feel successful and satisfied. Listen to Rita’s F’ing Up story to hear the full details! About Rita Cidre Rita Cidre is a marketer, professor and entrepreneur. She has 15 years of experience workin...
Carly DeFilippo has spent her career supporting companies through copywriting, marketing and brand strategy. Though she was fortunate enough to work for household names, Carly spent periods in her career where she felt stuck, not doing what she truly enjoyed, in unsupportive cultures. About Carly DeFilippo Carly DeFilippo is the co-founder of Cognoscenti Creative, a Denver-based branding and creative studio. Her career has spanned the fields of copywriting, marketing and brand strategy, with...
Liam Darmody is the kind of employee you want on your team. He’s driven, passionate, and has an appetite to learn. Despite this, Liam has experienced some unexpected twists and turns in his career journey that will take you by surprise. Listeners will be relieved to hear just how normal he is and how he, too, has experienced trials and tribulations in the workplace. About Liam Darmody After nearly two decades scaling operations at startup and mid-market technology companies, Liam Darmody j...
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 vulnerabil...
Alex Poon immigrated to the US during a pivotal time in his life, just in time for 8th grade. He encountered numerous challenges such as not knowing English, navigating cultural norms, and looking around and not seeing examples of himself. Alex pushed himself to work hard and overcome obstacles, but found himself struggling with the desire to always want more and finding it hard to be satiated. About Alex Poon Alex Poon is a three-time VC-backed founder. Most recently he co-founded&nbs...
Tessa Wolf spent the first several years of her career unhappy in her work. She had the drive to make something special of her career yet, she couldn’t seem to land somewhere in a role that matched her. Desperate to find her footing, she found herself in startups and felt seen for the first time in her career. She gave everything to her work and ultimately risked her health by not understanding the importance of healthy boundaries. About Tessa Wolf Tessa Wolf is a creative brand and ...
About Wen Hsu As an immigrant woman who spent 15+ years in the engineering leadership role in the tech industry, Wen Hsu knows intimately the challenge that immigrant women experience. She lost herself in the quest of climbing the corporate ladder, felt the need to show up in a certain way to gain the recognition she deserved, exhausted from the constant need to prove herself. As she continued advancing in her career, she felt a part of her being rejected and unfulfilled. That’s why she turne...
Toni Dada witnessed the benefits of a career in consulting and immediately knew that’s what she would want to pursue. Toni worked tirelessly to combat “new girl” experiences and health challenges and rose to start her own successful growth and innovation studio. About Toni Dada Toni Dada, is the founder of Enterscale, a growth and innovation studio that supports founders with strategy and growth execution. Toni is a data enthusiast and commercial leader with diverse experience...
Katy McFee is the Founder and CEO of Insights to Action Coaching & Consulting. She spends time helping women become executives and thrive as senior leaders. Katy, in her own journey, struggled to get to the top tier of leadership. It seemed no matter how successful and results driven she was, that top layer was constantly just out of reach. Katy shares honestly about her experience and how she overcame the hurdles, ultimately becoming an ally to others who experience the same struggle(s)....
Sarah Haggard is Founder and CEO at Tribute. Though she has a track record of success, it’s been layered with personal complications along the way including assisting a parental figure through substance abuse struggles. Sarah took on the role of adult at a young age which she later discovered stunted her in many ways when it came to actually growing up and then having to navigate the workforce. About Sarah Haggard Sarah is an impact-driven entrepreneur focused on increasing access to educat...
This recording is a trailer for the second season of the F'ing Up Podcast. The host, Deanne Rhynard, shares what to expect from the show this season. Episodes will be released on Wednesdays every other week beginning on September 20, 2023. 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 infor...
Season 1, Episode 11 with Chris Efthymiou was originally released on June 7, 2023. Chris Efthymiou is a successful business leader founding companies and rising up the way through insurance and tech. Despite the success, he fought uphill to find confidence in his career. Being introverted, nervous to speak in front of others and suffering from self-titled, RAPS (right arm perspiration syndrome) gave him plenty to overcome all while trying to take NYC by storm and encountering the effects o...
Season 1, Episode 10 with Sarah Moses was originally released on May 24, 2023. Sarah Moses rose to success quickly. She is in her dream job, at a dream company, working in partnership with an amazing CEO. However, Sarah nearly threw the opportunity in the garbage can when she first declined the opportunity. Listen to learn more about Sarah’s journey. About Sarah Moses: Sarah Moses is the Chief Operating Officer at Prefect, a global leader in Dataflow Automation. Sarah oversees finance,...
Season 1, Episode 9 with Christy Johnson was originally released on May 10, 2023. Christy Johnson is an award winning educator and deeply experienced strategist, owning and operating her own firm. One interaction with her and you are immediately impressed by both her intellect and immense kindness. She is impossible not to like, her care for others speeps out and it’s no wonder she’s so accomplished. All that said, she’s had struggles and F’ing Up moments in her career. She doesn’t shy away...
Season 1, Episode 8 with Everette Fortner was originally released on April 26, 2023. Everette Fortner is a leader in the career management field, spending a bulk of his career at the University of Virginia both on the main and Darden campus. Prior to his career in the Education Sector he spent a great deal of his career in Consumer Packaged Goods, having a lot of fun including increasing Oreo brand presence in Asia and managing the Oscar Meyer Weinermobile program. Though his success is obv...
Season 1, Episode 7 with Emily Ellis was originally released on April 12, 2023. Emily Ellis has worked at many cool-kid tech companies such as Living Social, 2U, Social Code and Lyft. Despite the appeal of those popular names, Emily, like us all, experienced F’ing Up along the way. She shares many stories including being thrown into management, managing a team that needed more than she had by way of experience, and dealing with the emotional journey of infertility while aiming to build on ...
Season 1, Episode 6 with Tori Horton was originally released on March 29, 2023. From a sales associate at Ann Taylor to CEO of Reset Your Nest, Tori Horton shares her stories related to when we felt she was F’ing Up along her career journey. Tori opens up about experiences such as never successfully getting hired following submitting an application and how she got back on her feet while simultaneously ending a career and facing the end of a marriage. About Tori Horton: Tori Horton is a st...
Season 1, Episode 5 with Matt Tucker was originally released on March 15, 2023. Matt Tucker, Senior Vice President of Squarespace and the Head of Tock, has ridden the technology wave. He’s had a lot of success riding in the Tube, but he’s also been in the Impact Zone more than anyone would care to experience. Matt shares stories of choosing between his career and being more available for his family, becoming experienced at conducting employee RIFs, and wondering how his transportation busin...
Season 1, Episode 4 with Mary Hendricks was originally released on March 1, 2023. Mary Hendricks is a Stay At Home Mom (SAHM) and Social Media Influencer, A Very Mary Life, shares her career journey which right now means being a 24/7 in-home child caretaker and manager. Mary addresses the reality of being misunderstood and not taken seriously by some. She highlights that Imposter Syndrome doesn’t discriminate whether you have an in-office job or a job raising humans. She keeps things raw wi...
Season 1, Episode 3 with Scott Callender was originally released on February 15, 2023. There’s hardly anyone with more coffee knowledge and expertise than Scott Callender. He spent his entire career falling in love with the thing that most people consume everyday. His appreciation took him to find a career building and innovating machines to achieve the best in-home coffee experience. Though he’s reached success in his career in coffee, it hasn't all been easy or straightforward. F’ing Up m...
Season 1, Episode 2 with Sharon Cao was originally released on February 1, 2023. Sharon Cao is co-founder and COO of Happied. Though her company made the Techstars 2021 list, she was listed in Forbes’ Next 1000 list, and she wears a C-suite and founder title of a tech startup, Sharon acknowledges F’ing Up along her career journey. She shares experiences where struggled with self identity, not knowing how to do her job, and navigating personal relationships in the workplace. Sharon is not af...
Season 1, Episode 1 with Amy Wilkinson was originally released on January 24, 2023. Some of us only dream of walking by individuals like Idris Elba, Kristen Bell, Kevin Bacon, Padma Lakshmi, and Selena Gomez. Amy Wilkinson sits down with celebrities like these regularly. Amy has built her career on interviewing some of the hottest names in Hollywood and sharing those experiences through major publications like MTV News, Entertainment Weekly, Women's Health, Vanity Fair, Cosmopolitan, V...
Chris Efthymiou is a successful business leader founding companies and rising up the way through insurance and tech. Despite the success, he fought uphill to find confidence in his career. Being introverted, nervous to speak in front of others and suffering from self-titled, RAPS (right arm perspiration syndrome) gave him plenty to overcome all while trying to take NYC by storm and encountering the effects of 9-11. About Chris Efthymiou Chris Efthymiou has been a Founder, Co-Founder, ...
Sarah Moses rose to success quickly. She is in her dream job, at a dream company, working in partnership with an amazing CEO. However, Sarah nearly threw the opportunity in the garbage can when she first declined the opportunity. Listen to learn more about Sarah’s journey. About Sarah Moses: Sarah Moses is the Chief Operating Officer at Prefect, a global leader in Dataflow Automation. Sarah oversees finance, operations, legal, and HR functions. She is responsible for scaling the orga...
Christy Johnson is an award winning educator and deeply experienced strategist, owning and operating her own firm. One interaction with her and you are immediately impressed by both her intellect and immense kindness. She is impossible not to like, her care for others speeps out and it’s no wonder she’s so accomplished. All that said, she’s had struggles and F’ing Up moments in her career. She doesn’t shy away from sharing about those experiences and knowing she’s come out better for them. ...
Everette Fortner is a leader in the career management field, spending a bulk of his career at the University of Virginia both on the main and Darden campus. Prior to his career in the Education Sector he spent a great deal of his career in Consumer Packaged Goods, having a lot of fun including increasing Oreo brand presence in Asia and managing the Oscar Meyer Weinermobile program. Though his success is obvious, Everette faced many of the hurdles that we face in our careers: accepting jobs th...
Emily Ellis has worked at many cool-kid tech companies such as Living Social, 2U, Social Code and Lyft. Despite the appeal of those popular names, Emily, like us all, experienced F’ing Up along the way. She shares many stories including being thrown into management, managing a team that needed more than she had by way of experience, and dealing with the emotional journey of infertility while aiming to build on her career success. About Emily Ellis: Emily Ellis is a People and Operations ent...
From a sales associate at Ann Taylor to CEO of Reset Your Nest, Tori Horton shares her stories related to when we felt she was F’ing Up along her career journey. Tori opens up about experiences such as never successfully getting hired following submitting an application and how she got back on her feet while simultaneously ending a career and facing the end of a marriage. About Tori Horton: Tori Horton is a startup veteran with over 20 years of experience working to launch early-stage compa...
Matt Tucker, Senior Vice President of Squarespace and the Head of Tock, has ridden the technology wave. He’s had a lot of success riding in the Tube, but he’s also been in the Impact Zone more than anyone would care to experience. Matt shares stories of choosing between his career and being more available for his family, becoming experienced at conducting employee RIFs, and wondering how his transportation business would survive immediately following the impacts of September 11. It should com...
Mary Hendricks is a Stay At Home Mom (SAHM) and Social Media Influencer, A Very Mary Life, shares her career journey which right now means being a 24/7 in-home child caretaker and manager. Mary addresses the reality of being misunderstood and not taken seriously by some. She highlights that Imposter Syndrome doesn’t discriminate whether you have an in-office job or a job raising humans. She keeps things raw with the hope of creating community and rebuilding the village that society has lost. ...
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