The Real F Word

10. Lost My Business and Almost Lost Myself | Levi Lindsay

Levi Lindsay, former cofounder of VidArmy and now CMO at Hona, sat down with Joe Grover to share his story of how he started VidArmy. Believing hustle would lead to success, he worked for years without pay but unfortunately battled cofounder disputes and lost himself in the process. As a recent college graduate, Levi started VidArmy after getting the idea from a friend. The first few years went well as they slowly gained clients and eventually added two more partners—without an official partner agreement—and a CEO. When COVID hit, a government loan provided their first real working capital. Instead of stabilizing the business, it fueled over-expansion and bad hires and forced the partners to work without a paycheck. Levi found himself on the edge of burnout and suffering panic attacks when one partner demanded a permanent 6% of future revenue. He had built his entire identity around VidArmy, convinced that walking away meant failure. But everything changed when he finally decided to step away as his wife requested, “I just want my husband back.” From his experiences, Joe and Levi discuss the importance of giving yourself permission to quit in order to find yourself again. They explore the dangers of the sunk-cost fallacy, how some leaders deplete themselves to the point of losing who they are, and the trap of the “I’ll be happy when” mentality. Links: Levi Lindsay: LinkedIn (https://www.linkedin.com/in/levilindsay/ [https://www.linkedin.com/in/levilindsay/]) Joe Grover: LinkedIn (www.linkedin.com/in/joelgrover/ [http://www.linkedin.com/in/joelgrover/]) This episode is sponsored by Amplēo, offering fractional executives in finance, marketing, and HR. Visit ampleo.com [http://ampleo.com] to learn more. Chapters: [0:00 - 1:44] Intro [1:44 - 5:26] The Birth of VidArmy and Early Struggles [5:26 - 10:44] Scaling Up [10:44 - 28:55] Partnerships, Paychecks, and Panic Attacks [28:55 - 41:53] The Breaking Point and Letting Go  [41:53 - 46:05 ] The Aftermath and Personal Recovery [46:05 - 57:59] I’ll be happy when . . . [46:05 - 1:00:00] Permission to Quit #TheRealFWord #PermissionToQuit #Failure #Entrepreneurship

9. Failure Isn’t the Real F Word, Fear Is | Kortney Osborne

In this episode, Kortney, a partner at Amplēo and former marketing executive at Qualtrics and Weave, flips the script on failure, believing that the real F word isn’t failure—it’s fear. From bombing on stage as a stand-up comedian to marketing ahead of product at Qualtrics, Kortney shares how embracing failure helped her iterate, learn, and ultimately drive success. At Qualtrics, she played a key role in pushing the company’s vision beyond what the product could do at the time, forcing innovation to catch up. She also helped launch X4, bringing in Barack Obama and Oprah Winfrey as keynote speakers. At Weave, she went through four CEOs in 12 months and witnessed firsthand how ego, fear-based decision-making, and reactive layoffs can damage a company’s culture in ways that some businesses never recover from. She reflects on moments in which she let fear and ego dictate her own responses and shares how therapy and self-awareness helped her shift toward leading with belief and intention. Throughout the conversation, Joe and Kortney dive deep into leadership, ego, and the cost of short-sighted decisions, whether in startups or personal growth. Kortney also shares her “First Fridays” practice—a commitment to actually enjoying the life she’s working so hard to build—as a way to combat fear and burnout. Links: Kortney Osborne: LinkedIn (www.linkedin.com/in/kortneyosborne/ [https://www.linkedin.com/in/kortneyosborne/]) Joe Grover: LinkedIn (www.linkedin.com/in/joelgrover/ [http://www.linkedin.com/in/joelgrover/]) This episode is sponsored by Amplēo, offering fractional executives in finance, marketing, and HR. Visit ampleo.com to learn more. Chapters: [0:00 - 0:49] The Real F Word Isn’t Failure—It’s Fear [0:49 - 2:40] Lessons from Stand-Up Comedy [2:40 - 18:59] Marketing at Qualtrics & Launching X4 [18:59 - 35:28] Fear-Based Decisions & Ego [35:28] - 39:51] Patterns of Failure in Business Growth [39:52 - 54:55] Redefining Success: First Fridays & Living with Intention #RealFWord #FearVsFailure #EntrepreneurMindset #OvercomingFear

8. What Defines You? From Startup Struggle to Venture Capitalist Success | Kristy Muir

In this episode of The Real F Word, venture capitalist Kristy Muir shares her deeply personal and inspiring journey of resilience, failure, and growth. Kristy opens up about the defining moments of her life—from navigating single motherhood on welfare and struggling to provide for her daughters to exiting her first startup. She reflects on the tough lessons learned through her entrepreneurial journey, her transition into tech leadership, and her current role as a venture investor. Kristy’s story is one of grit, vulnerability, and triumph. She discusses recognizing failure patterns, the importance of listening to customers, and the power of storytelling in business. Most memorably, she shares how a $30 pink tinsel Christmas tree became a lasting symbol of hope and light during the hardest times. Tune in for an honest, insightful conversation about overcoming adversity, embracing the hard, and building a life of purpose and impact. About Kristy Kristy is a seasoned senior executive and investor at Pelion Venture Partners. With a proven track record in customer experience, M&A, strategy and operations, she has successfully overseen multimillion-dollar business acquisitions and cross-functional teams of 70+ across five countries. This episode was recorded on December 6th, 2024. -Links- For (Kristy Muir): https://www.linkedin.com/in/kristylmuir/ For (Joe Grover): https://www.linkedin.com/in/joelgrover/ #RealFWord #Venture Capitalist #Failure #Hardearnedwisdom #Startup #Founder #Entrepreneur.

7. Sentenced to Life in a Maximum-Security Prison | Damon West

Joe Grover sits down with Damon West—3-time Wall Street Journal best-selling author and one of America’s most sought-after speakers—to explore the devastating impact of failure and the power of redemption. Damon shares his journey from having it all to losing everything after receiving a life sentence in a Texas maximum-security prison (talk about FAILURE.) They unpack the hard-hitting lessons Damon learned during his seven years behind bars and how the transformative "Coffee Bean" mindset helped him rebuild his life. With profound insights on overcoming failure, Damon inspires everyday entrepreneurs to turn their lowest moments into fuel for success. Links: Damon West: Instagram [https://www.instagram.com/damonwest7?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==] | LinkedIn [https://www.linkedin.com/in/damon-west-685168152] | Website [https://damonwest.org/] Joe Grover: LinkedIn [https://www.linkedin.com/in/joelgrover/] #RealFWord #OvercomingFailure #CoffeeBeanMindset #EntrepreneurInspiration Speaker Bio: Damon West, M.S. Criminal Justice, is an internationally known keynote speaker, 3 times Wall Street Journal bestselling author, and former crime boss in Dallas, who was sentenced to Life in prison for Organized Crime. USA Today calls him the “modern-day Shawshank Redemption and the most in-demand speaker in America.”  At 20 years old, he was a Division 1 starting quarterback at the University of North Texas, when he suffered a career-ending injury and turned to hardcore drugs to cope with disappointments of life. After graduation, he worked in the United States Congress and trained to be a stockbroker for United Bank of Switzerland (UBS).One day at UBS, he was introduced to methamphetamines; he became instantly hooked—and the lives of so many innocent people would forever be changed by the choices he made in order to feed his insatiable meth habit. After a fateful discussion during his incarceration with a seasoned convict, Damon had a spiritual awakening. He learned that, like a coffee bean changing with the application of heat and pressure, he was capable of changing the environment around him. Armed with a program of recovery, a renewed faith, and a miraculous second chance at life, Damon emerged from over seven years of prison a changed man. On parole in Texas until 2073, his story is one of hope, redemption, grit and the resilience of the Human spirit.

6. 92 Pitches, 18 Months, and a Shutdown | Jake Bengtzen

What happens when an ambitious startup faces the harsh reality of an insurmountable problem? In this episode, Joe Grover engages in a candid conversation with Jake Bengtzen, the founder of Zipper, as they explore the painful journey of his healthcare fintech startup. After 92 pitches, seven investors, and 18 months of relentless effort—during which Jake paid himself only three times—he ultimately hit rock bottom. After he launched Zipper Health with the goal of lowering healthcare costs for individuals and families, he faced challenges that proved overwhelming. Jake shares the moment he realized that the multitrillion-dollar healthcare issue was too vast to tackle and that it was time to shut down Zipper. Reflecting on his experience, he states, “There are a lot of people who choose unhappiness over uncertainty,” emphasizing the importance of what one chooses to do after experiencing failure. This episode dives deep into the emotional and psychological aspects of shutting down a dream. Jake discusses how failure shaped his perspective on entrepreneurship and resilience, offering insights into the difficult decision to pivot after such an investment of time and energy. Join them as they unpack the lessons learned from failure and what lies ahead for Jake as he contemplates his next steps in making a meaningful impact in the world. Links: Jake Bengtzen: LinkedIn [https://www.linkedin.com/in/jake-bengtzen-0a8ab365/] (https://www.linkedin.com/in/jake-bengtzen-0a8ab365/ [https://www.linkedin.com/in/jake-bengtzen-0a8ab365/]) Joe Grover: LinkedIn [https://www.linkedin.com/in/joelgrover/] (https://www.linkedin.com/in/joelgrover/ [https://www.linkedin.com/in/joelgrover/]) This episode is sponsored by Amplēo. Amplēo offers fractional executives in finance, marketing, and HR to companies of all sizes. Visit ampleo.com [http://ampleo.com/] to learn more.