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/)

Joe Grover: LinkedIn (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