18: Startup Fails, Shark Tank Tales, and Bad Boss Moments

This week on Bad Boss Confessional, host and EOS Implementor Beth Fahey sits down with Mike Shannon, CEO of Impruve and author of Sweaty Equity. From surviving Shark Tank to opening his first businesses, Mike opens up about his cringiest leadership missteps, the chaos of scaling to 120 employees, and how embracing systems thinking (and a few bad boss moments) helped him grow as a leader. Expect startup war stories, EOS insights, and a fresh look at how AI is transforming financial advising.

 

00:00 From Ball Boy to Shark Tank 04:11 Early Entrepreneurial Challenges 10:47 Optimizing Executive Team Meetings 17:48 Impact of Structured Meetings 24:25 Improve: AI for Financial Advisors 36:04 Fear, Failure, Pain, and Systems

 

About: Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube: https://www.youtube.com/@badbossconfessional Beth's Youtube:  https://www.youtube.com/@bethfaheyeos   Guest Links CEO at Impruve | Author of ‘Sweaty Equity: A Ball Boy, A Billionaire, and the Bonkers Startup Tale You’ve Never Heard’ LinkedIn: https://www.linkedin.com/in/mikeshannon101/ Email: mike@impruve.com

 

Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible:

• Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies.
• Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.