Episode #44: When the Pie Crumbles: What One Entrepreneur Learned About Leading Teams and Starting Over

What do pies, poetry, and global equity have in common? In this candid and compelling episode of Missing Conversations, hosts Amy Vodarek and Steven Jones welcome Paul O’Donnell, a former investment banker turned entrepreneur, and Sylvana Caloni, a leadership coach and former equity analyst, to explore the real story behind their book Humble Crumbles. Paul shares his rollercoaster journey of building—and ultimately shutting down—a gourmet pie business, while Sylvana offers sharp, reflective insights into the leadership habits that quietly make or break companies. Key Moments You’ll Want to Hear: 02:01 – Entrepreneurship and poetry? Paul and Sylvana connect the dots—why both require bold, nonlinear thinking. 04:04 – Sylvana uncovers the leadership gaps behind company failures. 09:22 – When the money runs low: Paul on facing financial challenges and reinventing the plan. 13:00 – Paul on discovering the power of listening to build a stronger team. 15:27 – Meet your new favorite advisors: Sylvana introduces the “positive naysayers” every leader needs. 20:30 – Numbers don’t lie, but they don’t tell the whole story. Sylvana on self-analysis as a business strategy. 23:42 – The importance of balancing a mood of possibility and collaborative engagement. 25:34 – Business failed, but I didn’t: Paul’s honest take on identity, loss, and starting over. 28:35 – Creating the conditions for clarity: Sylvana on how self-awareness and boundaries lead to optimal decisions. 34:56 – Want better teams? Have a conversation about motivations, expectations, and boundaries. Sylvana breaks down “Designing an Alliance.” 40:05 – Test. Learn. Tweak. Sylvana’s method for minimizing risks and building resilience. 43:55 – Your business is not your identity, and the value of renegotiating commitments when necessary. Leadership isn’t a solo game. It’s a team sport. ~ Sylvana Caloni About Paul O’Donnell Paul is an investment banker turned business consultant with decades of experience in Australia, the UK, and the USA in strategic leadership and business development for multinational financial institutions. He is also a serial entrepreneur, and mentors owners of small to medium-sized enterprises and students of entrepreneurship, He is a published author and a poet. Connect with Paul on LinkedIn: https://www.linkedin.com/in/paulmodonnell/ or Instagram: @pod.the.poet About Sylvana Caloni Sylvana Caloni is a leadership coach who works with clients internationally. In her early career in global financial markets, she was a bond dealer, equity analyst, and fund manager. She blends insights from the fast-paced financial services world and the latest training on learning and development to enable entrepreneurs, executives, and self-starting individuals to become more self-aware, more effective and more successful. Connect with Sylvana: https://www.linkedin.com/in/sylvanacaloni/ https://sylvanacaloni.com/ https://sylvanacaloni.com/humble-crumbles/ About the Book Growing Groups Into Teams: How do you turn a group of individuals into a highly effective, productive team? Growing Groups Into Teams is an unusually useful book written by a team of generative consultants and coaches who have helped thousands of groups become effective teams. Through real-life stories combined with pragmatic advice, this book strengthens your ability to see what’s needed and take effective action: What two promises turn a group into a team. How to engage people to make those promises. How to invite responsibility and accountability. How to include and inspire people across differences. How to build and rebuild trust, and more! Regardless of how productive your teams are today, the insights in this book will help you grow to the next level to drive your business or organization forward. Order your copy today! Order from Amazon: https://www.amazon.com/Growing-Groups-into-Teams-Real-life-ebook/dp/B0CJLC23VS Order directly: https://shop.ingramspark.com/b/084?l8SxF4Aexn9gq08iz7jFBbwutleujrftoZ2wAOFzCVH If you're looking to expand your leadership influence, shift your results, and develop a highly engaged, accountable team, we’d love to talk to you. Schedule a conversation with an Altus Team Member here: https://calendly.com/prollin-altusgrowth/zoom-video-30-min Follow us on social media: https://www.linkedin.com/company/altus-growth-partners https://www.facebook.com/AltusGrowth https://www.instagram.com/altusgrowthpartners/ Keywords: #Entrepreneurship #Leadership #Creativity #TeamBuilding #DecisionMaking #Resilience #SelfAwareness #BusinessChallenges #Mindset #OptimalDecisionMaking #GrowthMindset