Lay of The Land #210: Umberto Fedeli Round III — Patience & Persistence, Progress & Perfection, Rationality & Uncertainty
I’m very excited to welcome Umberto Fedeli back for his third conversation. In our first two conversations — episode 135 and episode 171 — we explored Umberto’s remarkable life journey, deep-rooted wisdom, and how he's mastered the craft of building authentic relationships and connecting people across business, politics, and philanthropy. Those episodes are timeless and packed with valuable insights — I highly recommend listening to them to set the stage for today’s discussion.
In this episode, we delve deeper into these foundational ideas, unpacking the origins of Umberto’s relentless commitment to relationships, mentorship, and personal growth. We explore how to navigate the delicate balance between patience and persistence, between progress and perfection, and ultimately, how to cultivate resilience and rationality during times of uncertainty. We also dive into Umberto's perspective on the current state of the world — from economics and politics to tariffs. We talk about volatility, the fundamental human need for love and connection, regrets, legacy, and much more.
Please enjoy this insightful, continued discussion with Umberto Fedeli.
On a technical note, due to unexpected issues with our recording equipment at the time of this session, portions of the episode were lost. These segments have been audibly enhanced using speech technology in an effort to restore clarity and continuity. We appreciate your understanding regarding any subtle auditory or phonetic inconsistencies.
-----
LINKS:
https://www.thefedeligroup.com/
-----
SPONSOR:
Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.
Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.
Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.
Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.
-----
Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.
Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.
Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/
Follow Lay of The Land on X @podlayoftheland