Guest: Ryan Frederick

What if I told you the most successful CEOs I've interviewed this quarter share one counterintuitive trait? They don't try to be the smartest person in the room. From architecture to military leadership to digital transformation, the pattern is unmistakable. 
Looking back at this quarter's most listened-to episodes—featuring Jonathan Moody (Moody Nolan), Rear Admiral Brian Luther (Navy Mutual), Ryan Frederick (Transform Labs), Harold Green (Global Emissionary), Eddie Solomon (Net at Work), Joe Yaccarino (MTF Biologics), Jeff Ostenso (Ironmark), and James Hyman (serial turnaround CEO)—I discovered something remarkable.
The golden thread connecting every transformative leader: They refuse to be the smartest person in the room.
From Jonathan's "create more footprints, not bigger shoes" philosophy to Brian's "reflected light leadership," from Ryan's embrace of "continuous not knowing" to Eddie's insight that "entrepreneurship belongs in psychology," these leaders share seven powerful traits:
→ Anti-ego leadership - Building teams instead of thrones→ Vulnerability as strength - Admitting what they don't know→ Empowerment over control - Creating conditions for others to succeed→ Psychological wisdom - Understanding leadership is about mindset→ Radical transparency - Building trust through openness→ Purpose-driven growth - Companies that matter, not just profit→ The learning advantage - Staying curious regardless of expertise
Whether it's Harold at 69 still having daily learning conversations, Joe asking "is that even legal?" and building from curiosity, Jeff realizing his company "feeds 500 people," or James discovering that Hollywood leadership doesn't work—the pattern is clear.
The most successful leaders amplify their impact by avoiding being the bottleneck.
Join me as we unpack the strategies that turn good companies into thriving communities where everyone succeeds together.
Some of the episodes in this list:
EP105: Reflected Light: Leading Through Your People
EP103: The Power of Humble Listening in Leadership
EP96: Making Carbon Reduction Measurable and Meaningful
EP87: Why This Successful Family Business Said No to Nepotism
EP83: Heroes at Every Level of Healthcare Innovation
EP81: How Teaching the Game of Business Built an Empire
EP63: A CEO’s Competitve Edge - Mastering the Art of Corporate Turnarounds
 
 
 

In last week's conversation with Ryan Frederick, Principal of Transform Labs, we explored the delicate balance between expertise and humility. Ryan shares how the companies that failed in his experience often stumbled due to assumption-driven leadership rather than curiosity-driven validation.
"I think there's a lot to be said in approaching things in a humble manner where you don't assume that you know," Ryan reflects. "You actually assume that you don't know and you're just sort of on a journey of continuous not knowing, but making progress along the path."
This commentary focuses on the key point of how genuine success comes not from positioning oneself as the expert with all the answers, but from creating effective conversations between systems, between people, and between organizations. As we navigate an era of unprecedented technological change and potential disruption, Ryan reminds us that while we get paid for what we know, the future belongs to those who remain open to what they have yet to discover.
Listen to his full episode here.
About Ryan Frederick:
Ryan Frederick, Principal at Transform Labs, is an entrepreneur, author, speaker, and advisor renowned for exploring technology’s impact on global economics, politics, labor, and society. With deep expertise in digital transformation, he has successfully founded, built, and invested in multiple technology companies. Ryan authored two influential books, "The Founder's Manual" and "Sell Naked," and regularly discusses AI’s macroeconomic and societal implications. Passionate about social impact, he founded i.c.stars, a nonprofit training under-employed adults in digital skills. Ryan’s experience uniquely positions him as a compelling voice on how technology reshapes economies, labor markets, and political landscapes worldwide.
Connect with Ryan on LinkedIn: https://www.linkedin.com/in/ryangfrederick/

Deborah Fell connects with Ryan Frederick of Transform Labs about strategic technology implementation. Ryan positions his firm as independent advisors rather than product reps, ensuring "our advice to clients is in the best interest of the client."
Ryan captures the uncertainty many CEOs face with a compelling metaphor: "It's almost like being in the woods on a foggy trail... you're not sure if you should turn right or left or if you should wait for the fog to sort of dissipate."
What makes this conversation valuable is Ryan's candid reflection on failures and how ego-based assumptions derailed even previously successful ventures. His advocacy for "continuous not knowing" offers a counterintuitive but powerful framework for leaders.
The episode explores why challenging clients with education, prioritizing questions over answers, and genuinely serving client interests separate successful professional services firms from the rest. Ryan concludes by discussing his book Sell Naked, which advocates stripping away "fancy pitch decks" to focus on authentic understanding of client needs.
About Ryan Frederick:
Ryan Frederick, Principal at Transform Labs, is an entrepreneur, author, speaker, and advisor renowned for exploring technology’s impact on global economics, politics, labor, and society. With deep expertise in digital transformation, he has successfully founded, built, and invested in multiple technology companies. Ryan authored two influential books, "The Founder's Manual" and "Sell Naked," and regularly discusses AI’s macroeconomic and societal implications. Passionate about social impact, he founded i.c.stars, a nonprofit training under-employed adults in digital skills. Ryan’s experience uniquely positions him as a compelling voice on how technology reshapes economies, labor markets, and political landscapes worldwide.
Connect with Ryan on LinkedIn: https://www.linkedin.com/in/ryangfrederick/