Guest: Ryan Frederick

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/