#285 Steve Monaghan: The Advantage of Age in the Age of AI

Steve Monaghan flips the script on innovation culture: experience isn’t a relic—it’s a strategic edge. 

As General Partner at FinMir.ai, Limited Partner at True Global Ventures, Independent Non-Executive Director at RAK Bank, and former Chief Digital Officer at both AIA and DBS Bank, Steve brings a cross-industry view forged through decades of deep transformation. From aviation to fintech to AI, he shows how age fuels better questions, sharper pattern recognition, and global insight in a world obsessed with novelty. 

Whether he’s building Asia’s first unicorn or designing systems that could restructure entire economies, Steve makes one thing clear: for Gen Xers tired of being underestimated, age isn’t a liability—it’s leverage.

>>Built to Learn, Not to Fit

“I wasn’t hired for my experience. I was hired for the questions I knew how to ask.”

Steve’s journey—from pilot to pricing guru to product architect—was never about titles. It was about learning faster than the system could teach him.

>>From N-O to K-N-O-W

“People don’t fear change. They fear not understanding it.”

Steve shares his framework for flipping resistance into insight. At DBS, it became a model: learning, venturing, capital. The goal? Turn skeptics into innovators.

>>Legacy Is Not a Headline

“This isn’t my next startup. It’s my swing-for-the-fences play.”

Steve’s current project could restructure economies by eliminating capital inefficiencies in payroll and supply chains. It’s big, bold—and designed to help the people most hurt by broken systems.

>>The Advantage of Age in the Age of AI

“Older workers know how to ask better questions. That’s the advantage.”

Forget the ageist myth. Steve explains why mature employees are becoming AI’s secret weapon—and why experience, not just coding, is the multiplier.

>>Mental Health Is Not a Risk Factor—It’s a Design Factor

“You can’t build resilient companies without resilient founders.”

As an investor, Steve supports founders with integrity, grit, and humility. That includes stepping back when needed—and being asked, not judged, for how you feel.

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Host: Vince Chan | Guest: Steve Monaghan

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