Entrepreneur, author, and former telecom executive Roy Osing joins me to talk about what it really means to survive getting the shit kicked out of you—and why meaningful differentiation is the only durable way back.
Most business conversations focus on growth tactics or recovery platitudes. This episode doesn’t. Roy and I walk through the reality of being demoted, sidelined, and underestimated—then rebuilding leverage not through ego or exits, but through performance, patience, and strategic clarity.
Roy shares how he helped grow an early-stage data and internet company to over a billion dollars in revenue, not by following playbooks, but by rejecting them. We break down why “blue ocean” thinking fails in the real world, how copying successful companies turns you into a commodity, and why differentiation only matters if customers actually care.
The conversation moves from corporate power dynamics to entrepreneurship, where Roy dismantles the myth that success comes from speed, scale, or selling quickly. Instead, he argues for building an “only” value proposition—one that satisfies customer cravings, not abstract needs—and for staying in the fight long enough to earn trust, credibility, and leverage.
This isn’t a story about avoiding failure. It’s about what to do after you hit the wall: when titles disappear, leverage evaporates, and the only thing left is how you perform when no one owes you anything.
The lesson isn’t bravado or revenge.
It’s humility, focus, and building something that can’t be copied.
TL;DR
Everyone who builds something meaningful gets knocked down eventually
Differentiation only works if customers actually care about it
Copying winners turns businesses into commodities with shrinking margins
“Blue oceans” are academic fantasies without practical execution
Real leverage comes from performance after setbacks, not ego or exits
Customers buy based on emotional cravings, not rational needs
Being “different” without value is just narcissism
The goal isn’t to stand out—it’s to be the only one who does what you do
Memorable Lines
“Be different or be dead.”
“Copying success is a form of insanity.”
“What you think of yourself doesn’t matter—what customers crave does.”
“If you stay after the demotion, you earn leverage through performance.”
“Differentiation without value is just narcissism.”
Guest
Roy Osing — Entrepreneur, author, and former telecom executive
Author of Be Different or Be Dead and six other books on practical business differentiation. Former senior executive who helped scale a data and internet company to over $1B in revenue, now advising leaders on building category-of-one strategies.
🔗 Website: https://www.roosing.com
🔗 LinkedIn: Roy Osing
Why This Matters
Modern careers don’t fail cleanly. They fracture.
Titles vanish. Strategies stop working. The market stops caring. What determines who survives isn’t confidence or speed—it’s whether you can perform, adapt, and rebuild value when your leverage is gone.
This episode reframes failure not as a personal flaw, but as an inevitable checkpoint. For founders, operators, and executives navigating volatility, Roy’s story offers a sober alternative to hustle myths: build something people crave, stay useful when it hurts, and let performance—not narratives—restore power.
Reinvention isn’t about starting over.
It’s about becoming impossible to ignore.
