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Audacious Execution: Roy Osing's Secrets to Building a Business with a Billion in Annual Sales



Be Different or Be Dead: The Audacious Path to Business Success with Roy Osing


On the latest episode of Pathways with Amber Stitt, guest Roy Osing shared a bold perspective that flips conventional business wisdom on its head. As a former president leading his company from startup to over a billion in annual sales, Roy’s playbook isn’t filled with complex strategies you’ll find in MBA textbooks. Instead, he champions actionable, simple truths—chief among them, the art of being “different” in ways that truly matter.


The Power of a “Human Being Lover”


Roy’s journey is peppered with powerful, almost counterintuitive insights. Central to his philosophy is the idea of hiring and empowering what he calls “human being lovers” (HBLs). In Roy’s world, dazzling customer service doesn’t happen by accident or through rigid scripts—it’s delivered by people who genuinely care about others. As he puts it, “You can’t train people to love people. You can train them how to have a smile in their voice, or grin, but you can’t teach them love, right?”


To identify these HBLs, Roy developed his signature “Hiring for Goosebumps” approach. Rather than relying on resumes, or canned interview answers, he asks candidates to tell stories that reveal their innate empathy and love for serving others. If the story gives him goosebumps, he knows he’s found the right person. This passionate approach helped develop a company culture where the customer experience became legendary.


Simple Acts, Massive Impact


Amber and Roy debunked the myth that audacity in business is reserved for founders or entrepreneurs. Roy emphasized, “Anybody can do this. But you have to believe that pain is a strategic concept.” Standing out requires a willingness to go against the grain—to take risks, weather criticism, and care more about impact than popularity.


One of his most memorable stories recounted a service failure where his team accidentally caused a major outage for a key client. Instead of hiding from the mistake, or looking for cover, Roy visited the client in person, delivered a $30,000 check, and—most importantly—gifted a cherished retro phone the client had always wanted. The result? Not only was the relationship salvaged, but the client became an evangelist for Roy’s company, spreading referrals and goodwill well beyond a single business transaction.


The key? Don’t run from mistakes; lean into them with integrity and genuine empathy. “If you understood the power of an ‘oops,’ you would have a strategy in place to leverage that mistake into creating a more loyal customer,” Roy explains.


Innovation and Differentiation from Within


You don’t need to be a CEO to make a mark. Roy argues that every employee—regardless of role—can cultivate “the be different lens.” By waking up each morning and asking, “What is the one thing I could do differently today?” you encourage creativity and ownership, sparking a quiet revolution from within.


He warns that conformity and complacency are the real killers in business—not external threats or cost pressures. “If you’re not different, you’re dead. Or soon will be.” Roy’s approach focuses relentlessly on delivering value in ways competitors haven’t imagined, playing into what people crave—not just what they “need.”


Mentorship and the “Only Statement”


Roy also advises seeking mentors who have a proven record of business achievement, not just academic prowess. His own litmus test for businesses boils down to one simple challenge: Define your “Only Statement.” Rather than claiming to be the best, or number one, clarify how you are the only one to provide a unique solution. Technology isn’t enough; relevance and distinctiveness are the ultimate survival tools.


Legacy of Audacity


Roy’s wisdom isn’t about being different for its own sake—it’s about aligning your actions with real-world needs and unleashing a culture of servant leadership, innovation, and relentless execution. If you want businesses and careers that leave a mark, it starts with caring deeply, acting boldly, and never shying away from the pain of pushing boundaries.


Timestamped Overview:

00:00 Treasured Collectible Named Albert

04:51 Mother's Resilient Influence

08:41 Trench-Level Leadership Essentials

11:01 "Shifting Marketing Strategy and Mishap"

14:43 Intrapreneurship Within Organizations

18:00 Embracing Big Energy in 40s

20:24 "Context-Driven Strategic Leadership"

25:15 Genuine Empathy vs. Superficiality

26:03 Goosebumps Hiring Process Critique

30:01 The Importance of Startup Differentiation

33:31 Redefining Target Market Needs

35:42 Exploring Goosebumps and Thoughtful Remarks


🔗 To connect with Roy Osing:







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