In this episode, Rob sits down with Kurt Wilkin—entrepreneur, advisor, and author of Who's Your Mike?—to unpack what it really takes to scale a business with the right team. Kurt shares why so many CEOs stall their own growth by holding onto the wrong people for too long, what “hiring better” actually looks like, and how to level up your leadership by embracing self-awareness. It’s a candid, BS-free conversation from someone who’s helped hundreds of founders build companies that grow—and last.

About the Guest

Kurt Wilkin is the co-founder of HireBetter, a strategic talent partner for growth-minded companies, and managing partner at Bee Cave Capital. With decades of experience advising entrepreneurs, Kurt brings a plainspoken, no-nonsense approach to leadership and scaling. He’s also the author of Who’s Your Mike?, a guide for founders navigating the messy human side of business growth.

Episode Highlight

“Who got you here won’t always get you there.”

Actionable Insights

• “Hiring better” starts with strategy, not resumes: Before posting a job, ask: Where are we going—and who do we need around the table to get there? [03:35]
• Next-level talent changes everything: Bringing in one experienced, high-performing leader can shift your company’s entire trajectory. [05:57]
• Founders need self-awareness to scale: If you think you’re the smartest person in the room, you're probably limiting your own growth. [08:35]
• Conflict-avoidant? You’ll struggle with legacy hires: Kurt shares how to approach tough conversations with longtime team members who’ve outgrown their role—with empathy and clarity. [09:14]

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More About Kurt Wilkin

Check out HireBetter. Connect with Kurt on LinkedIn.

More About Rob Levin & WorkBetterNow

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