In this live Case Studies event, Casey Baugh sits down with Jeff Kearl—entrepreneur, investor, and brand builder behind Skullcandy and Stance—to unpack the foundational principles of long-term business success. From early mentorship to building culture-first companies, Jeff shares the pivotal moments and hard-won lessons that shaped his journey.

Jeff dives into the power of believing in young talent, the pain of early failure during the dot-com crash, and why he swore never to build a business dependent on outside capital again. He shares frameworks for hiring based on cultural alignment, building leadership without ego, and how customer conviction drives real investment decisions. With personal stories, investment insights, and startup war stories, this episode is a masterclass in resilience, intentionality, and brand-building.

Chapters:

00:00 | Opening & Setting the Stage

00:45 | Early Days at Covey Leadership Center

02:30 | Lessons from Early Mentors

05:15 | Founding Freeport & The Dot-Com Crash

08:00 | Building Culture as a Differentiator

10:30 | Brand Strength Starts Inside

13:00 | From Operator to Venture Capitalist

15:00 | Building LogoWorks & Getting Acquired by HP

17:45 | The Skullcandy Bet & Power of Counter Positioning

20:30 | Pelion Capital & Investing in Digital Scarecrows

23:00 | Frameworks for Long-Term Leadership

26:00 | Building Stance and Redefining Culture

31:00 | Operating Without Ego and Hiring Right

37:00 | Fundraising and Bootstrapping Philosophy

42:00 | Building Boards and Governance the Right Way

48:00 | Investing with Conviction, Not Consensus

54:00 | Identifying the Next Big Consumer Trends

01:00:00 | Lessons from Failures and Personal Growth

01:07:00 | What Makes a Founder Exceptional

01:14:00 | Personal Operating System and Decision Frameworks

01:21:00 | Jeff’s Advice for Young Builders and Investors

01:30:00 | Final Reflections and Jeff’s Legacy

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