Learning as You Go: How Entrepreneurs Thrive Through Uncertainty

What if the secret to success isn’t having all the answers, but embracing the unknown?

In this episode of The Overlap Podcast, hosts Sid Sexton and Keith Glines dive deep into what it really means to learn as you go in business, fitness, and life. From messy starts and stubborn pivots to the surprising lessons of parenting and jiu-jitsu, they reveal why staying open-minded and humble might be the most valuable skill an entrepreneur can develop.

You’ll hear candid stories about running companies without perfect plans, pivoting when things don’t work, and keeping momentum even when failure feels relentless. This is a raw, practical look at how growth often comes from trial, error, and the courage to keep going.

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What You Will Learn

• Why entrepreneurs must get comfortable with ambiguity and limited information.

• The fine line between stubbornness and knowing when to pivot.

• How parenting and jiu-jitsu mirror the challenges of business ownership.

• Practical strategies for controlling negative self-talk.

• Why humility and openness to younger voices can fuel long-term success.

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Key Topics Discussed

• The role of mental health in an entrepreneur’s ability to pivot.

• Why making money quickly is usually a myth in business.

• The danger of ignoring market signals (Henry Ford’s “buggy whip” lesson).

• How new creative tools like Canva are replacing old standards like Photoshop.

• What parenting teaches us about learning on the fly.

• How resilience in jiu-jitsu reflects resilience in entrepreneurship.

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Memorable Quotes

• “If you’re going to be an entrepreneur, you have to be okay operating with limited information.” – Sid

• “Competition—whether in business or jiu-jitsu—is mostly mindset. If you just keep showing up, eventually you get there.” – Keith

• “It takes humility to know you don’t know everything—and that you can learn from everyone.” – Sid

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