#54 What is Success? | Stoppage Time with Uncle Rob

Entrepreneurial Thinkers with Rob Ryan

This week’s episode is a deep, honest, and timely reflection on the thin line between success and failure—and how those two words show up in the lives of entrepreneurs, parents, creatives, and anyone chasing big dreams.

As summer winds down and life picks up again, Rob shares a thought-provoking conversation with Lauren Gregor, founder of Rent-A-Romper, who recently sold her startup and opened up about what it truly felt like to “let go” of her company. It’s not just about exits, deals, and check sizes—it’s about identity, community, self-worth, and defining success on your own terms.

This episode is filled with honest stories from Rob’s own entrepreneurial journey and lessons from over 15 years of interviewing founders around the world. If you’ve ever wondered whether you’re doing enough, or if a quiet moment in your life is a sign of failure rather than growth, this conversation is for you.

Whether you're a founder, dreamer, investor, or just someone navigating life’s transitions, this is an invitation to slow down and listen deeply.

You're not alone—and your life is worth more than your startup.

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