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Index/Startups & Founders/The Happy Hustle Podcast
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Why Entrepreneurs Are the Loneliest People on Earth And How to Fix It with Cary Jack

The Happy Hustle Podcast · 2026-06-26 · 20 min

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Episode notes

Have you ever sat in a room full of people who admire you and still felt completely alone? If you're an entrepreneur chasing something big, there's a good chance you already know that feeling. You can have fifty thousand followers and not one person you'd actually call at two in the morning. In this solo episode of The Happy Hustle Podcast, I get into something most people in the hustle world don't want to talk about. Loneliness. Not the casual kind, the kind that creeps in after years of grinding, sacrificing, and building something from nothing while everyone around you slowly drifts away. I share my own story of burning out in my twenties, walking away from seven figure funding deals, and moving to Bangkok just to figure out how to feel like a human again. And I break down why entrepreneurs might be the loneliest people on the planet, plus exactly what to do about it. Here's the big shift I want you to sit with. We've been taught that connection is something that just happens if you're successful enough, likable enough, or busy enough doing big things. It's not. Connection is something you build on purpose, the same way you build a business.

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