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Don't Be a Jerk

Healey Cypher

👋 Hey there, Healey Cypher here. My brother once said all CEOs are inherently bad, and I get it. Headlines glamorize ruthless success, but there’s another story: leaders who win because they’re good people. “Don’t Be a Jerk” explores real-world examples and tactical insights proving kindness and integrity aren’t just nice; they’re strategic advantages. Each episode reveals actionable lessons to b... more

PublishesWeeklyEpisodes15Founded4 months ago
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ManagementBusiness

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Latest Episodes

What does it take to build a real community in a world that rewards hustle over humanity?

Espree Devora has spent over a decade answering that question.

She’s the founder of We Are LA Tech and host of Women in Tech, where she’s spent thousands of h... more

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What happens when you build a $400 million startup and then lose it all?

For James Beshara, the answer wasn’t another company. It was a complete rewiring of how to live.

In this episode, Healey Cypher sits down with the founder of Tilt (acquired by... more

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What if telling the truth faster could make your company more profitable, your culture stronger, and your life easier?

Robert Yuen, CEO of Monograph, believes it can. He has built an entire business around it.

In this episode of Don’t Be a Jerk, He... more

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Empathy is one of the most powerful tools we have for survival, leadership, and connection.

In this episode of Don’t Be a Jerk, Healey Cypher sits down with Jamil Zaki — Stanford psychology professor, empathy researcher, and author of The War for Ki... more

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When you think about “service,” you might picture a volunteer day with matching T-shirts or a line on a résumé. But for Shakirah Simley, service is deeper. It’s generational. It’s survival. And it’s the force that has guided her life and leadership. more

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When I first met Young Han, he wasn’t coming on my podcast. He was stepping in as a fractional CFO to help me lead through one of the hardest stretches of my career.

Within 15 minutes of our first meeting, he scrapped his entire plan and said: “We’r... more

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Aaron Schwartz has built and scaled companies you know — Modify Watches, Passport, Loop Returns — and now Orita.ai, helping 100+ brands land in inboxes instead of spam. But ask anyone who’s worked with him, and they’ll tell you his real superpower is... more

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This one’s different. No guests, no interviews. Just me, your questions, and a few stories from the trenches.

Over the last few weeks of Don’t Be a Jerk, I’ve had incredible conversations with founders, VCs, coaches, and comedians. But behind the sc... more

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1. My First Million
2. Am I the Jerk?
3. Am I the Genius?

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Don't Be a Jerk launched 4 months ago and published 15 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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