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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

PublishesWeeklyEpisodes10Founded3 months ago
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Latest Episodes

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

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

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

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

Born legally blind in rural India, Sam Maddula’s life changed forever thanks to a single act of kindness: a corneal transplant that restored his sight.

That early gift shaped everything that came after, including his philosophy as founder of Bank’s ... more

Most people dread negotiations, whether it’s salary discussions, sales deals, or even personal conflicts. But what if negotiating didn’t have to feel stressful, combative, or uncomfortable? What if you could negotiate like an elite expert without eve... more

What do rage rooms, co-founder breakups, and high-stakes feedback have in common?

They're all windows into how our brains process stress, and how most leaders are flying blind without even realizing it.

In this episode, Healey Cypher sits down with... more

Ever wondered how comedians manage to laugh their way through heartbreak, anxiety, or even funerals?

In Episode #3 of Don’t Be a Jerk, comedian Ben Gleib (Netflix, Comedy Central, host of “Idiotest”) shares how humor has been his ultimate self-thera... more

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1. All-In with Chamath, Jason, Sacks & Friedberg
2. The Diary Of A CEO with Steven Bartlett

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Don't Be a Jerk launched 3 months ago and published 10 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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