Don't Be a Jerk
Don't Be a Jerk
Podcast Description
👋 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 build success without compromising values. Let’s rewrite the narrative of leadership, one story at a time.
Podcast Insights
Content Themes
The podcast focuses on themes of leadership ethics, business authenticity, and emotional intelligence, with episodes covering topics such as the strategic advantages of vulnerability in venture capital and the impact of genuine communication in business transactions.
👋 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 build success without compromising values. Let’s rewrite the narrative of leadership, one story at a time.
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 scenes, I’ve also been getting a flood of DMs, texts, and Slack messages with questions about leadership, empathy, and what it actually means to “not be a jerk” at work.
So in this special solo episode, I sit down to answer them. We get into:
– Why I started this podcast in the first place
– How to be conflict-seeking without being an asshole
– The #1 mistake early leaders make that kills credibility
– How to repair when you realize you were the jerk
– The difference between expectations and agreements
– How to fire someone without being cruel
– The art of debriefs and BLUFs (bottom line up front)
– Two things you can do tomorrow to become a better person
– How to rebuild trust once it’s been broken
This episode is part playbook, part confession, part experiment, but at the core it’s about the same idea that launched this whole show: kindness in leadership isn’t weakness. It’s strategy.
If you’ve got more questions you want me to tackle in a future solo episode, drop them in the comments, DM me, or send a carrier pigeon. You never know, maybe your question makes the next one.
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