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Hosted by Healey Cypher · 🇺🇸 US · EN · 43 episodes
Established thought leaders with verified media credentials.
👋 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.
Healey Cypher hosts Don't Be a Jerk, a business show with 43 episodes published.
Bob Sutton has spent twenty years being asked to prove that decency pays. He can do it: the productivity data, the health data, the turnover math, all of it. He mostly refuses to. His actual argument is harder to shrug o
Charlie Munger said "show me the incentive and I'll show you the outcome." Dr. Amy Gershkoff Bolles has spent an entire career proving it from the inside. She built the media operation for Obama's 2012 campaign, served a
It's harder to place a 16-year-old intern than a $200,000 software engineer. Alex Funkhouser learned that the hard way: his firm SherlockTalent places senior engineers for a living, but when he volunteered to find intern
Chad Bernstein showed up at a juvenile detention center with his band, ready to play, and the guards stopped him at the door. The guitar strings, they said, could be used as weapons. So he walked in empty-handed, into a
Most foundations write a check and walk away. Carolina Jayaram does the opposite. As founding CEO of The Elevate Prize Foundation, she gives changemakers $300,000 and then carves $50,000 of it out for the leader, not the
A clip from Don't Be a Jerk went viral for the wrong reasons. It was a vulnerable story: Healey's friend Danh Trang, a little person, recounting how a CEO once used a slur and how Danh responded with grace instead of ang
Kevin Kissi spent years at Microsoft leading teams that shipped software to hundreds of millions of people. Then he walked away to build Zof AI with no institutional funding, betting on one idea most of the industry stil
Kevin Kissi spent years at Microsoft leading teams that shipped software to hundreds of millions of people. Then he walked away to build Zof AI with no institutional funding, betting on one idea most of the industry stil
Most people think selling is about the pitch. Kalina Bryant built $9 million in six months doing the opposite through relationships, built so well that the customers came to her. As she puts it, once you learn the art of
Paul Bakaus started coding at 11, sold his first company to Zynga, and spent years at Google working on Search, Chrome, and ultimately as their first head of creator relations with a focus on bringing creators back to th
Blake Hudelson is my co-founder at BoomPop (and we probably spend more time with each other than we do with our wives). We met at a startup studio in San Francisco six years ago. I proposed we try three companies simulta
Danh Trang was standing near the finish line when the 2013 Boston Marathon bombs went off. He was watching friends and family. He came back the following year and ran it. At 4'2", in 5:36. Raised $14,000 for Little Peopl
What happens when a prosecutor walks into a prison, sits across from someone she could have sent there, and realizes she can't say she wouldn't have done the same thing in their shoes? That's the story of Hillary Blout.
What separates the people everyone wants to be around from the people who quietly drive others away? In this solo episode, Healey Cypher breaks down the 7 behaviors that make someone genuinely great to be around and the
Brianne Kimmel is the founder and managing partner of Worklife Ventures, a $45M early-stage venture firm backed by Marc Andreessen and Eric Yuan. Her portfolio includes Deel, Supabase, Public, and Metronome (zero to $1B
Sam started a podcast because he was tired of feeling helpless. He was consuming the news the way most of us do… headlines that made him anxious, stories that seemed designed to make the world feel like it was falling ap
Avni Barman joined Don’t Be a Jerk this week. she already has 1 million people in her community, 60 million monthly views, a 150,000-subscriber newsletter, and a venture fund where her own audience is the real investment
Andrew Dudum built Hims & Hers from zero into a multi-billion-dollar consumer publicly-traded consumer health company by doing something most founders avoid: leaning directly into discomfort. He’s able to lead the hard c
David Flink got kicked out of four schools. Then he went to Brown, then Columbia and spent the next 28 years building systems so that nobody else has to earn their humanity through performance. David is the founder of th
Rafael Burde holds one of the most quietly powerful jobs on the planet. As Co-Lead of Global Search Policy at Google, he helps decide what information billions of people see (or don't see) when they search online. Google
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Don't Be a Jerk is hosted by Healey Cypher. The show is categorised under business (management) and has published 43 episodes.
Don't Be a Jerk has published 43 episodes.
Don't Be a Jerk regularly covers business, management. It sits in the business category, with a management focus.
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Don't Be a Jerk hasn't explicitly signalled guest openness in recent episodes. That doesn't rule out pitching. your hook just needs to be especially compelling and relevant to their recent content.
Episodes of Don't Be a Jerk average 49 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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