
A year ago, Healey Cypher started Don't Be a Jerk as a personal quest to prove that being a jerk isn't the way to get ahead. Twelve guests later, the evidence keeps pointing the same way: most people are fundamentally...


business
Hosted by Healey Cypher · business · EN
👋 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.
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Contact path
Public web form
Booking probability
31%
Guest openness
Selective
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Signup to Generate a Pitch👋 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.
Don't Be a Jerk is hosted by Healey Cypher. The show has published 49 episodes to date.
Recent episodes include "How to Win In Life (And Business) Without Being a Jerk | Best of Year 1 on DBAJ" (6 October 2026, 15 minutes), "He Hires the People Everyone Else Screens Out | Keba Konte, Red Bay Coffee" (29 September 2026, 33 minutes), and "Why Kind CEOs Actually Make More Money | Emiliana Simon-Thomas @ UC Berkeley" (22 September 2026, 55 minutes).
Don't Be a Jerk publishes roughly weekly, with episodes averaging 44 minutes across 49 episodes.
Booking probability for Don't Be a Jerk is 31%, and the host is rated Selective on guests. Don't Be a Jerk requires a Pod Score of 80 or higher. Don't Be a Jerk's contact route on record: public web form.
The strongest fits for Don't Be a Jerk are Holding Companies & Corporate HQs and Business & Management Consulting. Don't Be a Jerk has a business audience.
Healey Cypher hosts Don't Be a Jerk, a business podcast with 49 episodes published.
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A year ago, Healey Cypher started Don't Be a Jerk as a personal quest to prove that being a jerk isn't the way to get ahead. Twelve guests later, the evidence keeps pointing the same way: most people are fundamentally...

In 1994 Keba Konte flew to South Africa to photograph the first election where everyone could vote. He had no press credential, so when Mandela appeared, the fifty accredited photographers had the front position and...

When Emiliana Simon-Thomas was a teenager in Berkeley, a man named Mr. Charles stood on a street corner every morning and told strangers they were beautiful. Decades later she ran a study with tens of thousands of...

Most of your day already happened without you. The drive to work, the meeting you walked into cold, the ten minutes after you got home. You didn't decide how any of it would go, so it went however it went. Healey Cypher...

Don't Be a Jerk
There's an award for everything in our society. The Emmys give awards for giving awards. Nobody gives one for kindness. Alan Ross noticed that during Covid, on a walk in the Berkeley Hills, when he passed a girl handing...

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...

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...

Don't Be a Jerk
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...

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...

Don't Be a Jerk
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...

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...

<p>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...

Don't Be a Jerk
<p>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...

<p>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...

Don't Be a Jerk
<p>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...

Don't Be a Jerk
<p>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...

Don't Be a Jerk
<p>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?</p><p><br></p><p>That's the...

<p>What separates the people everyone wants to be around from the people who quietly drive others away?</p><p><br /></p><p>In this solo episode, Healey Cypher breaks down the 7 behaviors that make someone genuinely...

<p>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...
Recent guests on Don't Be a Jerk. Study who booked and why before you pitch.
Founder & CEO, Stealth AI Startup, Renaissance Geek, Inc.
CEO and Founder, Hims & Hers Health
Founder and Director of the Survey Center on American Life, Rochester Community Unit School District 3A
attorney, entrepreneur, serial business founder, Thomas Metcalf Laboratory School at Illinois State University
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