Don't Be a Jerk artwork

Management · Healey Cypher

Don't Be a Jerk

by 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 build success without compromising values. Let’s rewrite the narrative of leadership, one story at a time.

Latest episodes

Showing 20 · updated from the feed

How to Win In Life (And Business) Without Being a Jerk | Best of Year 1 on DBAJ

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 point

Oct 6
14 min

He Hires the People Everyone Else Screens Out | Keba Konte, Red Bay Coffee

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 accred

Sep 29
33 min

Why Kind CEOs Actually Make More Money | Emiliana Simon-Thomas @ UC Berkeley

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 late

Sep 22
54 min

How to Build Willpower (hint: it’s NOT what you think) with Healey Cypher

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 wo

Sep 15
6 min

How This Ethics Professor Launched a $1,000-a-Month Kindness Award | Alan Ross @ UC Berkeley

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

Sep 1
39 min

"The No A**hole Rule” and When The Rule Can Be Broken | Bob Sutton @ Stanford

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 re

Aug 18
49 min

How the Wrong Incentives Can Kill Your Team | Amy Gershkoff Bolles

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 m

Aug 4
55 min

How to Engineer a Sense of Agency in Any Young Person with Alex Funkhouser @ GetMyIntern

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 fo

Jul 21
42 min

How Music Education Transformed 15,000 Kids’ Lives | Chad Bernstein

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

Jul 14
48 min

Why Leading With Love Is a Radical Act with Elevate Prize CEO Carolina Jayaram

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 the

Jul 7
54 min

The Science Behind Why People Are Crueler Online Than IRL (and How to Deal with Trolls)

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 slu

Jun 30
17 min

Why This Founder Says Humility is #1 Trait for the Best Hires with Kevin Kissi

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 fund

Jun 23
55 min

The Lost Art of Building Relationships: A Masterclass in Selling Without Selling | Kalina Bryant

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

Jun 16
41 min

The Social Skill Every Great Founder Has (That Nobody Teaches You) with Paul Bakaus

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 rela

May 12
56 min

Why 65% of Co-Founders Fail (and How to Prevent That) with BoomPop Co-Founder Blake Hudelson

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 ye

May 5
1 h 10 min

The 4’2” VC Who Ran Boston 7 Times and Spots Potential Before Everyone Else | Danh Trang

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.

Apr 28
46 min

The Former Prosecutor Who Built a Legal System to Bring Prisoners Home with Hillary Blout @ For The People

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 i

Apr 21
50 min

7 Ways to be a Great Person and 5 Traps That Can Make You Seem Like a Jerk

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

Apr 14
17 min

How Brianne Kimmel Built a $45M Fund Around the Founders Nobody Else Believed In

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 D

Apr 7
1 h 01 min

What Happens When an 11-Year-Old Decides to Stop Waiting for Better News and Make It Himself with Sam

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 des

Mar 24
35 min

Chart positions

Where Don't Be a Jerk ranks today in each Apple Podcasts chart (US, Oct 24, 2026).

#79 NEW Management US

More podcasts like Don't Be a Jerk

Popular shows in Management, for your next listen.

Browse charts by category

Daily updated Apple Podcasts rankings for the United States.

About Don't Be a Jerk on Reason.fm

Here you find the Apple Podcasts chart positions of Don't Be a Jerk, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

Contact

Questions or issues? Reach us at hello@reason.fm

0:000:00