Podcast · Business

Don't Be a Jerk

by Healey Cypher · English · Business

👋 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 i

New episodes: Weekly
Typical length: 49 min
Latest: 6 Oct 2026
Language: English

Latest episode

6 Oct 2026 · 15 min

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 pointing the same way: most people are fundamentally good, and the jerks just get more airtime. For the show's one-year anniversary, Healey pulls together his favorite moments from year one. The guests include the Stanford psychologist behind The No Asshole Rule, an 11-year-old who produces his own podcast, negotiation coaches, a VC, founders, and leading researchers on empathy and happiness from Stanford and UC Berkeley. You'll…

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Earlier episodes 29 most recent

29 Sep 2026 · 33 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 accredited photographers had the front position and Keba was stuck in the stands with the crowd. Then Mandela turned his back on the press, faced the people, and raised his fist. Keba got the frame. He has been standing on that side ever since. Twenty years later he started Red Bay Coffee in Oakland, roasting at home on a popcorn popper after the bank declined his loan. He was in his late forties with two careers already behind…
22 Sep 2026 · 55 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 later she ran a study with tens of thousands of people across more than 200 countries to find out whether small acts like that actually change anything. Emiliana is the Science Director of UC Berkeley's Greater Good Science Center and one of the researchers behind the Big Joy Project. She and Healey get into what seven days of tiny, deliberate acts of kindness did to people's mood, their sense of agency, and their willingness to…
15 Sep 2026 · 6 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 would go, so it went however it went. Healey Cypher has a fix that takes about ten seconds, and it's older than every productivity book on your shelf. It's called segment intending: you break the day into small pieces, and before each one you say what you want out of it. In this solo episode he walks through the practice, why he thinks of willpower as a muscle rather than a trait, and what changed in his calendar and his…
1 Sep 2026 · 40 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 the Berkeley Hills, when he passed a girl handing out free cookies because she thought everyone seemed sad. Four years later he writes a $1,000 check every month, out of his own pocket, to a stranger who did something quietly extraordinary: a gas station attendant, a locker room attendant, an 86-year-old who's folded origami at Children's Hospital every Thursday for a decade. Most of them try to give the money back. Alan has…
18 Aug 2026 · 50 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 refuses to. His actual argument is harder to shrug off. Sutton is a Stanford professor emeritus who got the idea for the most famous management book with a swear word in its title from his father, at the San Diego Zoo, when he was about four years old. He also once flew across the country for heart surgery, past a hospital two miles from his house, in part because the Cleveland Clinic's CEO told him something Stanford's…
4 Aug 2026 · 56 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 media operation for Obama's 2012 campaign, served as a C-level executive at companies including Zynga, Ancestry, and Levi Strauss & Co., and sits on public and private company boards. The throughline: most bad behavior at work isn't malice. It's good people responding rationally to a broken system. In this conversation with Healey Cypher, Amy turns that lens on the everyday problems leaders misdiagnose: the sales team…
21 Jul 2026 · 43 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 for a living, but when he volunteered to find internships for Miami high schoolers, a full year of work placed exactly eight kids. So he built the machine himself. GetMyInterns has now launched over 40,000 student careers, and this summer alone put more than 3,000 Miami-Dade teenagers into paid, insured internships that cost employers nothing. Healey sits down with Alex to unpack his central claim: agency can be engineered.…
14 Jul 2026 · 49 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 as weapons. So he walked in empty-handed, into a room of kids with crossed arms and cold stares, and the distance between them felt impossible to cross. Then the band started playing with nothing but their voices and a beat on the table, and within seconds the whole room cracked open. That afternoon became Guitars Over Guns, an organization that has now reached thousands of young people across four cities. Chad is a working…
7 Jul 2026 · 54 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 then carves $50,000 of it out for the leader, not the mission. Her argument is blunt: a depleted founder can't carry the work forward, so funding the human isn't a perk, it's the investment. Healey sits down with Carolina in Miami to unpack the two bets behind Elevate. "Make Good Famous" treats storytelling as the line item philanthropy forgot, the same marketing muscle every for-profit company spends millions on. "Whole…
30 Jun 2026 · 17 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 slur and how Danh responded with grace instead of anger. The CEO apologized and grew. It was the show in two minutes. Then it hit 400,000 views, and the comment section filled with cruelty from people whose own profiles said "man of God," "artist," "classical violinist." Healey's first reaction was anger. His second was curiosity. In this solo episode he goes down the rabbit hole of why decent people turn cruel the moment…
23 Jun 2026 · 55 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 funding, betting on one idea most of the industry still gets wrong: a system that looks perfect but can't be trusted has already failed. Born in Accra, raised between Ghana, Atlanta, and the snows of North Dakota and Minnesota, Kevin built a worldview where transparency beats polish and humility beats ego. In this conversation with Healey Cypher, he explains why he wants his own team to forget he's the boss, how he reads a…
16 Jun 2026 · 42 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 to her. As she puts it, once you learn the art of relationships, you'll never sell a day in your life. Kalina is the Founder and CEO of UnapologeTECH and was the first head of customer advocacy at Asana, where she turned community into one of the company's highest-converting revenue engines. She's a Forbes 30 Under 30 honoree and now an Executive in Residence at First Round Capital. In a moment when every inbox is flooded…
12 May 2026 · 57 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 relations with a focus on bringing creators back to the open web. Later on at Spotter, he built AI tools for creators like Dude Perfect and MrBeast. He's now the founder of Renaissance Geek and building Impeccable, an AI-powered creative tool for YouTube creators. In this episode, Paul and Healey get into the social skill that separates good leaders from great ones, why most people are terrible at asking the right questions, and…
5 May 2026 · 1 hr 10 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 years ago. I proposed we try three companies simultaneously to see what clicked. He said yes without hesitating. That tells you everything about him. Six years, a lot of 11pm calls, a few near-death moments, and one company (BoomPop) we're really proud of later… Blake is our Chief Product & Design Officer and still one of my favorite people to talk to every single day. 65% of high-potential startups fail because co-founders…
28 Apr 2026 · 47 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. At 4'2", in 5:36. Raised $14,000 for Little People of America. He's done it seven times since and cut 73 minutes off his time. He also won gold representing Team USA in para-badminton in 2016. Professionally: Citigroup, Bridgewater Associates, early product hire at Blend (IPO at $4B), years quietly helping his wife Dr. Ilana Nankin build Breathe for Change, which trained 20,000+ teachers and reached 20 million students. Now…
21 Apr 2026 · 50 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 in their shoes? That's the story of Hillary Blout. She spent six years as a prosecutor in the San Francisco DA's office handling violent crimes against women and children. She was good at her job. Then she visited a prison, heard the stories of the people inside, and couldn't keep going. So she left. And she built something that had never existed: a legal pathway for prosecutors to bring people back to court and recommend…
14 Apr 2026 · 17 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 make someone genuinely great to be around and the 5 traps that make you look like a jerk, even when you have the best intentions. The science is real, and the examples are specific. And none of it costs you a thing. You'll learn why the brain treats criticism like physical danger (and what to do instead), how smiling triggers a chain reaction of dopamine in everyone around you, why real listening has become one of the rarest…
7 Apr 2026 · 1 hr 1 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 Deel, Supabase, Public, and Metronome (zero to $1B exit). She recently opened Worklife Studios: a physical gathering space for founders, creators, and technologists who believe the best work happens when real humans are in the room together. But before all of that: Youngstown, Ohio. Rust belt. Ukrainian immigrant family. A journalism degree from Kent State. A move to Sydney, Australia alone at 22 and four years there, chasing…
24 Mar 2026 · 35 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 designed to make the world feel like it was falling apart, a constant drip of fear and outrage that left him feeling worse, not better. And at some point, instead of just complaining about it, he made something. Sam built No Bad News: a podcast for kids and families that specifically spotlights what's working, who's solving problems, and where communities are getting things right. He was 10 years old. He pitched his own guests,…
17 Mar 2026 · 50 min
Why Trust Beats Product: How Avni Barman Built a 60-Million-View Media Empire by Giving Everything Away
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 thesis. She's the founder and CEO of Gen She: a media company and venture fund reimagining what it looks like to lead as a woman in business today. And the way she built it? By doing almost everything the conventional playbook says not to. Give everything away for free. Lead with generosity before you have leverage. Tell people what you admire about them before you know if…
10 Mar 2026 · 51 min
Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers
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 conversations that most leaders avoid. In this episode, Andrew and I talk candidly about what it actually takes to scale a company and stay grounded while doing it. We unpack the lessons he learned by understanding mortality early, the emotional whiplash of running a public company, and why “being nice” is often the least kind thing a leader can do. Andrew shares the moment at…
3 Mar 2026 · 1 hr 15 min
The Rules of Rule Breaking: David Flink on Why the System Was Never Built for You
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 the Neurodiversity Alliance (reaching 600+ schools nationwide), author of Thinking Differently , CNN Hero, and recipient of the Bezos Courage & Civility Award, which came with $5 million to direct toward the cause he's dedicated his life to. His second book, 20% Smarter , drops in 2027. But more than any of that, David is one of the most practically wise people I've ever sat…
24 Feb 2026 · 49 min
The Man Who Quietly Decides What Billions See On Google: Rafael Burde
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 processes 14 billion searches per day, and Raf's team writes the policies that govern all of it. His guiding principle? "Safeguarding without sanitizing." He navigates the ultimate high-wire act: keeping the internet open and useful while protecting users from harm. But this conversation goes far beyond tech and trust. Raf and I met at Penn, lost touch for years, then…
17 Feb 2026 · 51 min
Why No One Has Quit Her Company in 5 Years with Dr. Ilana Nankin
In a world where employees change jobs every 18 months, Dr. Ilana Nankin has had zero voluntary resignations in five years at Breathe For Change. Ilana is a former public school teacher, holds a PhD in education, and is the co-founder and co-CEO of Breathe For Change , an organization dedicated to educator well-being and human-centered leadership. Since she stated the organization 10 years ago, they have trained over 20,000 educators to become more mindful, grounded leaders. What started as research into burnout has evolved into a company culture so strong that people simply don’t want to…
3 Feb 2026 · 43 min
Why Most Wellness Brands Lose Trust and How to Avoid It with Dan Cox
Too many wellness brands try to sell a feeling. Dan Cox decided to sell the truth. You might recognize Dan as the ultra-fit guy from The Bachelorette . What you probably don’t know is that instead of riding the influencer wave, he opened nutrition stores, built multiple supplement brands, and quietly made integrity the core of his business. In this episode, we talk about what it actually looks like to do things the “right” way when it’s harder, slower, and more expensive. We get into: - Why Dan barely spends on ads and relies on trial and word-of-mouth instead - The real tension between…
27 Jan 2026 · 21 min
Why Most Goal Setting Fails (and the Exercise That Fixed It for Me)
Every January, we’re told to set goals. More goals. Bigger goals. Smarter goals. And yet… most of us still feel weirdly unclear about what we actually want. In this solo episode of Don’t Be a Jerk , I share a goal-setting exercise that completely reframed how I think about my life. It started with a single line from a friend that stopped me cold: “Most people set goals for their resume. You should be setting goals for your tombstone.” Then, I stumbled across a book called Creative Visualization by Shakti Gawain while I was on vacation, and it changed everything for me. These ideas sent me…
21 Jan 2026 · 44 min
Why the Best Founders Don’t Try to Sound Smart with Mike Jones
What if the most important skill for founders isn’t intelligence, hustle, or speed but empathy? In this episode of Don’t Be a Jerk, I sit down with Mike Jones, co-founder and CEO of Science Inc., former CEO of MySpace, and early backer of companies like Dollar Shave Club and Liquid Death. Mike has spent decades working with founders at every stage. What he’s learned runs counter to most startup advice. The best founders aren’t the loudest in the room. They don’t try to prove how smart they are. And they definitely don’t lead with ego. Instead, they lead with curiosity, humility, and a deep…
13 Jan 2026 · 49 min
Why Inclusion Wins in the Long Run with Damian Pelliccione
What if the thing investors call a “liability” is actually your biggest edge? In this episode of Don’t Be a Jerk, I sit down with Damian Pelliccione, co-founder & CEO of Revry, an LGBTQ+ streaming network built on a simple, powerful belief: diversity isn’t charity… it’s a competitive advantage. We talk about what it really takes to lead diverse teams across generations, build an identity-driven business that’s also ruthlessly pragmatic, and keep going when the world tells you “no” (over and over again). Damian is hilarious, sharp, and deeply real about the operator journey. You’ll learn:-…
7 Jan 2026 · 32 min
A Letter From My 80-Year-Old Self
This episode started with a hard moment of self-awareness. It was a quiet comment from my wife and a security camera clip I didn’t expect to watch. Then, I had a realization that I was rushing through the very moments I’ll one day miss the most. So I tried an exercise that stopped me in my tracks. I wrote a letter, as if I were 80 years old , waking up in my 41-year-old body for one single day . What came out was emotional, grounding, and deeply clarifying. In this solo episode, I slow everything down and walk through the exercise, the moments that inspired it, and the mindset shifts that…

About Don't Be a Jerk

Don't Be a Jerk is a English business podcast from Healey Cypher. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: Healey Cypher
Language: English
Category: Business
New episodes: Weekly
Typical length: 49 min
Latest episode: 6 Oct 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id1826689477
Rights: Healey Cypher

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