Don't Be a Jerk

Healey Cypher
  • 5.0 (1)
  • Management
  • Updated weekly

👋 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.

  1. 3 days ago

    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 taught at Berkeley Haas for 36 years and has been the business school's only ethics teacher for 25 of them, which means every Haas graduate has passed through his classroom. He opens each semester by asking how many students would be there if the class weren't required. His record answer is ten out of 240. He tells Healey about it laughing. In this episode: - Why Alan says he could never win his own award, and means it - The case against gratitude, and what he'd replace it with - What the New York banker making seven figures told him about "just $100K more" - How to gamify kindness with your kids at the drive-through window - Why nobody has ever faked their way to the $1,000 in four years - The student whose entire Harvard interview became about a kindness award - What Alan would put on a billboard a billion people could see Subscribe for more conversations about doing well without being a jerk. New episodes on YouTube, Spotify, and Apple Podcasts. Learn more or nominate someone at chriskindnessaward.org Timestamps: 00:00 Intro 01:39 What the Chris Kindness Award actually is 02:46 The cookie stand that started it 03:11 An award for everything in our society except kindness 04:02 Who Chris was 05:25 Why handing over the check is the best day of his month 05:50 The origami volunteer at Children's Hospital 07:05 Why he says he could never win his own award 09:48 What spending money on others does to happiness 10:41 Abstraction, and how people become numbers 12:20 The New York banker and just a hundred thousand more 14:44 Writing down his real top ten goals 15:51 The hours you don't get back 19:39 The ripple effect 21:34 The fifth grader on why the news is all bad 26:34 The interview that starts with how you treat the waiter 27:45 Gamifying kindness at the drive-through 30:32 The ethics class, and why nobody has faked it in four years 31:24 The student whose Harvard interview became about the award 38:40 What he'd put on a billboard

  2. 18 Aug

    "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 wouldn't: you reward a**hole heart surgeons, and I fire them. Healey and Bob get into the moral case, the business case, and the uncomfortable middle where jerks really do win. It's the rare conversation about workplace behavior that never once sounds like an HR training. In this episode: - Why Sutton has given up arguing decency on ROI, and what he says instead - The one sentence that tells you everything about a company's culture - The hidden-tape-recorder study on coaches who lose it at halftime, and why the nice ones get results - How to tell whether you're the difficult person in the room - Why calling someone a jerk is the most reliable way to turn them into one - What Google did to cut interviews from 25 rounds to four - The Kurt Vonnegut poem Sutton wrote a letter to get permission to use, and the postcard he got back Subscribe for new episodes of ‘Don’t Be a Jerk’ every week. Watch on YouTube, listen on Spotify and Apple Podcasts. Find Bob at bobsutton.net or on LinkedIn.

  3. 4 Aug

    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 fighting the support team, the "cost center" incentivized to hang up on customers, the marketing budget spread too thin to work. She shares the exact fixes that sent revenue "through the roof," why she asks every new hire what they want in twelve months (not five years), and why a Princeton Ph.D's real value was learning how to learn, a skill she argues matters more than ever now that AI can write the code while you sleep. She also makes the case for the generalist, the discipline of saying "I will find out," the campaign trick of going broke on purpose, and why, after 20 years in big tech, she's betting on Main Street. In this episode: - The one change that erased the war between a sales team and its support staff - Why customer-support incentives quietly destroy customer loyalty, and how to balance them - The marketing budget mistake ("love all your children equally") that starves your best products - The question Amy asks every new hire to unlock "exponential" performance - Why AI can hand you the answer but never the fortitude to act on it - The hidden penalty generalists pay, and why the boardroom finally rewards it - How to sound confident when you don't know the answer - The Obama-campaign discipline of being "bankrupt by election day" Subscribe to Don’t Be a Jerk for more conversations on leadership, incentives, and building companies worth working at.

  4. 21 Jul

    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. Give a young person a real mission, a learning contract they write themselves, actual decision-making authority, and real consequences, and the switch can flip in a single day. Alex has watched it happen 40,000 times, starting with a timid student who was raised not to talk to strangers and ended her first day of cold-calling glowing. Highlights: - Why placing a 16-year-old is harder than placing a $200K engineer, and what Alex built to fix it - The "learning contract" that hands ownership to kids who've never had it - How Hard Rock Stadium turns 1,000 interns into its full-time hiring pipeline - Alex's contrarian take on AI: kids don't need jobs, they need missions - The one human skill he says you can't outsource to a model - What employers actually ask for from Gen Z hires (it's not technical) - The 1966 Mustang he bought at 15 with lawn-mowing money and rebuilt nut by nut Subscribe to Don't Be a Jerk for more proof that good people finish first. Watch on YouTube, or listen on Spotify and Apple Podcasts.

  5. 14 Jul

    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 trombonist who's played with Pitbull, Shakira, and members of James Brown's band, earned a doctorate studying his own program, and sat as a Governor on the Grammys board. On this episode of Don't Be a Jerk, he and Healey get into what musicians understand about leadership that most MBAs never learn: how to listen, when to create space, why vulnerability is a tool instead of a weakness, and how to build the kind of safety where people finally stop bracing and do their best work. It's a conversation about the spaces between the notes, and why the people who master them tend to lead better than everyone else. In this episode: - Why the guards confiscated the guitars, and how the band won the room with no instruments - The five words from one kid that changed the entire direction of Chad's life - Why "failure" is an official value at Guitars Over Guns, and what that unlocks - What a brain scan reveals about the "self-auditing" switch that keeps people from taking risks - The Fred Wesley line about leaving "space for God to walk through," and what it means for any leader - Why the most powerful move in a negotiation (and a jam session) is 7 seconds of silence - How to build psychological safety before you ever ask anyone to perform🎧 Subscribe to Don't Be a Jerk for more conversations on leading like a good human.

  6. 7 Jul

    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 Leader" treats founder wellbeing as a structural problem instead of a personal one. Along the way she explains why she stopped using the word "unrestricted," what a five-day retreat in Mexico actually does for a burned-out leader, and why one still person can change an entire room. This is a conversation about doing good and being honest about what it takes from the people who do it. In this episode: - Why "the most underfunded line item in philanthropy" is the one every business spends millions on - The $50K-to-the-leader bet and how Carolina makes the case for it - Why she traded the word "unrestricted" for "trust-based" and what changed - The playwright who was about to quit the week she got the call - How a forest's underground network reframed how she thinks about a team - Why meditation is "for the crisis, not the pillow" - What leading with love "unapologetically" looks like inside a foundation Subscribe for new episodes of Don’t Be a Jerk every week. Watch on YouTube, listen on Spotify and Apple Podcasts. Learn more about Carolina's work at elevateprize.org.

  7. 30 Jun

    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 they're behind a screen, pulling in the research that explains it and landing somewhere more useful than "just be nicer." This is the most on-brand episode the show could make: the exact behavior it's named against, happening at full volume, met with curiosity instead of a lecture. In this episode: - Why the internet is an "empathy removal machine," and the 2004 study that named it - The 47-likes finding: how cruelty gets socially rewarded until it becomes a group's identity - What Healey found when he actually looked up the people leaving the comments - Why the algorithm pulls negative people deeper into negativity - The "reverse dogpile" idea: what happens if you flood cruelty with kindness - Why leaving cruel comments costs you more than the person you aim them at - The one question to ask yourself before you ever hit post Subscribe to Don't Be a Jerk on YouTube, Spotify, and Apple Podcasts, so you never miss an episode!

  8. 23 Jun

    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 single conversation to know whether to hire someone, and why he treats his mental energy like a budget he refuses to overspend. It's a conversation about reliability, in software and in people, and the courage it takes to build things that admit when they're broken. In this episode: - Why Kevin says "perfect without trust is failure," and what he builds instead - The restaurant test for whether you're actually leading or just managing - How he spots a bad hire by listening for one missing trait - The Friday memo habit that revealed how much his team relied on him - Why he walked away from a degree, a math professorship, and Microsoft - How he budgets his mental energy like a bank account - Building AI agents that carry human judgment instead of removing it Subscribe to Don't Be a Jerk for conversations with leaders who prove you can build great things while doing good in the world.

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About

👋 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.

Information

  • Creator
    Healey Cypher
  • Years Active
    2025 - 2026
  • Episodes
    45
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

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