Don't Be a Jerk

Healey Cypher
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👋 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. hace 2 días

    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.

  2. 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.

  3. 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.

  4. 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.

  5. 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!

  6. 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.

  7. 16 jun

    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 and every message sounds AI-generated, she makes the case that genuine human connection is the last real advantage left in business. Healey and Kalina get into why the hard sell is dead, how she courts a customer like it's a first date, and what the best salespeople do that makes you forget you're being sold at all. In this episode: - Why "always be closing" is the worst advice in modern sales - How she built $9M in six months with "dinners that weren't really dinners" - Why she treats every customer relationship exactly like dating - The reason the best salespeople never sound like they're selling - How to turn a single cup of coffee into a deal that lasts years - Why your credibility is the one asset you can't afford to spend carelessly - What it actually means to be human in a transactional world Subscribe to Don't Be a Jerk for more on the business case for being a good human.

  8. 12 may

    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 why being nice at work can be the unkindest thing you do. In this episode, we get into: - Why everyone in the room is the main character of their own story, and how the best communicators use that to win every room they walk into - The pitch deck trick Paul watched a colleague use at Google to get promoted every single time, and what it actually reveals about how people make decisions - Why being nice and being kind are completely different things, and how California's passive-aggressive culture gets this exactly backwards - What FBI hostage negotiators and top Google executives have in common when it comes to getting people to say yes - Why the world's best car salesman outperformed everyone else by 10x using a single postcard - How AI sycophancy is actively making you worse at thinking, and what to do about it - Why Paul's team at Renaissance Geek now needs a one-hour standup just to stay aligned, and what that tells us about where product teams are headed - The open source move that made Paul "criminally" generous, and why it kept coming back to him in ways money couldn't buy - Why most early managers kingdom-build out of fear, and what Paul did when he flipped the script entirely This full episode of Don’t Be a Jerk is live on Spotify, Apple Podcasts, and YouTube.

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👋 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.

Información

  • Creador
    Healey Cypher
  • Años de actividad
    2025 - 2026
  • Episodios
    43
  • Clasificación
    Explícito
  • Copyright
    © Healey Cypher
  • Mostrar sitio web
    Don't Be a Jerk

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