Don't Be a Jerk

Healey Cypher
  • 4.1 (10)
  • 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. 1D AGO

    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, scheduled his own interviews, edited his own audio, and published it himself. He's now 11. He's gearing up for the NPR Student Podcast Challenge. And he's on this show not as a novelty, not because it's heartwarming to watch a young person do grown-up things… but because his philosophy is EXACTLY what Don't Be a Jerk is about. In this episode, Sam and I dig into why negativity dominates media (and why the system is literally built to reward fear), what "good news" actually means versus fake positivity, how he runs his show like a real founder, and what adults might be missing about the relationship between what we consume and how we feel. This is one of my favorite conversations in the history of this show. What We Cover in This Episode: - Why bad news wins: the economics of negativity bias and how the attention economy turned news into an anxiety machine - What Sam was feeling that made him say "I'm not just going to complain, I'm going to make something" - The difference between solutions journalism (agency-building) and denial (toxic positivity) and why Sam understands the difference intuitively - How No Bad News is structured and what makes a story Sam will actually cover - Sam's full production workflow: pitching, booking, recording, editing, publishing, repeat - What repeated exposure to distressing news is doing to kids and what the research actually says - The one media rule Sam would teach every adult if he could - Why hope isn't something you wait for… it's something you engineer - What Sam is building toward with the NPR Student Podcast Challenge - What I learned about my own media habits from a conversation with an 11-year-oldIf you've ever felt like the news is making you worse, this episode is for you. And if you've got kids who consume media, this conversation will change how you think about their information diet too.

    35 min

  2. MAR 17

    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 they'll respond. In this episode, we talk about what it actually means to run a business, and a life, with that philosophy as the foundation. You'll hear: - Why "give someone their flowers while they can still smell them" is more than a nice idea… it's how she built her entire business - The one-sentence DM she sent to a self-made female billionaire and the 8-hour, one-on-one meeting that followed - The character test that never lies: what the way you treat a server at lunch reveals about how you lead - Why we actually DO care what other people think and what to do about it - Why venture capital is going to matter far less in the next decade and what's replacing it - How to guarantee you're in the top 1% of something without being the most talented person in the room - Why posting 8 times a day and having "negative minutes" for bad comments is a philosophy, not just a schedule Avni is one of the most generous and clear-eyed operators I've come across. Full episode is live everywhere you get your podcasts.

    50 min

  3. MAR 10

    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 age 12 that shaped his entire worldview, what it’s really like leading a public company through wild emotional and financial swings, and why the leaders who scale fastest are often the ones most willing to admit what they don’t know. What We Cover in This Episode: - How Andrew built Hims & Hers from an idea into a multi-billion-dollar public company without losing his values - Why learning to be comfortable being uncomfortable became his greatest leadership skill - The moment at age 12 that shaped how he thinks about responsibility, truth, and hard conversations - What running a public company actually feels like during extreme highs and brutal lows - Why the best leaders obsess over details most people dismiss - The difference between niceness vs. kindness and why avoiding conflict hurts teams long-term - Why the strongest CEOs hire people smarter than themselves and expect roles to evolve every year - How crisis reveals who truly belongs in your inner circle - Why success just amplifies who you already are If you’re a founder, operator, or leader trying to build something meaningful without losing yourself in the process, we hope this one will stick with you. Timestamps: 00:02 — How Andrew and I first met 06:45 — Building Hims & Hers from scratch without a medical background 09:30 — The moment at age 12 that changed Andrew’s view on responsibility forever 14:20 — Why information isn’t scary and why avoidance is 17:40 — Niceness vs. kindness (and why leaders get this wrong) 23:10 — Hiring people smarter than you 31:00 — What it actually feels like running a public company 38:45 — Why obsession over small details scales better than most strategies 46:30 — How hardship reveals who truly belongs in your life 56:10 — Andrew’s advice to founders riding extreme highs and lows

    51 min

  4. MAR 3

    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 across from. The throughline of everything David believes: misalignment isn't a personal failure. It's a design failure. And the moment you internalize that (about your employees, your kids, yourself) everything about how you lead and live starts to shift. In this episode, we cover: — Why there's no such thing as a bad employee (only a bad manager, a broken expectation, or a context nobody updated) — The critical difference between expectations and agreements and why one of them is silently destroying your team — The "work IEP": the user manual every person on David's team fills out, and why you'd be "nuts" to lead someone without it — His get-out-of-jail-free card framework: how to give people the benefit of the doubt before you spiral into assumption and blame — The one-liner that stops you mid-trigger: "It's hard work being a person, which means it's hard work for everyone else you're talking to too" — The three gates every story you tell yourself has to pass through — Why psychological safety has to be rebuilt every time the team changes — What the invention of the newspaper has to do with Gen Z's cognitive decline — Why curiosity is the single most underrated tool for both leadership and conflict resolution — What it means to truly leave every interaction better than you found it This one is for you if you're a founder, manager, teacher, or parent who wants to lead the actual humans in front of you, not the idealized, neurotypical, always-performing version of them. David talks about kindness with spine. The kind that still demands excellence, still holds standards, but starts from a place of genuine curiosity about who's actually in the room. Don't Be a Jerk is hosted by Healey Cypher — founder, CEO of BoomPop, and someone who believes that being a good leader and being a good human are the same job. New episodes every week. Subscribe so you never miss one.

    1h 15m

  5. FEB 24

    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 randomly reconnected at Whole Foods in 2019. Since then, I've had a front-row seat to watching someone navigate immense responsibility with remarkable humility. In this episode, we explore: - The framework Raf uses to make decisions affecting billions: "What's the harm? What's our role? What's proportionate?" - Resume virtues vs. eulogy virtues and why most of us are optimizing for the wrong one - The meaning crisis, and Raf's definition: "The things you want to endure once you're gone and the contributions you're going to make to it" - Suffocation vs. abdication in parenting, leadership, and platform governance - Why 54% of Americans don't know their neighbors and what we're losing - Why intergenerational friendships are the most underinvested asset - The Two Pockets Principle: "The world was created for you" AND "You are nothing but dust and ashes" Rafael is also a Bay Area community leader, father, and someone who's proof that you can hold immense power and still lead with humility, nuance, and care. This conversation on ‘Don’t Be a Jerk’ changed how I think about meaning, responsibility, and what actually matters. I hope it does the same for you. Resources Mentioned in the Episode: - Eulogy vs resume virtues - Brooks, Road to Character - "Not your duty to finish the work, nor are you at liberty to neglect it" - Pirkei Avot 2:16 - Two pockets teaching: Carry two slips of paper, one in each pocket. One reads "the world was created for me", the other "I am but dust and ashes" (ancient Jewish teaching - no consensus source) - "Meaning = what you care about enduring once you're gone, and the contributions you make to it" (John Vervaeke) - "If you want to succeed once, set a goal. If you want to succeed over time, build a system" (Clear, Atomic Habits) - Effective platform regulation avoids the extremes of both abdication and suffocation (Jonathan Zittrain) Timestamps 0:00 - Intro 1:19 - Co-leading global search policy at Google 8:37 - The AI search race & the war for how we make sense of the world 16:22 - The two pockets teaching: confidence vs. humility 17:37 - Why community is Rafael's secret weapon 24:29 - Résumé virtues vs. eulogy virtues 29:53 - How Rafael defines meaning 36:55 - The case for intergenerational friendships 41:03 - Abdication vs. suffocation in parenting & leadership 47:28 - Advice for anyone stepping into a seat of power

    49 min

  6. FEB 17

    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 leave. In this episode of Don’t Be a Jerk, we go deep into the specific practices behind that culture and why they work even in high-pressure, remote-first environments. We cover: Why Ilana starts meetings with a two-word emotional check-in and how it takes less than 30 seconds How gratitude and appreciation rituals actually increase performance instead of lowering the bar The hiring mistake she made early on that nearly broke her culture Why psychological safety is the foundation for honest feedback and real accountability The moment she led a room of skeptical investors through a two-word check-in and why one later called it the best pitch he’d ever seen How these practices don’t cost time… they give time backThis conversation isn’t about being “nice.” It’s about building teams that perform with gratitude in mind, stay connected, and don’t burn out when things get hard. If you’re a founder, leader, or manager trying to build something that actually lasts, this episode will change how you think about culture.

    51 min

  7. FEB 3

    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 profit and integrity when deadlines hit - How wellness trends go from “helpful for a few” to misleading for everyone - Why expectations, not effort, derail most weight loss journeys - What it means to build a brand you can sleep at night running This is a grounded conversation about building trust, resisting shortcuts, and choosing the long game in an industry that rewards the opposite. If you’re building something and trying not to lose yourself in the process, this one’s for you.

    43 min

  8. JAN 27

    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 down a rabbit hole of reflection, journaling, and some uncomfortable honesty about what I’ve been optimizing for (and what I haven’t). In this episode, we talk about: - Why traditional goal setting often leaves people feeling empty - The difference between resume goals and life goals - The five most common regrets people have at the end of their lives - Why clarity about the end can change how you live right now - And how a simple writing exercise helped me realign my priorities around love, family, work, and fulfillment This is about designing a life you’d be proud to look back on. If you’ve ever felt successful but still slightly off, I think this one will resonate with you.

    21 min
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Ratings & Reviews

4.1
out of 5
10 Ratings

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
    30
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

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