Don't Be a Jerk

Healey Cypher
  • 4.0 (9)
  • 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. 2D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. JAN 21

    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 connection to the people they’re building for. We talk about why there’s a growing global empathy problem in tech, how that shows up in products and leadership, and what founders can actually do to fix it. This episode is a breakdown of why empathy, mission, and humility quietly outperform raw IQ and brute force. In this episode, we cover:- Why a University of Washington study found humility beats IQ as a predictor of performance - The difference between mercenary founders and missionary founders - Why trying to sound smart in a pitch is usually a losing strategy - How to evaluate decisions using the “deathbed test” - Why founders who ask better questions win more often - How mission clarity makes hiring, marketing, and decision-making easier - Why asking for help early can save companies from dying quietly - How Mike designs his life around focus, family, and long-term thinking This conversation is especially relevant if you’re a founder, operator, or leader who’s tired of the “brilliant jerk” myth and wants to build something meaningful without burning bridges or yourself. If you care about building great companies and being a decent human along the way, this one’s for you.

    44 min

  7. JAN 13

    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:- Why Damian believes “no is a motivator” and how to reframe rejection into momentum - Why diversity of thought beats “more resources” (and how to build teams that challenge assumptions) - The investor red flags Damian wishes they’d seen earlier and how to avoid “poster child” capital - The business case behind the $1.7T “rainbow economy” and why “June-only” marketing is a trap - The intersectionality lesson every B2C brand needs right now: “It drives dollars.” - The mindset pattern that separates elite performers (and founders): your bounce-back after a miss - Why “founder therapy” (aka your cohort/tribe) can be the difference between quitting and surviving 🎧 If you’re a founder, exec, marketer, or anyone building teams in 2025, this one will change how you think about inclusion, performance, and leadership. Watch / listen now and if it resonates, send it to one person on your team who needs to hear it. Timestamps 00:00 — “Diversity is the ultimate competitive advantage” (opening theme) 00:05 — Meet Damian + the most intersectional founding team I’ve met 00:08 — Sheryl Sandberg / “pods” + why diverse teams outperform 00:10 — “Diversity is not charity.” 00:13 — VCs, bias, and the comment Damian will never forget 00:15 — Fundraising lesson: don’t chase money, choose partners 00:19 — “I’m motivated by no.” The rejection reframe 00:20 — Top 5 vs Top 25 tennis players: the bounce-back mindset 00:22 — Near-death startup moments + how Revry survived 00:28 — The scrappy SF Pride launch (yes… porta-potties) 00:32 — The $1.7T rainbow economy + why Pride-month-only is “rainbow washing” 00:39 — Founder neutrality: having a voice vs fiduciary reality 00:47 — Leading across generations + building a mission-driven culture 00:52 — “Founder therapy” + why you need a tribe 00:54 — Damian’s advice to their 25-year-old self

    49 min

  8. JAN 7

    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 followed. This isn’t a productivity episode. It’s a presence episode. If you’ve ever felt like life is moving too fast, you’re always optimizing for “later”, or you’re succeeding on paper but missing something real: this one is for you. In this episode, we explore:- The moment I saw myself clearly (and didn’t like what I saw) - The letter I wrote from my 80-year-old self (and why it broke me open) - Why the “arrival fallacy” keeps us chasing the next milestone - A simple daily prompt that changed how I show up as a father, partner, and leader - How imagining the ending can radically improve the way you live today - Why helping others may be the clearest path to a meaningful life This episode is raw, personal, and intentionally slower than usual. You don’t need to be a parent to listen. You don’t need to be 41. You just need to be human. If it changes even one ordinary day for you, it did its job. ⏱️ TIMESTAMPS 00:00 – A hard conversation & an uncomfortable realization 02:00 – Watching myself through someone else’s eyes 04:30 – The exercise that changed everything 05:00 – Reading the letter from my 80-year-old self 13:30 – Why ordinary days are the ones we’ll miss most 19:50 – A dark career moment and the mindset shift that saved me 26:00 – “Everything works out in my favor” (and why it works) 37:50 – Imagining the ending as a daily decision-making tool 40:30 – The question I ask before every moral decision 42:00 – The one lesson I hope my kids remember 45:00 – A quiet closing invitation to try this yourself

    32 min
See All (27)

Ratings & Reviews

4
out of 5
9 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
    27
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

You Might Also Like