Don't Be a Jerk

Healey Cypher
  • 3.9 (8)
  • 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

    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

  2. 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

  3. 12/16/2025

    The Hidden Success Behind 100 No. 1 Debuts and the The YouTube Creator Economy, with Bing Chen

    What if your success has nothing to do with you? That is the worldview of Bing Chen. And it has shaped two massive revolutions: the YouTube creator economy and the rise of Asian representation in Hollywood. Bing and I go all the way back to Wharton. We were in the same senior society. After college we’d grab coffee in New York and he’d casually say things like, “I think millions of people will make their full-time living on YouTube.” He was right. He helped build it. Today he is the CEO and Co-Founder of Gold House. Under his leadership the collective has supported over 600 projects, helped 100 films and shows reach #1 total debuts, and driven billions in revenue. But none of that is why this conversation blew me away. The real story is Bing’s philosophy. This is a conversation about generosity, legacy, culture, and what leadership actually looks like when you center it on others. ⏱️ Timestamps 00:00 – Why Bing and I still feel like caffeinated college kids 03:00 – The early YouTube years and the birth of the creator economy 07:00 – Bing’s definition of success and how losing his father changed everything 10:00 – Why real givers never count who owes them 11:30 – Naming the “creator.” The internal battles inside YouTube 15:00 – How Gold House accidentally came to life 16:00 – The strategy behind rallying a global diaspora 17:00 – The three universal human desires (health, love, meaning) 20:00 – The truth behind #GoldOpen and engineering cultural wins 23:00 – Why 100 films and shows reached number one in total debuts 25:00 – How community movements are intentionally built 28:00 – The manifesto of Gold House and why it is built on giving 29:30 – Why they chose the color gold and how brand identity shapes culture 31:00 – Being “the first call” when people win or fall 33:00 – Building a Marvel-scale creative universe about death 36:00 – Why contemplating mortality makes you more generous 41:00 – How to design community experiences that spark real impact 44:30 – Ethics, character checks, and the courage to excommunicate the wrong people 47:00 – The leadership principle Bing wishes he learned earlier 50:00 – How to be “the only one,” not the best one 55:00 – Final reflections on kindness, ambition, and legacy This episode is a masterclass in impact, community, and leadership. If you’ve ever wondered how to build something bigger than yourself, Bing is the blueprint. 🎧 Listen to the full episode of “Don’t Be a Jerk” now on Spotify, Apple, YouTube, or wherever you get your podcasts.

    57 min

  4. 12/09/2025

    The Quantum Physicist Who Proves Soft Skills Beat IQ

    Most people meet a quantum physicist and think they have nothing in common. But Anastasia Marchenkova is built different. She went from breaking the servers at Georgia Tech to building quantum chips at Rigetti, to investing in deep-tech startups, to teaching introverts how to communicate. And along the way she discovered something surprising. Being smart is not the hard part. Being human is. In this episode, we talk about how Anastasia rewrote her entire identity. From shy scientist to founder to creator to someone who believes empathy is a core technology. You will hear: - The night she accidentally took down Georgia Tech’s internet and got seed funding for it - Why scientists struggle to admit “I don’t know” and how it kills innovation - The “misogyny is a skill issue” problem in tech and what confident people do differently - Why 85 percent of career success comes from people skills, not IQ - How she taught herself charisma using physics-level study habits - Why scientists should fire clients faster - The rule she lives by online: never punch down - How to handle haters who can’t spell “your” - The moment she realized asking for help is a superpower - How boundaries make you kinder, not harsher - The real cost of being the smartest person in the room This conversation is part science, part philosophy, and part survival guide for anyone who has ever felt like their intelligence outran their communication skills. EPISODE TIMESTAMPS 00:00 — The supervillain origin story 03:00 — Breaking Georgia Tech’s servers and starting a company 07:00 — The academic mindset vs the startup mindset 11:30 — Why saying “I don’t know” increases innovation 15:00 — The danger of needing to be the smartest person in the room 17:30 — Why founders should fire faster 20:00 — People skills as a competitive advantage 27:00 — Misogyny as a skill issue 30:00 — Handling online hate and setting boundaries 35:00 — The psychology of communication in deep tech 40:00 — What scientists can teach founders (and vice versa) 48:00 — The most important question every technical leader should ask 🎧 Listen to this episode of Don’t Be A Jerk wherever you get your podcasts. Follow along for more conversations on leadership, kindness, and the future of work: IG: @healeycypher | @dontbeajerkpodcast LinkedIn: linkedin.com/in/healeycypher

    55 min

  5. 12/02/2025

    How Jesse Pujji Rewired His Mind (and Built Multiple 8-Figure Companies)

    What happens when you build everything you ever wanted… and still feel empty? For Jesse Pujji, that moment came after bootstrapping Ampush to a multi-eight-figure exit and realizing that money and titles weren’t enough. So he stepped back, did the inner work, and started Gateway X, a venture studio built around one radical idea: you can scale businesses and stay human. Jesse and I met as college kids at Wharton 20+ years ago. He was the calm, wise one. Let’s just say I was… not that. That’s why this conversation felt like a full circle moment for me. In this conversation, Jesse and I talk about what happens behind the curtain of “success” and how fear, ego, and self-awareness shape everything from our leadership style to our happiness. You’ll hear: Why fear and extrinsic motivation (money, titles, status) will get you far but can’t take you all the way. The 5 motivators that drive every founder (and how to choose yours consciously). How to find your “one thing you can’t NOT do.” Why Jesse left a $1M offer on the table to start his company. How to turn anxiety into presence: in real time, even in a meeting. The difference between treating people like employees vs. adults. What it means to run your business as a spiritual practice. The moment humility became Jesse’s superpower.This episode is for for anyone building something big and trying to stay grounded while they do it.⏱️ TIMESTAMPS 00:00 — How Healey and Jesse met at Wharton (and the TA story that started it all) 03:30 — Why Jesse left Wall Street to build a company from scratch 06:00 — The crash after the win: what happens when external success stops working 07:30 — The 5 motivators that drive all human behavior (and how to choose your fuel) 10:00 — When money stopped motivating and what filled the gap 11:50 — “What’s the one thing you can’t not do?” Finding purpose through practice 13:20 — From purpose to play: how to live in your “zone of genius” 18:00 — The decision to leave a $1M job offer and follow intuition 25:30 — “Fear is excitement without breath.” How to reframe fear as energy 27:00 — Aliveness as the compass: how to know you’re on your path 30:00 — Work as a spiritual pursuit (and how to turn frustration into curiosity) 33:00 — Mirrors, ego, and the parts of ourselves we don’t want to see 38:00 — The moment Jesse said “I feel scared” in a meeting (and how it changed the room) 42:00 — Why presence is contagious and awareness builds trust 44:30 — Treating people like adults (and why “loving candor” works better than control) 47:00 — How humility became Jesse’s leadership advantage 50:00 — What he wishes someone told him earlier about money, fear, and fulfillment 52:30 — Where to find Jesse today and what he’s building next — 🎧 Listen now to Don’t Be a Jerk wherever you get your podcasts. Follow for more conversations on leadership, kindness, and the inner work of building something that lasts. IG: @healeycypher | @dontbeajerkpodcast LinkedIn: Healey Cypher

    53 min

  6. 11/18/2025

    Personal Branding for Introverts: What Every Leader Can Learn from Goldie Chan

    What happens when authenticity becomes your superpower? For Goldie Chan, she turned her authentic, vulnerable story into a personal brand everyone wants. She’s the founder of Warm Robots, a Forbes contributor, and the author of Personal Branding for Introverts, a guide to building influence without pretending to be someone you’re not. Dubbed the “Oprah of LinkedIn,” Goldie built one of the most trusted voices in storytelling and leadership by doing something revolutionary in the age of algorithms: leading with heart. In this episode, Healey Cypher sits down with Goldie to talk about how stories shape trust, why vulnerability is magnetic, and what it really takes to connect in a world run by metrics. You’ll hear: How emotional intelligence beats IQ in leadership and influence The two versions of every great story (and when to use each) Why authenticity builds more trust than perfection ever could How to make one-to-many communication feel one-to-one Why “Yes, and…” might be the secret to better teams and conversations How Goldie’s cancer story became a masterclass in vulnerability The storytelling framework that every founder should stealThis conversation is equal parts strategy and soul. It’s about turning your humanity into your advantage and proving that empathy, not ego, is the real growth engine. ⏱️ EPISODE TIMESTAMPS 00:00 — The story behind Don’t Be a Jerk (and Adam Grant’s advice) 05:00 — Meet Goldie Chan: from poetry to the “Oprah of LinkedIn” 10:00 — Why storytelling is the most human skill we have left 14:30 — “Broetry,” bad writing, and how to actually hook your reader 19:00 — Vulnerability as a superpower: Goldie’s cancer story 22:00 — The two versions of every story: short vs. long 26:30 — Authenticity → Trust → Performance: the leadership loop 31:00 — The improv rule that transforms conversations 34:00 — How to make one-to-many feel one-to-one 40:00 — Confidence vs. ego — and why both are contagious 47:00 — Storytelling as a muscle: how to keep it strong 55:00 — Goldie’s final lesson: tell the story that resonates 🎧 Listen now to this episode of Don’t Be a Jerk wherever you get your podcasts. Follow along for more conversations on leadership, empathy, and storytelling in the age of AI: IG: @healeycypher @dontbeajerkpodcast LinkedIn: Healey Cypher

    52 min

  7. 11/04/2025

    What 50 Cent, Disneyland, and Cancer Taught Lucy Aragon About Happiness

    What happens when life throws you something you can’t control? For Lucy Aragon, the answer was to keep dancing. She’s been to 105 countries, built a life around optimism and adventure, and faced her husband’s cancer diagnosis with humor, perspective, and a contagious belief that joy isn’t luck. It’s work. In this episode, Healey Cypher sits down with Lucy to talk about the art of staying light when life gets heavy. From her solo travels through war zones to the lessons she learned about resilience, confidence, and perspective, Lucy’s story is a reminder that happiness isn’t something you find. It’s something you create. You’ll hear: - How travel rewires your empathy and your brain - Why “the rules were invented by people way stupider than you” - The moment in Yemen that changed how she sees courage - How humor became her greatest survival tool - Why optimism is a health advantage, not a personality trait - The 50 Cent quote that helped her beat anxiety and depression - What lighting poop on fire taught her about leadership and joy This conversation is equal parts philosophy and laughter. It’s about choosing perspective over panic, humor over fear, and joy as a daily act of rebellion. ⏱️ EPISODE TIMESTAMPS 00:00 — How Healey and Lucy met (and why she lights up every room) 04:00 — Travel as a teacher: empathy, perspective, and the Yemen story 10:00 — “The rules were invented by people way stupider than you” 15:30 — Disneyland, the 8-year-old, and the moment Lucy realized most rules are fake 24:30 — Facing cancer with confidence, humor, and perspective 31:00 — Why optimism isn’t denial 35:45 — How comparison became the thief of modern joy 39:00 — Travel, gratitude, and the psychology of happiness 45:20 — “Depression is a luxury” from 50 Cent 49:00 — Anxiety, control, and the mental rewiring that joy requires 55:00 — The loneliness epidemic and how to fight it with connection 01:05:00 — The art of humor (even when life is serious) 01:10:00 — Lighting poop on fire (yes, really) and parenting through joy 01:17:00 — Why intention matters more than perfection 01:22:00 — Lucy’s final lesson: You can just be happy, without being rich or successful — 🎧 Listen now to this episode of Don’t Be a Jerk wherever you get your podcasts. Follow along for more conversations on leadership, kindness, and the science of joy: IG: @healeycypher | @dontbeajerkpodcast LinkedIn: https://www.linkedin.com/in/healeycypher/

    1h 6m

  8. 10/28/2025

    Why True Leadership Starts with Loving Yourself, with Espree Devora

    What does it take to build a real community in a world that rewards hustle over humanity? Espree Devora has spent over a decade answering that question. She’s the founder of We Are LA Tech and host of Women in Tech, where she’s spent thousands of hours connecting entrepreneurs, creators, and founders (and learning the hard way what it means to lead with empathy). In this episode, Healey Cypher sits down with Espree to explore the science and soul of connection. From raising venture capital with no introduction to Sequoia, to learning the power of boundaries, breathwork, and burnout recovery, Espree shares how to build communities that last, starting with yourself. You’ll hear: - Why community is a human survival tool, not a marketing strategy - The simple mindset shift that made Espree fall in love with herself - How to set boundaries without shutting people out - Why “curious compassion” can fix almost any conflict - The real reason most founders burn out - What Tony Hsieh taught her about culture and core values - How to build belonging without losing yourself in the process This conversation is equal parts tactical and deeply human. It’s about self-worth, leadership, and why the most successful communities are built on something simple but radical: love. 🎧 Listen now to this episode of Don’t Be a Jerk on Spotify, Apple Podcasts, or wherever you get your shows. Follow along for more conversations on empathy, leadership, and the art of human connection: @healeycypher | @dontbeajerkpodcast

    59 min
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Ratings & Reviews

3.9
out of 5
8 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
    21
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

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