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. 12H AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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
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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
    25
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

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