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

    Why 65% of Co-Founders Fail (and How to Prevent That) with BoomPop Co-Founder Blake Hudelson

    Blake Hudelson is my co-founder at BoomPop (and we probably spend more time with each other than we do with our wives). We met at a startup studio in San Francisco six years ago. I proposed we try three companies simultaneously to see what clicked. He said yes without hesitating. That tells you everything about him. Six years, a lot of 11pm calls, a few near-death moments, and one company (BoomPop) we're really proud of later… Blake is our Chief Product & Design Officer and still one of my favorite people to talk to every single day. 65% of high-potential startups fail because co-founders can't get along. We’re grateful we found a way to get along (and thrive) on this crazy journey. If you’re a co-founder (or looking for a co-founder), you’re going to want to tune into this one. Here's what we get into: 1. How we actually met and why we tried three companies first 2. Why our most pivotal moments always came from disagreement 3. The "Swoop and Poop” problem 4. The pre-parade and pre-mortem: two exercises every co-founding pair needs 5. Why telling your team the real problem is your strongest tool 6. Why being too similar is the actual danger zone for co-founders 7. Integrity in the micro-decisions and why it's the whole architecture 8. The outsider advantage, and when it runs outSubscribe and listen to this episode of “Don’t Be a Jerk” wherever you get your podcasts!

    1h 10m

  2. APR 28

    The 4’2” VC Who Ran Boston 7 Times and Spots Potential Before Everyone Else | Danh Trang

    Danh Trang was standing near the finish line when the 2013 Boston Marathon bombs went off. He was watching friends and family. He came back the following year and ran it. At 4'2", in 5:36. Raised $14,000 for Little People of America. He's done it seven times since and cut 73 minutes off his time. He also won gold representing Team USA in para-badminton in 2016. Professionally: Citigroup, Bridgewater Associates, early product hire at Blend (IPO at $4B), years quietly helping his wife Dr. Ilana Nankin build Breathe for Change, which trained 20,000+ teachers and reached 20 million students. Now he's a partner at South Park Commons, a $275M fund that invests in founders before they've decided what to build. Portfolio includes Gamma, Baseten, Render, and Profound, among many others. Danh and I went to Wharton together. He's one of my closest friends. Somehow I had never asked him most of what we talked about in this conversation. In this episode, we get into: - Why SPC watches founders for 9-12 months before writing a check, and what you actually learn when someone can't perform anymore - What Danh reads in body language during a pitch and why he trusts it less than 9 months of watching someone in the wild - Why the #1 cause of startup failure is team dysfunction, not the product or the timing - Marshall Rosenberg's four-step nonviolent communication framework and why the smallest word swap changes everything - What happened when a CEO called him the M word, and how he responded with more grace than most of us could manage - Why the first three minutes of a hard conversation determine the entire outcome - What his parents taught him about belief and persistence and how it now shapes everything about how he invests - Why the best thing SPC gives a founder is the room full of the right people. Danh has spent his entire career running toward the hard thing. This one is going to stay with you. Full episode is live on Spotify, Apple Podcasts, and YouTube. Follow Danh at: https://x.com/danh_trang Check out South Park Commons at: https://www.southparkcommons.com/

    47 min

  3. APR 21

    The Former Prosecutor Who Built a Legal System to Bring Prisoners Home with Hillary Blout @ For The People

    What happens when a prosecutor walks into a prison, sits across from someone she could have sent there, and realizes she can't say she wouldn't have done the same thing in their shoes? That's the story of Hillary Blout. She spent six years as a prosecutor in the San Francisco DA's office handling violent crimes against women and children. She was good at her job. Then she visited a prison, heard the stories of the people inside, and couldn't keep going. So she left. And she built something that had never existed: a legal pathway for prosecutors to bring people back to court and recommend shorter sentences. She drafted the nation's first Prosecutor-Initiated Resentencing law, founded the nonprofit For The People, and has since helped resentence over 1,000 people across six states. In this conversation, Hillary and Healey explore: - Why she couldn't sit in judgment after hearing the full stories of incarcerated people - The 500% increase in women in American prisons and the trauma-to-prison pipeline - Why perspective-taking outperforms emotional empathy in changing minds (76% success rate, per Stanford/Kellogg research) - The data: 3-8% recidivism for resentenced people, up to $287M saved in one county, 97% court success rate - Why everyone loves a comeback story, except in the one place people need it most This is a conversation about justice, leadership, and what happens when you choose partnership over combat. Whether you're running a company, managing a team, or trying to change someone's mind about anything, Hillary's playbook applies.

    50 min

  4. APR 14

    7 Ways to be a Great Person and 5 Traps That Can Make You Seem Like a Jerk

    What separates the people everyone wants to be around from the people who quietly drive others away? In this solo episode, Healey Cypher breaks down the 7 behaviors that make someone genuinely great to be around and the 5 traps that make you look like a jerk, even when you have the best intentions. The science is real, and the examples are specific. And none of it costs you a thing. You'll learn why the brain treats criticism like physical danger (and what to do instead), how smiling triggers a chain reaction of dopamine in everyone around you, why real listening has become one of the rarest skills in business, the one word that activates more brain regions than anything else in language, and why arguing almost always makes things worse. You'll also hear about the weird trap of being "too polished," why trying to convince someone is the least effective way to change their mind, and the billboard study that increased voter turnout by 41% just by asking a single question. This episode is about how people feel when they walk away from you and whether they want to come back. Listen wherever you get your podcasts!

    17 min

  5. APR 7

    How Brianne Kimmel Built a $45M Fund Around the Founders Nobody Else Believed In

    Brianne Kimmel is the founder and managing partner of Worklife Ventures, a $45M early-stage venture firm backed by Marc Andreessen and Eric Yuan. Her portfolio includes Deel, Supabase, Public, and Metronome (zero to $1B exit). She recently opened Worklife Studios: a physical gathering space for founders, creators, and technologists who believe the best work happens when real humans are in the room together. But before all of that: Youngstown, Ohio. Rust belt. Ukrainian immigrant family. A journalism degree from Kent State. A move to Sydney, Australia alone at 22 and four years there, chasing something she couldn't quite name. She came back and started writing $1,000 angel checks to founders most people hadn't heard of, helping them get into rooms with Andreessen Horowitz before she had any leverage to offer. She had a philosophy instead: lead with generosity before you have anything else. In 2019, inspired by Robert Putnam's Bowling Alone and a personal craving for real connection she couldn't shake, she launched Worklife Ventures. The mission: make work more human. This episode is about a thesis Brianne has been building her entire career: that corporate culture stripped something essential out of us, that the internet took another 100 things we haven't gotten back, and that the best founders are the ones Silicon Valley keeps overlooking: the ones with zigzag lives, real taste, and a reason that's bigger than the exit. In this conversation, Brianne and I get into:- Why the MBA founder almost always builds a generic company and what the zigzag life produces that no business school can teach - The "culture sourcing" strategy that gave her more deal flow than anyone chasing it the conventional way - Why Gen Z hates dating apps for the exact same reason they hate bad workplaces and what it tells us about the future of work - Why the "next door millionaire" (the plumber, the contractor, the skilled tradesperson) has more job security in the AI era than the Ivy League entry-level software engineer - The science of luck and why the unlucky person is usually trying too hard - Why vulnerability in the workplace isn't a nice-to-have but actually the foundation of high-performing teams - How becoming unrelatable is the number one thing that kills careers, even wildly successful ones - Why a mission without a "why" can't attract great people, no matter how good the salary is - What it means to "get outside the bubble" and why it's the most important leadership move of this decade Brianne is one of the most original thinkers I've had on this show. She leads like she believes humans actually matter. This one is going to stay with you. Full episode is live on Spotify, Apple Podcasts, and YouTube.

    1h 1m

  6. MAR 24

    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

  7. 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

  8. 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
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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
    35
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

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