Don't Be a Jerk

Healey Cypher
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👋 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. 3d ago

    Why This Founder Says Humility is #1 Trait for the Best Hires with Kevin Kissi

    Kevin Kissi spent years at Microsoft leading teams that shipped software to hundreds of millions of people. Then he walked away to build Zof AI with no institutional funding, betting on one idea most of the industry still gets wrong: a system that looks perfect but can't be trusted has already failed. Born in Accra, raised between Ghana, Atlanta, and the snows of North Dakota and Minnesota, Kevin built a worldview where transparency beats polish and humility beats ego. In this conversation with Healey Cypher, he explains why he wants his own team to forget he's the boss, how he reads a single conversation to know whether to hire someone, and why he treats his mental energy like a budget he refuses to overspend. It's a conversation about reliability, in software and in people, and the courage it takes to build things that admit when they're broken. In this episode: - Why Kevin says "perfect without trust is failure," and what he builds instead - The restaurant test for whether you're actually leading or just managing - How he spots a bad hire by listening for one missing trait - The Friday memo habit that revealed how much his team relied on him - Why he walked away from a degree, a math professorship, and Microsoft - How he budgets his mental energy like a bank account - Building AI agents that carry human judgment instead of removing it Subscribe to Don't Be a Jerk for conversations with leaders who prove you can build great things while doing good in the world.

    55 min

  2. Jun 16

    The Lost Art of Building Relationships: A Masterclass in Selling Without Selling | Kalina Bryant

    Most people think selling is about the pitch. Kalina Bryant built $9 million in six months doing the opposite through relationships, built so well that the customers came to her. As she puts it, once you learn the art of relationships, you'll never sell a day in your life. Kalina is the Founder and CEO of UnapologeTECH and was the first head of customer advocacy at Asana, where she turned community into one of the company's highest-converting revenue engines. She's a Forbes 30 Under 30 honoree and now an Executive in Residence at First Round Capital. In a moment when every inbox is flooded and every message sounds AI-generated, she makes the case that genuine human connection is the last real advantage left in business. Healey and Kalina get into why the hard sell is dead, how she courts a customer like it's a first date, and what the best salespeople do that makes you forget you're being sold at all. In this episode: - Why "always be closing" is the worst advice in modern sales - How she built $9M in six months with "dinners that weren't really dinners" - Why she treats every customer relationship exactly like dating - The reason the best salespeople never sound like they're selling - How to turn a single cup of coffee into a deal that lasts years - Why your credibility is the one asset you can't afford to spend carelessly - What it actually means to be human in a transactional world Subscribe to Don't Be a Jerk for more on the business case for being a good human.

    42 min

  3. May 12

    The Social Skill Every Great Founder Has (That Nobody Teaches You) with Paul Bakaus

    Paul Bakaus started coding at 11, sold his first company to Zynga, and spent years at Google working on Search, Chrome, and ultimately as their first head of creator relations with a focus on bringing creators back to the open web. Later on at Spotter, he built AI tools for creators like Dude Perfect and MrBeast. He's now the founder of Renaissance Geek and building Impeccable, an AI-powered creative tool for YouTube creators. In this episode, Paul and Healey get into the social skill that separates good leaders from great ones, why most people are terrible at asking the right questions, and why being nice at work can be the unkindest thing you do. In this episode, we get into: - Why everyone in the room is the main character of their own story, and how the best communicators use that to win every room they walk into - The pitch deck trick Paul watched a colleague use at Google to get promoted every single time, and what it actually reveals about how people make decisions - Why being nice and being kind are completely different things, and how California's passive-aggressive culture gets this exactly backwards - What FBI hostage negotiators and top Google executives have in common when it comes to getting people to say yes - Why the world's best car salesman outperformed everyone else by 10x using a single postcard - How AI sycophancy is actively making you worse at thinking, and what to do about it - Why Paul's team at Renaissance Geek now needs a one-hour standup just to stay aligned, and what that tells us about where product teams are headed - The open source move that made Paul "criminally" generous, and why it kept coming back to him in ways money couldn't buy - Why most early managers kingdom-build out of fear, and what Paul did when he flipped the script entirely This full episode of Don’t Be a Jerk is live on Spotify, Apple Podcasts, and YouTube.

    57 min

  4. May 5

    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

  5. 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

  6. 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

  7. 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

  8. 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
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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
    38
  • Rating
    Explicit
  • Copyright
    © Healey Cypher
  • Show Website
    Don't Be a Jerk

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