👋 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.
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The Former Prosecutor Who Built a Legal System to Bring Prisoners Home with Hillary Blout @ For The People
Tuesday, April 21, 2026 • Duration 50:13
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.
7 Ways to be a Great Person and 5 Traps That Can Make You Seem Like a Jerk
Tuesday, April 14, 2026 • Duration 17:26
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!
How Brianne Kimmel Built a $45M Fund Around the Founders Nobody Else Believed In
Tuesday, April 7, 2026 • Duration 01:01:06
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
What Happens When an 11-Year-Old Decides to Stop Waiting for Better News and Make It Himself with Sam
Tuesday, March 24, 2026 • Duration 35:16
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"
Why Trust Beats Product: How Avni Barman Built a 60-Million-View Media Empire by Giving Everything Away
Tuesday, March 17, 2026 • Duration 49:51
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 Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers
Tuesday, March 10, 2026 • Duration 50:59
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
The Rules of Rule Breaking: David Flink on Why the System Was Never Built for You
Tuesday, March 3, 2026 • Duration 01:14:31
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:
The Man Who Quietly Decides What Billions See On Google: Rafael Burde
Tuesday, February 24, 2026 • Duration 48:41
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"
Why No One Has Quit Her Company in 5 Years with Dr. Ilana Nankin
Tuesday, February 17, 2026 • Duration 51:15
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 back
This 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.
Why Most Wellness Brands Lose Trust and How to Avoid It with Dan Cox
Tuesday, February 3, 2026 • Duration 42:53
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.
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- 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.
- 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.
- 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.
- 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
"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.
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.
- "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
If you’re a founder, leader, or manager trying to build something that actually lasts, this episode will change how you think about culture.
