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PODCAST

Don"t Be a Jerk

👋 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

business management

All Episodes

00:42:53

Why Most Wellness Brands Lose Trust and How to Avoid...

Don"t Be a Jerk ·

2026/02/03

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

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00:20:31

Why Most Goal Setting Fails (and the Exercise That...

Don"t Be a Jerk ·

2026/01/27

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

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00:44:12

Why the Best Founders Don’t Try to Sound Smart with...

Don"t Be a Jerk ·

2026/01/21

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

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00:48:51

Why Inclusion Wins in the Long Run with Damian...

Don"t Be a Jerk ·

2026/01/13

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

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00:31:40

A Letter From My 80-Year-Old Self

Don"t Be a Jerk ·

2026/01/07

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

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00:56:52

The Hidden Success Behind 100 No. 1 Debuts and the...

Don"t Be a Jerk ·

2025/12/16

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

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00:54:33

The Quantum Physicist Who Proves Soft Skills Beat IQ

Don"t Be a Jerk ·

2025/12/09

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

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00:52:46

How Jesse Pujji Rewired His Mind (and Built Multiple...

Don"t Be a Jerk ·

2025/12/02

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

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00:51:48

Personal Branding for Introverts: What Every Leader...

Don"t Be a Jerk ·

2025/11/18

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:

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01:06:13

What 50 Cent, Disneyland, and Cancer Taught Lucy...

Don"t Be a Jerk ·

2025/11/04

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,

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00:59:29

Why True Leadership Starts with Loving Yourself, with...

Don"t Be a Jerk ·

2025/10/28

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

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01:03:34

Why Stillness Beats Hustle (and Other Lessons from a...

Don"t Be a Jerk ·

2025/10/21

What happens when you build a $400 million startup and then lose it all?For James Beshara, the answer wasn’t another company. It was a complete rewiring of how to live.In this episode, Healey Cypher sits down with the founder of Tilt (acquired by Airbnb) and Magic Mind to talk about the unseen side of ambition: the waves you catch, the ones you miss, and the peace that comes when you stop fighting the current.James shares how public failure became the best thing that ever happened to him, why

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00:51:23

Radical Transparency: The CEO’s Shortcut to Trust...

Don"t Be a Jerk ·

2025/10/14

What if telling the truth faster could make your company more profitable, your culture stronger, and your life easier?Robert Yuen, CEO of Monograph, believes it can. He has built an entire business around it.In this episode of Don’t Be a Jerk, Healey sits down with Robert to unpack what radical transparency really looks like in practice. They discuss everything from open dashboards and revenue lines visible to every employee, to investor meetings where Robert leads with the hard stuff

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00:41:36

The War for Kindness: Why Empathy Is a Superpower...

Don"t Be a Jerk ·

2025/10/07

Empathy is one of the most powerful tools we have for survival, leadership, and connection.In this episode of Don’t Be a Jerk, Healey Cypher sits down with Jamil Zaki — Stanford psychology professor, empathy researcher, and author of The War for Kindness — to explore why empathy is under siege and how we can build it back, stronger than ever.Jamil shares:Why empathy has declined 40% in the past few decades and why that’s reversible.How reading fiction can be a “gateway drug” for empathy.A simple

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00:48:48

The Life-Changing Power of Service with Shakirah Simley

Don"t Be a Jerk ·

2025/09/30

When you think about “service,” you might picture a volunteer day with matching T-shirts or a line on a résumé. But for Shakirah Simley, service is deeper. It’s generational. It’s survival. And it’s the force that has guided her life and leadership.Shakirah grew up in Harlem and the South Bronx, raised by a family of Black women leaders, social workers, and activists. Today, she’s the Executive Director of the Booker T. Washington Community Service Center in San Francisco, where she’s quintupled the

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00:47:15

The Relationship OS: Young Han’s System for Human...

Don"t Be a Jerk ·

2025/09/23

When I first met Young Han, he wasn’t coming on my podcast. He was stepping in as a fractional CFO to help me lead through one of the hardest stretches of my career.Within 15 minutes of our first meeting, he scrapped his entire plan and said: “We’re meeting three nights a week at 7pm until we get through this.” And then he did. Night after night, Young sat down with me and helped me push through. That’s who he is.Today, Young is a serial founder, fractional COO/CFO, coach, and host of The Girl Dad

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00:48:57

The ROI of Generosity: Aaron Schwartz @Orita.ai on...

Don"t Be a Jerk ·

2025/09/16

Aaron Schwartz has built and scaled companies you know — Modify Watches, Passport, Loop Returns — and now Orita.ai, helping 100+ brands land in inboxes instead of spam. But ask anyone who’s worked with him, and they’ll tell you his real superpower isn’t just building businesses. It’s building people.In this conversation, we dig into:- Why sharing problems faster leads to better solutions (and stronger relationships).- The inner circle of advisors that Aaron has relied on for years, and how you can

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00:20:24

Why I Started Don’t Be a Jerk (and the Questions...

Don"t Be a Jerk ·

2025/09/09

This one’s different. No guests, no interviews. Just me, your questions, and a few stories from the trenches.Over the last few weeks of Don’t Be a Jerk, I’ve had incredible conversations with founders, VCs, coaches, and comedians. But behind the scenes, I’ve also been getting a flood of DMs, texts, and Slack messages with questions about leadership, empathy, and what it actually means to “not be a jerk” at work.So in this special solo episode, I sit down to answer them. We get into:- Why I started

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00:56:03

From Blind at Birth to Million-Dollar Founder: Sam...

Don"t Be a Jerk ·

2025/08/19

Born legally blind in rural India, Sam Maddula’s life changed forever thanks to a single act of kindness: a corneal transplant that restored his sight.That early gift shaped everything that came after, including his philosophy as founder of Bank’s Apothecary Specialty Pharmacy, a company he scaled to $300M in annual revenue before selling at an industry-leading valuation.In this episode of Don’t Be a Jerk, Sam shares the radical leadership principles that fueled his success, from paying employees

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01:09:13

Why “Nice” Negotiators Win More: Master the Soft...

Don"t Be a Jerk ·

2025/08/12

Most people dread negotiations, whether it’s salary discussions, sales deals, or even personal conflicts. But what if negotiating didn’t have to feel stressful, combative, or uncomfortable? What if you could negotiate like an elite expert without ever feeling like a jerk?In this episode of Don’t Be a Jerk, Healey sits down with Derek Blazensky and Todd Camp, negotiation advisors who’ve coached executives from some of the largest companies in the world, helping them navigate billion-dollar deals with

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24 results

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