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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

00:41:36

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

en

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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01:06:21

The Psychology of High-Performing Founders, with Dr....

Don"t Be a Jerk ·

2025/08/07

What do rage rooms, co-founder breakups, and high-stakes feedback have in common?They're all windows into how our brains process stress, and how most leaders are flying blind without even realizing it.In this episode, Healey Cypher sits down with Dr. Faith Cohen, one of the top executive coaches in the world, to explore the neuroscience behind great leadership. Dr. Cohen has coached leaders at companies like Harry’s, Athletic Greens, Warby Parker, and IVP, helping them navigate stress, scale

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00:51:29

Ben Gleib on Why Humor is the Best Therapy and How to...

Don"t Be a Jerk ·

2025/07/29

Ever wondered how comedians manage to laugh their way through heartbreak, anxiety, or even funerals?In Episode #3 of Don’t Be a Jerk, comedian Ben Gleib (Netflix, Comedy Central, host of “Idiotest”) shares how humor has been his ultimate self-therapy, saving him from life’s most painful moments and turning struggles into strength.Ben reveals the surprising power behind self-deprecation, why being authentically flawed makes you a better public speaker, and how comedy helped him handle being bullied

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00:56:15

Winning the War Within: How Adam Greenfeld Silenced...

Don"t Be a Jerk ·

2025/07/23

In this episode of Don’t Be a Jerk, host Healey Cypher sits down with Adam Greenfeld, co-founder of Frij and former co-founder of Thesis, to explore how his greatest obstacle wasn’t building companies… it was his relentless inner critic.Known for transforming brands into thriving businesses, Adam opens up about his battle with self-doubt and perfectionism, revealing powerful insights and practical tools for founders and leaders to cultivate true self-compassion, clarity, and success.In this honest

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00:56:09

Why Nice Guys Win: Jules Maltz on The Power of...

Don"t Be a Jerk ·

2025/07/15

In the very first episode of Don’t Be a Jerk, host Healey Cypher sits down with legendary investor Jules Maltz, the VC behind investments in iconic companies like Slack, Dropbox, Grammarly, Zendesk, and more.Jules breaks every stereotype of the typical cutthroat investor. Known for his kindness and humility, Jules reveals why authenticity, vulnerability, and imperfection are strategic superpowers.In this honest and insightful conversation, you’ll discover:Why perfection can actually make people

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31 results

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