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Artwork for Don't Be a Jerk

Don't Be a Jerk

Healey Cypher
Leadership
Empathy
Entrepreneurship
Mental Health
Emotional Intelligence
Personal Growth
Relationships
Gratitude
Personal Development
Cancer
Goal Setting
Trust
Generosity
Happiness
Humor
Negotiation Techniques
Workplace Empathy
Radical Transparency
Self-Reflection
Neuropsychology

👋 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 b... more

PublishesWeeklyEpisodes33Founded9 months ago
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Artwork for Don't Be a Jerk

Latest Episodes

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 pros... more

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 li... more

YouTube

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 Wor... more

YouTube

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 ... more

YouTube

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Recent Guests

Damian Pelliccione
Co-founder of Revry, an LGBTQ+ media company
Revry
Episode: Why Inclusion Wins in the Long Run with Damian Pelliccione
Bing Chen
Co-founder of Gold House and former YouTube executive
Gold House
Episode: The Hidden Success Behind 100 No. 1 Debuts and the The YouTube Creator Economy, with Bing Chen
Goldie Chan
A successful digital marketer and author, recognized for her storytelling skills online.
Episode: Personal Branding for Introverts: What Every Leader Can Learn from Goldie Chan
Jamil Zaki
Professor of Psychology at Stanford and author of The War for Kindness
Stanford University
Episode: The War for Kindness: Why Empathy Is a Superpower with Jamil Zaki, Psychology Professor @ Stanford
Young Han
Fractional CFO known for his expertise in building human connections and relationships within business
Episode: The Relationship OS: Young Han’s System for Human Connection
Derek Blazensky
Foundational leader at The Pareto Group specializing in negotiation coaching.
The Pareto Group
Episode: Why “Nice” Negotiators Win More: Master the Soft Skills That Close Big Deals, with Derek Blazensky & Todd Camp @ The Pareto Group
Todd Camp
Foundational leader at The Pareto Group focused on negotiation strategies.
The Pareto Group
Episode: Why “Nice” Negotiators Win More: Master the Soft Skills That Close Big Deals, with Derek Blazensky & Todd Camp @ The Pareto Group
Dr. Faith Cohen
An executive coach psychologist who has spent over 30,000 hours in one-on-one sessions to help people become high-performing leaders.
Episode: The Psychology of High-Performing Founders, with Dr. Faith Cohen

Host

Healey Cypher
Host focused on leadership with emphasis on kindness, integrity, and practical, strategic insights.

Reviews

4.2 out of 5 stars from 11 ratings
  • This podcast is blah

    The host of this podcast has great intentions, but The execution of this podcast is painfully stereotypic and generic.

    Apple Podcasts
    1
    Gotchayeah
    United States4 months ago

Listeners Say

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Listeners note strong intentions and practical leadership lessons, but some critique the show for perceived stereotypes or formulaic delivery.

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Talking Points

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Why the Best Founders Don’t Try to Sound Smart with Mike Jones
Q: What would be one thing you want tech CEOs or founders to internalize about leadership?
To measure decisions against what truly matters, particularly what you would reflect on in your deathbed regarding memories with loved ones over professional achievements.
Why the Best Founders Don’t Try to Sound Smart with Mike Jones
Q: How important is it to you that you hear that authenticity, empathy, lived experience part of that?
It's really important that a founder has a deep connection to the problem they're addressing, as it fuels their passion and perseverance.
From Blind at Birth to Million-Dollar Founder: Sam Maddula’s People-First Playbook
Q: What would you tell your 25 year old self about your career that maybe at that point you would disagree with, but now you know to be true?
Hold your head up high. Don't be so self conscious and believe in yourself.
The ROI of Generosity: Aaron Schwartz @Orita.ai on Luck, Boundaries, and Building People
Q: If you could go back to the earliest stage of your career, what would you tell yourself?
Be more open more quickly about the challenges and don't be afraid to share problems so others can help.
Why I Started Don’t Be a Jerk (and the Questions You’ve Been Asking Me)
Q: How do you fire someone and not be a jerk?
The most critical thing is to not surprise them. Establish clear agreements about expectations and performance from the beginning so that when you have to deliver bad news, it's based on mutual understanding.

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Frequently Asked Questions About Don't Be a Jerk

What is Don't Be a Jerk about and what kind of topics does it cover?

This show centers leadership, culture, and human-centric business strategies, highlighting how kindness, psychological safety, and authentic communication can drive durable success. Episodes frequently explore topics like empathy in leadership, inclusion and belonging in teams, personal growth, and practical frameworks for building trust and high-performing organizations. A notable pattern is translating science-backed insights and real-world founder experiences into tactical takeaways for leaders who want to win without compromising values. A standout aspect is inviting guests with deep expertise in psychology, community-building, and entrepreneurship to unpack how humane practices correlate with performance and resilience.

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Which podcasts are similar to Don't Be a Jerk?

These podcasts share a similar audience with Don't Be a Jerk:

1. A Bit of Optimism
2. The Mel Robbins Podcast
3. Good Hang with Amy Poehler
4. Throughline
5. IMO with Michelle Obama and Craig Robinson

How many episodes of Don't Be a Jerk are there?

Don't Be a Jerk launched 9 months ago and published 33 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Don't Be a Jerk?

Recent guests on Don't Be a Jerk include:

1. Damian Pelliccione
2. Bing Chen
3. Goldie Chan
4. Jamil Zaki
5. Young Han
6. Derek Blazensky
7. Todd Camp
8. Dr. Faith Cohen

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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