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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
Happiness
Generosity
Trust
Education
Negotiation Techniques
Radical Transparency
Humor
Workplace Empathy
Self-Reflection

👋 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

PublishesWeeklyEpisodes42Foundeda year ago
Number of ListenersCategories
ManagementBusiness

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Artwork for Don't Be a Jerk

Latest Episodes

It's harder to place a 16-year-old intern than a $200,000 software engineer. Alex Funkhouser learned that the hard way: his firm SherlockTalent places senior engineers for a living, but when he volunteered to find internships for Miami high schoolers... more

Chad Bernstein showed up at a juvenile detention center with his band, ready to play, and the guards stopped him at the door. The guitar strings, they said, could be used as weapons. So he walked in empty-handed, into a room of kids with crossed arms... more

YouTube

Most foundations write a check and walk away. Carolina Jayaram does the opposite. As founding CEO of The Elevate Prize Foundation, she gives changemakers $300,000 and then carves $50,000 of it out for the leader, not the mission. Her argument is blun... more

YouTube

A clip from Don't Be a Jerk went viral for the wrong reasons. It was a vulnerable story: Healey's friend Danh Trang, a little person, recounting how a CEO once used a slur and how Danh responded with grace instead of anger. The CEO apologized and gre... more

YouTube

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Recent Guests

Carolina Garcia Jayaram
CEO of Elevate Prize Foundation
Elevate Prize Foundation
Episode: Why Leading With Love Is a Radical Act with Elevate Prize CEO Carolina Jayaram
Kevin Kissi
Founder and CEO of zof.ai
zof.ai
Episode: Why This Founder Says Humility is #1 Trait for the Best Hires with Kevin Kissi
Kalina Bryant
Founder/CEO of Unapologetic, inclusive tech career platform
Unapologetic
Episode: The Lost Art of Building Relationships: A Masterclass in Selling Without Selling | Kalina Bryant
Paul Bakaus
Founder/CEO; Google's first head of creative relations; AI tool creator
Renaissance Geek / Google
Episode: The Social Skill Every Great Founder Has (That Nobody Teaches You) with Paul Bakaus
Blake Hudelson
Co-founder of BoomPop
BoomPop
Episode: Why 65% of Co-Founders Fail (and How to Prevent That) with BoomPop Co-Founder Blake Hudelson
Danh Trang
Venture investor at South Park Commons; former Wall Street executive
South Park Commons
Episode: The 4’2” VC Who Ran Boston 7 Times and Spots Potential Before Everyone Else | Danh Trang
Hillary Blout
Former prosecutor, founder of For The People
For The People
Episode: The Former Prosecutor Who Built a Legal System to Bring Prisoners Home with Hillary Blout @ For The People
Brianne Kimmel
Investor who writes early checks for overlooked founders
All Main Spectrum / VC investor (All Spectrum)
Episode: How Brianne Kimmel Built a $45M Fund Around the Founders Nobody Else Believed In
Avni Barman
Creator, founder and investor at Gen She
Gen She
Episode: Why Trust Beats Product: How Avni Barman Built a 60-Million-View Media Empire by Giving Everything Away

Host

Healey Cypher
Host of Dont Be a Jerk

Reviews

4.4 out of 5 stars from 20 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 States7 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Production could tighten up pacing and topic focus.
Guests are strong, but the format sometimes underdelivers on standout insights.
The host has good intentions but execution can feel stereotypic and generic.
Some episodes feel like they lean on clichés rather than deep analysis.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Why This Founder Says Humility is #1 Trait for the Best Hires with Kevin Kissi
Q: Why is admitting failures early so critical to trust and effectiveness?
Admitting mistakes early demonstrates transparency, invites feedback, prevents hidden issues from growing, and ultimately strengthens team trust and decision-making.
Why This Founder Says Humility is #1 Trait for the Best Hires with Kevin Kissi
Q: What does it mean to hire people who are better than you at certain things, and how does alignment matter?
He emphasizes hiring top performers, aligning motivations with shared context, and letting capable people make decisions in service of common goals rather than commanding them, which accelerates progress.
Why This Founder Says Humility is #1 Trait for the Best Hires with Kevin Kissi
Q: How have you woven transparency and humility into your leadership and team-building approach?
Kevin explains staying close to the teams, being accessible, and leading by example with open discussions about challenges, which fosters trust and self-management rather than micromanagement.
The Lost Art of Building Relationships: A Masterclass in Selling Without Selling | Kalina Bryant
Q: What are the core elements that make a sales process feel non-transactional and relationship-first?
Focus on genuine curiosity, learning about the other person's life and needs, and building a meaningful experience rather than pushing a deal. Demonstrate value through relationships and let trust lead to long-term collaboration.
Why Trust Beats Product: How Avni Barman Built a 60-Million-View Media Empire by Giving Everything Away
Q: Why do you emphasize giving away resources and knowledge for free?
Because genuine impact and long-term success come from building trust and value upfront; generous, transparent sharing creates an engaged community and opens doors to opportunities that money alone cannot buy.

Audience Metrics

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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 on leadership done right, highlighting kindness, integrity, and practical tactics that drive sustainable success. Across episodes, guests range from founders and investors to researchers and creators who emphasize empathy, inclusive leadership, transparent communication, and personal growth as core business strategies. Unique angles include radical transparency, the creator economy, and the deliberate use of soft skills to navigate tech, startups, and culture. Listeners can expect actionable takeaways for building teams and brands without compromising values, making it appealing to growth-minded professionals who want to lead with humanity.

Noteworthy aspects include a strong emphasis on culture and psychological safety, ... more

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

1. Huberman Lab
2. Hard Fork
3. Pod Save America

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

Don't Be a Jerk launched a year ago and published 42 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. Carolina Garcia Jayaram
2. Kevin Kissi
3. Kalina Bryant
4. Paul Bakaus
5. Blake Hudelson
6. Danh Trang
7. Hillary Blout
8. Brianne Kimmel

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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