Episodes 35
Avg. Duration 53m
Activity Highly Active
Apple Rating 4.1 (10)
Since Jul 2025
Latest Episode May 2026

Publishing Details

Schedule
Weekly
Format
Episodic
Consistency
66%
Hosting
anchor.fm

About This Podcast

👋 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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Recent Episodes

Why 65% of Co-Founders Fail (and How to Prevent That) with BoomPop Co-Founder Blake Hudelson

May 05, 2026 1h 10m

Blake Hudelson is my co-founder at BoomPop (and we probably spend more time with each other than we do with our wives). We met at a startup studio in San Francisco six years ago. I proposed we try…

The 4’2” VC Who Ran Boston 7 Times and Spots Potential Before Everyone Else | Danh Trang

Apr 28, 2026 46m

Danh Trang was standing near the finish line when the 2013 Boston Marathon bombs went off. He was watching friends and family. He came back the following year and ran it. At 4'2", in 5:36. Raised…

The Former Prosecutor Who Built a Legal System to Bring Prisoners Home with Hillary Blout @ For The People

Apr 21, 2026 50m

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…

7 Ways to be a Great Person and 5 Traps That Can Make You Seem Like a Jerk

Apr 14, 2026 17m

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…

How Brianne Kimmel Built a $45M Fund Around the Founders Nobody Else Believed In

Apr 07, 2026 1h 1m

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…

What Happens When an 11-Year-Old Decides to Stop Waiting for Better News and Make It Himself with Sam

Mar 24, 2026 35m

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…

Why Trust Beats Product: How Avni Barman Built a 60-Million-View Media Empire by Giving Everything Away

Mar 17, 2026 49m

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…

Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers

Mar 10, 2026 50m

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.…

The Rules of Rule Breaking: David Flink on Why the System Was Never Built for You

Mar 03, 2026 1h 14m

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…

The Man Who Quietly Decides What Billions See On Google: Rafael Burde

Feb 24, 2026 48m

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…

Why No One Has Quit Her Company in 5 Years with Dr. Ilana Nankin

Feb 17, 2026 51m

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…

Why Most Wellness Brands Lose Trust and How to Avoid It with Dan Cox

Feb 03, 2026 42m

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…

Why Most Goal Setting Fails (and the Exercise That Fixed It for Me)

Jan 27, 2026 20m

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…

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

Jan 21, 2026 44m

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.,…

Why Inclusion Wins in the Long Run with Damian Pelliccione

Jan 13, 2026 48m

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…

A Letter From My 80-Year-Old Self

Jan 07, 2026 31m

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 Hidden Success Behind 100 No. 1 Debuts and the The YouTube Creator Economy, with Bing Chen

Dec 16, 2025 56m

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…

The Quantum Physicist Who Proves Soft Skills Beat IQ

Dec 09, 2025 54m

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…

How Jesse Pujji Rewired His Mind (and Built Multiple 8-Figure Companies)

Dec 02, 2025 52m

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…

Personal Branding for Introverts: What Every Leader Can Learn from Goldie Chan

Nov 18, 2025 51m

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…

Frequently Asked Questions

How many episodes does Don't Be a Jerk have?

Don't Be a Jerk has published 35 episodes since July 2025, covering topics in Business, Management.

Is Don't Be a Jerk still active?

Don't Be a Jerk is currently highly active with new episodes weekly. Average episode length is 53m.

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