Don't Be a Jerk
Don't Be a Jerk
Podcast Description
👋 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.
Podcast Insights
Content Themes
The podcast focuses on themes of leadership ethics, business authenticity, and emotional intelligence, with episodes covering topics such as the strategic advantages of vulnerability in venture capital and the impact of genuine communication in business transactions.
👋 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.
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 and walk through the exercise, the moments that inspired it, and the mindset shifts that followed. This isn’t a productivity episode. It’s a presence episode.
If you’ve ever felt like life is moving too fast, you’re always optimizing for “later”, or you’re succeeding on paper but missing something real: this one is for you.
In this episode, we explore:– The moment I saw myself clearly (and didn’t like what I saw)
– The letter I wrote from my 80-year-old self (and why it broke me open)
– Why the “arrival fallacy” keeps us chasing the next milestone
– A simple daily prompt that changed how I show up as a father, partner, and leader
– How imagining the ending can radically improve the way you live today
– Why helping others may be the clearest path to a meaningful life
This episode is raw, personal, and intentionally slower than usual. You don’t need to be a parent to listen. You don’t need to be 41. You just need to be human.
If it changes even one ordinary day for you, it did its job.
⏱️ TIMESTAMPS
00:00 – A hard conversation & an uncomfortable realization
02:00 – Watching myself through someone else’s eyes
04:30 – The exercise that changed everything
05:00 – Reading the letter from my 80-year-old self
13:30 – Why ordinary days are the ones we’ll miss most
19:50 – A dark career moment and the mindset shift that saved me
26:00 – “Everything works out in my favor” (and why it works)
37:50 – Imagining the ending as a daily decision-making tool
40:30 – The question I ask before every moral decision
42:00 – The one lesson I hope my kids remember
45:00 – A quiet closing invitation to try this yourself
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