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.
Most people think selling is about the pitch. Kalina Bryant built $9 million in six months doing the opposite through relationships, built so well that the customers came to her. As she puts it, once you learn the art of relationships, you'll never sell a day in your life.
Kalina is the Founder and CEO of UnapologeTECH and was the first head of customer advocacy at Asana, where she turned community into one of the company's highest-converting revenue engines. She's a Forbes 30 Under 30 honoree and now an Executive in Residence at First Round Capital. In a moment when every inbox is flooded and every message sounds AI-generated, she makes the case that genuine human connection is the last real advantage left in business.
Healey and Kalina get into why the hard sell is dead, how she courts a customer like it's a first date, and what the best salespeople do that makes you forget you're being sold at all.
In this episode:
– Why ”always be closing” is the worst advice in modern sales
– How she built $9M in six months with ”dinners that weren't really dinners”
– Why she treats every customer relationship exactly like dating
– The reason the best salespeople never sound like they're selling
– How to turn a single cup of coffee into a deal that lasts years
– Why your credibility is the one asset you can't afford to spend carelessly
– What it actually means to be human in a transactional world
Subscribe to Don't Be a Jerk for more on the business case for being a good human.
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