Don't Be a Jerk

What happens when life throws you something you can’t control? For Lucy Aragon, the answer was to keep dancing. She’s been to 105 countries, built a life around optimism and adventure, and faced her husband’s cancer diagnosis with humor, perspective, and a contagious belief that joy isn’t luck. It’s work. In this episode, Healey Cypher sits down with Lucy to talk about the art of staying light whe...

What does it take to build a real community in a world that rewards hustle over humanity? Espree Devora has spent over a decade answering that question. She’s the founder of We Are LA Tech and host of Women in Tech , where she’s spent thousands of hours connecting entrepreneurs, creators, and founders (and learning the hard way what it means to lead with empathy). In this episode, Healey Cypher si...

What happens when you build a $400 million startup and then lose it all? For James Beshara, the answer wasn’t another company. It was a complete rewiring of how to live. In this episode, Healey Cypher sits down with the founder of Tilt (acquired by Airbnb) and Magic Mind to talk about the unseen side of ambition: the waves you catch, the ones you miss, and the peace that comes when you stop fighti...

What if telling the truth faster could make your company more profitable, your culture stronger, and your life easier? Robert Yuen, CEO of Monograph, believes it can. He has built an entire business around it. In this episode of Don’t Be a Jerk , Healey sits down with Robert to unpack what radical transparency really looks like in practice. They discuss everything from open dashboards and revenue...

Empathy is one of the most powerful tools we have for survival, leadership, and connection. In this episode of Don’t Be a Jerk, Healey Cypher sits down with Jamil Zaki — Stanford psychology professor, empathy researcher, and author of The War for Kindness — to explore why empathy is under siege and how we can build it back, stronger than ever. Jamil shares: Why empathy has declined 40% in the past...

When you think about “service,” you might picture a volunteer day with matching T-shirts or a line on a résumé. But for Shakirah Simley, service is deeper. It’s generational. It’s survival. And it’s the force that has guided her life and leadership. Shakirah grew up in Harlem and the South Bronx, raised by a family of Black women leaders, social workers, and activists. Today, she’s the Executive D...

When I first met Young Han, he wasn’t coming on my podcast. He was stepping in as a fractional CFO to help me lead through one of the hardest stretches of my career. Within 15 minutes of our first meeting, he scrapped his entire plan and said: “We’re meeting three nights a week at 7pm until we get through this.” And then he did. Night after night, Young sat down with me and helped me push through....

Aaron Schwartz has built and scaled companies you know — Modify Watches, Passport, Loop Returns — and now Orita.ai , helping 100+ brands land in inboxes instead of spam. But ask anyone who’s worked with him, and they’ll tell you his real superpower isn’t just building businesses. It’s building people. In this conversation, we dig into: - Why sharing problems faster l eads to better solutions (and...

This one’s different. No guests, no interviews. Just me, your questions, and a few stories from the trenches. Over the last few weeks of Don’t Be a Jerk , I’ve had incredible conversations with founders, VCs, coaches, and comedians. But behind the scenes, I’ve also been getting a flood of DMs, texts, and Slack messages with questions about leadership, empathy, and what it actually means to “not be...

Born legally blind in rural India, Sam Maddula’s life changed forever thanks to a single act of kindness: a corneal transplant that restored his sight. That early gift shaped everything that came after, including his philosophy as founder of Bank’s Apothecary Specialty Pharmacy, a company he scaled to $300M in annual revenue before selling at an industry-leading valuation. In this episode of Don’t...

Most people dread negotiations, whether it’s salary discussions, sales deals, or even personal conflicts. But what if negotiating didn’t have to feel stressful, combative, or uncomfortable? What if you could negotiate like an elite expert without ever feeling like a jerk? In this episode of Don’t Be a Jerk , Healey sits down with Derek Blazensky and Todd Camp, negotiation advisors who’ve coached e...

What do rage rooms, co-founder breakups, and high-stakes feedback have in common? They're all windows into how our brains process stress, and how most leaders are flying blind without even realizing it. In this episode, Healey Cypher sits down with Dr. Faith Cohen, one of the top executive coaches in the world, to explore the neuroscience behind great leadership. Dr. Cohen has coached leaders...

Ever wondered how comedians manage to laugh their way through heartbreak, anxiety, or even funerals? In Episode #3 of Don’t Be a Jerk , comedian Ben Gleib (Netflix, Comedy Central, host of “Idiotest”) shares how humor has been his ultimate self-therapy, saving him from life’s most painful moments and turning struggles into strength. Ben reveals the surprising power behind self-deprecation, why bei...

In this episode of Don’t Be a Jerk , host Healey Cypher sits down with Adam Greenfeld, co-founder of Frij and former co-founder of Thesis, to explore how his greatest obstacle wasn’t building companies… it was his relentless inner critic. Known for transforming brands into thriving businesses, Adam opens up about his battle with self-doubt and perfectionism, revealing powerful insights and practic...

In the very first episode of Don’t Be a Jerk , host Healey Cypher sits down with legendary investor Jules Maltz, the VC behind investments in iconic companies like Slack, Dropbox, Grammarly, Zendesk, and more. Jules breaks every stereotype of the typical cutthroat investor. Known for his kindness and humility, Jules reveals why authenticity, vulnerability, and imperfection are strategic superpower...