Don't Be a Jerk

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 few decades and why that’s reversible.How reading fiction can be a “gateway drug” for empathy.A simple tactic to de-escalate conflict (marriage fights included): list what you don’t know and what you already agree on.Why organizations that lead with empathy have lower turnover, more innovation, and stronger profits.How to move from a “warrior mentality” to a guardian mentality in leadership.Why nobody says hi… but everybody says hi back (and what that reveals about loneliness).The contagious nature of kindness and how to spark a ripple effect in your team.Why Jamil believes the empathy deficit is less about supply, and more about demand.This is empathy with receipts: science, data, and tactical frameworks you can use today. Whether you’re running a company, managing a team, or just trying to argue better with your spouse, this episode is for you.

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 Director of the Booker T. Washington Community Service Center in San Francisco, where she’s quintupled the budget, quadrupled the staff, and transformed the center into a thriving hub of housing, education, food justice, and wellness.In this conversation, Shakirah and Healey explore:- Why research shows service makes us healthier, happier, and even live longer- The difference between “resume service” and service that truly transforms communities- Why low-income and marginalized communities are often the most generous- How to prevent burnout when your job is helping others- Shakirah’s framework for service: time, treasure, and talent- The connection between service, empathy, and stronger democracies- Why humility isn’t optional if you want to lead with impactThis conversation is about building trust, resilience, and joy through the act of giving back.If you’ve ever thought “I’m too busy to volunteer” or wondered how to make service a real part of your life, this episode will change how you think.

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. That’s who he is.Today, Young is a serial founder, fractional COO/CFO, coach, and host of The Girl Dad Show. He’s on a mission to build 20 businesses to $1M ARR each. But more importantly, he’s built an operating system for human connection.In this episode we cover:- Why Starbucks taught him that relationships can outweigh even product quality- His 4-step framework for building trust instantly- The Rule of 100 and how it increases your surface area for luck- Why the future belongs to the emotionally fluent, not just the technically brilliant- Why diversity is a competitive advantage- How to prepare for interactions without being transactionalYoung’s story is part playbook, part inspiration, and all high-energy. If you want to learn how to scale not just your business but your relationships, this one’s for you.Full episode is live now on Spotify, Apple Podcasts, and YouTube.

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 leads to better solutions (and stronger relationships).- The inner circle of advisors that Aaron has relied on for years, and how you can build one too.- His personal framework for paying it forward without burning out.- Why he only advises founders he’d be willing to work for himself.- The surprising ROI of generosity (including the story of how a casual meeting in Bryant Park turned into co-founding Orita).- How to be authentic without oversharing, and the boundaries that protect trust.- Balancing the weight of being a founder with the realities of family, guilt, and joy.- The books Aaron rereads to stay focused and grounded when life gets loud.This one’s about generosity, luck, boundaries, and the human side of building. I walked away with a new perspective on who I help, how I help, and what I say yes to. And I think you will too.Full episode is live now on Spotify, Apple Podcasts, and YouTube.

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 a jerk” at work.So in this special solo episode, I sit down to answer them. We get into:- Why I started this podcast in the first place- How to be conflict-seeking without being an asshole- The #1 mistake early leaders make that kills credibility- How to repair when you realize you were the jerk- The difference between expectations and agreements- How to fire someone without being cruel- The art of debriefs and BLUFs (bottom line up front)- Two things you can do tomorrow to become a better person- How to rebuild trust once it’s been brokenThis episode is part playbook, part confession, part experiment, but at the core it’s about the same idea that launched this whole show: kindness in leadership isn’t weakness. It’s strategy.If you’ve got more questions you want me to tackle in a future solo episode, drop them in the comments, DM me, or send a carrier pigeon. You never know, maybe your question makes the next one.

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 Be a Jerk, Sam shares the radical leadership principles that fueled his success, from paying employees 2–3x the market rate to designing company outings where work talk is banned. His approach flips traditional corporate logic on its head — and proves that taking care of your people isn’t just “nice,” it’s the smartest business strategy there is.We cover:- The incredible origin story that shaped Sam’s people-first leadership style.- Why paying 2–3x market rate can *increase* profitability.- How to build “unreasonable loyalty” in your team.- The tactic Sam uses to make offshore employees feel true ownership in the company.- Why culture eats strategy for breakfast and how to make sure yours is strong.- What private equity can learn from people-first companies.If you’ve ever wondered whether you can “do good” and still scale big, Sam’s story is proof that you can. And that it might even be the fastest way to win.Listen now on Spotify, Apple Podcasts, or YouTube.

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 executives from some of the largest companies in the world, helping them navigate billion-dollar deals with ease and empathy.Here’s just a taste of the practical negotiation tactics and strategies you’ll walk away with:- The Four Reasons People Say No: Learn exactly why someone rejects your idea or offer (hint: it’s never personal), and discover how to address each issue to get to “yes.”- How to Ask Better Questions: Small adjustments to your phrasing can immediately disarm defensiveness and make tough conversations collaborative instead of combative.- Why Saying “No” Is Essential (and Powerful): Derek and Todd break down why the most successful negotiators actively embrace hearing and saying “no” — turning rejection into opportunity.- Advanced Negotiation Mindset: Discover how to stay calm, confident, and clear-headed even in tense situations, transforming challenging conversations into win-win outcomes.If you’ve ever struggled with negotiations, felt stuck after a rejection, or simply want to become a more confident, empathetic negotiator, this episode is your tactical playbook.Tune in to the episode now wherever you get your podcasts (Spotify, Apple, YouTube, and more).

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 at companies like Harry’s, Athletic Greens, Warby Parker, and IVP, helping them navigate stress, scale companies, and build emotionally intelligent teams.Together, they unpack:- Why 65% of startups fail due to co-founder dysfunction- How to give feedback without triggering fight-or-flight- What displaced aggression looks like in the workplace- The surprising power of self-compassion as a leadership advantage- The CUBE framework for handling difficult conversations- Why creating a sense of psychological safety isn’t just ethical—it’s smart businessThis is part science, part story, and all real talk for anyone building or leading something ambitious🎧 Listen to this episode if you:- Lead a team under pressure- Struggle with giving hard feedback- Want to build a more emotionally intelligent culture- Believe leadership starts with how you treat yourselfFull episode is live wherever you get your podcasts!

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 being authentically flawed makes you a better public speaker, and how comedy helped him handle being bullied as a kid. He even hilariously breaks down Barack Obama’s public speaking, proving nobody, not even the greatest orators, nails it every time.In this conversation, Ben also discusses:Why laughing through heartbreak can turn pain into your best material.How humor creates genuine safety (not just for others, but for yourself).Why canned lines will never outperform genuine listening and connection.How even the darkest moments can become lighter once you find the joke.Recorded after Healey and Ben hit it off at a recent conference, this episode feels less like an interview and more like two friends jamming about life, love, and the comedic absurdity of it all. If you’ve ever felt nervous about speaking up, overwhelmed by tough situations, or just need proof that laughing at yourself can heal pretty much anything — this one’s for you.Tune in now on Spotify, Apple Podcasts, YouTube, or wherever you listen.

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 practical tools for founders and leaders to cultivate true self-compassion, clarity, and success.In this honest and eye-opening conversation, you’ll discover:How Adam realized the inner voice pushing him to be perfect was actually holding him back—and the practical steps he took to break free from it.Why an “exit lifestyle” isn’t something you need to wait until your company is acquired to experience—and exactly how Adam started living his ideal life decades ahead of schedule.How intentional pauses can radically transform your day-to-day interactions, relationships, and overall happiness.Why Adam believes self-love isn’t just a nice-to-have. It’s the essential foundation of sustainable success and happiness.Adam’s unique daily journaling practice that helped him uncover hidden truths, reduce anxiety, and clarify his real purpose.How your internal state and mindset directly shape your external leadership style—and why your “vibe” matters far more than your words.Powerful lessons Adam learned from working closely with high-profile entrepreneurs like Adam Neumann, including how visionary leaders consistently inspire excitement rather than chase happiness.If you’re tired of the endless hustle, internal negativity, and chasing false definitions of success, Adam’s story is your invitation to step into a kinder, more intentional way of leading and living.Join Healey and Adam for this vulnerable yet empowering episode—and learn how silencing your inner critic can be your greatest competitive advantage, both professionally and personally.Listen and subscribe wherever you get your podcasts!