Healey Cypher

"If you do something 100% for four months, your entire life can change overnight." - @avnibarman_ Most people never find out because they never go ALL IN. Don't be most people. 💜

@avnibarman_ New episode of DBAJ with Avni: youtu.be/IUBgqcaOgZg

NEW episode of Don’t Be a Jerk is live everywhere! This week, I sat down with @avnibarman_ to discuss how she’s grown her independent media company into 60 million monthly views, launched a venture fund, runs a 750,000-person community, AND writes newsletter read by 75k people a week. Avni blew me away in this conversation. Here are a few things you'll learn: 1. The character test that never lies: how you treat someone you have nothing to gain from 2. Why "giving someone their flowers" is one of the most underrated leadership moves in business 3. How one sentence, sent cold to one of five self-made female billionaires in the world, led to 8 hours one-on-one with her and "confidence that could last a lifetime" 4. Why we actually DO care what other people think and what the most self-aware leaders do about it 5. Why venture capital is going to matter a lot less in the next decade and what replaces it 6. How to beat 99% of your competition in any field without being more talented or better resourced 7. Why giving everything away for free is the highest-ROI strategy for building lasting trust Avni is one of the most generous and clear-eyed operators I've come across. She leads like her reputation is always on the line, because for her, it always is. Full episode is live now on Spotify, Apple, and YouTube.

@AndrewDudum @wearehims @wearehers Full episode with Andrew is live everywhere you get your podcasts! youtu.be/IAYCA-whKUM

I’ve known @AndrewDudum for a long time. And what’s always stood out isn’t how smart he is. It’s how calm he stays when things feel scary or tough. In this episode, Andrew Dudum (founder of @wearehims & @wearehers) He says that the biggest super power for a founder is being able to get comfortable being uncomfortable. He doesn’t try to out-run it. He just recognizes these challenging moments for what they are. If you can’t sit there without rushing to fix, numb, or avoid it, you won’t scale anything that matters. This might be the most underrated trait in leadership.

@AndrewDudum youtu.be/IAYCA-whKUM

When @AndrewDudum was 12 years old, his dad sat him down and told him: “I’m dying. Everyone’s dying. I just might know what kills me.” His Dad had stage IV colon cancer at 38. The night before surgery, his dad took off the Mother Mary pendant he’d worn his entire life and handed it to Andrew. “You’re the oldest son,” he told him. “You’re the man of the house now. Take care of your mom.” Thankfully, his dad survived and Andrew was able to give the pendant back to his Dad. But that moment in his life re-shaped everything for Andrew and into the DNA of Hims & Hers, which he founded in 2017. Below are some of my favorite ideas that Andrew shared on the pod: - Why Andrew is obsessed with having hard conversations early - Why he draws such a sharp line between niceness vs. kindness - How life filters your people for you and who really matters - And why he’s built a company around being comfortable in deeply uncomfortable territory We talked about all of this and so much more in this latest episode of Don’t Be a Jerk. I’m really not sure anyone embodies this philosophy of not being a jerk more than Andrew. I’ve known Andrew long before @wearehims & @wearehers was even an idea. Before the headlines and the public scrutiny of building a public company that forces people to confront the most uncomfortable parts of their health… we were just 2 friends in SF trying to build meaningful things without becoming assholes in the process. This really is one of the most honest conversations I’ve had on the show. So excited and honored to share it with you today. Full episode is live! Link in next tweet 👇️

@AndrewDudum @wearehims @wearehers Follow and subscribe to ‘Don’t Be a Jerk’ so you can get this episode with Andrew Dudum right when it drops 🤝 youtu.be/IAYCA-whKUM

@AndrewDudum. Founder & CEO of @wearehims& @wearehers. Tomorrow. March 11, 2026. Available everywhere you get your podcasts.

@AndrewDudum @wearehims @wearehers Follow and subscribe to ‘Don’t Be a Jerk’ so you can get this episode with Andrew Dudum right when it drops 🤝 youtu.be/IAYCA-whKUM

Only took me an hour to get to the point. Humanity at all costs. @healeycypher is one of the most generous hosts and humans I have ever met. What a joy to be on his Don't Be A Jerk Podcast.

@DaveFlink Full episode is live right here: youtu.be/JXMUvNO80G0

1 in 5 people are neurodivergent. @DaveFlink has spent 28 years making sure workplaces and schools stop treating that like a problem to fix. What struck me most about this conversation was just how USEFUL everything he said was. Immediately actionable and oh so wise. David is the founder of the @theNDalliance, a recognized CNN Hero, Bezos Award winner, and one of the most generous thinkers I've had on this show. In this episode of Don't Be a Jerk: - The critical difference between expectations and agreements (and why one quietly destroys teams) - Why "bad employees" almost never exist and what's really going on instead - His simple practice for giving people get-out-of-jail-free cards before you judge them - Why psychological safety has to be rebuilt every time your team changes And so much more. I could have talked to David for hours and hours on end. I hope you enjoy this one as much as I did. My conversation with David Flink on Don't Be a Jerk is live everywhere you get your podcasts! 🎙️

54% of Americans don't know their neighbor. Let that sink in for a second. The biggest problem with this is that we NEED to know our neighbors. We need community more than ever. And here’s why: The longest social sciences study ever conducted started at Harvard in 1938 and ran for nearly 80 years. They were asking one simple question: what leads to the longest, happiest life? It turns out it wasn’t wealth, status, or achievement. It was COMMUNITY. Specifically: longitudinal friendships… real relationships held consistently over the course of a lifetime. And yet more than half of us don't even know the person living 10 feet away. We are wired for connection. We crave belonging. It's literally in our biology. The gap between what we need and how we're actually living has never been bigger. We have work to do. 🫂

Resume virtues get you the job or the career you want. Eulogy virtues make life REALLY worth living. ❤️ Choose wisely what you optimize for over the long-run. @RafaelBurde (Co-lead of Global Search Policy @Google) is live on Don't Be a Jerk, everywhere you get your podcasts.

This new Navan offering powered by @BoomPopHQ is a game-changer for planning and booking group travel and events

@Navan @BoomPopHQ @BoomPopHQ is VERY pumped to get this out to the world. AI can now plan events. Let’s goooo! 🚀

BOOM: One single end-to-end platform for the entire event lifecycle ✨ Introducing Navan’s all new events functionality, powered by the integration of @BoomPopHQ AI-driven platform. Now, organizers can: ✔️ Instantly source venues with AI ✔️ Gain total visibility into all event costs ✔️ Seamlessly manage agendas, RFPs, and room blocks ✔️ Provide attendees with a single, unified itinerary Watch the video below to see our SVP & GM of Meetings & Events, Galen Grady, dive into how we’re transforming corporate events, removing barriers, and channeling a fragmented process into a seamless experience.

@RafaelBurde @Google Check out the full episode here! youtu.be/tVe2Q94rPbs

@RafaelBurde holds one of the most powerful jobs on the planet. He co-leads Global Search Policy at @Google, leading the decisions behind what billions of people see or don't see when they search for anything online. Think about that for a second. His decisions help shape the information diet of the entire internet… Raf and I met at Penn, reconnected randomly at Whole Foods in SF in 2019, and now our kids tear apart each other's houses together. This episode isn't what you'd expect. Sure, we talk about stewarding trust at the scale of billions. About safeguarding without sanitizing. About the framework he uses to make calls that affect literally everyone online. But we also go deep on: - The meaning crisis and how to build a life around what endures - Suffocation vs. abdication (in parenting, leadership, and life) - Why intergenerational friendships are massively underinvested Raf is brilliant, grounded, and one of the most thoughtful people I know about what it means to hold power responsibly. The full episode of ‘Don’t Be a Jerk’ is live everywhere you get your podcasts!