Don't Be a Jerk

Most foundations write a check and walk away. Carolina Jayaram does the opposite. As founding CEO of The Elevate Prize Foundation, she gives changemakers $300,000 and then carves $50,000 of it out for the leader, not the mission. Her argument is blunt: a depleted founder can't carry the work forward, so funding the human isn't a perk, it's the investment. Healey sits down with Carolina...

A clip from Don't Be a Jerk went viral for the wrong reasons. It was a vulnerable story: Healey's friend Danh Trang, a little person, recounting how a CEO once used a slur and how Danh responded with grace instead of anger. The CEO apologized and grew. It was the show in two minutes. Then it hit 400,000 views, and the comment section filled with cruelty from people whose own profiles said...

Kevin Kissi spent years at Microsoft leading teams that shipped software to hundreds of millions of people. Then he walked away to build Zof AI with no institutional funding, betting on one idea most of the industry still gets wrong: a system that looks perfect but can't be trusted has already failed. Born in Accra, raised between Ghana, Atlanta, and the snows of North Dakota and Minnesota, Ke...

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 comm...

Paul Bakaus started coding at 11, sold his first company to Zynga, and spent years at Google working on Search, Chrome, and ultimately as their first head of creator relations with a focus on bringing creators back to the open web. Later on at Spotter, he built AI tools for creators like Dude Perfect and MrBeast. He's now the founder of Renaissance Geek and building Impeccable, an AI-powered c...

Blake Hudelson is my co-founder at BoomPop (and we probably spend more time with each other than we do with our wives). We met at a startup studio in San Francisco six years ago. I proposed we try three companies simultaneously to see what clicked. He said yes without hesitating. That tells you everything about him. Six years, a lot of 11pm calls, a few near-death moments, and one company (BoomPop...

Danh Trang was standing near the finish line when the 2013 Boston Marathon bombs went off. He was watching friends and family. He came back the following year and ran it. At 4'2", in 5:36. Raised $14,000 for Little People of America. He's done it seven times since and cut 73 minutes off his time. He also won gold representing Team USA in para-badminton in 2016. Professionally: Citigro...

What happens when a prosecutor walks into a prison, sits across from someone she could have sent there, and realizes she can't say she wouldn't have done the same thing in their shoes? That's the story of Hillary Blout. She spent six years as a prosecutor in the San Francisco DA's office handling violent crimes against women and children. She was good at her job. Then she visited a...

What separates the people everyone wants to be around from the people who quietly drive others away? In this solo episode, Healey Cypher breaks down the 7 behaviors that make someone genuinely great to be around and the 5 traps that make you look like a jerk, even when you have the best intentions. The science is real, and the examples are specific. And none of it costs you a thing. You'll learn w...

Brianne Kimmel is the founder and managing partner of Worklife Ventures, a $45M early-stage venture firm backed by Marc Andreessen and Eric Yuan. Her portfolio includes Deel, Supabase, Public, and Metronome (zero to $1B exit). She recently opened Worklife Studios: a physical gathering space for founders, creators, and technologists who believe the best work happens when real humans are in the room...

Sam started a podcast because he was tired of feeling helpless. He was consuming the news the way most of us do… headlines that made him anxious, stories that seemed designed to make the world feel like it was falling apart, a constant drip of fear and outrage that left him feeling worse, not better. And at some point, instead of just complaining about it, he made something. Sam built No Bad News:...

Avni Barman joined Don’t Be a Jerk this week. she already has 1 million people in her community, 60 million monthly views, a 150,000-subscriber newsletter, and a venture fund where her own audience is the real investment thesis. She's the founder and CEO of Gen She: a media company and venture fund reimagining what it looks like to lead as a woman in business today. And the way she built it? B...

Andrew Dudum built Hims & Hers from zero into a multi-billion-dollar consumer publicly-traded consumer health company by doing something most founders avoid: leaning directly into discomfort. He’s able to lead the hard conversations that most leaders avoid. In this episode, Andrew and I talk candidly about what it actually takes to scale a company and stay grounded while doing it. We unpack th...

David Flink got kicked out of four schools. Then he went to Brown, then Columbia and spent the next 28 years building systems so that nobody else has to earn their humanity through performance. David is the founder of the Neurodiversity Alliance (reaching 600+ schools nationwide), author of Thinking Differently , CNN Hero, and recipient of the Bezos Courage & Civility Award, which came with $5...

Rafael Burde holds one of the most quietly powerful jobs on the planet. As Co-Lead of Global Search Policy at Google, he helps decide what information billions of people see (or don't see) when they search online. Google processes 14 billion searches per day, and Raf's team writes the policies that govern all of it. His guiding principle? "Safeguarding without sanitizing." He navigates the ultimat...

In a world where employees change jobs every 18 months, Dr. Ilana Nankin has had zero voluntary resignations in five years at Breathe For Change. Ilana is a former public school teacher, holds a PhD in education, and is the co-founder and co-CEO of Breathe For Change , an organization dedicated to educator well-being and human-centered leadership. Since she stated the organization 10 years ago, th...

Too many wellness brands try to sell a feeling. Dan Cox decided to sell the truth. You might recognize Dan as the ultra-fit guy from The Bachelorette . What you probably don’t know is that instead of riding the influencer wave, he opened nutrition stores, built multiple supplement brands, and quietly made integrity the core of his business. In this episode, we talk about what it actually looks lik...

Every January, we’re told to set goals. More goals. Bigger goals. Smarter goals. And yet… most of us still feel weirdly unclear about what we actually want. In this solo episode of Don’t Be a Jerk , I share a goal-setting exercise that completely reframed how I think about my life. It started with a single line from a friend that stopped me cold: “Most people set goals for their resume. You should...

What if the most important skill for founders isn’t intelligence, hustle, or speed but empathy? In this episode of Don’t Be a Jerk, I sit down with Mike Jones, co-founder and CEO of Science Inc., former CEO of MySpace, and early backer of companies like Dollar Shave Club and Liquid Death. Mike has spent decades working with founders at every stage. What he’s learned runs counter to most startup ad...

What if the thing investors call a “liability” is actually your biggest edge? In this episode of Don’t Be a Jerk, I sit down with Damian Pelliccione, co-founder & CEO of Revry, an LGBTQ+ streaming network built on a simple, powerful belief: diversity isn’t charity… it’s a competitive advantage. We talk about what it really takes to lead diverse teams across generations, build an identity-drive...

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 . W...

What if your success has nothing to do with you? That is the worldview of Bing Chen. And it has shaped two massive revolutions: the YouTube creator economy and the rise of Asian representation in Hollywood. Bing and I go all the way back to Wharton. We were in the same senior society. After college we’d grab coffee in New York and he’d casually say things like, “I think millions of people will mak...

Most people meet a quantum physicist and think they have nothing in common. But Anastasia Marchenkova is built different. She went from breaking the servers at Georgia Tech to building quantum chips at Rigetti, to investing in deep-tech startups, to teaching introverts how to communicate. And along the way she discovered something surprising. Being smart is not the hard part. Being human is. In th...

What happens when you build everything you ever wanted… and still feel empty? For Jesse Pujji, that moment came after bootstrapping Ampush to a multi-eight-figure exit and realizing that money and titles weren’t enough. So he stepped back, did the inner work, and started Gateway X, a venture studio built around one radical idea: you can scale businesses and stay human. Jesse and I met as college k...

What happens when authenticity becomes your superpower? For Goldie Chan, she turned her authentic, vulnerable story into a personal brand everyone wants. She’s the founder of Warm Robots , a Forbes contributor, and the author of Personal Branding for Introverts, a guide to building influence without pretending to be someone you’re not. Dubbed the “Oprah of LinkedIn,” Goldie built one of the most t...