Don't Be a Jerk

In 1994 Keba Konte flew to South Africa to photograph the first election where everyone could vote. He had no press credential, so when Mandela appeared, the fifty accredited photographers had the front position and Keba was stuck in the stands with the crowd. Then Mandela turned his back on the press, faced the people, and raised his fist. Keba got the frame. He has been standing on that side eve...

When Emiliana Simon-Thomas was a teenager in Berkeley, a man named Mr. Charles stood on a street corner every morning and told strangers they were beautiful. Decades later she ran a study with tens of thousands of people across more than 200 countries to find out whether small acts like that actually change anything. Emiliana is the Science Director of UC Berkeley's Greater Good Science Center...

Most of your day already happened without you. The drive to work, the meeting you walked into cold, the ten minutes after you got home. You didn't decide how any of it would go, so it went however it went. Healey Cypher has a fix that takes about ten seconds, and it's older than every productivity book on your shelf. It's called segment intending: you break the day into small pieces, a...

There's an award for everything in our society. The Emmys give awards for giving awards. Nobody gives one for kindness. Alan Ross noticed that during Covid, on a walk in the Berkeley Hills, when he passed a girl handing out free cookies because she thought everyone seemed sad. Four years later he writes a $1,000 check every month, out of his own pocket, to a stranger who did something quietly...

Bob Sutton has spent twenty years being asked to prove that decency pays. He can do it: the productivity data, the health data, the turnover math, all of it. He mostly refuses to. His actual argument is harder to shrug off. Sutton is a Stanford professor emeritus who got the idea for the most famous management book with a swear word in its title from his father, at the San Diego Zoo, when he was a...

Charlie Munger said "show me the incentive and I'll show you the outcome." Dr. Amy Gershkoff Bolles has spent an entire career proving it from the inside. She built the media operation for Obama's 2012 campaign, served as a C-level executive at companies including Zynga, Ancestry, and Levi Strauss & Co., and sits on public and private company boards. The throughline: most bad...

It's harder to place a 16-year-old intern than a $200,000 software engineer. Alex Funkhouser learned that the hard way: his firm SherlockTalent places senior engineers for a living, but when he volunteered to find internships for Miami high schoolers, a full year of work placed exactly eight kids. So he built the machine himself. GetMyInterns has now launched over 40,000 student careers, and t...

Chad Bernstein showed up at a juvenile detention center with his band, ready to play, and the guards stopped him at the door. The guitar strings, they said, could be used as weapons. So he walked in empty-handed, into a room of kids with crossed arms and cold stares, and the distance between them felt impossible to cross. Then the band started playing with nothing but their voices and a beat on th...

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...