June 4, 2025
Real kindness feels like your stomach tightening right before you tell someone the truth they need to hear. It feels like watching their face fall before it lifts with understanding. It feels like choosing the conversation that might end a friendship today to build something deeper tomorrow.
I know because I have this feeling at least twice a week.
We've confused being nice with being kind.
Nice feels good in the moment. Kind does good in the long run. And in the pressure cooker of a startup, this difference can kill you.
I grew up professionally at a hedge fund famous for its culture of brutal honesty (Bridgewater), where people would tell you to your face that your ideas were terrible and why. When I left to start my own company, everyone warned me I'd need to soften. Be more "founder-friendly." Build a "positive culture."
Every day, I'm tempted.
Because these conversations are brutal. I've watched friendships fracture. I've seen people walk out. I've laid awake wondering if I should have just kept my mouth shut.
But then, usually about two years later, I get the text:
"Hey, I've been thinking about that conversation we had. Thank you."
The gap between impact and gratitude is measured in years, not moments. That's the brutal math of real kindness - you pay the price today for a thank you that might never come. You watch relationships end and hope they transform into something deeper with time.
Real kindness feels uncomfortable. It feels like choosing to have the conversation you've been avoiding for two weeks. It feels like your voice getting quiet because the stakes are high.
Nice feels like relief. Like dodging a bullet. Like keeping the peace. But that relief is borrowed from the future, and the interest rate is brutal.
I used to think emotional intelligence meant reading the room, smoothing things over, keeping everyone comfortable. Then I built a startup and learned that comfort is a luxury small teams can't afford.
Real kindness sounds like: "That's not going to work, and here's why."
Nice sounds like: "Interesting approach!" followed by silence.
I've fired people I've avoided giving feedback to. That's not leadership - that's theft. I stole their chance to improve.
The highest-stakes conversations happen in the smallest voices. You lean in. You speak carefully but clearly. You watch their eyes to make sure they're really hearing you, not just waiting for it to end.
My co-founder and I have a rule: if something bothers you for more than 24 hours, you have to say it out loud. The first few times, it felt like defusing a bomb. Now it feels like breathing.
I optimize for being respected in ten years, not liked today. I care more about whether people will appreciate me when they reflect on their career than whether they enjoy this particular Tuesday's standup.
Here's the thing about deathbeds: no one says "I'm so glad my first boss never gave me hard feedback." They say "That person who told me the truth when I needed to hear it changed my life."
But being that person? It sucks in the moment. Every single time.
The kindest thing you can do for someone who's betting years of their life on your shared mission is to be unflinchingly honest with them.
They didn't join your startup for comfort. They joined to build something real. Treat them like they can handle reality.
It would be so much easier to be nice. To dodge. To smooth over. To be the founder everyone likes working for today. But I've seen what happens to teams built on polite fictions. They move slowly, then they die quickly.
The paradox is that teams built on this kind of real kindness - the kind that doesn't feel nice - actually like each other more in the long run. Once you know that someone will tell you the truth, you can finally relax. You stop performing. You stop wondering what they really think. You just build.
Nice is optimizing for comfort in the moment.
Kind is optimizing for growth and trust over time.
Choose kind. Even when - especially when - it doesn't feel nice.