Why I Started Don’t Be a Jerk (and the Questions You’ve Been Asking Me)

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.

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