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 broken

This 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.