I was doing this talk, which I’d done dozens of times before. Good, well-practiced deck. I was speaking to CTO-types (current and aspirational) as a favor to a friend. This was a monthly morning coffee chat for this crew, and they invited folks like me to speak. It was on a weekday morning near Slack… More

I’ve worked at three successful start-ups and one failure. I’ve also worked at post-IPO successes such as Borland, Netscape, and Apple, which means I’ve seen a lot of different founders who, if you measure success financially, were quite successful. My backstory aside and with deep respect, most founders fail. You’ve heard of the stories of… More

Awkward. Seven of us now. Sitting around the table. Five minutes since the start of the meeting. We’ve used up our chit-chat allowance and wonder if you will show. In the scheme of things relevant to a company’s success, showing up late to a meeting is not the end of the world. When it happens… More

Say their name if you think they aren’t listening. In a meeting with five or more humans, it’s ok if someone checks out of part of the conversation. Not every topic is of equal interest to all humans. When you know the conversation is steering back to a human who isn’t listening, say their name.… More

I asked DALL-E to draw a flowchart on how to make a decision. This is spot on.

Remember. Monday. It’s not Wednesday when everything is already blowing up. Monday is a blank slate before 9am; this is my chance to set the tone. While it is still quiet, get a fresh cup of coffee (I prefer black and strong). Not a coffee drinker? Great, try Chai or just a glass of water.… More

Do you remember your first job? Correction: not your first job, but the first job you wanted. This is my career. This is what I want to do. I don’t want to screw this up. I was a grocery store clerk, a butcher, a video store clerk, the guy who backed up the system onto… More

In the hallway, late on Thursday, someone tells a bit of information about your product that is 100% provably not true. You laugh, wink at the person, and say, “That’s goofy. What reasonable human would believe that?” And that conversation moves on. Two hours later, different locations, different humans, and different contexts. Same exact piece… More

One of my least favorite moments as a leader, specifically your leader, is when you ask me to make the decision. First, yes, I know it’s my job to make these decisions, especially the complicated and high-risk ones. Second, it’s true I’ve acquired ample experience over the last thirty years, and the chance I can… More