Post by Monty Ngan

Uber's CEO set a tough rule for his team: if they don't respond to his Saturday email, they should expect a follow-up on Sunday demanding an explanation. Dara Khosrowshahi made waves recently on The Diary Of A CEO podcast when he laid out his leadership philosophy pretty bluntly. To him, it's work hard or get out- and part of that is responding on weekends if you don't want to be flagged. On paper, you'd think his philosophy checks out: Uber turned around from burning $2.5B a year into generating over $9.8B in free cash flow. At first it looks hard to argue with those numbers. And even I get his conviction - grit compounds and output follows obsession. I've lived that firsthand -- during our early days Isaac and I were deep in the trenches fighting for a mission to close the global opportunity gap with no VC safety net in sight. But where I disagree with Dara's approach is how his company builds a culture where his team never really gets to switch off. There's a version of "work hard" that's about personal drive, internal fire, and the desire to build something real. Dara has that, and most founders I know also have that. And I do genuinely think it's non-negotiable. But once you turn hard work into a system that expects you to be on all the time, that's when it turns into an unsustainable work ethic. Instead of building great teams, it creates burned-out ones who eventually perform worse and stop caring about the mission altogether. I protect my team's weekends - not because I'm soft on standards, but because I've seen what happens when someone comes into Monday rested and fired up vs someone who spent Sunday anxious about an unanswered email. The latter rarely does their best thinking. If your team needs a Sunday check-in to stay engaged, that's not an accountability system - it's a sign the people running it built the wrong culture to begin with. True accountability comes when your people are motivated to put their best every single day.