I think we're all rooting for the narrative that it's possible to get ahead working 9-5. But it's hard for me to ignore the survivorship bias at play here. Yes, if your company has a market cap in the billions, you probably don't need to be grinding on the weekends anymore. If you've built a company with amazing programmers and predictable revenue (e.g., dhh/Jason Fried) you probably don't need to grind weekends.

But when you're at the front lines, striving to create something new, you'll be competing against very motivated entrepreneurs. These entrepreneurs will often have more resources than you, and zero aversion to working weekends. In those circumstances, Tobi's lifestyle probably isn't going to cut it. When an entrepreneur is working to create that spark, it pays to be completely obsessed, sometimes for years.

Thankfully, very few of us are on the front lines struggling to launch something momentous. Tobi once was, but he was smart and surrounded by great people, and now he's in scaling mode, which seems like a much different beast. I'm grateful that he and other successful tech leaders don't force their teams to work as hard as they needed to in the early days.