Sam Schillace (00:00:00): We tend to undervalue the things we're good at. We tend to think work has to be unpleasant. And so if something is easy and fun, we don't tend to think it's valuable. So I think lots of people gravitate in this direction of like, let's go do unpleasant things and grind our way through the career because that's the way to make it. But the reality is you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can. If you get pleasure from doing something that people want to pay you for, do it the best you can do it, as hard as you can do it. And if that's messing around and playing around with cool ideas, do the hell out of that. Work doesn't necessarily have to be hard. Lenny (00:00:37): Today my guest is Sam Schillace. Sam has an incredible resume that is very hard to summarize succinctly. I'll give it a shot. Currently, he is corporate vice president and deputy chief technology officer at Microsoft, where he leads efforts in the consumer product space, infrastructure, and AI. Sam is most known for basically inventing Google Docs with his company Writely, which was acquired by Google, and became the foundation for what is now Google Workspace, which currently has over one billion active users a month. (00:01:06): After joining Google, Sam ended up responsible for many of Google's consumer applications, including parts of Gmail, Maps, Automotive, Groups, Reader, and more. He's also founded six startups, was senior vice president of engineering at Box through their IPO. He's also worked at Intuit, Macromedia. He was even a VC at Google Ventures for a time. As you'd suspect, we had a fairly wide-ranging conversation, but the core focus was around innovation, how to think big, how to come up with original ideas, why optimism is so important and powerful, and also a ton of career advice. Sam is hilarious and not what I imagined a corporate vice president...