Sam Schillace
Sam Schillace is deputy CTO and corporate vice president at Microsoft. Prior to working at Microsoft, Sam started a company called Writely, which was acquired by Google and became the foundation of what today is Google Docs. While at Google, Sam helped lead many of Google’s consumer products, including Gmail, Blogger, PageCreator, Picasa, Reader, Groups, and more recently Maps and Google Automotive Services. Sam was also a principal investor at Google Ventures, has founded six startups, and was the SVP of engineering at Box through their IPO.
Career (separate track) Skills
High-value work often feels surprisingly easy and fun to you; follow the path where your natural talents make work feel like play.
"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 d..."
Discovery & Research Skills
Innovative thinking requires actively shifting from a critical 'why not' mindset to an imaginative 'what if' framework that focuses on possibilities.
"I think the more interesting ones are the what-if questions, like, what if this does work? Just use your imagination. Think about, how far can I extend the curve? What are the implications of that?"
Overlay: Zero-to-One / Founder Skills
True disruption is characterized by extreme polarization—where users either love or hate a product—rather than broad, lukewarm acceptance.
"And that bifurcation of love it, hate it, is really how you have an idea of whether you have impact in what you're building. If you get more of the bell curve of modern indifference and maybe mild lik..."
Distinguish real value from hype by evaluating if the technology provides a clear, transformational user benefit once its core problems are solved.
"SpaceX is a great example where people are like, 'That doesn't make any sense.' And Elon's like, 'Well, what if you could land rockets and reuse them and they get really cheap? That's pretty amazing...."