Sam Schillace
Corporate VP & Deputy CTO at Microsoft
Sam Schillace is Corporate VP and Deputy CTO at Microsoft leading consumer products, infrastructure, and AI. He is most known for inventing Google Docs through his company Writely, which became the foundation for Google Workspace (1B+ monthly users).
Dimension Profile
Key Themes
Episode Summary
Sam Schillace shares the origin story of Google Docs — from three rented Windows servers in Texas to a billion monthly users — and his counterintuitive career advice: do the thing you feel guilty getting paid for. He argues that most people undervalue their natural strengths because they believe work must be unpleasant, and that following your pleasure leads to better outcomes than grinding through discomfort.
Leadership Principles
- → Do the thing you feel guilty getting paid for — if something is easy and fun, that's your strength
- → We undervalue things we're good at because we think work has to be unpleasant
- → If you get pleasure from doing something people want to pay you for, do the hell out of it
Notable Quotes
"You should go do the thing that you feel guilty to get paid for. 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."
— On career advice based on decades of experience from Google Docs to Microsoft AI
"We tend to undervalue the things we're good at. We think work has to be unpleasant. So if something is easy and fun, we don't think it's valuable."
— On why people choose careers that don't match their strengths
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