Question 1

What are the key takeaways from Sam Schillace's episode on Lenny's Podcast?

Accepted Answer

1. Ask 'what if' questions instead of 'why not' questions - the more disruptive an idea, the dumber it looks at first, and pessimism has a much smaller prize than optimism in moments of technological change. 2. The love-it-or-hate-it bifurcation is the real signal of disruptive impact - if your product gets polite indifference, it's incremental; if it gets passionate love and passionate hate, you're onto something. 3. Users are fundamentally lazy and only adopt products that deliver at least 10X more value than the effort required to use them - remove all friction and focus ruthlessly on genuine user value over features or marketing. 4. Be rigid about your mission but flexible about your feedback - product builders must blend stubborn vision with genuine openness to being wrong, like a samurai sword that is hard on one side and flexible on the other. 5. Do the thing you feel guilty getting paid for with maximum intensity - the most career impact comes not from grinding through unpleasant work, but from leaning hard into what comes naturally and feels almost like play.

Question 2

What does Sam Schillace say about disruptive-innovation and optimism?

Accepted Answer

"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? I'm an engineer, and engineers are fundamentally pessimistic people. Somebody once told me engineers come into the world broken. They just look at everything as a problem to be solved. But I feel like I've missed out more by being pessimistic than I have by being too optimistic too early." - Sam Schillace "There's just not that much of a prize for being pessimistic and right, particularly in a moment like this. It's much better to be optimistic and wrong than pessimistic and right, I think." - Sam Schillace "Every new idea looks dumb at first. Unfortunately, the dumb ideas also look dumb at first. But the more disruptive they are, the more dumb you're going to feel they are. If you hear people saying something's a toy, that's often a really good signifier that it's actually something real and threatening, and they can't think of a better criticism for it than it's just a toy right now." - Sam Schillace

Question 3

What are Sam Schillace's views on disruptive-innovation, optimism, experimentation?

Accepted Answer

Sam Schillace: "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? I'm an engineer, and engineers are fundamentally pessimistic people. Somebody once told me engineers come into the world broken. They just look at everything as a problem to be solved. But I feel like I've missed out more by being pessimistic than I have by being too optimistic too early." Sam Schillace: "There's just not that much of a prize for being pessimistic and right, particularly in a moment like this. It's much better to be optimistic and wrong than pessimistic and right, I think."

Sam Schillace

How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

TRANSCRIPT

Sam Schillace

How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

Sam Schillace

How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

TRANSCRIPT

Sam Schillace

How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)