Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs.

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In today’s episode, we discuss:

Sam’s advice for future engineers
What’s next for AI
How to develop technical taste
The importance of asking “what if” questions
Lessons on market timing
Scaling a software company in 2024

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Referenced:

Amazon: https://amazon.com
Box: https://www.box.com/
Elon Musk: https://twitter.com/elonmusk
Google Docs: https://docs.google.com
Itzhak Perlman: https://itzhakperlman.com/
Microsoft: https://www.microsoft.com
Netflix: https://www.netflix.com
Tesla: https://www.tesla.com/
The Innovator’s Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244
TurboTax: https://turbotax.intuit.com/
Uber: https://www.uber.com/
Walmart: https://www.walmart.com/
Workday: https://www.workday.com/
Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/

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Where to find Sam Schillace:

LinkedIn: https://www.linkedin.com/in/schillace/
Newsletter: https://sundaylettersfromsam.substack.com/
Twitter/X: https://twitter.com/sschillace

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Where to find Brett Berson:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson

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Where to find First Round Capital:

Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast

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Timestamps:

(00:00) Introduction

(02:54) Lessons on market timing

(07:30) Developing technical taste

(09:51) Asking “what if” questions

(14:03) Building Google Docs

(19:32) The decline of Google apps

(20:57) The Innovator’s Dilemma facing Microsoft

(22:53) The differences between Google and Microsoft

(24:42) How to build a winning product

(27:46) Becoming an optimist

(29:12) Why engineering teams aren’t smaller

(32:00) Sam’s prediction about AI

(34:11) Capturing the value of AI

(37:43) How you should think about AI

(45:33) Advice for future engineers

(48:18) What makes a great engineer

(49:45) One thing the best engineers do

(51:37) Microsoft’s new leverage

(56:01) Scaling software in 2024

(59:50) The future of AI across several sectors

(64:28) What Sam and a violinist have in common

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