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.

–

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

–

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/

–

Where to find Sam Schillace:

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

–

Where to find Brett Berson:

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

–

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

–

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