Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft)
Episode description
Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent.
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In today’s episode, we discuss:
- Lessons from Amazon, Microsoft, and Square
- “Minimum Remarkable Products” versus Minimum Viable Products
- Navigating different work cultures in big tech
- Insider reactions to the disruptive launch of AWS
- “Pioneer” versus “fast-follower” companies
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Referenced:
- Amazon: https://www.amazon.com
- Amazon Web Services: https://aws.amazon.com
- Bill Gates: https://www.linkedin.com/in/williamhgates
- Block, Inc: https://block.xyz
- Cash App: https://cash.app
- Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one
- Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1
- Jack Dorsey: https://twitter.com/Jack
- James Hamilton: https://www.linkedin.com/in/jameshamilton4
- Jeff Bezos: https://twitter.com/jeffbezos
- Microsoft: https://www.microsoft.com
- Oracle Corporation: https://www.oracle.com
- Sarah Friar: https://www.linkedin.com/in/sarah-friar
- Square: https://squareup.com
- Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817
- WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424
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Where to find Alyssa Henry:
- LinkedIn: https://linkedin.com/in/alyssa-henry-0905692
- Twitter/X: https://twitter.com/alyssahhenry
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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: 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
(02:20) Lessons from Microsoft and Amazon
(08:29) Noticeable consistencies in the human condition
(10:50) Differences in culture at Amazon, Microsoft and Square
(13:27) Why “customers come first,” even above employees and community
(14:01) Why fast-followers can be less customer-focused
(15:50) The challenge of commercializing research projects
(18:58) Joining Square and “building a picture” of the org
(24:55) Knowing what to replicate from past companies
(27:45) Questioning norms in new companies
(28:41) The importance of effective communication systems
(31:31) How to operationalize company values
(33:38) Why shared beliefs are crucial for good company culture
(37:05) Building Minimal Remarkable Products at Square
(38:13) How to scale an aesthetic
(42:46) Org design lessons from Square
(50:06) How to align different teams behind business priorities
(52:57) Lessons learned from fierce competition
(57:39) The “fast follower” vs “pioneer” playbook
(61:05) The original thinking behind AWS
(66:08) The unlikely origin of Amazon CloudFront and other products
(73:47) How Jeff Bezos influenced Alyssa