Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble

20VC

Oct 13, 2025

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Mike Cannon-Brookes is the Co-Founder and CEO of Atlassian, the $50BN software giant behind products like Jira, Confluence, and Trello. Since founding the company in 2002, he has scaled it to over 300,000 customers globally, generating more than $5BN in annual revenue. Atlassian now employs over 10,000 people across 13 countries and is one of the most successful bootstrapped-to-IPO stories in tech history. Mike is also a leading climate investor and co-owner of several major sports teams.

In Today’s Episode We Discuss:

Lessons from 20 years as co-CEOs with Scott Farquhar

Becoming solo CEO & making bold AI-era moves

Are tech valuations insane? Mike’s investor reality check

Why design, not data, will define the AI era

The future of engineers in an AI world

How Atlassian survives by protecting creativity

Fighting the “entropy of ambition"

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