Mike Cannon-Brookes is the Co-Founder and CEO of Atlassian, the company behind Jira, Confluence, Trello and Loom. Atlassian generated $6.5BN in ARR in 2026, and serves more than 350,000 customers, including over 85% of the Fortune 500. Today, Mike is leading its expansion into enterprise AI through Rovo and the Teamwork Graph, connecting company knowledge with AI agents.
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Timestamps:
00:00 Intro
01:24 Do AI Agents Turn Traditional Software Into Just Databases?
03:31 Why “Headless” Software Is a Brainless Bet
05:02 Why Design Becomes More Important in the AI Era
08:46 Is Company Context the Real Moat in Enterprise AI?
10:17 The Biggest Unsolved Design Problems With AI Agents
14:14 Will We Stop Caring Whether Content Is AI-Generated?
17:04 Will Enterprises Ever Trust Chinese AI Models?
21:21 Is Building Your Own AI Model a Losing Bet?
25:35 Can AI Startups Survive When They Finally Have to Care About Costs?
28:36 Why Model Routing Will Become a Core AI Capability
32:12 What Happens When AI Gets Cheaper Than Anyone Expects?
33:46 Why Technology Is Being Built Faster Than Customers Can Consume It
35:07 From Information Asymmetry to Imagination Asymmetry
38:43 Why Proprietary Company Context Matters More Than External Data
44:48 What Happens When OpenAI and Anthropic Come for Your Customers?
46:43 Atlassian vs Linear: Does Design Become the Differentiator?
48:53 Why Are Young Founders Cashing Out More Than Ever?
54:16 What Mike Changed His Mind on About AI
54:28 What Does Nobody Tell You About Getting Rich?
56:49 The Best Advice Mike Cannon-Brookes Has Ever Received
57:23 Why Leaders Need to Learn How to Slow Down
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