Anthropic's Super Bowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded?

20VC

Feb 12, 2026

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Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the software giant behind products like Jira, Confluence, and Trello. Under his leadership, Atlassian has become one of the world’s most successful enterprise software companies, serving over 250,000 customers globally and valued at more than $50 billion.

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more.

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.

In Today's Episode We Discuss:
  • Anthropic Predicts $149B in ARR in 2029

  • Will FDEs Become More or Less Powerful

  • Harvey Raises $200M at an $11BN Valuation

  • Is Customer Support a Terrible or Terrific Investment Category

  • Anthropic's Super Bowl Ad: Who Won and Who Lost

  • Do CEOs Have to Work Harder Today Than Ever

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