The Twenty Minute VCAnthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded?
Episode Details
EPISODE INFO
- Released
- February 12, 2026
- Duration
- 1h 24m
- Channel
- The Twenty Minute VC
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
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. 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. ----------------------------------------------- Timestamps: 00:00 Intro 01:06 Anthropic Predicts $149B in ARR in 2029 11:33 Mike’s Thoughts on SaaS Today 26:26 Harvey Raises $200M at an $11BN Valuation 45:56 Is Customer Support a Terrible or Terrific Investment Category? 01:00:58 Anthropic's Super Bowl Ad: Who Won & Lost 01:15:58 Do CEOs Have to Work Harder Today Than Ever ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll Follow Mike Cannon-Brookes on X: https://twitter.com/mcannonbrookes Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #atlassian #anthropic #openai #superbowl #harvey #saas
SPEAKERS
Mike Cannon-Brookes
guestCo-Founder and CEO of Atlassian.
Rory O’Driscoll
guestGeneral Partner at Scale Venture Partners focused on enterprise software investing.
Harry Stebbings
hostFounder and host of The Twenty Minute VC (20VC).
Jason Lemkin
guestFounder of SaaStr and a venture investor focused on SaaS.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Mike Cannon-Brookes and Rory O’Driscoll, Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? explores aI reshapes SaaS: TAM debates, agentic support, and hype signals Anthropic’s $149B ARR projection sparks a debate about whether AI is zero-sum within fixed CIO budgets or primarily TAM-expanding via productivity gains and shifting spend from services (e.g., consulting and integration) into software.
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