The Twenty Minute VCEventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan
Episode Details
EPISODE INFO
- Released
- December 4, 2025
- Duration
- 1h 11m
- Channel
- The Twenty Minute VC
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
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 01:01 Thrive and OpenAI Partnership 04:07 Databricks Raising $5BN at $134BN Valuation: Cheap or Not? 20:41 Eventbrite Acquired by Bending Spoons for $500M 23:02 Pagerduty's $1BN Market Cap, Just 2x Revenue 26:37 The TAM Trap: Why SaaS Is Like Japan 38:13 Lessons from Companies Hitting $100M ARR 42:43 The Future of Labour Markets is F****** 49:27 The Importance of Compounding in Investments 56:26 The Relevance Game in Venture Capital 01:08:05 Supabase at $5BN or Lovable at $6BN: Which One? ---------------------------------------------------------------------------------------------- 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 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 #ai #thrive #lovable #openai #eventbrite #TAM #pagerduty
SPEAKERS
Rory O’Driscoll
guestVenture capitalist (Scale Venture Partners) focused on SaaS and enterprise software investing.
Jason Lemkin
guestFounder of SaaStr and a SaaS-focused investor and operator.
Harry Stebbings
hostFounder and host of 20VC, interviewing and moderating discussions with leading investors and founders.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Jason Lemkin, Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan explores saaS valuations, TAM traps, AI pricing shifts, and venture relevance battles Thrive’s OpenAI partnership is framed as more about VC power-law focus—going deeper with a winner—than a strategically pivotal move for OpenAI.
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