The Twenty Minute VCWhy VC Today is Worse than 2021
Episode Details
EPISODE INFO
- Released
- October 23, 2025
- Duration
- 1h 34m
- 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 00:53 Everett Randle joins Benchmark 02:16 Ambition, career moves & the VC shuffle 04:15 Are VCs still the best paid? 06:25 Carry payouts & delayed returns 07:00 Revolut's $75B valuation explained 09:40 The TAM myth in startups 12:30 Why founders must expand their markets 17:05 Are AI Verticals overhyped? 19:55 The "Covid mistake" in AI investing 24:00 The rush to buy AI tools before the window closes 28:10 Will AI markets boom or deflate? 31:00 When to sell vs hold your startup 33:40 The truth about vertical SaaS 40:10 AI is changing the legal industry 41:34 OpenAI's billion dollar cloud play 46:44 Poolsuite builds its own data center 50:19 The rising cost of competing in AI ---------------------------------------------------------------------------------------------- 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 #revolut #ai #meta #openai #supabase #investing #venturecapital
SPEAKERS
Rory O’Driscoll
guestVenture capitalist (partner at Scale Venture Partners) focused on technology investing.
Jason Lemkin
guestFounder of SaaStr and a longtime SaaS-focused investor and operator.
Harry Stebbings
hostFounder and host of 20VC (The Twenty Minute VC), interviewing leading venture capitalists and founders.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Jason Lemkin, Why VC Today is Worse than 2021 explores vC returns look tougher as AI hype reshapes markets rapidly Venture has become a slower, harder liquidity game as companies stay private longer, carry takes longer to distribute, and billion-dollar outcomes no longer feel like “real exits.”
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