# @20vc on YouTube

- **Type:** Video
- **Original URL:** https://youtube.com/watch?v=I5vRmsMS3ms
- **Gondola URL:** https://gondola.cc/posts/34467737-20vc-youtube
- **Thumbnail:** https://img.gondola.cc/tr:w-,h-,fo-auto/postThumbnails/cb681bf863.jpg
- **Posted:** 2025-09-11T13:58:53.000+00:00
- **Account Owner:** 20VC with Harry Stebbings (@20vc) — https://gondola.cc/20vc

## Caption

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.

Jeff Lawson is the co-founder and former CEO of Twilio (TWLO), the developer-first cloud communications platform that pioneered APIs for voice, messaging, email (via SendGrid), and customer data (via Segment). Previously he was the founding CTO at StubHub, a product manager at AWS, co-founded Versity.
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In Today’s Episode We Discuss:

00:00 Intro 
01:16 Elon Musk's Trillion Dollar Pay Package
04:26 Compensation Trends for Founders and CEOs
19:03 Ramp at $1B ARR, Brex at $700M - Is AI Causing All Boats To Rise?
24:34 Sierra at $100M ARR Worth $10B - Bubble or Brilliant Bet?
30:18 Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF?
36:48 $10B in OpenAI Secondaries — What Happens When 1,000 New Millionaires Hit SF?
42:30 Anthropic Pays $1.5B to Authors — Fair Deal or Pure Piracy?
46:44 Why Did ASML Just Invest into Mistral at $14BN?
55:26 Atlassian Buys the Browser Company for $610M - Genius Move or Panic Buy?
01:09:25 The Next Wave of Aggressive Acquirers
01:26:32 IRL CEO Arrested for Fraud: Is More To Come?
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Subscribe on Spotify:
https://open.spotify.com/show/3j2KMcZ...

Subscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast...

Follow Harry Stebbings on X:
  / harrystebbings  

Follow Jason Lemkin on X:
  / jasonlk  

Follow Rory O’Driscoll on X:
  / rodriscoll  

Follow Jeff Lawson on X:
  /  jeffiel

Follow 20VC on Instagram:
  / 20vchq  

Follow 20VC on TikTok:
  / 20vc_tok  

Visit our Website:
https://www.20vc.com

Subscribe to our Newsletter:
https://www.thetwentyminutevc.com/con...
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#20vc #harrystebbings #roryodriscoll #jasonlemkin #jefflawson #canva #ramp #anthropic #saas #openai #elonmusk #irl #sierra #twilio

## Stats

- **Views:** 9,760
- **Likes:** 143
- **Shares:** 0
- **Comments:** 41

## Credits

| Name | Username | Profile | Role |
| --- | --- | --- | --- |
| 20VC with Harry Stebbings | @20vc | https://gondola.cc/20vc | Podcast |

## Tags

harrystebbings, anthropic, saas, irl, canva, roryodriscoll, elonmusk, jefflawson, sierra, jasonlemkin, 20vc, twilio, ramp, openai

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