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Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare

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 01:10 Brex Acquisition by Capital One for $5.15BN 09:06 Does Brex's Acquisition Help or Hurt Ramp? 15:13 TikTok Deal Completed: Who Won & Who Lost: Analysis 18:38 Anthropic Inference Costs Higher Than Expected 39:05 OpenEvidence Raises at $12BN from Thrive and DST 46:41 a16z Companies are 2/3 AI Revenues 57:24 Wealthront IPO Disaster: Is $1.5BN IPO Too Small? 01:12:19 Salesforce Wins $5BN Army Contract: The Last Laugh for SaaS ---------------------------------------------------------------------------------------------- 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 #a16z #brex #ramp #anthropic #tiktok #openevidence #ai

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
Jan 29, 20261h 18mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
January 29, 2026
Duration
1h 18m
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 01:10 Brex Acquisition by Capital One for $5.15BN 09:06 Does Brex's Acquisition Help or Hurt Ramp? 15:13 TikTok Deal Completed: Who Won & Who Lost: Analysis 18:38 Anthropic Inference Costs Higher Than Expected 39:05 OpenEvidence Raises at $12BN from Thrive and DST 46:41 a16z Companies are 2/3 AI Revenues 57:24 Wealthront IPO Disaster: Is $1.5BN IPO Too Small? 01:12:19 Salesforce Wins $5BN Army Contract: The Last Laugh for SaaS ---------------------------------------------------------------------------------------------- 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 #a16z #brex #ramp #anthropic #tiktok #openevidence #ai

SPEAKERS

  • Rory O’Driscoll

    guest

    Venture capitalist, partner at Scale Venture Partners.

  • Harry Stebbings

    host

    Founder and host of 20VC (The Twenty Minute VC).

  • Jason Lemkin

    guest

    Founder of SaaStr and a venture investor (SaaStr Fund).

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Harry Stebbings, Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare explores big tech deals, soaring AI costs, and shaky IPOs reshape markets Brex’s $5.15B sale to Capital One is framed as a strong founder outcome but also a case study in “hubristic financing” after raising at $12B in 2021.

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