Skip to content
The Twenty Minute VCThe Twenty Minute VC

Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings

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. 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. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 00:54 Was GPT-5 the Biggest AI Letdown Yet? 16:12 Should Perplexity Really Try to Buy Chrome for $34.5B? 27:35 The $3B N8N Deal: Genius Bet or Bubble FOMO? 39:06 Why Datadog’s Best Quarter Ever Still Tanked the Stock 45:30 Palantir’s 50% Growth at Scale – Can It Last? Is Palantir Overpriced? 01:01:33 Shopify’s Ruthless Path to 91% Revenue Growth With 30% Fewer Staff 01:14:19 Are Seed and Series A Valuations Now at Dangerous Highs? 01:20:29 Can a Single Founder Build a Unicorn? 01:28:46 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- 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 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... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #chatgpt5 #palantir #datadog #shopify #perplexity

Rory O’DriscollguestJason LemkinguestHarry Stebbingshost
Aug 14, 20251h 34mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

GPT-5 fizzles, Chrome bid stuns, and lean SaaS wins big

  1. The panel frames GPT-5 as commercially important but emotionally underwhelming, signaling a shift from AGI hype toward incremental productization, price competition, and a code-focused token war with Anthropic.
  2. Perplexity’s reported $34.5B Chrome bid is treated as mostly about AI distribution and marketing optics, highlighting how browsers regain strategic value as subscription AI can monetize default traffic.
  3. The $3B n8n round is read as an example of “workflow automation + LLM attach” creating sudden step-function growth, and a reminder that founder speed in shipping AI features determines who wins crowded categories.
  4. Public-market reactions (e.g., Datadog down despite a record quarter) are described as inherently hard to predict because investors price expectations, concentration risk, and second-order effects—not just reported beats.
  5. Palantir and Shopify are used to argue a new operating model: massive growth with fewer employees, rising revenue-per-employee, and AI-driven ruthlessness—reshaping careers, equity concentration, and what “winning” looks like in B2B.

IDEAS WORTH REMEMBERING

5 ideas

GPT-5’s “meh” moment may be healthy for the category.

They argue the launch deflates AGI grandiosity and marks entry into the “grind it out” phase: simplify model choices, improve enterprise workflows (documents, extraction), and compete on cost and reliability like mature software markets.

Price cuts are a strategic attack on Anthropic’s coding revenue pool.

Even if Claude remains best-in-class for some coding tasks, a “good enough” model at materially cheaper tokens changes buyer behavior (mix cheap where possible, premium where necessary) and pressures competitors’ margins and distribution partners.

Chrome’s value is mostly derivative: the buyer determines the monetization.

A browser doesn’t inherently print cash, but it can be a gateway to search payments or AI subscriptions; the panel’s core point is that owning default distribution can create a conversion engine similar to ChatGPT’s free-to-paid funnel.

In AI, marketing and narrative placement are a growth prerequisite, not optional.

They interpret Perplexity’s Chrome move partly as “stay in the top-two conversation” signaling, arguing that hackathons, founder visibility, and constant press are now table stakes to sustain AI adoption velocity.

n8n illustrates how AI can re-rate an existing category overnight.

Workflow automation was previously noisy and hard to differentiate; attaching LLMs shifts it from “automate a bit” to “do the work,” expanding ROI and accelerating ARR—rewarding founders who ship fast and re-position decisively.

WORDS WORTH SAVING

5 quotes

My big aha is it's like dealing with a deranged madman trying to estimate what the street will do. I spend no time on it. Utterly unknowable.

Rory O’Driscoll

You don't need half your company, and Palantir and Shopify are proving it. You don't need half your company.

Jason Lemkin

The Department of Justice gets around to killing American companies and technology just when they've become irrelevant anyway.

Rory O’Driscoll

Shopify is doing 91% more revenue with 30% fewer employees.

Jason Lemkin

AI's smarter than most humans already. Pre, pre-AGI, it is smarter.

Jason Lemkin

GPT-5 launch reaction and pricing strategyOpenAI vs Anthropic competition in coding/toolsChrome as AI distribution and DOJ-driven assetn8n’s AI-enabled workflow automation surgeDatadog earnings, OpenAI concentration risk, and market psychologyPalantir re-acceleration and valuation debateShopify’s headcount cuts and productivity metricsSeed/Series A valuation highs vs deal concentrationOne-founder/one-person unicorn debate and AI orchestration roles

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.