Cover art for The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: OpenAI & SpaceX S1 Drops | NVIDIA's $81BN Revenue Quarter | Cloudlfare and ClickUp Do Controversial Layoffs | Exa, OpenRouter and Polsia Raise Mega Rounds | Uber and Microsoft Declare AI ROI for Developers is Questionable

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Published
May 28, 2026
Duration
1h 25m
Summary source
description
Last updated
Jul 25, 2026

Discusses openai, anthropic, investing.

Summary

AGENDA: 05:16 Nvidia Blowout Quarter: $81BN Revenues and Stock… Flat! 10:39 Uber and Microsoft Declare Productivity Gains Questionable from AI 25:26 The Layoffs Continue: ClickUp and Cloudflare 34:39 OpenAI S1: Is it a Race? How Will it be Received? 38:28 Do Anthropic Rush Out Their IPO Also? 45:49 SpaceX S-1: "Why I Would Never Invest" 48:06 Why Colossus…

Anthropic laps OpenAI in revenue growth, SpaceX drops a wild S1 worth debating, Nvidia prints $56B profit in a quarter, and AI layoffs accelerate—Jason & Rory break it all down.

Key takeaways

  • Anthropic matched all of last year's GAAP revenue in Q1 alone and expanded gross margins from 38% to 70%, projecting $559M operating profit in Q2—signaling it is on track to surpass OpenAI on revenue, growth rate, and profitability simultaneously.
  • OpenAI is filing its S1 now out of strategic necessity: waiting risks going public visibly smaller, slower-growing, and less profitable than Anthropic, making 'first mover' narrative its strongest remaining differentiator.
  • SpaceX's S1 attributes 90% of its $28T TAM to AI despite having no established AI product a year ago, with critics arguing the $2–3T valuation reflects an 'Elon premium' and financial engineering rather than DCF-supportable fundamentals.

Why this matters

The simultaneous S1 filings from OpenAI and SpaceX, combined with Anthropic's profitability inflection, are forcing enterprise buyers, public market investors, and B2B technology leaders to confront whether AI infrastructure spend will deliver measurable ROI—a question that will define capital allocation strategies across the industry for the next 12–24 months.

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Show notes

AGENDA: 05:16 Nvidia Blowout Quarter: $81BN Revenues and Stock… Flat! 10:39 Uber and Microsoft Declare Productivity Gains Questionable from AI 25:26 The Layoffs Continue: ClickUp and Cloudflare 34:39 OpenAI S1: Is it a Race? How Will it be Received? 38:28 Do Anthropic Rush Out Their IPO Also? 45:49 SpaceX S-1: "Why I Would Never Invest" 48:06 Why Colossus is a Stroke of Genius By Elon 51:31 Data Centers In Space is BS and Will Not Be Core to SpaceX 58:04 Polsia Raises $30M at $250M Price: Is thi

Themes

  • openai
  • anthropic
  • investing