EQUITY RESEARCH DR. JOSH C. SIMMONS
OpenAI vs Anthropic: The Race to IPO
LIVE
OPENAI PRE-IPO
$840B POST-MONEY
$0B ARR (FEB '26)
0M WEEKLY USERS
$0B+ TOTAL RAISED
$0B CASH BURN '30 PROJECTED
REVENUE TRAJECTORY (ARR $B) 2022 - 2030P
FINANCIAL OVERVIEW
METRIC VALUE NOTE
Gross Margin33%Down from 40% (2024)
Revenue Multiple33x ARRvs 20x (Anthropic)
MSFT Rev Share20%Through 2032
Paying Consumers50M5%+ of WAUs
Business Users9M4x since Sep '25
Compute Spend '30~$600BRevised down 57%
Cash-Flow Positive2030TARGET
$110B MEGA-ROUND (FEB 27, 2026) LARGEST PRIVATE ROUND IN HISTORY
INVESTOR AMOUNT TERMS
Amazon$50B$35B contingent on IPO/AGI
NVIDIA$30B3GW inference commitment
SoftBank$30B~11% ownership, $64.6B total
MicrosoftDID NOT PARTICIPATEAlready owns 27%
RISK FACTORS HIGH
  • Musk trial jury selection Apr 27 — seeking $79B-$134B
  • $665B cumulative cash burn projection through 2030
  • Gross margins declining: 40% → 33%
  • Ad rollout on free tier risks alienating user funnel
VS
ANTHROPIC PRE-IPO
$380B POST-MONEY
$0B ARR (MAR '26)
0% ENTERPRISE REV
$0B TOTAL RAISED
$0B COMPUTE '30 1/6TH OF OAI
REVENUE TRAJECTORY (ARR $B) JAN 2025 - 2027P
FINANCIAL OVERVIEW
METRIC VALUE NOTE
Revenue Multiple20x ARRvs 33x (OpenAI)
API Revenue70-75%Pay-per-token
Claude Code Run-Rate$2.5B+Doubled since Jan 1
$100K+ Customers7x YoYGrowth
Fortune 10 Clients8 of 10Enterprise penetration
GitHub Commits4%Of all public commits worldwide
Cash-Flow Positive2028TARGET (2yr ahead of OAI)
$30B SERIES G (FEB 12, 2026) 850% VALUATION INCREASE IN 15 MONTHS
INVESTOR ROLE NOTE
GIC (Singapore)CO-LEADSovereign wealth fund
CoatueCO-LEADGrowth equity
D.E. Shaw, Founders FundCO-LEAD+ ICONIQ, MGX
Sequoia, BlackRock, FidelityPARTICIPANT+ Goldman, JPM, Morgan Stanley
RISK FACTORS CRITICAL
  • Pentagon designated "supply chain risk" — Mar 4
  • Sued DoD in two courts — TODAY (Mar 9)
  • 6-month DoD transition away ordered by Hegseth
  • 79% of OAI customers dual-buy — loyalty thin