A Red-Hot IPO
One giant is ready for Wall St. The other is telling itself it is.
Two predictions today. Grab your coffee.
1) Sam Altman will step down as OpenAI CEO in 2026.
According to Rob Toews at Radical Ventures, Altman will be replaced by Fidji Simo in a choreographed transition ahead of a public listing.
OpenAI needs ~$150B to fund its commitments. That’s IPO territory.
Simo’s profile is perfect. She led Instacart through its IPO and scaled a consumer platform at Facebook under intense regulatory pressure.
Altman’s legacy is secured. Running a public company is a different beast.
A clean handover suits everyone.
But Sam Altman and Open AI are unique. There’s a version of events where he stays precisely because investors believe the AGI story requires him to unlock that $150B.
Why it matters: A Simo appointment signals a shift from “build AGI at all costs” to “show me the numbers,” and says volumes about where the AI race is heading.
What to watch: An org change giving Simo operating authority before any formal handover. Then watch for the S-1: if Altman is still listed as CEO → this call is dead.
2) Anthropic will IPO in 2026, OpenAI will not.
Again from Rob Toews at Radical Ventures. Public markets prefer clean narratives and stories they can model.
Anthropic = less capital, clean structure, clear narrative
OpenAI = more capital, messy structure, chaotic narrative
The math tells the story. Anthropic needs $20B to reach profitability. OpenAI needs $150B+. Investors can model a path to Anthropic’s number. OpenAI requires heroic assumptions.
OpenAI’s structure is awkward. OpenAI is a capped-profit company under a nonprofit parent. Institutional investors want absolute clarity on ownership and governance. This offers neither.
Anthropic has a better story. Enterprise-first, safety-forward, revenue concentrated in large contracts. That’s what public markets reward. OpenAI’s consumer and API strategy is harder to price.
The balance sheet helps too. Google and Amazon have put in billions. That investor profile signals a company going public on its own terms, not squeezed to exit by liquidity pressure.
But Anthropic may not want to go public in 2026. An IPO means scrutiny, a slower pace, and public markets that may not reward safety as a North Star. Another large private round preserves flexibility, while OpenAI’s structure delays its own listing anyway.
Why it matters: If Anthropic goes public first, it sets the valuation benchmark. Anthropic lists at $400B, OpenAI needs to justify a massive premium or compress its valuation expectations significantly.
What to watch: The appointment of a lead underwriter always leaks. Watch for a named bookrunner before Q3 2026:
If Goldman Sachs or Morgan Stanley get the mandate → game on.
If OpenAI isn’t structurally clean by mid-2026 → no IPO window.
My view:
1) I get the business logic, but I can’t see it happening. When the Board "fired" Altman in November 2023 he returned with more power, not less. He doesn’t seem the type to walk away from this, so a voluntary step-down feels psychologically unlikely in the near term. If Altman doesn’t want it, I can’t see the new Board pressuring for this either. More likely this turns into a Zuckerberg - Sandberg, Musk - Shotwell type situation where Simo powers the business and Altman manages the “vibes” (aka. valuation).
2) We’re 25% through the year and no mandates yet. Tech valuations have come down across the board this year. Without this contraction in valuations I would have assigned a much higher probability. But the macro environment shifts the probability. As I sit here today in March 2026 it’s hard to assign a probability >50%, for either company, given they have other sources of funding to see through this dip.
What do you think?