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OpenAI's reported $1.25 trillion valuation works out to about 30 times its $50 billion annualized revenue run rate, by the math of Jason Calacanis, host and owner of This Week in Startups, who covered the week's news with co-host Lon Harris.
A year earlier, speculative targets of $2 trillion to $4 trillion implied something closer to 100 times revenue. Jason said the lower number is the more defensible one, and that he would still buy at it.
"If in the year of our Lord, October 23rd, 2026, it's at 30 times price of sales, and the thing's doubling every year, tripling every year, I think it closes the gap, and it's probably a good buy if you were holding it for 10 years." — Jason Calacanis
Jason invests in early-stage startups, and he said he has watched one deal term, a put right that lets investors demand their money back, blow up one of his own portfolio companies. That is why he reads a headline valuation for its terms first.
The full episode is covered here so you can skip it. 93 minutes of audio, 11 minutes of reading.
Here are the 11 calls that matter.
This Week in Startups · Oct 24, 2026 · 1h 33m · 82m saved
Key Takeaways
A headline valuation means little without the deal's protective terms, such as liquidation preferences and put rights
OpenAI at about 30 times its $50B run rate is a defensible price for a company growing this fast
A year earlier, the talk was of 100 times revenue
Jason would put 30% of a 20-year retirement account into SpaceX, OpenAI and Anthropic, with 20% in SpaceX alone
Starlink Mobile could bring a family's home, car and phone service down to about $200 a month on one bundle
Every Tesla on the road would double as a secure hotspot for nearby phones
Meta's deal to keep Zuckerberg in California will help the wealth tax pass, not stop it, Jason said, against a 23% Polymarket price
A tax on margin loans against stock, refunded when the loan is repaid, would do the wealth tax's job with less damage
Jason does not let Claude write final copy: the AI assembles and edits, and a person writes
1. Valuations Hide the Terms
CNBC reported that OpenAI is close to raising up to $30 billion at a $1.25 trillion pre-money valuation, led by UAE-backed investors. Bloomberg had put the same $30 billion target at $1.4 trillion in late September.
Protective provisions can matter more than the headline price
"We don't have complete information here about the terms of the deals, protective provisions, etc... do they have a minimum amount? Do they have the ability to call back the investment?" — Jason Calacanis
Jason listed the terms that can sit behind a big number: liquidation preferences, minimum guaranteed returns and put rights. A liquidation preference pays certain investors first in a sale. A put right lets investors demand their money back after a fixed period, the clause he said once blew up one of his own portfolio companies.
