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Great Expectations

A startup with 10 employees is now worth $5 billion

That’s more than what Macy’s is worth

A million dollars isn't cool, you know what's cool?
A billion dollars.

That’s what a young Justin Timberlake told his castmates in a scene from The Social Network — the 2010 film about the rise of Facebook.

Back then, as Silicon Valley was entering its golden era, startups seeking to change the world were doing really well if they were valued at a few million dollars. Any mention of the “B” word was typically reserved for companies making serious waves, with a billion-dollar valuation typically taking years and a revenue (or user) chart that looked like a hockey stick.

Zero to one (billion of cash)

Things have obviously changed a lot since the early 2000s. But few things in the startup world in the intervening years have been quite as remarkable as the news that Safe Superintelligence (SSI), a startup co-founded by OpenAI's former chief scientist Ilya Sutskever, has raised $1 billion in a round of investment that values the company at $5 billion, according to an exclusive report from Reuters. The company has 10 employees.

That valuation is more than what iconic department store Macy’s ($4.2 billion) is worth. It’s more than triple what pizza giant Papa John’s International is worth.

SSI valuation $5 billion
Sherwood News

The wave of AI hype that took Nvidia to a $3 trillion market cap is filtering all the way through the economy, and venture capitalists with deep pockets are willing to take bets that, even just 5 or 6 years ago, would have seemed ludicrous. Clearly, SSI is a special case and the expertise that someone like Ilya Sutskever brings is substantial, but with that kind of deal it is no wonder that nearly all of Silicon Valley’s ambitious founders say they’re working on AI in some shape or form.

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OpenAI’s ARR reached over $20 billion in 2025, CFO says

Sam Altman’s $500 billion artificial intelligence behemoth hit a major financial milestone last year, according to a new blog post over the weekend from OpenAI CFO Sarah Friar, as the company confirmed it had hit a more than $20 billion annual revenue run rate at the end of 2025.

Elsewhere in the blog post, Friar spent time addressing the company’s shifting goals, referencing plans to “close the distance between where intelligence is advancing and how individuals, companies, and countries actually adopt and use it.” As has become customary in the AI company press release genre, the CFO was also keen to tout the unending growth of the business, writing:

  • Both our Weekly Active User (WAU) and Daily Active User (DAU) figures continue to produce all-time highs. This growth is driven by a flywheel across compute, frontier research, products, and monetization.

  • Compute grew 3X year over year or 9.5X from 2023 to 2025: 0.2 GW in 2023, 0.6 GW in 2024, and ~1.9 GW in 2025.

And, perhaps most importantly for current backers and those keeping an eye on the private company before its rumored mega IPO:

  • Revenue followed the same curve growing 3X year over year, or 10X from 2023 to 2025: $2B ARR in 2023, $6B in 2024, and $20B+ in 2025. This is never-before-seen growth at such scale.

That latest figure has certainly set tongues in the tech world wagging, just as the company announced it would begin rolling out ads to free and ChatGPT Go users. It also puts the chatbot giant a fair way ahead of competitors like Anthropic, the company behind Claude.

OpenAI Anthropic ARR race
Sherwood News

Elsewhere in the blog post, Friar spent time addressing the company’s shifting goals, referencing plans to “close the distance between where intelligence is advancing and how individuals, companies, and countries actually adopt and use it.” As has become customary in the AI company press release genre, the CFO was also keen to tout the unending growth of the business, writing:

  • Both our Weekly Active User (WAU) and Daily Active User (DAU) figures continue to produce all-time highs. This growth is driven by a flywheel across compute, frontier research, products, and monetization.

  • Compute grew 3X year over year or 9.5X from 2023 to 2025: 0.2 GW in 2023, 0.6 GW in 2024, and ~1.9 GW in 2025.

And, perhaps most importantly for current backers and those keeping an eye on the private company before its rumored mega IPO:

  • Revenue followed the same curve growing 3X year over year, or 10X from 2023 to 2025: $2B ARR in 2023, $6B in 2024, and $20B+ in 2025. This is never-before-seen growth at such scale.

That latest figure has certainly set tongues in the tech world wagging, just as the company announced it would begin rolling out ads to free and ChatGPT Go users. It also puts the chatbot giant a fair way ahead of competitors like Anthropic, the company behind Claude.

OpenAI Anthropic ARR race
Sherwood News

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