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OpenAI is shopping a round at $1.2 trillion while its CEO explains why now is a bad time to go public and Salesforce chose the week of its own 40,000-person conference to stop working across six countries.

Let's get into it.

The One Number

$1.2 trillion

OpenAI has started early conversations with investors about a private round at $1.2 trillion or more, per the Financial Times, and Fortune has Sam Altman on the record Tuesday saying "right now would be an ill-advised moment to go public." The IPO is now a 2027 story at the earliest. The last round, in March, raised $122 billion at an $852 billion valuation.

So the ask is up $348 billion in six months. That is a 41 percent markup, or about $1.9 billion of paper value a day, on a company whose product has not changed in kind since March. Put another way, the increase alone is nearly three times the size of the March round, which was itself the largest private raise anyone had seen.

OpenAI makes ChatGPT and the models underneath it, sells access to both, and spends most of what it takes in on compute. Nothing about that changed over the summer. What changed is that Dario Amodei published an essay asking the labs to slow down, Altman said he would match it, and by Tuesday the company was citing "everything happening with safety" as the reason not to list.

The obvious reading is that a company pausing its IPO over safety is being careful. The more useful reading is about who holds the risk while it waits. A public listing would have priced the safety question in front of everyone with a brokerage account. A private round at $1.2 trillion prices it in front of a few dozen funds who are, by the sound of it, offering $1.2 trillion and being told that is a little low.

For founders, the mechanic to notice is that "we are not ready to go public" and "we would like a higher number" are now the same sentence. The valuation went up because the IPO went away. That is the theory anyway.

The Fact Sheet

Anew Labs ($290M Raised, $1.5B Valuation). ByteDance's AI drug discovery unit, spun out in Shanghai with about 50 core staff and four drug candidates, taking outside money for the first time. ByteDance keeps 56 percent, which is roughly $840 million of paper in a company with no approved drug. Backed by HSG and Hillhouse.

Ridgeline ($250M Raised, $1.425B Valuation, Series E). Investment management software that replaces the six to nine systems an asset manager usually runs. The round was invitation-only and led by the company's own founder, Dave Duffield of PeopleSoft and Workday. Backed by Dave Duffield and Motley Fool Ventures.

Factory ($200M Raised, $5B Valuation). Enterprise coding agents it calls Droids, which route each task to whichever model fits and now run inside Nvidia, Adobe and RBC. The company was worth $1.5 billion in April, which makes this the third round in five months. Backed by Khosla Ventures and Sequoia.

CADDi ($114M Raised, $1.2B Valuation, Series D). Manufacturing data platform that turns drawings and quotes into something a procurement team can search, up from $470 million in March 2025. It has more customer success staff than salespeople. Backed by Salesforce Ventures and Woven Capital.

Thatch ($108M Raised, $1B Valuation, Series C). A marketplace where the employer sets a fixed health budget and each employee buys an individual plan, which is legal because of a 2020 federal rule almost nobody had used. Revenue is up about 7x since the $410 million Series B in April 2025. Backed by Index Ventures and Andreessen Horowitz.

Headlines, No Fluff

→ Mark Zuckerberg has picked a side in the AI slowdown fight, and it is Jensen Huang's. Dario Amodei's weekend essay calling for slower capability gains got an endorsement from Sam Altman and a slap from President Trump. Zuckerberg's answer, posted Tuesday, is that labs which fail to focus on alignment "will fall behind," framing safety as a product feature rather than a reason to brake. Huang told Mad Money that AI-specific regulation is "just completely unnecessary." All four men made their case at Dreamforce, Salesforce's own conference. The AI safety debate is now a panel format at a sales event.

→ Salesforce went down across six countries in the middle of its own Dreamforce week. The outage started around 4:30 AM ET Wednesday and hit hundreds of instances across the US, Japan, India, the UK, France, and Germany, with an internal login service stalling and eating server resources. A fix rolled out region by region, though some customers were still reporting dead scheduled jobs mid-morning. Roughly 40,000 people are in San Francisco for Dreamforce right now. At one point the status page noted the outage "also affects support case creation," so for a while you could not even file a ticket about it.

→ India now has a nine-figure venture fund that invests in nothing but AI. Activate, founded by Aakrit Vaish and Pratyush Choudhury, closed its debut fund at $105 million, split between an $85 million early-stage vehicle and $20 million for growth checks. The fund came together within a year of launch and has already made ten investments in nine months, including Sarvam AI, ElevenLabs, and Wispr Flow. Ten checks in nine months. In venture, that counts as a hustle.

→ This is the second-biggest IPO year on record, and enterprise software was not invited. US venture-backed tech companies have raised nearly $90 billion in public offerings this year, per Crunchbase, but SpaceX alone accounts for 83% of it and Cerebras for another 6%. The other 21 listings split less than $10 billion combined. Energy supplied about a quarter of the year's offerings while SaaS was a no-show, with VCs funding AI-first replacements instead. Anthropic and OpenAI dominate the pipeline chatter. The plot twist is not currently scheduled.

On Vesting

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Open Doors

Fresh:

  • Innovation Crossroads, Cohort 2027 (Oak Ridge National Lab): two-year hard-tech fellowship with R&D support. Applications opened yesterday and close October 30, 8 PM ET.

  • a16z Alpha Fellowship: join a breakout a16z startup, or get up to $250K to build your own. Deadline October 11.

  • Y Combinator Winter 2027: batch runs January to March in SF. On-time deadline November 2, 8 PM PT; decision by December 11.

  • Antler Residency: rolling cohort start dates across cities.

  • Thiel Fellowship: $250K over two years to build instead of sitting in a classroom.

    Always rolling: Z Fellows: $10K, one week, mostly virtual.

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The Vesting Team (Brycent, Ajay, and Kamil)