Menlo Ventures announced $3 billion in funds on Tuesday, the largest raise in its 50-year history, driven in large part by its AI portfolio, especially Anthropic. Its stake in the model maker is now worth about $14 billion, sources told Bloomberg.

To hear the folks at Menlo talk about it, they were white-knuckling it when they made a bet-the-firm $750 million investment in Anthropic in 2024, preemptively leading the model maker’s Series D. At the time, that round quadrupled the startup’s valuation to $18.4 billion.

While the bet itself was arguably not wildly risky, the means by which the firm raised that kind of capital was more so.

Menlo had been an early investor, before Anthropic had a product. By 2024, long before Claude Code and Claude Mythos, the company was showing signs of success. It had landed a $4 billion deal from Amazon and was being hotly pursued by VCs, having been founded by former OpenAI researchers, including siblings CEO Dario Amodei and president Daniela Amodei. It was a rising-star AI company, as so many startups founded by OpenAI alum still are today.

But how Menlo raised the funds was eye-popping. In 2024, the venture world was just rebounding from the post-pandemic VC winter, with big-money firms like SoftBank and Tiger Global still licking their wounds. No one was writing checks for three-quarters of a billion dollars.

Menlo structured the bulk of deal, about $500 million worth, as a special purpose vehicle, or SPV — a one-off investment entity created to pool money from multiple sources for a single deal. Menlo also contributed $250 million from its own fund and contributions from Menlo insiders, sources told Forbes at the time, bringing the total round to $750 million.

Since then, AI SPVs have become as commonplace as cockroaches, with Anthropic a particular target — so much so that the AI company issued a warning last month, calling all unauthorized SPVs and secondary markets claiming to sell its stock “scams.”

But for those investors in Menlo’s authorized 2024 deal, the aggressive push paid off handsomely. Menlo went on to invest in the company’s Series E and F.

On top of that, Menlo followed up by launching a $100 million startup fund with Anthropic in 2024, which they cutely named Anthology. That fund has since ballooned into capital deployed to date closer to $250 million, a source with knowledge of the fund tells TechCrunch. It has not only backed 60+ companies (and offered them support, like access to Anthropic leaders and credits for Claude), but has also produced a number of returns already. These include Graphite, acquired by Cursor, and Astrix Security, acquired by Cisco.

The fund has allowed Menlo to get its finger of the pulse of AI startups, categories, and tech, at the earliest stages. The VC firm has since built a broader rep for AI investing, counting AI stars like OpenRouter, Higgsfield, Legora, Lovable, OpenEvidence, and many others in its portfolio.