Do the headline valuations of leading AI labs translate into correspondingly large returns for their early venture investors?

Harry Stebbings · Apr 18, 2025

No venture investor is going to make money from investing in LLM companies

The rounds cost so much money that investors are heavily diluted over successive rounds, and stock-based comp makes it even more dilutive

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Harry Stebbings · May 5, 2025

Early Anthropic investors at a $4B valuation have only realized roughly 3.5-4x after dilution and employee stock payouts, which is unimpressive given the headline 12x markup

Investors who bought Anthropic at $4B have only made roughly 3.5–4x once dilution and employee stock payouts are accounted for, despite a 12x headline mark

Scope: excludes OpenAI

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Harry Stebbings · Aug 25, 2025

The opportunity cost of writing nine-figure checks into mega-rounds is high because dilution crushes the realized multiple.

A friend who invested in Anthropic at a $4B valuation only had a ~3.8x when it was marked at $60B, because of dilution — and that cash could have been deployed elsewhere.

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Harry Stebbings · Oct 17, 2025

OpenAI has not actually been a great venture investment — early investors are sitting on roughly 25x, no better than a great SaaS outcome, because of how dilutive the business is; the AI wave is the greatest transfer of wealth from VCs to founders and employees.

Enormous capital requirements dilute early investors, so returns lag the headline valuation

Scope: 25x is still an amazing outcome

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Martin Mignot · Aug 11, 2025 · hedged

Early-stage multiples on LLM/foundation-model investments will likely be lower than past categories because of heavy dilution, but absolute returns can still be very high.

The size of the outcomes and especially the speed at which they are reached means a lot of capital can be deployed profitably even with more dilution.

Scope: 'we'll see at the end of the journey'; multiple 'maybe slightly lower'; requires ability to deploy a lot of capital

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Byron Deeter · Aug 25, 2025

Anthropic is a generational company that could be one of the next hyperscalers and a trillion-dollar business, making it a potential 30x rather than a 3.8x.

Reports suggest it may be raising at $170B and buyers at that price believe it becomes a hyperscaler; the investment thesis is generational upside, not the interim mark.

Scope: depends on being right; these businesses could still go to zero

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Larry Aschebrook · Jun 16, 2025

Anthropic is a buy at $61B all day long, and future dilution is irrelevant to that decision

What matters is the dollar price paid versus the dollar price you sell at — he is solving for DPI, not MOIC

72:40 Future dilution is irrelevant what matters is entry price versus exit price not moic