The smart money won't sell

For three decades, secondaries were how insiders cashed out — at the top of today's market, the insiders refuse

// Share
The smart money won't sell

OPENAI'S October tender offer was supposed to clear $10.3 billion; it cleared $6.6 billion. The $4 billion gap reflected a quiet verdict from the people closest to the asset: at a $500 billion valuation, employees holding shares declined to sell to investors who had bid up the round in size and aggression and were now left holding their checkbooks. Anthropic's most recent tender, run earlier this year, fell short of its $6 billion target by similar logic, according to one investor in the company. Two of the three most valuable private companies in the world ran tenders this year that drew more buyer demand than the sellers were willing to fulfill.

The venture secondary market in 2025 reached $106.3 billion in transaction value by PitchBook's tally, nearly double the 2024 total and roughly tenfold the level of a decade ago. Concentration is extreme. The top 20 names traded on Hiive, a private-stock marketplace, accounted for 86.4% of fourth-quarter volume; the top five — OpenAI, Anthropic, SpaceX, and a small handful of others — represented 55.6%. Capital chasing this short list has piled up. Dedicated VC secondary funds held $11.8 billion in dry powder by mid-2025, a 2.8-fold increase from 2022, and secondary SPVs on Sydecar, a fund-administration platform, are up 682% from 2023, with capital raised through them up 1,340%. Buyers are willing to pay at or near last-round prices — sometimes premiums — for stakes in the top names.

// Members only

This article is for Vector members. Start a 7-day free trial to keep reading.

Start your free trial

// The Daily

Get Vector in your inbox.

A free morning briefing on the AI revolution. Weekdays at 6am CT.