Missing market context in private secondaries
Dan Akivis, senior associate at Expansion VC, on selling secondary and managing LP relationships
The real bottleneck in private secondaries is not company quality, it is missing market context. In practice, a buyer is being asked to wire millions for common stock in a company they cannot diligence like a public name, with no steady disclosures, no reliable trading history, and often no help from management. That pushes buyers toward blunt discounts, makes off cycle sales hard to clear, and keeps even strong unicorn stakes illiquid outside company run processes.
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Akivis describes buyers anchoring to generic discounts because they do not know the business well enough, even when sellers know an up round is coming. He also notes that companies rarely want to spend time educating outside buyers for a sale that only helps one shareholder.
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That pattern shows up more broadly in the market. Most tender offers are priced at or below the last round, and closed door tenders usually rely on an existing insider buyer. Without fresh information and broader investor access, pricing lags company progress and liquidity stays narrow.
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The market has built execution rails before it built trust and research. Platforms and brokers can move shares, aggregate cap tables, and settle trades, but they still struggle to answer the basic buy side question, which is why this company at this price right now. That is why issuer cooperation and disclosure matter so much.
The next phase of private liquidity will look less like one off brokering and more like a light version of investor relations. The winners will be the companies and infrastructure providers that create repeat disclosure, repeat trading windows, and repeat buyer familiarity, because that is what turns a hard to explain private stake into an asset that can actually clear at scale.