Poor matchmaking in private secondaries

The real bottleneck in private secondaries is not just finding a buyer, it is finding a buyer the company will trust, the seller can reach, and the buyer can underwrite with thin information. Dan Akivis is describing a market where most trades still depend on brokers, personal networks, and scattered whispers, so smaller or lesser known names struggle to clear even when the underlying company is doing well.

• In practice, matchmaking breaks because sellers, buyers, and issuers want different things. Sellers want liquidity, buyers want a discount for uncertainty, and issuers want control of the cap table. That leaves many trades stuck unless the company itself sponsors the process or already knows the buyer.
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• The market is still highly fragmented. Most secondary volume historically came through brokered deals and issuer run tenders, not a deep open order book. Even newer software platforms often improve paperwork and settlement more than they solve discovery, diligence, and trust.
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• Poor matchmaking shows up directly in pricing. Tender data showed 83% of transactions priced at or below the last round, with average participation around 37%. When buyers are limited and information is sparse, the side that most needs liquidity usually accepts the worse price.
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The next phase of the market is likely to look less like a single open exchange and more like better infrastructure around trusted distribution, recurring issuer approved programs, and broker tooling. As disclosure becomes more systematic and company approved liquidity windows become more common, matchmaking should shift from relationship hunting to a more repeatable market process.