Marketplace investing has its own math: liquidity, take rate, cold-start strategy, and the failure modes that kill 90% of two-sided businesses.
Marketplaces are the highest-variance category in venture. The winners are enormous; the failures are common. Investors look at a very specific set of signals.
For buyers: % of searches that convert to a transaction. For sellers: % of listings that transact within N days. Below a category-specific threshold, the marketplace feels dead and both sides leave.
Consumer marketplaces: 10-30% (Airbnb, Uber). B2B marketplaces: 3-15%. Vertical / high-service marketplaces can go higher; commodity marketplaces stay lower. Take rate is set by the value the marketplace adds — matching, trust, payments, logistics.
Pick one side to solve first (usually supply). Concentrate in one geography or vertical. Simulate the other side manually if needed. Airbnb photographed apartments, DoorDash ran restaurant deliveries themselves — the pattern repeats.
Disintermediation (both sides transact off-platform). Weak network effects (buyers indifferent to seller count above a low threshold). Constant subsidy needed to keep either side. Regulator risk that changes economics overnight.
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