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Founder secondary stock related business ideas – marketplaces and funds for secondary txs. My notes: 1) When you’re fully VC backed, it’s simplest to sell as part of a round. You already have the buyers lined up (the investors in that round, or the ones who wanted in but didn’t get an allocation). Either opportunistically if the round is heavily oversubscribed, or done intentionally up-front as a part of the round.  2) Founders don’t really think about doing secondaries outside of rounds. And even if they did, they’d go via their insiders. The investors generally have ROFRs on secondary txs too. 3) For the great companies, this is a solved problem (doing it as part of a round). For the companies that aren’t already hot, there’s value in creating demand for their shares. 4) For companies that raised a round, are making good money, but are no longer VC track and not growing fast, there may be some value there. But why not negotiate a distribution to all investors? 5) There’s demand from investors that don’t have access to hot private companies to get access, but this is tough too. It’s a marketplace for lemons: the sellers have all the info. The buyer knows less than the seller. The seller will either sell only if desparate, or if they believe the buyer is overpaying, based on their information asymmetry.  6) Some companies are utilizing the high-demand dynamic by doing big secondary offerings, via a network of kind-of SPV middlemen, e.g. CoreWeave. 7) Founders don’t want employees selling unless they can control price, and access/captable. Generally have veto rights. 8) "Secondaries are bought not sold." 9) If there are 5-10 big winners, then a marketplace doesn’t really work. If 100+, then it might. 10) Buying stock in private companies in exchange for ongoing dividends could be interesting. Would founders sell at an attractive price, relative to the dividend, though?  11) But also, people have made good money on secondary stock purchases (SpaceX, others), and the dollar amounts involved in the transactions are often large (7-8 figures, sometimes more). See also: Chris Sacca’s Twitter secondary stock purchases. 12) You can sell financial products people want to buy (like Destiny Tech100), or you can buy financial products people don’t want to buy at your price (yet) but where you can own it long enough that they’ll come around. A fund seems like the better move, but then you’re an investor, not running a marketplace. See also: EquityZen, Collective Liquidity, 137 Ventures. Destiny Tech100, Carta (Carta exited the secondary business). Thank you to mike yu, Timothy Wee, David Zheng 🍉, Eric Chen, Justin Mares, and Chris Yeh, for your quick reactions and input.

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