Don’t think @sacca gets enough credit for mainstreaming secondaries as a investment strategy vs. purely as a tool for founder liquidity.
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I think most bootstrapped founders don't want to sell that equity, but if they do, they sell it only to close friends to look for a mutually benefitial trade.
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I'm not so sure about that. Jason Fried and DHH famously had Bezos buy some of their equity in Basecamp early on. They were able to take millions off the table (personally) and just focus on growing the company (without anxiety, because they had $ in their personal bank accnts).
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I think you could structure something interesting if a) there’s a clear stream of dividends or b) a structured event down the road for the buyer to acquire the remainder / majority of the business Tough to do if neither are true w/ a minority position w/o a clear path for exit
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Agree - a small slice of an illiquid entity with no defined exit opportunities (held in perpetuity) is not very appealing.
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