Now *that* is an intriguing idea. A refinement might be something like a "Employees of YC Winter 2019 Class" syndicate, which might be even more employee-friendly, due to the diversification factor, and might alleviate some social concerns internal to a company.https://twitter.com/HarveyMultani/status/1123932050950639616 …
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To elaborate a little bit here: Most employees are probably over-exposed to the future of their company by both equity ownership and the implicit current value of their future career prospects both being a) heavily correlated to the company and b) very large relative to wealth.
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So if somebody was early-career and asked me "Hey should I buy more stock in my employer", even if ceteris paribus that were available at an attractive price, that is probably not a great financial decision in most cases.
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Additionally, compensation schemes at a company run into some fraught issues with employee-to-employee fairness, and one underappreciated dimension that employees are different on is "Has this person e.g. benefited from 1+ exits before?"
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It could plausibly do unwonderful things to internal morale if two peers mutually know that they're approximately equal with regards to how the company evaluates status but because one of them was around for the last IPO and one wasn't their effective comp is very different.
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I think that is plausibly defanged a little bit by emphasizing that the perk is mostly about investing in other-than-one's-employer companies, because Silicon Valley is basically OK with capitalism outdoors but often tends towards socialism indoors.
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