I wonder if there's a market for angel investing (w/o followon) in dating startups SPECIFICALLY to become friends/familiar with great early-in-career founders, to try to invest in their second, presumably non-dating startup.
i.e. throw down $25k on whatever valuation purely to build a relationship with 10 teams/year, with the hope one might survive as a business, and one or two might be stellar teams who fail for reasons specific to dating, but will come to you first when they do their next startup. $250k/yr isn't that expensive, and you could pre-screen by just investing in 100% of the YC dating-or-adjacent companies.
Extra points for going out of your way to be helpful vs. maximizing your return, and being super helpful during inevitable wind-down.
i.e. throw down $25k on whatever valuation purely to build a relationship with 10 teams/year, with the hope one might survive as a business, and one or two might be stellar teams who fail for reasons specific to dating, but will come to you first when they do their next startup. $250k/yr isn't that expensive, and you could pre-screen by just investing in 100% of the YC dating-or-adjacent companies.
Extra points for going out of your way to be helpful vs. maximizing your return, and being super helpful during inevitable wind-down.