February 24 2023 Jason is in Japan Stripe Needs $4B for RSUs 4square is letting early employee stock options expire Does it make sense to wait as long as possible before going public? Apparently if stock options are granted and its been 10 years they have to refresh it or something and so IRS deems that an event and so you need money to cover it Apparently ADYEN is very profitable Stripe has added way too many employees Stripe has to hire a lot more people to fund tons of features to go after tail customers Adyen goes after head customers so they have to build fewer features So in hindsight Stripe should have gone public 2018-2019 Not clear if there is long term profitability in tail products Sacks post on Enterprises vs SMBs Enterprises provide better Annual Contract Value but SMBs are better early adopters Both strategies are good Its about founder market fit - better sales founder = Enterprise, better product founder = SMBs If you start with SMBs and do well then...