E117: Did Stripe miss its window? Plus: VC market update, AI comes for SaaS, Trump's savvy move

(0:00) Bestie intro: Jason's Japan trip! (1:04) Stripe's precarious situation: Did it miss the window? Breaking down its $4B tax bill, slowing growth curve, enterprise vs SMB customers, scalability issues, and more (23:07) Lessons for founders: How ZIRP can skew CAC and LTV calculations, burn multiple (29:40) VC market update: ZIRP mistakes, VC as a "must-have" asset class for LPs, how the 2021 vintage can be saved (39:05) AI's outsized impact on SaaS and real-world businesses (55:16) Advice from Steve Jobs on customer-first product development, Section 230 update (1:00:29) Trump's savvy visit to East Palestine and 2024 strategy, Biden's visit to Ukraine, China's position (1:14:24) Tinfoil hat corner (1:23:25) Bestie wrap up!

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Intro Music Credit: https://rb.gy/tppkzl https://twitter.com/yung_spielburg

Intro Video Credit: https://twitter.com/TheZachEffect

Referenced in the show: https://www.theinformation.com/articles/inside-stripes-55-billion-pitch-to-investors https://www.theinformation.com/articles/the-private-tech-company-that-let-employee-stock-grants-evaporate https://techcrunch.com/2013/09/11/zuckerberg-says-he-was-too-afraid-of-taking-facebook-public https://sacks.substack.com/p/enterprises-vs-smbs-whos-the-better-customer-for-b2b-saas-startups-9a0d4efe69e9 https://sacks.substack.com/p/the-burn-multiple-51a7e43cb200 https://twitter.com/tylertringas/status/1627449217294958592 https://chamathreads.substack.com/p/higher-rates-will-lead-to-the-next https://twitter.com/Jason/status/1628851245644644352 https://signalvnoise.com/posts/3497-you-know-one-of-the-things-that-really-hurt https://www.scotusblog.com/2023/02/not-like-the-nine-greatest-experts-on-the-internet-justices-seem-leery-of-broad-ruling-on-section-230 https://www.whitehouse.gov/briefing-room/statements-releases/2023/02/20/on-the-record-press-call-by-senior-administration-officials-on-president-bidens-trip-to-ukraine https://www.washingtonpost.com/politics/2023/02/20/secrecy-security-biden-trip-to-kyiv https://www.yahoo.com/news/joe-biden-makes-surprise-visit-095627966.html https://twitter.com/nytimes/status/1626984889449959430 https://www.nytimes.com/interactive/2023/02/23/world/russia-ukraine-geopolitics.html https://www.bbc.com/news/world-europe-26079957 https://openai.com/blog/how-should-ai-systems-behave