How Many Startups Will Survive OpenAI? | E2288

This Week In Startups is made possible by:Pilot -⁠ https://Pilot.com/TWIST⁠Grasshopper Bank -⁠ https://Grasshopper.bank/TWIST⁠Quo -⁠ https://Quo.com/TWiST⁠Plaud - ⁠https://Plaud.ai/twist⁠Anthropic just declared every unauthorized secondary sale of its stock "void" — naming Hiive, Forge, Sydecar, Upmarket, and others in a public hit list. Jason and Alex sit down with Jenny Fielding (Everywhere Ventures), Dave McClure (Practical VC), and Sam Lessin (Slow Ventures) to unpack what the AI lab's move to limit secondary trades means for SPV operators, brokers, and the founders trying to keep control of their cap tables. Plus: a real story of a founder who returned a $15M Series A six months after closing because Claude was going to eat his startup, SaaS moats, and just what does it mean to be rich?Timestamps:0:00 Guest introductions0:48 Anthropic voids unauthorized SPV trades8:41 Accredited investor reform & the SEC sophisticated investor test8:58 Quo (formerly OpenPhone) - Quo gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at https://quo.com/TWiST11:43 Naval's USVC closed-end fund as a workaround16:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!17:48 Pro-rata rights battles: when Series A investors push seed investors out19:36 Grasshopper Bank: Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.29:13 Pilot: Focus on your product, let Pilot handle your bookkeeping. Pilot provides the most reliable accounting, CFO, and tax services for startups and small businesses. Head to https://pilot.com/twist and get $1,200 off your first year.30:23 Storing wealth in stories vs. cash flows34:19 Cerebras and Fervo Energy IPOs — meaningful liquidity?37:54 Will SpaceX, Anthropic, OpenAI IPOs redistribute capital or compound it?45:58 The $15M Series A founder who returned the money because of Claude50:01 Should founders pivot or return capital when the world changes?56:43 OpenAI's $6.6B tender and Shruti Gandhi's viral SF cost-of-living tweet1:00:25 Intercom rebrands to Fin: the AI-first late-stage pivotSubscribe to the TWiST500 newsletter:⁠ https://ticker.thisweekinstartups.com⁠Check out the TWIST500:⁠ https://www.twist500.com⁠Subscribe to This Week in Startups on Apple:⁠ https://rb.gy/v19fcp⁠Follow Lon:X:⁠ https://x.com/lons⁠Follow Alex:X:⁠ https://x.com/alex⁠LinkedIn:⁠ ⁠https://www.linkedin.com/in/alexwilhelm⁠Follow Jason:X:⁠ https://twitter.com/Jason⁠LinkedIn:⁠ https://www.linkedin.com/in/jasoncalacanis⁠Check out all our partner offers:⁠ https://partners.launch.co/⁠Great TWIST interviews:⁠ Will Guidara,⁠⁠ Eoghan McCabe⁠,⁠ Steve Huffman⁠,⁠ Brian Chesky⁠,⁠ Bob Moesta,⁠⁠ Aaron Levie⁠,⁠ Sophia Amoruso⁠,⁠ Reid Hoffman⁠,⁠ Frank Slootman⁠,⁠ Billy McFarland⁠Check out Jason's suite of newsletters:⁠ https://substack.com/@calacanis⁠Follow TWiST:Twitter:⁠ https://twitter.com/TWiStartups⁠YouTube:⁠ https://www.youtube.com/thisweekin⁠Instagram:⁠ https://www.instagram.com/thisweekinstartups⁠TikTok:⁠ https://www.tiktok.com/@thisweekinstartups⁠Substack:⁠ https://twistartups.substack.com⁠

Episode metadata supplied by the publisher feed · Published May 13, 2026

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