How Many Startups Will Survive OpenAI? | E2288

How Many Startups Will Survive OpenAI? | E2288

Author: Jason Calacanis May 14, 2026 Duration: 1:25:16

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


Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 100

This Week in Startups
Podcast Episodes
SpaceX and Cursor team up to topple Claude Code | E2279 [not-audio_url] [/not-audio_url]

Duration: 1:13:29
This Week In Startups is made possible by:LinkedIn Jobs - linkedIn.com/twistGrasshopper Bank - grasshopper.bank/twistNotion - notion.comToday’s show:This week, SpaceX announced that it was partnering with AI coding start…
Why Your Company Should Own Its AI Model | E2278 [not-audio_url] [/not-audio_url]

Duration: 1:16:59
This Week In Startups is made possible by:Quo - https://quo.com/TWiST Vanta - https://vanta.com/twist Pilot - https://pilot.com/twist Plaud - https://Plaud.ai/twistToday’s show:*Eragon CEO Josh Sirota believes that you s…
Bittensor’s (alleged) $10M rug pull (feat. Mark Jeffrey) | E2275 [not-audio_url] [/not-audio_url]

Duration: 1:18:38
This Week In Startups is made possible by:Sentry - https://sentry.io/twist Deel - https://deel.com/twist Netsuite - https://netsuite.com/twist Plaud - https://Plaud.ai/twistToday’s show:*TAO just had its worst week since…
Bittensor Drama! TAO down 15%! | E2274 [not-audio_url] [/not-audio_url]

Duration: 1:21:54
This Week In Startups is made possible by:Pilot - https://pilot.com/TWISTSquarespace -https://squarespace.com/TWISTNorthwest Registered Agent - https://northwestregisteredagent.com/TWISTPlaud - https://Plaud.ai/twistCrow…
Anthropic’s Mythos is a cyber-weapon, so you can’t have it | E2273 [not-audio_url] [/not-audio_url]

Duration: 1:16:48
Anthropic just built a model so dangerous, they’re not even going to release it (for now). On TWiST, Jason, Alex, and Neurometric CEO Rob May discuss whether or not this is just another frontier model or a potential weap…
3 AI Agents That Actually Replaced Human Jobs | E2272 [not-audio_url] [/not-audio_url]

Duration: 1:19:09
Anthropic just pulled the plug on Claude subscriptions for OpenClaw and every third party agentic tool. So Jason and Lon welcome back three of our top TWiST OpenClaw experts to break down what it means, how much it’s goi…