How Many Startups Will Survive OpenAI? | E2288
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Anthropic 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?
Guest Links:
Sam Lessin
https://www.linkedin.com/in/wlessin/
Slow Ventures
https://slow.co/
Dave McClure
https://www.linkedin.com/in/davemcclure/
Practical Venture Capital
https://practicalvc.com/
Jenny Fielding
https://www.linkedin.com/in/jennyfielding/
Everywhere VC
https://www.everywhere.vc/
Discussion Links:
Anthropic saying no to SPVs
https://support.claude.com/en/articles/13704655-unauthorized-anthropic-stock-sales-and-investment-scams
OpenAI saying no to SPVs
https://openai.com/policies/unauthorized-openai-equity-transactions/
Cerebras raises IPO guidance
https://www.cautiousoptimism.news/with-gas-prices-spiking-going-to-office-is-now-a-pay-cut/
Fervo Energy goes public
https://www.renaissancecapital.com/IPO-Center/News/118998/Geothermal-energy-developer-Fervo-Energy-prices-upsized-IPO-at-$27-above-th
Coverage of OpenAI secondary
https://techcrunch.com/2025/10/02/openai-is-the-worlds-most-valuable-private-company-after-private-stock-sale/
USVC
https://usvc.com/
Ryan Hoover's Weekend Fund IV
https://x.com/rrhoover/status/2052405380655825140
Intercom rebrands to Fin
https://www.intercom.com/blog/today-intercom-becomes-fin/
Other:
Equitybee
https://equitybee.com/
Dave McClure's podcast
https://open.spotify.com/show/3WH5Br0CPTqSPcrK1FxC7J
Sam Lessin's podcast
https://moreorlesspod.com/
Launch Festival
https://www.launchfestival.com/#
Timestamps:
0:00 Guest introductions
0:48 Anthropic voids unauthorized SPV trades
8:41 Accredited investor reform & the SEC sophisticated investor test
8:58 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/TWiST
11:43 Naval's USVC closed-end fund as a workaround
16:41 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 out
19:36 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 flows
34:19 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 Claude
50:01 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 tweet
1:00:25 Intercom rebrands to Fin: the AI-first late-stage pivot
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