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This Week in Startups

How Many Startups Will Survive OpenAI? | E2288

This Week in Startups

Jason Calacanis

Technology

4.2 • 1.4K Ratings

🗓️ 13 May 2026

⏱️ 85 minutes

🧾️ Download transcript

Summary

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

Transcript

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0:00.0

People don't want to talk about it because it's scary to admit that this is happening.

0:03.8

A founder that closed a $15 million Series A from a top tier VC and then a half year later,

0:09.8

they plan to return the cash to investors.

0:12.4

You add that Clyde will displace the product and I wrote the value.

0:15.1

This is really happening.

0:16.1

Most people are not talking about it.

0:17.4

It's kind of wild.

0:18.7

It's running a zombie company to put your nose to the

0:22.1

grindstone at a startup for 10 years, 15 years, and the outcome is unknown. Or you get a guaranteed,

0:29.4

you know, 10, 20, 30 million dollar package from Open AI. Do you think that the companies in your

0:35.2

portfolio that are facing the similar chasm going from the SaaS era to the AI era or the agentic era are going to make it?

0:40.9

Probably 50% that I think might make it. It might not be the money printing free cash flow machine that people think it's going to be.

0:48.7

This week in startups is brought to you by Pilot. Focus on your product. Let Pilot handle your bookkeeping. Pilot provides the most

0:55.6

reliable accounting, CFO and tax services for startups and small businesses. Head to pilot.com

1:01.8

slash twist and get $1,200 off your first year. Grasshopper Bank. Time is money. Don't waste either.

1:07.7

Go to grasshopper.com bank slash twist and get an exclusive $500 cash bonus just for

1:13.5

opening an account. And Quo, formerly open phone. It gives you a clean, modern way to handle every

1:18.8

customer call, text, and thread all in one place. Try it free and get 20% off your first six months

1:25.3

at quo.com slash twist. That's QUO.com slash twist. Hey, everybody and welcome back to Twist. Today is May 13th. It's Wednesday, which means it's Venture Capital Roundtable Day. I'm joined by Abevius of some of my favorite people, including, of course, my usual co-host, Jason Callicanus. Jason, how are you? I'm well. Excited for today. We also have Jenny Fielding from Everywhere Adventures. Jenny, how's life on your end? It's good. I'm excited to be back. It's been a while. It has been a while. If you don't know her firm, Everywhere Adventures does essentially raises capital from a collection of about 500 founders and then sources deals from the same group. Portfolio companies include

2:01.0

StarCloud, Headway, Devo, and others. Jenny, good to have you here. Now, Sam, slow ventures. How are you doing? I'm great, man. Glad to have you here. Major portcoes include next door Robin Hood, human interest, air table, et cetera, et cetera, et cetera, busy man. And then finally, we have Dave McClure from Pactical Venture Capital. Dave, how you doing?

2:18.8

Fantastic. Good to have you back. You run a secondaries-focused fund that also buys GP and LP commits, which is a big deal because we're going to start today by talking about the most important thing in the world, which is news that Anthropic and OpenAI dropped successive bombs on the SPV market. And if you don't know what that means and you're listening to this, imagine that you can't buy shares in Anthropical Urban AI because you're not a VC. You're not an employee. So you go to somebody in a back alley behind a dumpster. They have a couple of shares in there. And they say, don't worry. Got some anthropic for you here. Yeah, exactly. Just caught with a little bit of like, you know, sugar or something.

2:56.1

In this case, the fentanyl is the layered fees and it turns out that the two companies in question

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