Is Anthropic Making the Biggest Mistake in AI History | E2258

Is Anthropic Making the Biggest Mistake in AI History | E2258

Author: Jason Calacanis March 5, 2026 Duration: 1:20:55

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Today’s show:

It’s a packed TWiST Today! WITH US, we’ve got Erik Voorhees of VeniceAI and Logan Allin of Fin Capital on to talk agents, crypto, and… you guessed it, OPENCLAW!

Where does agentic AI meet the financial system? How will agents transact? And what does privacy look like in a world with omnipresent AI?

Stick around for some demos! We’ve got George Pickett to demo OpenClaw studio and David Kaufman to show us what he’s building at Siteline!


Timestamps:


00:04:31 What was Logan’s original thesis in Circle?


10:08 LinkedIn Jobs - Thanks to our partners at @LinkedIn! Post your job for free at https://⁠linkedIn.com/twist⁠ then promote it to get access to LinkedIn Jobs’ new AI assistant.


00:11:52 Logans thoughts on Open vs. Closed Source


00:15:33 How to maintain privacy in AI


20:02 Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit https://⁠deel.com/twist⁠ to learn more.


00:23:29 Why LAUNCH’s token usage is trending higher than payroll!


00:25:05 How Fin capital uses personality types and AI to assess investments


00:29:45 Why Erik thinks Anthropic’s defiance of the federal gov. is bravery!


32:10 Iru - Iru unifies identity, endpoint security, and compliance into one platform. TWiST listeners get 20% off when they book a demo at https://⁠iru.com⁠/twist!


00:42:23 How Siteline is helping understand companies and their agent traffic.


00:57:15 OpenClaw Studio makes OpenClaw as user friendly as possible.


01:10:09 The layers and layers of Microstrategy’s business model.


01:11:44 Which AI tools are the most indispensable?


01:12:25 How Jason uses the Grok button on threads


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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland


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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
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