Clawdbot is an inflection point in AI history | E2240

Clawdbot is an inflection point in AI history | E2240

Author: Jason Calacanis January 27, 2026 Duration: 1:02:14

This Week In Startups is made possible by:


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Today’s show: 


Jason is back from Davos and Tokyo! We are jumping right back in with a group of Clawdbot power users: Alex Finn, Matt Von Horn, and Dan Penguine.


Clawdbot is a hot open source AI project that lets users automate… everything! Dan helped his automate his aging parent’s tea shop, Matt built news sourcing bots, and Alex runs his one-man SAAS startup with Clawdbot as an AI employee!


But with all of that power comes the responsibility of making sure you are not giving your AI too many authorizations that could come under fire! Whether fisching emails, “injections”, or bad decision making from incorrect information online.


Check out how these 3 experts, Jason and Alex are thinking about the bleeding edge of AI!


Timestamps:


(00:00) Introducing today’s Clawdbot experts!


(04:09) How Matt Von Horn makes “Skills” with Clawdbot


(10:53) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST.


(13:25) Dan Penguine’s “Normy” use case: automating his parent’s tea shop


(19:50) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist


(22:23) Alex Finn breaks down how Clawdbot lets him run a one man startup


(24:28) Alex Finn on Clawdbot autonomously building apps within his business


(28:33) Security concerns with Clawdbot, can your AI get hacked?


(32:46) Northwest Registered Agent. Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity —  Learn more at https://www.northwestregisteredagent.com/twist


(35:07) Why is everyone buying Mac Minis?


(37:39) How to think about LLM Token usage


(46:02) Clawdbot will build CRMs, project management software, etc without being asked. Is this the end of SAAS?


(46:58) Matt live uploads his new Clawdbot skill on aire!


(48:22) Why was Clawdbot able to move so much quicker than Anthropic and OpenAI?


(50:17) What is Clawdbot’s business model as an open source AI?


(53:27) Matt’s recursive AI prompt loop and how AI prompts layer


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Follow Lon:


X: https://x.com/lons


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Follow Alex:


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LinkedIn: https://www.linkedin.com/in/alexwilhelm/


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LinkedIn: https://www.linkedin.com/in/jasoncalacanis/


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Thank you to our partners:


(10:53) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST


(19:50) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist


(32:46) Northwest Registered Agent. Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity —  Learn more at www.northwestregisteredagent.com/twist


Check out all our partner offers: https://partners.launch.co/


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.
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