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Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot Paywall for AI Agents | E2167

Aug 20, 2025 • 59 mins

Today’s show: In this TWiST 500 double feature, Alex sits down with two breakout founders: Chalk’s Marc Freed-Finnegan & Tollbit’s Toshit Panigrahi! First, Chalk’s CEO Marc Freed-Finnegan is tackling one of AI’s biggest bottlenecks—data freshness. Instead of relying on stale batch jobs, Chalk delivers real-time pipelines for inference compute, automatically transpiling Python into C++/Rust so it can run blazing fast in production. Investors are calling it the ‘next Databricks’—and after hearing this convo, you’ll see why. Then, Tollbit’s CEO Toshit Panigrahi returns after raising a $24M Series A and signing up 1,400+ publishers. With RAG traffic exploding and robots.txt losing its teeth, their ‘bot paywall’ could reshape how AI agents pay for the content they consume. Are we heading for a Spotify moment for data licensing? A must-watch if you care about the economics of AI, from data pipelines to publisher monetization.

Key Points

Chalk is revolutionizing machine learning by enabling real-time data retrieval at inference time, significantly enhancing the freshness and relevance of AI model outputs.
Tolbit's bot paywall solution addresses the growing issue of AI agents scraping content without providing equivalent value, ensuring publishers can monetize automated traffic effectively.
The rise in AI-driven autonomous traffic is reshaping the economics of the Internet, with publishers increasingly looking to Tolbit to manage and monetize these interactions.

Speakers

Marc Fried Finnegan

Guest • 26%

Alex Wilhelm

Host • 34%

Tosit Panagrahi

Guest • 33%

Partners

Chapters

0:00	Introduction to Chalk's data pipelines for machine learning and AI models
0:23	Sponsor: Dot Tech, Lemon.io, Squarespace
2:07	Chalk's role in the AI inference era and its impact on data freshness
5:55	Chalk's impact on Whatnot's recommendation system
9:54	Challenges and solutions for real-time data pipelines
11:46	Sponsor: Squarespace
14:45	Chalk's data processing capabilities, pricing, and deployment strategy
21:23	Chalk's open source strategy and industry adoption
25:08	Accessibility of Chalk's technology to non-tech companies
27:06	Chalk's hiring and company growth
28:01	Introduction to Tolbit and retrieval augmented generation (RAG)
30:37	Use cases for RAG and implications of increased AI bot traffic
33:17	Ethical considerations and bot paywall strategies for AI companies
40:36	Tolbit's approach to publisher relations and piracy debate
43:16	Challenges for AI companies on the open Internet
43:59	Pricing models and publisher experiences with AI crawlers
47:34	Incentives and partnerships for publishers with Tolbit
50:02	Notable publishers and recent growth of Tolbit
53:59	Future projections and milestones for Tolbit
55:54	Tolbit's state of the bots report and hiring needs

Transcript

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