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

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. Timestamps: (0:00) Intro + sponsors (1:03) Alex tees up two Twist 500 interviews: Chalk & Tolbert (2:47) Why AI is shifting from training compute to inference compute (4:41) Data freshness & real-time inference explained (10:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST (12:00) How Chalk transpiles Python into C++/Rust for speed (18:52) Chalk's business model, margins & $500M valuation (20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (21:24) Show Continues… (28:02) Tollbit returns: $24M Series A & the rise of RAG bot traffic (30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today. (31:41) Show Continues… (36:53) Robots.txt losing relevance & the case for bot paywalls (39:19)Publishers, AI agents & the future economics of the web Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (10:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST (20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today. Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916