Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot Paywall for AI Agents | E2167
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 20 August 2025
⏱️ 59 minutes
🧾️ Download transcript
Summary
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
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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
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Transcript
Click on a timestamp to play from that location
| 0:00.0 | training jobs, these training data pipelines, Chalk is able to get fresh data to machine learning |
| 0:06.8 | and AI models in context at inference time, which means when someone clicks a button, when they |
| 0:12.3 | load a page, we can help a model fetch the data from the source, so it's really fresh and |
| 0:18.2 | really relevant to what you're doing in in that application. |
| 0:23.4 | This week in startups is brought to you by dot tech. |
| 0:27.6 | Say it without saying it. |
| 0:29.7 | Head to get. |
| 0:30.5 | Dot tech slash twist or your favorite registrar to get a clean, sharp. |
| 0:35.4 | Dot Tech domain today. |
| 0:37.4 | Lemon.io. |
| 0:38.9 | Hire pre-vetted remote developers |
| 0:40.7 | and get 15% off your first four weeks of developer time |
| 0:44.3 | at lemon.io slash twist. |
| 0:48.1 | And Squarespace, turn your idea into a beautiful website. |
| 0:52.4 | Go to squarespace.com slash twist for a free trial. |
| 0:56.0 | When you're ready to launch, use offer code twist to save 10% off your first purchase of a website or domain. |
| 1:02.4 | Hey everybody. |
| 1:03.2 | Welcome back to Twist. |
| 1:04.4 | This is Alex. |
| 1:05.3 | And today we have two Twist 500 interviews for you. |
| 1:08.8 | I did both of these and I'm incredibly excited about both these companies. |
| 1:11.8 | All right. |
... |
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