This Week in AI
Hosted by Jason Calacanis
A weekly roundtable where tech investor Jason Calacanis and CEO-level guests candidly debate the business and strategy of the AI industry.
A graduate-level conversation about the business of AI, framed as a roundtable of peers. Host Jason Calacanis brings on 2-3 founders or CEOs to analyze current events, like SpaceX's M&A strategy or Apple's latest announcements, through the lens of operators. The show bypasses basic explainers to focus on second-order effects: competitive moats, go-to-market strategy, talent wars, and the economics of building with and on top of foundational models.
“Unlike purely technical or interview-based AI podcasts, this show's 'roundtable' format fosters a candid, multi-sided debate on strategy and market dynamics. Calacanis's role as both host and active investor adds a layer of skin-in-the-game analysis, often pushing guests on their business models and competitive threats from a VC perspective.”
Who hosts this show
This Week in AI is an expert-focused podcast hosted by veteran technology entrepreneur and angel investor Jason Calacanis. Presented as 'the All In Podcast for AI,' the show features roundtable discussions with founders and executives who are actively building and funding AI companies. Episodes dissect the week's news, from major acquisitions and platform shifts to the underlying economics and competitive dynamics shaping the artificial intelligence landscape.
Credentials & credits
- Internet Entrepreneur & Angel Investor
- Author, "Angel: How to Invest in Technology Startups"
- Founder, LAUNCH Accelerator & This Week in Startups
- Co-founder, Weblogs, Inc. (sold to AOL)
- Co-host, All-In Podcast
- B.A. in Psychology, Fordham University
Other ventures
- This Week in Startups (podcast)
- All-In (podcast)
- LAUNCH (accelerator, fund, events)
- The Syndicate (investment syndicate)
- Inside.com (newsletter platform)
- Founder University (pre-accelerator)
What kind of podcast
- Country
- United States
- Region
- usa
When new episodes drop
- 01Are world models the unlock for Physical AI? | Episode 19Jun 25, 2026 · 1h 13m
- 02Why AI Models Aren’t the Product Any More | TWiAI Ep 18Jun 18, 2026 · 1h 21m
- 03Hermes Agent, NotebookLM & LiveKit Founders on the AI Agent Race | TWiAI 17Jun 10, 2026 · 1h 29m
- 04How to Move From ChatGPT to an AI Coworker | Claude CoworkJun 8, 2026 · 7 min
- 05
- 06How I Build Real Apps Without Writing Code | Lovable TutorialMay 29, 2026 · 6 min
- 07The Pope Wants to "Disarm" AIMay 27, 2026 · 1h 07m
- 08Grads boo AI, Reese Witherspoon gets dunked + Karpathy joins Anthropic | TWiAI E14May 20, 2026 · 1h 39m
Notable episodes
- 01Hermes Agent, NotebookLM & LiveKit Founders on the AI Agent Race | TWiAI 17
A quintessential roundtable where founders of competing AI agent companies debate strategy, costs, and the threat of major platforms like Apple entering their space.
- 02Why AI Models Aren’t the Product Any More | TWiAI Ep 18
This episode captures a key strategic shift in the AI industry, arguing that value is moving from foundational models to the application and agent layers built on top.
- 03Are world models the unlock for Physical AI? | Episode 19
A deep dive into a specific, complex AI topic ('world models') with founders applying the technology in different physical domains like construction and space robotics.
What you'll be asked on this show
As a roundtable facilitator, Calacanis sets the agenda with a topical news hook, like a major acquisition or a cultural controversy around AI. He then poses strategic questions to the panel, often pitting one guest's approach against another's or against a major platform like Apple or Google. He frequently uses analogies to simplify complex topics and challenges guest assumptions with direct, sometimes provocative questions about their business model, data policies, or competitive vulnerabilities. He also shares his own war stories from his career as an investor and founder to elicit similar candor from his guests.
The primary format is a roundtable discussion with Jason Calacanis and multiple expert guests, sometimes facilitated by a moderator. Calacanis actively participates with his own opinions, anecdotes, and direct questions. Shorter, solo-hosted episodes occasionally feature hands-on demos of new AI products and workflows.
Questions Jason Calacanis keeps coming back to
12 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when Jason Calacanis reaches for it.
controversy
2- Q.01
“What's your take on the current [controversy/backlash] surrounding AI?”
Often used as an opener to frame the conversation around a timely, culturally relevant event.
- Q.02
“Are you sure [major company] isn't training on customer data?”
A provocative question used to challenge common assumptions about Big Tech data policies.
business
1- Q.01
“How do you plan to compete with or beat [major competitor/platform like Apple, Google, or Siri]?”
He asks this to force guests to articulate their strategic moat against incumbent giants.
product
1- Q.01
“Can you give us the current pitch for your product?”
A standard question to get an up-to-date description of the guest's company and its market position.
future
2- Q.01
“Who do you predict will win the [specific AI category, e.g., 'agent race']?”
This question is used to elicit forward-looking predictions and analysis of market leaders.
- Q.02
“When will AI be capable of [specific high-stakes task, e.g., representing someone in court]?”
This seeks a concrete timeline for significant AI milestones and capabilities.
strategy
1- Q.01
“What's the thinking behind a 'build vs. buy' decision for [specific technology]?”
Probes the strategic rationale behind major corporate M&A or R&D decisions.
money
1- Q.01
“What are the economics of your business, like token costs or pricing models?”
Calacanis frequently digs into the unit economics and financial viability of AI business models.
industry
1- Q.01
“What's the capability gap between open-source and frontier models, and when will it close?”
A recurring question to gauge the competitive dynamics between open and closed AI ecosystems.
advice
1- Q.01
“How would you build a disruptive, AI-first version of [established product like Slack]?”
He poses this as a thought experiment to brainstorm new startup ideas and attack vectors.
personal
2- Q.01
“Do you have any wild stories from the venture capital world?”
Asked near the end of an episode to elicit entertaining, behind-the-scenes anecdotes from guests.
- Q.02
“When does Fable come back?”
A recurring, lighthearted closing question that serves as an inside joke for regular listeners.
Signature segments
- · Roundtable Format
- · AI Slop Roundup
- · Weekly AI Demos
- · Asking about the video game 'Fable'
Topics covered repeatedly
Who gets booked here
The show books founders and CEOs of venture-backed AI startups, often from companies that are building agentic AI, foundational models, or developer tools. Guests are typically 'in the trenches' and willing to speak candidly about their strategy, fundraising, and the competitive landscape.
- Boris Sofmanon Are world models the unlock for Physical AI? | Episode 19
- Jeff Hawkon Are world models the unlock for Physical AI? | Episode 19
- Ethan Barajason Are world models the unlock for Physical AI? | Episode 19
- Ali Ansarion Why AI Models Aren’t the Product Any More | TWiAI Ep 18
- Ryan Danielson Why AI Models Aren’t the Product Any More | TWiAI Ep 18
- Steven Berlin Johnsonon Hermes Agent, NotebookLM & LiveKit Founders on the AI Agent Race | TWiAI 17
- Jeffrey Quesnelleon Hermes Agent, NotebookLM & LiveKit Founders on the AI Agent Race | TWiAI 17
Where to find this show
Audience & reach
The primary sponsor is PayPal Open. The angle is to reach an influential audience of technology founders, executives, and investors who are making decisions about financial infrastructure for their companies.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
Pitch Jason Calacanis
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People also ask
- Who is the host of This Week in AI?
- The host is Jason Calacanis, a technology entrepreneur, angel investor, and host of the 'All-In' and 'This Week in Startups' podcasts.
- What is the format of the show?
- Most episodes are a roundtable discussion where Jason Calacanis and 2-3 expert guests (typically founders or CEOs) debate the latest news and trends in the AI industry. Some shorter episodes are solo demos of new AI tools.
- Is This Week in AI still producing new episodes?
- Yes, the podcast is active and releases episodes on a weekly basis.
- Who is the target audience for this podcast?
- The show is aimed at an 'experts-only' audience of tech industry professionals, including founders, investors, and executives who are already familiar with the AI space.
- Where can I listen to the podcast?
- The podcast is available on major platforms like YouTube and Apple Podcasts.
- How can I pitch a guest for the show?
- The podcast's description does not provide a public method for pitching guests; they typically book CEO-level experts and founders from venture-backed AI companies.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
- [01]Jason Calacanis - Wikipediaen.wikipedia.org
- [02]This Week in AI - YouTubeyoutube.com
- [03]Jason Calacanis Biography | All-In Podcastallinpodcast.co
- [04]LAUNCH | We Back Builderslaunch.co
- [05]Jason Calacanis Biography | Booking Infoallamericanspeakers.com
- [06]This Week in AI - Apple Podcastspodcasts.apple.com
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