Podcast · 653 episodes
This Week in Startups
by Jason Calacanis · English
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.
Latest episodes
Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344Flashback episode of This Week in Startups (E2344) revisiting Justin Kan’s path from Justin.tv to Twitch and Airbnb cofounder Brian Chesky’s early rejections, plus broader discussion on startup…30 Sep 2026 · 1 h 18 min
Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338Jason runs a $5,000 bounty contest for building a Chrome extension for Annotated.com: users can highlight text or media on the web, attach a comment/dispute, and publish a permalink-style “annotation…28 Sep 2026 · 41 min
The 5 Companies Apple Must BuyThe episode is a “fantasy draft” discussion of which companies Apple should acquire, framed around Apple’s tendency to do small “tuck-in” tech buys but the hosts arguing Apple should make bigger…28 Sep 2026 · 50 min
All episodes
Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344Flashback episode of This Week in Startups (E2344) revisiting Justin Kan’s path from Justin.tv to Twitch and Airbnb cofounder Brian Chesky’s early rejections, plus broader discussion on startup…30 Sep 2026 · 1 h 18 min · 30 chapters
Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338Jason runs a $5,000 bounty contest for building a Chrome extension for Annotated.com: users can highlight text or media on the web, attach a comment/dispute, and publish a permalink-style “annotation…28 Sep 2026 · 41 min · 12 chapters
The 5 Companies Apple Must BuyThe episode is a “fantasy draft” discussion of which companies Apple should acquire, framed around Apple’s tendency to do small “tuck-in” tech buys but the hosts arguing Apple should make bigger…28 Sep 2026 · 50 min · 21 chapters
A rogue OpenAI agent hacked Australia’s government. Does this matter? | E2342The episode discusses an OpenAI “agent” breach of Australia’s Medicare statistics portal, arguing about whether it’s a meaningful security failure or mostly a terms-of-service/controls issue.25 Sep 2026 · 1 h 26 min · 37 chapters
VCs Would Bet on Open-Source AI Over OpenAI and Anthropic | E2341A This Week in VC panel debates AI risk and regulation (liability shields, monitoring, “AI agents” misfires), whether open-source AI will outperform closed frontier models, and how extreme…23 Sep 2026 · 1 h 27 min · 34 chapters
Bill Gates foresees massive AI job loss: these VCs disagree | E2330Bill Gates’ 6,000-word essay “The Turbulent AI Era Is Here” and whether AI will cause massive job loss; how to coordinate society (taxes, job “reservation,” retraining/UBI vs other models); and a…26 Aug 2026 · 1 h 31 min · 34 chapters
You Can't Fire a VC From Your Board: Here's Why | Wilson Sonsini Startup Legal BasicsVenture-backed startup board governance—when to add a board, what board seats vs observer roles mean, how independents are chosen/compensated, and why removing a VC director is hard.25 Aug 2026 · 25 min · 11 chapters
China wants you to cheer for the robots taking your job | E2329The episode discusses China’s World Robot Conference and World Humanoid Robot Games in Beijing, arguing the events are designed to make audiences cheer for robots (rather than fear job loss).25 Aug 2026 · 1 h 20 min · 30 chapters
Open source is going to win it all: Harvey proves it | E2328The episode argues that open-source AI will “win it all” in enterprise because companies won’t want to give their sensitive training data to frontier model providers, especially as those providers…21 Aug 2026 · 1 h 9 min · 22 chapters
Taste is the new programming language (w/ Astrocade CEO Amir Sadeghian) | AI BasicsHow Astrocade uses generative AI to let anyone create and publish interactive games via natural-language prompts, with “taste” as the remaining key barrier.20 Aug 2026 · 21 min · 10 chapters
Neurosymbolic AI outperforms chatbots and product search | E2327Onton’s neurosymbolic AI “vibe” search for e-commerce (with explainable, non-hallucinating results and real-time learning), plus a related discussion of in-space refueling (Spacium) and why it…19 Aug 2026 · 54 min · 26 chapters
Bittensor creator Const on Affine, dTAO, "mining reasoning," and more | E2326BitTensor’s “mining” model for AI—how it adapts Bitcoin-style permissionless proof-of-work to create decentralized networks (“subnets”) that compete on measurable AI services (training, inference,…17 Aug 2026 · 1 h 25 min · 30 chapters
What we'll learn from Anthropic's $2-$3T IPO | E2325The episode covers (1) rumors and expectations around Anthropic’s planned October IPO with a $2–$3T valuation, (2) Anthropic’s reported $6B acquisition talks for Descartes AI, and (3) a guest…15 Aug 2026 · 1 h 20 min · 34 chapters
These robots could cut delivery costs by 80% | Next UnicornsTwo founders discuss “physical AI for commerce” and automated vision testing.12 Aug 2026 · 1 h 4 min · 23 chapters
Zuck's AI manifesto is a data center PR masterclass | E2323The hosts discuss Mark Zuckerberg’s 6,500-word AI essay “The Future is for Everyone, The Path to a Positive AI Future,” arguing it’s both an AI manifesto and a PR/data-center pitch.11 Aug 2026 · 1 h 20 min · 29 chapters
How AI splits startups into winners and losers | E2322Markets and SaaS “winners vs losers” driven by AI adoption; stock-based compensation (SBC) as a signal; and energy for AI/data centers via floating small modular nuclear reactors.7 Aug 2026 · 1 h 18 min · 31 chapters
Airtable's 80% off value crash: VCs explain why it's still a win | E2321The episode is a VC roundtable focused on the “SaaSpocalypse” and what happens when high-multiple SaaS companies stop growing.5 Aug 2026 · 1 h 13 min · 27 chapters
How Bespoke faked AI until it actually worked (w/ Akemi Tsunagawa) | E2320Akemi Tsunagawa (Bespoke) explains how her company “faked AI” with human-in-the-loop chatbots for Japan tourism support, then expanded into multilingual video-based training for foreign workers, and…3 Aug 2026 · 1 h 2 min · 24 chapters
Why AI has no taste and how to fix it (w/ Thais Castello Branco) | E2319The episode argues that today’s AI systems “have no taste” in subjective domains (design, writing, tweets) because they’re optimized for objective correctness and tend to regress to the mean.31 Jul 2026 · 1 h 15 min · 30 chapters
While other cultivated meat companies are collapsing, this one turned a profit | E2317This Week in Startups in Japan interviews Dr. Yuki Hanyu (Integrity Culture) about why some cultivated-meat firms fail while Integrity Culture became profitable, and what “stunt” and niche products…27 Jul 2026 · 44 min · 17 chapters
Why quantum has been "10 years away" for 30 years | E2316The episode explains why quantum computing has been “10 years away” for decades, focusing on hardware difficulty, qubit error rates, and the path to practical systems.24 Jul 2026 · 45 min · 22 chapters
Why this longevity startup raised in Japan, not Silicon Valley | TWiST Tokyo | E2315Longevity startup Iki Labs’ mission and product, plus founder lessons on building in Japan (Tokyo/Okinawa), raising seed capital, and balancing short-term revenue vs long-term R&D.22 Jul 2026 · 1 h 12 min · 27 chapters
The AI Securing Your Workforce Before a Mistake Ever Becomes a Breach | E2314Int’s on-device “endpoint agent” uses AI embeddings and corporate policy context to detect risky or unsanctioned actions (including human clicks and agent behavior) and stop them in sub-second time,…20 Jul 2026 · 42 min · 12 chapters
The dawn of surgery bots + buy a home for $250 (w/ Andromeda & Mogul) | E2313Episode “The dawn of surgery bots + buy a home for $250” (E2313) covers two themes: (1) Andromeda Surgical’s push toward increasingly autonomous, AI-assisted surgery; (2) Mogul’s “syndicate” model…17 Jul 2026 · 47 min · 18 chapters