Jason Calacanis

This Week in Startups

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.

Author

Jason Calacanis

Category

Technology

Podcast website

thisweekinstartups.com

Latest episode

Jul 10, 2026

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Episodes

Exits Are Back, QSB Stock & The New America Party? | E2148 07.07.2025

Today's show: Startup exits are heating up with $67.7B in Q2 activity, QSBS just got a major expansion, and Robinhood is pushing boundaries with tokenized SPVs. In this episode, @Jason and @alex break down what it all means for founders and investors, plus the rise of Elon's "America Party," TikTok's potential reboot, and why SaaS startups must rebrand around AI to stay competitive. A must-watch f...

Startup Valuations, Biotech's Crunch & AI's Massive TAM | E2147 02.07.2025

Today's show: It's another blockbuster panel of insiders, as Alex sits down with Astasia Myers from Felicis, Matt Turck from First Mark Capital, and D.A. Wallach of Time BioVentures. AI is reshaping early-stage investing, with startups raising record-setting rounds adn chasing $100B+ markets. Meanwhile, biotech faces a "Great Depression" as public markets stay shut, putting added pressure on priva...

The Grammarly–Superhuman Megadeal, plus TWiST 500 chats with LabelBox and Apptronik's founders | E2146 01.07.2025

Today's show: Grammarly is acquiring the beloved email app Superhuman! In today's extremely timely episode, @alex sits down with Grammarly CEO Shishir Mehrotra and Superhuman founder Rahul Vohra to unpack why they're merging, how they plan to combine apps and AI agents, and what it means for the future of email and work. PLUS they reveal how Grammarly's 40M+ daily users already rely on email—and w...

Rebuilding Civilization from First Principles: Inside Balaji's Network State Vision | E2145 30.06.2025

Today's show: Jason sits down with Balaji Srinivasan in Singapore to explore how he's turning years of theory into reality with Network School—the first node of a broader vision for internet-native, decentralized societies. Balaji explains how these "sharp societies" combine education, co-living, and startup culture to create physical communities aligned by values, not geography. From digital noma...

Travis' Uber Comeback, AGI's Stakes, Meta's $100M AI Hires & Prediction Market Gold Rush | E2144 27.06.2025

Today's show: EVs are igniting a global tariff war, and Xiaomi's shockingly cheap, high-quality electric cars threaten to obliterate Western automakers, sparking fears of a manufacturing wipeout. In today's brand-new TWiST, Jason and Alex dive into the EV price war, Uber's rumored plan to team up with Travis Kalanick on a self-driving takeover, and DoorDash's mega-drones giving us a glimpse of the...

Multi-Agent AI, Open Protocols & Startup Acceleration with Saurabh Tiwary | AI Basics 26.06.2025

In this episode, Jason dives deep into the future of multi-agent systems with Saurabh Tiwary , VP & GM of Cloud AI at Google. They explore how teams of AI agents —not just single models—can collaborate to solve complex problems, helping startups scale faster with fewer resources. Saurabh introduces Google Cloud's open frameworks: Agent Development Kit (ADK) for building flexible, debuggable agents...

VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143 26.06.2025

Today's show: In this powerhouse VC roundtable, @Jason sits down with Sequoia's Doug Leone and Cyberstarts' Gili Raanan to share brutally honest insights on startup recruiting, evaluating second-time founders, and how to truly find product-market fit. They break down why big-tech résumés can be misleading, how to structure early teams, and what separates "missionary" talent from mercenaries. Plus,...

AI Producers, Tesla Robotaxis & the Rise of the "Tiny Teams" Era | E2142 24.06.2025

Today's show: Tesla's robotaxi launch, AI producers, job destruction, and smart toilets? In this episode of This Week in Startups , @Jason and @alex break down Tesla's cautious rollout strategy, how AI is quietly replacing producers and employees, why second-movers like Tesla and Ramp often win, and how Throne Science is turning gut health into a billion-dollar market—with cameras in your toilet....

The Strip Mining Era of LLMs—And Why It's About to End | E2141 21.06.2025

Today's show: AI has been feasting on the open web—but is the free lunch over? In this explosive episode, @Jason and @alex call out OpenAI and others for "strip mining" the internet's content without paying creators. As lawsuits pile up and new defenses like AI-robots.txt emerge, a reckoning looms. Will AI be forced to pay for its training data? Dive into the legal, ethical, and business implicati...

From Drones to Dystopia: The Future of Jobs, Fires & Meta's AI Land Grab | E2140 18.06.2025

Today's show: In this episode, @Jason and @alex explore how AI is reshaping the economy—from Pano AI's $44M raise to fight wildfires with drones, to Amazon CEO Andy Jassy's memo foreshadowing white-collar job cuts, to Meta's stealth move poaching Scale AI talent. They dig into the collapse of early-career roles, the slow disappearance of the gig economy safety net, and why founders may want to thi...

Meta, Scale, and the Future of AI Labeling: Did Zuck Just Kill a Category? | E2139 17.06.2025

Today's show: Meta just took a 49% stake in Scale AI, and the shockwaves are hitting the entire AI ecosystem. In this episode, @Jason and @alex unpack the deal's implications: Google ($150M customer!) and others are fleeing Scale, worried Meta will hoard its RLHF infrastructure and cut off competitors. Startups like Labelbox, Turing, and Handshake are already seeing a demand surge. Is this smart v...

Stripe's Crypto Wallet, M&A Momentum, and Robots Replacing Soul-Crushing Jobs | E2138 13.06.2025

Today's show: In this episode of This Week in Startups, @Jason and @Alex break down Stripe's big bet on crypto wallets with its latest acquisition of Privy, the return of major M&A activity from Meta, DoorDash, and Stripe, and the rapid rise of robotics replacing soul-crushing warehouse jobs. They dive into why today's toy-like robot arms will become tomorrow's billion-dollar tools, how stablecoin...

TWIST VC Roundtable: Startup Valuations, Secondary Markets & the YC Revenue Illusion | E2137 12.06.2025

Today's show: Alex moderates a TWIST VC Roundtable with Jason, Paige Doherty (Behind Genius), and Altimeter's Megan Reynolds about the state of early-stage venture capital. They break down the rise of secondary markets as a key liquidity path for VCs, analyze the resurgence in M&A activity from major players like Meta, Databricks, and OpenAI, and question whether inflated ARR figures from YC start...

YC Valuations, VC Slowdown, and Office Hours with CustomerIQ | E2136 10.06.2025

Today's show: Jason and Alex dive into why Y Combinator startups are raising at sky-high valuations with relatively low ARR—what does that mean for investors and founders? VC funds are slowing down and returning to pre-ZIRP pacing, signaling a reset in the market. Plus, in this week's Office Hours, Sean Steigerwald, founder of CustomerIQ, demos his AI sales agent that lives in your inbox, drafting...

Circle's IPO Soars, The Future of VC and Cursor's Crazy Growth | E2135 07.06.2025

Today's show: Jason and Alex dicuss stories shaping the tech and startup world: Circle's explosive IPO and what it signals about crypto regulation and public market sentiment, the potential for tokenized venture capital funds to bring liquidity and transparency to startup investing, and Cursor's extraordinary growth—scaling to over $500M in ARR in just six months. Timestamps: (0:00) Episode Teaser...

Anthropic Cuts Off Windsurf, Deel Rewrites the Narrative and Flock Safety's Surveillance Tech | E2134 04.06.2025

Today's show: Alex and Lon discuss Windsurf getting abruptly cut off from Anthropic just before a rumored $3B acquisition by OpenAI, sparking questions around platform risk and foundation-model politics; Deel defends itself by arguing the information it allegedly took was public or obvious, complicating its ongoing legal saga; and Flock Safety's neighborhood-focused surveillance tech—combining LPR...

Grammarly's $1B Round, Brain Computers, and NYT Licenses To Amazon | E2133 02.06.2025

Today's show: Jason and Alex discuss the hottest tech and startup news: Grammarly secures a massive $1B investment from General Catalyst to fuel its AI ambitions and expand into deeper enterprise offerings; a DARPA-backed brain-computer interface startup emerges as a serious Neuralink rival, signaling renewed momentum in the neurotech space; and The New York Times signs a licensing deal with Amazo...

How AthenaHQ and Browser Use Are Building the Next Layer of the Internet | E2132 30.05.2025

Today's show: Alex interviews two cutting-edge startups shaping the future of AI: AthenaHQ, pioneering "GEO" (Generative Engine Optimization) to help brands rank in AI-powered search engines like ChatGPT and Gemini, and Browser Use, building infrastructure that lets AI agents take real actions on the web—from form-filling to workflow automation. Both teams dive deep into how fast AI is evolving, h...

Google's AI Design Tool, Salesforce's $8B Comeback Deal, and M&A Momentum Builds | E2131 28.05.2025

In this episode, we cover three major stories shaping the startup and tech landscape. First, Google unveils Stitch , an AI-powered web design tool with one-click export to Figma—signaling a major disruption for freelance design marketplaces. Then, Salesforce returns to M&A with its $8B acquisition of Informatica , aiming to broaden its AI data stack beyond CRM. Finally, we break down the surge in...

Apple's Tariff Trouble, Anthropic's New Models, and Our Founder Friday Finale | E2130 23.05.2025

Today's show: Trump takes aim at Apple with a potential 25% iPhone tariff, Anthropic releases two powerful new Claude models claiming top performance in coding tasks, and two founders go head-to-head in the final round of Founder Fridays. In this packed episode, Jason, Alex, and Lon unpack what Trump's latest trade threat really means, why Anthropic's AI progress could reshape the dev landscape, a...

David Friedberg on AI-First Startups & the Future of Biology, Business & Creativity | AI Basics with Google Cloud 22.05.2025

In this episode, Jason chats with David Friedberg—CEO of Ohalo Genetics and co-host of the All-In Podcast—about how AI is transforming agriculture and startups. David introduces Ohalo's "Boosted Breeding" technology, which enables plants to inherit 100% of genes from both parents, potentially doubling crop yields. They also discuss building AI-first companies, genome language models, and the futur...

Jony Ive Joins OpenAI, Waymo Hits 10M Rides, and How to Launch a Marketplace from Scratch | E2129 21.05.2025

Today's show: Jason and Alex dicsuss Jony Ive's $6.5B deal with OpenAI and what it means for the future of AI hardware, Tesla's push into robotaxis vs. Waymo's 10M paid rides, and Microsoft's latest move partnering with xAI. We dive into the GENIUS Act and what it means for stablecoin regulation, explore practical, gritty tactics for launching and scaling a marketplace from scratch, and debate the...

Drones, Design, and Digital Espionage | E2128 20.05.2025

Today's show: Jason and Lon explore the wild edges of tech innovation and regulation — from a student-built acoustic weapon that takes down drones (without harming humans) to the legal gray areas of drone defense over private property. They also unpack the escalating espionage drama between Rippling and Deel, and dive into FireCrawl's viral move to hire AI agents as employees. Plus, a deep look at...

Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 16.05.2025

Today's show: Microsoft lays off 6,000 employees despite record profits, signaling a ruthless new phase in big tech. Jason, Lon, and Alex discuss what it means for the talent market, why tightening U.S. immigration could cripple startup innovation, and whether AI startup Windsurf is selling too early as OpenAI circles. Plus, Klarna's AI customer service backfires, IPO momentum returns, and Office...

Chime's IPO, Databricks' $1B Acquisition & Dave Rubin's Media Empire | E2126 15.05.2025

Today's show: Chime is finally going public with strong financials and a shot at matching its $25B 2021 valuation, signaling real momentum in the IPO market. Databricks just made a $1B bet on agentic AI by acquiring Neon, a Postgres-as-a-service startup riding the new database wave. Then, Dave Rubin joins to share how he built and sold Locals, his uncancellable creator platform, all while navigati...

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