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PODCAST

This Week in Startups

Jason Calacanis

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.

technology

All Episodes

01:27:24

The Grammarly–Superhuman Megadeal, plus TWiST 500...

This Week in Startups ·

2025/07/01

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 why this deal is the key to building the ultimate communication assistant. Don’t miss this deep dive into

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01:04:08

Rebuilding Civilization from First Principles: Inside...

This Week in Startups ·

2025/06/30

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 nomads to aspiring founders, people are opting into these new systems as an alternative to broken

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01:07:45

Travis’ Uber Comeback, AGI’s Stakes, Meta’s $100M AI...

This Week in Startups ·

2025/06/27

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 future of food delivery. Plus, Tesla’s cautious safety driver rollout shows we’re only in the early

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00:19:51

Multi-Agent AI, Open Protocols & Startup Acceleration...

This Week in Startups ·

2025/06/26

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 agentsAgent-to-Agent (A2A) Protocol, now part of the Linux FoundationThe emerging Multi-Agent Collaboration

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01:08:51

VC Roundtable: Recruiting Secrets, Second-Time...

This Week in Startups ·

2025/06/26

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, the myth of early ARR, the art of founder-board trust, and how AI is (and isn’t) reshaping startup

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01:11:25

AI Producers, Tesla Robotaxis & the Rise of the “Tiny...

This Week in Startups ·

2025/06/24

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. Buckle up.Timestamps:(02:11) Introducing… PRODUCER CLAUDE!(04:21) Tesla’s Robotaxis are out and about! But

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01:15:25

The Strip Mining Era of LLMs—And Why It’s About to...

This Week in Startups ·

2025/06/21

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 implications—including Substack’s stance, Cloudflare’s firewall, and Perplexity’s lawsuits—in what may be a

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01:11:41

From Drones to Dystopia: The Future of Jobs, Fires &...

This Week in Startups ·

2025/06/18

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 think twice before building in public.Timestamps:(1:52) Travel chaos, laundry issues, and the Airbnb

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01:09:25

Meta, Scale, and the Future of AI Labeling: Did Zuck...

This Week in Startups ·

2025/06/17

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 vertical integration or anti-competitive overreach? Jason shares tactical advice for founders on how to

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01:03:53

Stripe’s Crypto Wallet, M&A Momentum, and Robots...

This Week in Startups ·

2025/06/13

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 stablecoins are quietly transforming fintech, and why Disney is going to war with AI platforms over IP theft. A

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01:11:22

TWIST VC Roundtable: Startup Valuations, Secondary...

This Week in Startups ·

2025/06/12

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 startups are distorting valuations. Jason shares his year-zero investment thesis and offers tactical

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01:03:55

YC Valuations, VC Slowdown, and Office Hours with...

This Week in Startups ·

2025/06/10

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 follow-ups using CRM context. It’s a deep look at early-stage investing, startup efficiency, and where

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00:46:03

Circle’s IPO Soars, The Future of VC and Cursor’s...

This Week in Startups ·

2025/06/07

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(2:25) Circle’s IPO is Soaring and What This Means for Tech(10:21) LinkedIn Jobs - Post your first job for

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01:09:55

Anthropic Cuts Off Windsurf, Deel Rewrites the...

This Week in Startups ·

2025/06/04

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 cameras and drones—positions itself as a privacy-conscious tool that gives elected officials control

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01:04:10

Grammarly’s $1B Round, Brain Computers, and NYT...

This Week in Startups ·

2025/06/02

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 Amazon, suggesting that traditional media may be starting to find common ground with large language

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00:59:13

How AthenaHQ and Browser Use Are Building the Next...

This Week in Startups ·

2025/05/30

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, how brands and developers can stay competitive, and why adaptability and technical precision are key in

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00:58:02

Google’s AI Design Tool, Salesforce’s $8B Comeback...

This Week in Startups ·

2025/05/28

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 startup M&A activity, with billion-dollar deals from OpenAI, DoorDash, and others—hinting at a

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01:04:52

Apple’s Tariff Trouble, Anthropic’s New Models, and...

This Week in Startups ·

2025/05/23

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, and which startup—an AI ad network or industrial automation platform—comes out on top. A fast-paced look

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00:41:23

David Friedberg on AI-First Startups & the Future of...

This Week in Startups ·

2025/05/22

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 future of creativity in an AI-driven world.*Timestamps:(0:00) David Friedberg joins Jason to

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01:05:17

Jony Ive Joins OpenAI, Waymo Hits 10M Rides, and How...

This Week in Startups ·

2025/05/21

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 ethics of AI-powered smart glasses and always-on recording. Plus, Jason reflects on the legacy of

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1,266 results

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