This Week in Startups - podcast cover

This Week in Startups

Jason Calacanisthisweekinstartups.com
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.

Episodes

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

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...

Jun 27, 20251 hr 8 min

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

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 Agent-to-Agent (A2A) Protocol , now part of the Linux Foundation The emerging Multi-Agent Colla...

Jun 26, 202520 min

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

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 ...

Jun 26, 20251 hr 9 min

AI Producers, Tesla Robotaxis & the Rise of the “Tiny Teams” Era | E2142

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 a...

Jun 24, 20251 hr 11 min

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

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 t...

Jun 21, 20251 hr 15 min

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

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 ...

Jun 18, 20251 hr 12 min

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

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 ...

Jun 17, 20251 hr 9 min

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

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 the...

Jun 13, 20251 hr 4 min

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

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 ...

Jun 12, 20251 hr 11 minEp. 2137

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

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 wh...

Jun 10, 20251 hr 4 minEp. 2136

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

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 j...

Jun 07, 202546 minEp. 2135

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

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 contro...

Jun 04, 20251 hr 10 minEp. 2134

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

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 model...

Jun 02, 20251 hr 4 minEp. 2133

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

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 ...

May 30, 202559 minEp. 2132

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

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 a...

May 28, 202558 min

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

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 l...

May 23, 20251 hr 5 minEp. 21320

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

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 discuss A...

May 22, 202541 min

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

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 S...

May 21, 20251 hr 5 minEp. 2129

Drones, Design, and Digital Espionage | E2128

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 how world-class design and systems thinking can set startups apart. Packed with insights, laughs, a...

May 20, 20251 hr 4 minEp. 2128

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

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 Hours with airfive founder Jeremy Redman pitches a bold new prepaid SaaS model. Timestamps: (0:00) E...

May 16, 20251 hr 4 minEp. 2127

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

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 navigating the intense media landscape. Timestamps: (0:00) Episode Teaser(1:14) Jason and Alex open the show...

May 15, 20251 hr 7 minEp. 2126

Agentic AI Meets Cybersecurity + Solar Robots in the Desert | E2125

Today’s show: Alex interviews founders from two frontier technologies reshaping our world. First, ZioSec is tackling the cybersecurity risks of AI agents with continuous adversarial testing before real attacks happen. Then, Terabase shows how mobile robotic factories are transforming solar energy deployment, assembling massive solar farms directly in the desert. With AI scaling across enterprises and clean energy demand surging, these startups are building critical infrastructure for our future....

May 13, 202552 minEp. 2125

Anti-Work Uprising, Copyright Wars & the StreamFog Solution | E2124

Today’s show: Jason, Lon & Alex are back with a spicy Monday episode of This Week in Startups. Jason goes off on unions vs capitalism, we dig into why fewer seed startups are making it to Series A, and look at OpenAI’s quiet copyright land grab. Plus: YC says Google should be broken up (then kind of walks it back), Perplexity’s wild $14B valuation, and Saudi Arabia wants its own national AI. We wrap with an Office Hours chat with Kevin Bondzio from Streamfog on the future of AR ads in livest...

May 13, 20251 hr 31 min

OpenAI Scoops Instacart’s CEO, AI in the Courtroom & Off-Road Startups | E2123

Today’s show: Jason, Alex, and Lon break down OpenAI’s latest power move: hiring Instacart CEO Fidji Simo to lead its consumer apps. They also dive into the ethical storm brewing around an AI-generated victim statement used in court — is this the future of legal testimony? Plus, they explore how late-stage funding rounds like a “Series G” don’t automatically spell trouble anymore, and what The Checklist Manifesto can teach startup founders. Stick around for another Office Hours, where WhereToWhe...

May 10, 20251 hr 13 min

Zoox Crash Fallout, COATUE’s $1B Open Fund, and Office Hours with FusionAds | E2122

Today’s show: Jason, Lon & Alex discuss the day’s hottest tech and startup news. Zoox’s robotaxi crash and voluntary recall, COATUE’s innovative open-ended venture fund that could democratize private tech investing, the NSO Group's massive $167M fine for spyware abuse, Uber’s record-setting earnings and in-person work push, and a candid AI wake-up call from Fiverr’s CEO urging employees to embrace automation or fall behind. From regulatory shakeups to funding innovation and the rise of AI pr...

May 08, 20251 hr 7 minEp. 2122

Cursor’s $9B Round, AI-Powered Toys & CloudNuro’s SaaS Fix | E2121

Today’s show: Cursor’s explosive growth, hitting $200M in ARR and a massive $9B valuation. They also explore the buzz around Magical Toys’ new AI-powered dinosaur, where LLMs meet playtime. The conversation turns to “vibe coding” and how AI dev tools are changing the way product teams build. Plus, Jason shares stories from his Formula 1 poker table, Uber’s latest autonomous vehicle partnerships get analyzed, and we bring you highlights from our Founder Fridays pitch showdown, featuring Kippy fro...

May 06, 20251 hr 26 min

Apple’s App Store Loss, AI Persuasion, and an Interview with Tyler Denk of Beehiiv | E2120

Today’s show: Jason, Lon, and Alex break down a loaded week in tech: Apple’s 27% App Store “link-out” fee gets shut down by a judge—unlocking margin for startups and slashing CAC; AI bots on Reddit’s r/ChangeMyView are now 6x more effective than humans at changing minds, signaling a seismic shift in online discourse; and Beehiiv CEO Tyler Denk joins to discuss building in public, rapid product iteration, and the irony of being critiqued like a market leader for innovating too fast. The big takea...

May 02, 20251 hr 15 minEp. 2120

What's Next for AI Infrastructure with Amin Vahdat | AI Basics with Google Cloud

In this episode of AI Basics , Jason sits down with Amin Vahdat, VP of ML at Google Cloud, to unpack the mind-blowing infrastructure behind modern AI. They dive into how Google’s TPUs power massive queries, why 2025 is the “Year of Inference,” and how startups can now build what once felt impossible. From real-time agents to exponential speed gains, this is a look inside the AI engine that’s rewriting the future. * Timestamps: (0:00) Jason introduces today’s guest Amin Vahdat (3:18) Data movemen...

May 01, 202528 min

Bittensor’s Rise, Meta’s Llama Goes Cloud, & AI Now Writes Your Code | E2119

Today’s show: Jason, Alex, Lon and Special Guest Mark Jeffrey of Hash Rate, cover the explosive rise of Bittensor, a decentralized AI compute network some are calling the “third great coin” after Bitcoin and Ethereum, explore Meta’s bold move to host its open-source LLaMA models via partnerships with Groq and Cerebras—potentially setting the stage for a future AWS competitor—and unpack shocking revelations from the Wall Street Journal about Meta AI chatbots engaging in inappropriate conversation...

May 01, 20251 hr 5 minEp. 2119

Meta’s Dangerous Chat, Protect AI & Founder Fridays Pitch Comp | E2118

Today’s show: we break down the wild story behind Meta’s AI chatbots going completely off the rails — including a bombshell WSJ exposé about bots flirting with minors. Then they cover Palo Alto Networks’ huge $500M+ acquisition of Protect AI, and sit down with the founder of Formulate, who’s building a robotic kitchen for chemicals and cosmetics. Plus, we get into some spicy takes on the secret group chats shaping tech behind the scenes, whether AI can clean up bad code faster than humans, and a...

Apr 29, 20251 hr 27 min
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