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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.
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Episodes

AUTOMATING HEALTH CARE, THERMODYNAMIC COMPUTING, AND PRODUCT VELOCITY | E2155

Today’s show: TWiST is back with a three more hugely insightful (and also fun!) founder interviews. First up, Trey Holterman from Tennr tells us why getting in to see a specialist is so time consuming, and how AI is making the entire health care industry more streamlined.THEN Gill Verdon from Extropic AI unpacks deterministic vs. probabilistic computing, and how thermodynamics can make everything from robots to VR more effective.FINALLY, Tyler Denk from our fav newsletter platform Beehiiv walks ...

Jul 23, 20251 hr 21 min

Manufacturing in the US, Building in Open Source… and more | E2154

Today’s show: TWiST is back with a trio of can’t miss interviews with some of our favorite TWiST 500 founders. First up, John Harris of Harbinger Motors tells us about making his EV batteries right here in the USA, and why the loss of EV tax credits might not hurt the business as much as you’d think… THEN, we’re talking to James Hawkins of PostHog about how keeping his burn rate low opened up a wealth of new opportunities for his company… THEN Yoshi Yokokawa from Alpaca HQ stops by to talk about...

Jul 21, 20251 hr 23 min

Inside Substack’s $100M Push to Fend Off Beehiiv | E2153

Today’s show: WHY DOES @SUBSTACKINC NEED $100M IN NEW FUNDING?HOW DO THEY PLAN TO STAY AHEAD OF @BEEHIIV?Jason and Alex are debating the future of indie publishing on an all-new TWiST, considering the future of these rival platforms, plus Patreon and more.PLUS they’re digging into Lovable’s latest raise and what it says about the current economics of vibecoding, surveying the automated driving landscape in light of Uber’s new agreement Lucid and Euro, explaining Jason’s “meme processing” theory ...

Jul 18, 20251 hr 13 min

Thinking Machines’ RECORD seed round, VC Geoff Lewis, and MORE | E2152

Today’s show: Jason and Alex tackle a full tech and business news docket on today’s show, including Jason’s big SF trip with Launch Accelerator’s 34th cohort, some peculiar social media posts from VC Geoff Lewis, a look inside the HUGE seed rounds being commanded by early-stage AI startups, crunching the numbers on how much compute data centers need to sell before they’re profitable, Polymarket asks who will be the next CEO of X and MUCH MUCH MORE. Join us for the longest-running and most in-dep...

Jul 17, 20251 hr 8 min

Blitzhiring and the Complicated Case of Windsurf, OpenAI and Google | E2151

Today’s show: On today’s show… Jason and Alex are considering the fallout of Windsurf’s OpenAI deal, the company’s latest agreements with both Google and Cognition AI, and how “blitzhiring” is actually playing out in real-world startups.Plus Jason’s short- and medium-term predictions for AI’s impact on the job market, Tesla’s latest expansion of its Austin robotaxi service, Mistral giving the EU a real stake in the AI model race, a look back at the SnapStream live TV archiving service, AND an up...

Jul 14, 20251 hr 1 min

Grok 4 Beats OpenAI + The $300 AI Agent Era | E2150

Today’s show: Grok 4 just leapfrogged OpenAI to become the top AI model—and it’s not just hype. In this episode, @Jason and @alex break down Grok’s AGI-level performance, the massive drop in LLM pricing, and why some companies are raising prices anyway. They also dive into the Missouri AG’s investigation into AI “bias,” the future of First Amendment protections for LLMs, and how autonomous vehicles are creating a new category: “autonomous commerce.” If you’re building with AI or betting on the f...

Jul 12, 20251 hr 11 min

Orchestrating Smarter AI Systems with AI21 Labs’ Yoav Shoham | AI Basics with Google Cloud

In this episode of AI Basics , Jason sits down with Yoav Shoham — Stanford professor emeritus and co-founder of AI21 Labs , creators of Jurassic-2, Wordtune, and the new orchestration system Maestro . They unpack: Why enterprise AI struggles with reliability What orchestration really means (and why LLMs alone aren't enough) The pitfalls of “agent-washing” Small vs large models, agent-to-agent protocols, and where real opportunities lie This one is for founders building with AI — if you're naviga...

Jul 10, 202522 min

Starlink + Tesla? $4T Nvidia? Perplexity Browser? Linda Yaccarino Steps Down? | E2149

On a brand new TWiST, Jason and Alex ponder… What if every Tesla doubled as a Starlink-powered Wi-Fi hotspot? Plus, Nvidia’s historic $4T valuation, Perplexity’s fancy new AI browser that literally books flights, Linda Yaccarino steps down as X CEO, Waymo launches teen accounts, and maybe recording everything all the time has some disadvantages? Later, Tim Ranzetta joins to explain how his nonprofit is making personal finance mandatory in high schools. A must-watch for founders, investors, and a...

Jul 09, 20251 hr 6 min

Cloud Seeding, Conspiracies & the Texas Floods | BONUS EPISODE!

Today’s show: Cloud seeding startup Rainmaker faced a viral backlash after deadly floods in Texas—so @Jason hosted an emergency X Spaces with founder Augustus Doricko to unpack what really happened. Did Rainmaker cause the floods? How much water can cloud seeding actually produce? Is it safe, and should we even be doing it? They dive into the science, conspiracy theories, regulation, and how cloud seeding compares to desalination as a tool to fight drought and preserve ecosystems. A fascinating,...

Jul 09, 202526 min

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

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 for anyone building, investing, or navigating tech in 2025. Timestamps: (04:29) Jason’s thoughts on E...

Jul 07, 20251 hr 7 min

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

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 private capital. In healthcare, AI-powered virtual doctors promise to bring world-class medical advice to...

Jul 02, 20251 hr 17 min

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

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 ...

Jul 01, 20251 hr 27 min

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

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 tradit...

Jun 30, 20251 hr 4 min

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
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