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

In this episode of This Week in Startups, Jason Calacanis and Alex Wilhelm delve into the effects of tariff wars on car manufacturers and startups. They explore Travis Kalanick's potential return to Uber and discuss advancements in drone delivery with companies like DoorDash and Zipline. The conversation shifts to industry consolidation in the self-driving and food delivery sectors, followed by an overview of prediction markets with Kalshi and Polymarket. They examine investor roles in prediction markets, OpenAI-Microsoft dynamics, and strategies for startups inspired by major partnerships. The episode concludes with Meta's AI team expansion, talent acquisition, and the challenges of moving from academia to startups.

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

In this episode of This Week in Startups, Jason Calacanis hosts Doug Leone and Gili Raanan. They explore recruiting strategies, integrating new team members, and Doug Leone's retirement journey. Gili Raanan discusses Wiz and balancing innovation with practical constraints. The conversation covers managing talent, equity splits, AI's impact on startup efficiency, company building speed, overfunding challenges, and venture capital compensation dynamics. The episode wraps up with insights into early-stage investment strategies and success predictors in venture capital.

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

In this episode of This Week in Startups, Jason chats with Alex Wilhelm and Giram Taitana about AI and business. They discuss AI data sourcing, Meta's financial strategies, and Midjourney's video AI advancements. The conversation covers AI scraping's impact on content creators and the regulation debate. Giram shares insights into medical tourism, focusing on design's role in building trust. They also explore Doctours' fundraising and AI's influence on employment, highlighting new job roles and the gig economy. The episode wraps up with Tesla's robo taxi launch and its potential effects on urban transport.

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

In this episode of This Week in Startups, Jason talks with Alex Wilhelm and Rishab Gupta about key tech and business issues. They discuss Andy Jassy's memo on labor, AI's role in workforce evolution, and challenges in job training for white-collar roles. They also examine the stock market's resilience amid changing media trends and strategic communication approaches. The episode explores future firefighting technology, AI's impact on insurance, and TikTok's implications for US-China relations. Rishab introduces Actuality's AI-driven RFP response platform, emphasizing its human-in-the-loop design and potential impact on the construction industry.

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

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 capitalize when incumbents stumble—hire ex-Scale talent, build “Scale AI alternative” SEO pages, and hit the podcast circuit. Don’t miss this deep dive into AI’s shifting power dynamics.

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

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 must-watch if you’re building, investing, or just trying to understand where tech is headed next.

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 advice on secondary structuring and identifying high-quality revenue. Whether you're raising, investing, or building, this episode delivers essential insights into the evolving early-stage landscape.

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 where AI is headed in enterprise.

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.

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 control over community data governance.

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 models.

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

Today’s show: Alex interviews wo 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 the era of intelligent search and autonomous agents.

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

Today’s show: 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 major Q2 rebound. Don’t miss Jason’s insights on what these trends mean for founders and investors.

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

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 at the volatility, breakthroughs, and ambition defining today’s startup ecosystem.

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.

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

Today’s show: Jason and Alex 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 Scott Adams and the power of systems thinking.

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, and cutting-edge ideas across defense tech, AI, and startup strategy.

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

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.

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.

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.