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

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 of internet humor, AND looking ahead to Christopher Nolan’s IMAX epic “The Odyssey.” Join us for the longest-running and most in-depth podcast on Earth for startup founders.

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-depth podcast on Earth for startup founders.

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

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 update on how much more time we have until all our servers are obsolete.All that and more on a brand new Monday edition of This Week in Startups.

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 future of tech, don’t miss this one.

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 anyone navigating the future of tech.

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

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 everyone, while fertility tech could revolutionize IVF by automating embryo handling and slashing costs. Hear our VC experts exclusive thoughts on these trends and much more!

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

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 one of the most exciting AI acquisitions yet!

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.