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Jason Calacanis · Business

This Week in Startups

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

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

26 Jun 2025
1h 8m
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In this episode of "This Week in Startups," Jason Calacanis interviews Doug Leone, a veteran venture capitalist from Sequoia Capital, and Gili Raanan, who runs CyberStarts, a cybersecurity-focused venture firm. The discussion revolves around the secrets to successful venture investing, particularly in cybersecurity. Th...

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

24 Jun 2025
1h 11m
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The Strip Mining Era of LLMs—And Why It’s About to End | E2141

21 Jun 2025
1h 15m
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From Drones to Dystopia: The Future of Jobs, Fires & Meta’s AI Land Grab | E2140

18 Jun 2025
1h 11m
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Meta, Scale, and the Future of AI Labeling: Did Zuck Just Kill a Category? | E2139

17 Jun 2025
1h 9m
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Stripe’s Crypto Wallet, M&A Momentum, and Robots Replacing Soul-Crushing Jobs | E2138

13 Jun 2025
1h 3m
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TWIST VC Roundtable: Startup Valuations, Secondary Markets & the YC Revenue Illusion | E2137

12 Jun 2025
1h 11m
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YC Valuations, VC Slowdown, and Office Hours with CustomerIQ | E2136

10 Jun 2025
1h 3m
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In this episode of This Week in Startups, Jason Calacanis and Alex Wilhelm discuss various topics relevant to the startup ecosystem. Jason shares his experiences from a recent trip to Singapore, noting a shift in sentiment among international elites regarding the U.S. and its impact on startups. They analyze venture ca...

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

07 Jun 2025
46m
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In this episode of This Week in Startups, Jason Calacanis and Alex Wilhelm discuss Circle's successful IPO and its implications for the crypto market, regulatory environment, and public markets, highlighting Jeremy Allaire's entrepreneurial success and the potential for future crypto IPOs like Gemini. They analyze the ...

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

04 Jun 2025
1h 9m
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Grammarly’s $1B Round, Brain Computers, and NYT Licenses To Amazon | E2133

02 Jun 2025
1h 4m
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How AthenaHQ and Browser Use Are Building the Next Layer of the Internet | E2132

30 May 2025
59m
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Google’s AI Design Tool, Salesforce’s $8B Comeback Deal, and M&A Momentum Builds | E2131

28 May 2025
58m
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In this episode of "This Week in Startups," Jason is joined by Lon and Alex to discuss a range of topics, starting with the ClearSpace app designed to limit screen time through shame and social sharing, and then pivoting to Google's Stitch, an AI tool for website design. They explore the concept of viral marketing stun...

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

23 May 2025
1h 4m
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David Friedberg on AI-First Startups & the Future of Biology, Business & Creativity | AI Basics with Google Cloud

22 May 2025
41m
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Jony Ive Joins OpenAI, Waymo Hits 10M Rides, and How to Launch a Marketplace from Scratch | E2129

21 May 2025
1h 5m
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Drones, Design, and Digital Espionage | E2128

20 May 2025
1h 3m
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Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127

16 May 2025
1h 4m
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Chime’s IPO, Databricks’ $1B Acquisition & Dave Rubin’s Media Empire | E2126

15 May 2025
1h 6m
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Agentic AI Meets Cybersecurity + Solar Robots in the Desert | E2125

13 May 2025
51m
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This episode explores the cybersecurity risks associated with the increasing adoption of AI agents in enterprise environments, followed by a discussion on leveraging automation to enhance solar power plant construction. The conversation begins with ZioSec's Aaron Walls and Andruis Oshetkas defining AI agents and highli...

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